A member of the class of quinolines that is quinoline substituted by a 6-[4-(piperazin-1-yl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl group at position 5. It is a potent ALK inhibitor (IC50 values of 2.4, 1.3, 85.8, 2,133 and 9,276 nM for ALK1, ALK2, ALK3, ALK4 and ALK5, respectively).


A pyrazolopyrimidine that is pyrazolo[1,5-a]pyrimidine substituted by phenyl and 4-[2-(morpholin-4-yl)ethoxy]phenyl groups at positions 3 and 6, respectively. It is an inhibitor of VEGFR-2 (IC50 = 0.16 muM).


A dipeptide zwitterion resulting from transfer of a proton from the carboxy to the amino group of any L-histidyl-L-alpha-amino acid; major species at pH 7.3.


L-lysyl-L-alpha-amino acid(1+)

A dipeptide cation that is the conjugate acid of any L-lysyl-L-alpha-amino acid; major species at pH 7.3.


A dipeptide cation that is the conjugate acid of any L-aminoacyl-L-lysine; major species at pH 7.3.


L-aminoacyl-L-histidine zwitterion

A dipeptide zwitterion resulting from transfer of a proton from the carboxy to the amino group of any L-aminoacyl-L-histidine; major species at pH 7.3.


A dipeptide cation that is the conjugate acid of any L-aminoacyl-L-arginine; major species at pH 7.3.


Lys-Asp zwitterion

A dipeptide zwitterion resulting from transfer of protons from the carboxy groups to the amino groups of Lys-Asp; major species at pH 7.3.


A member of the class of aminoquinolines that is is quinoline substituted by 5-methylfuran-2-yl, (1-methylpiperidin-4-yl)amino, methoxy, and 3-(pyrrolidin-1-yl)propoxy groups at positions 2, 4, 6 and 7, respectively. It is a dual G9a/DNA methyltransferases inhibitor with antitumor activity. It inhibits G9a, DNMT1, DNMT3A, DNMT3B and GLP (IC50 = 8 nM, 382 nM, 85 nM, 1200 nM and 2 nM, respectively).


A member of the class of carbazoles that is 1,3-di(9H-carbazol-9-yl)propan-2-ol in which the hydroxy group is replaced by a 2-hydroxy-3-[(propan-2-yl)amino]propoxy group. It is a DNA methyltransferase 1 inhibitor (IC50 = 1.7 muM).


Major species at pH 7.3.


cyclosporin A sulfate

An organosulfate oxoanion that is the conjugate base of cyclosporin A hydrogen sulfate resulting from the deprotonation of the sulfooxy group. It is a metabolite of cyclosporin A found in human bile and plasma.


TETRAHYDROBERBERINE

A berberine alkaloid that is 5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline substituted by methoxy groups at positions 9 and 10.


caprolactams

A lactam in which the amide bond is contained within a seven-membered ring, which includes the amide nitrogen and the carbonyl carbon.


carbamoyl group

The univalent carboacyl group formed by loss of -OH from the carboxy group of carbamic acid.


carbohydrate-containing antibiotic

Any carbohydrate derivative that exhibits antibiotic activity.


A 7-hydroxyflavonol that is kaempferide substituted by a 1,1-dimethylallyl group at position 8.


carbonates

Organooxygen compounds that are salts or esters of carbonic acid, H2CO3.


name: EC 4.2.1.1 (carbonic anhydrase) inhibitor

description: An EC 4.2.1.* (hydro-lyases) inhibitor that interferes with the action of carbonic anhydrase (EC 4.2.1.1). Such compounds reduce the secretion of H(+) ions by the proximal kidney tubule.


A 7-hydroxyflavonol that is  3-methylgalangin substituted by a 1,1-dimethylallyl group at position 8.


VERRUCARIN A

A trichothecene antibiotic which incorporates a triester macrocyclic structure and an exocyclic methylene epoxide group.


name: Hydroxyethyl myristyl oxyhydroxypropyl decanamide


A trihydroxyflavone that is galangin substituted by a 1,1-dimethylallyl moiety at position 8. It is isolated from the buds of Platanus acerifolia.


name: N-(3-Aminopropyl)-N-methylcarbamic acid tert-butyl ester


name: 24-fluoro-25-hydroxyvitamin D3 / 24-fluoro-25-hydroxycholecalciferol


A 7-hydroxyflavonol that is 3-O-methylgalangin  substituted by a prenyl group at position 8.


carotene

Hydrocarbon carotenoids.


carotenoid

One of a class of tetraterpenoids (C40), formally derived from the acyclic parent, psi,psi-carotene by hydrogenation, dehydrogenation, cyclization, oxidation, or combination of these processes. This class includes carotenes, xanthophylls and certain compounds that arise from rearrangement of the skeleton of psi,psi-carotene or by loss of part of this structure. Retinoids are excluded.


cyclosporin A hydrogen sulfate

A cyclosporin A derivative that is cyclosporin A  in which the hydroxy group at the MeBmt (butenylmethylthreonine) amino acid is replaced by a sulfooxy group.


Ac-Tyr-Val-Ala-Asp-chloromethylketone

A tetrapeptide composed of L-tyrosine, L-valine, L-alanine, and L-aspartic acid joined in sequence by peptide linkages and in which the amino terminus in substituted by an acetyl group and the carboxy terminus is substituted by a chloromethyl group.


carveol

A limonene monoterpenoid that is cyclohex-2-en-1-ol substituted by a methyl group at position 2 and a prop-1-en-2-yl group at position 5.


Major microspecies at pH 7.3.


An acyl-CoA(4-) species arising from deprotonation of the phosphate and diphosphate OH groups of cis-dodec-5-enoyl-CoA; major species at pH 7.3.


metformInium

Major species at pH 7.3.


gentamicin C1(5+)

major species at pH 7.3


Major microspecies at pH 7.3


carvones

Any p-menthane monoterpenoid having the carvone skeleton as part of its structure.


(-)-coniine

A 2-propylpiperidine that has R-configuration.


MS023 is a type I PRMTs inhibitor.


StemRegenin 1

Inhibitor of the aryl hydrocarbon receptor


name: dihydroprecondylocarpine acetate (enamine form)

description: Major species at pH 7.3.


mevociclib

Mevociclib (SY-1365) is a selective CDK7 inhibitor. Mevociclib exhibits anti-proliferative and apoptotic effects in solid tumor cell lines. Mevociclib possesses anti-tumor activity in hematological and multiple aggressive solid tumors.


NVP-2 is a potent and selective ATP-competitive cyclin dependent kinase 9 (CDK9) probe. NVP-2 induces cell apoptosis.


AGI-5198 (IDH-C35) is a potent and selective mutant IDH1 R132H inhibitor


BMS641 (BMS-209641) is a selective RARbeta agonist.


BMS 753 is an isotype-selective retinoic acid receptor alpha (RARalpha) agonist


BMS961 is a selective retinoic acid receptor gamma (RARgamma) agonist


CMS-121 is a quinolone derivative and an orally active acetyl-CoA carboxylase 1 (ACC1) inhibitor. CMS-121 protects HT22 cells against ischemia and oxidative damage. CMS-121 has strong neuroprotective, anti-inflammatory, antioxidative and renoprotective activities.


pinometostat

Pinometostat (EPZ-5676) is a potent DOT1L histone methyltransferase inhibitor.


GSK547 (GSK'547) is a highly selective and potent inhibitor of receptor-interacting serine/threonine protein kinase 1 (RIPK1), inhibits macrophage-mediated adaptive immune tolerance in pancreatic cancer.


GSK591 (EPZ015866) is a potent and selective inhibitor of protein methyltransferase 5 (PRMT5).


GSK805 is an orally active and CNS penetrant RORgammat inhibitor. GSK805 inhibits RORgamma and Th17 cells differentiation. GSK805 inhibits the function of Th17 cells. GSK805 can be used for the research of immunity.


PLX5622 is a highly selective brain penetrant and orally active CSF1R inhibitor. PLX5622 allows for extended and specific microglial cells elimination, preceding and during pathology development. PLX5622 demonstrates desirable PK properties in varies animals. PLX5622 is mostly used in the way of feed free diet.


A dihydroxyflavone that is chrysin substituted by a prenyl group at position 8.


A member of the class of indoles that is 1H-indole substituted by a 5-chloro-2-[3-(4-{[(2E)-4-(dimethylamino)but-2-enoyl]amino}benzamido)anilino]pyrimidin-4-yl group at position 3. It is a selective and potent covalent inhibitor of CDK7 that exhibits anti-proliferative effects in cancer cell lines.


TMP269 is a novel and selective class IIa histone deacetylase (HDAC) inhibitor.


TMP778 is a potent and selective RORgt inverse agonist.


TMP920 is a highly potent and selective RORgt antagonist. TMP920 inhibits RORgt binding to the SRC1 peptide.


UNC1999 is a SAM-competitive, potent and selective inhibitor of EZH2/1.


X5050 is a REST inhibitor.


apilimod

Apilimod (STA 5326) is a potent IL-12/IL-23 inhibitor, and strongly inhibits IL-12 in IFNg/SAC-stimulated human PBMCs and SAC-treated monkey PBMCs. Apilimod is a potent and highly selective PIKfyve inhibitor.


ARV-825 is a PROTAC connected by ligands for Cereblon and BRD4. ARV-825 binds to BD1 and BD2 of BRD4.


birabresib

Birabresib (OTX-015) is a potent bromodomain (BRD2/3/4) inhibitor.


Major species at pH 7.3.


Defencath

A mixture containing taurolidine (a thiadiazinane antimicrobial) and heparin sodium (an anti-coagulant). It is used to reduce the incidence of catheter-related bloodstream infections in adult patients with kidney failure receiving chronic hemodialysis through a central venous catheter.


heparin sodium

The organic sodium salt of heparin.


sulfosungeidine F

Major microspecies at pH 7.3.


hexafluoropropylene oxide trimer acid

A polyfluoroalkyl substance with formula C9HF17O4. It is an environmental contaminant found in drinking water, food, and human blood samples at low levels. It enters the environment through wastewater treatment plants or by atmospheric deposition and causes health effects in laboratory animals and humans leading to changes in thyroid hormone levels, decreased fertility rates, increased cholesterol levels, liver damage, and developmental toxicity.


CATECHIN

Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.


ADAMTS-5 Inhibitor

ADAMTS-5 Inhibitor


compound 38 [PMID: 24915291]

A member of the class of pyrimidines that is pyrimidine substituted by (3-{[N-(prop-2-enoyl)glycyl]amino}phenyl)amino and {2-methyl-5-[3-(trifluoromethyl)benzamido]benzoyl}nitrilo groups at positions 2 and 5, respectively. It is a covalent BTK inhibitor with potential anti-proliferative activity. It exhibits more potent anti-proliferative effects than ibrutinib in multiple cellular and in vivo preclinical models of B-cell lineage malignancy, including tumor cell lines and mouse xenograft models.


A member of the class of N-benzylacetamides that is benzene substituted by acetylnitrilo, methyl, and butyl groups at positions 1, 2 and 4, respectively. It is a SKP2 E3 ligase inhibitor and a selective apoptosis inducer of human prostate cancer cells.


sulfosungeidine E

Major microspecies at pH 7.3.


A member of the class of benzocycloheptapyridines that is 5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one substituted by 1-methyl-1H-pyrazol-4-yl and [{[(2R)-1,4-dioxan-2-yl]methyl}(methyl)sulfamoyl]amino groups at positions 3 and 7, respectively. It is a novel ATP-competitive multi-targeted inhibitor of activated c-Met (IC50 = 2.5 nM).


name: 25-hydroxy-16,17,23,24-tetradehydrovitamin d3 / 25-hydroxy-16,17,23,24-tetradehydrocholecalciferol


name: (6r)-1alpha,25-dihydroxyvitamin d3 6,19-sulfur dioxide adduct / (6r)-1alpha,25-dihydroxycholecalciferol 6,19-sulfur dioxide adduct


name: 4,4-difluoro-1alpha,25-dihydroxyvitamin d3 / 4,4-difluoro-1alpha,25-dihydroxycholecalciferol


name: 25-hydroxy-16,17,23,23,24,24-hexadehydrovitamin d3 / 25-hydroxy-16,17,23,23,24,24-hexadehydrocholecalciferol


name: 1alpha,25-dihydroxy-19-nor-22-oxavitamin d3 / 1alpha,25-dihydroxy-19-nor-22-oxacholecalciferol


name: (24r)-25-fluoro-1alpha,24-dihydroxy-24-methylvitamin d3 / (24r)-25-fluoro-1alpha,24-dihydroxy-24-methylcholecalciferol


name: glucose isomerase from streptomyces rubiginosus


cephalosporin

A class of beta-lactam antibiotics differing from the penicillins in having a 6-membered, rather than a 5-membered, side ring.  Although cephalosporins are among the most commonly used antibiotics in the treatment of routine infections, and their use is increasing over time, they can cause a range of hypersensitivity reactions, from mild, delayed-onset cutaneous reactions to life-threatening anaphylaxis in patients with immunoglobulin E (IgE)-mediated allergy.


name: 5-Isoxazoleacetic acid, 4,5-dihydro-3-(4-hydroxyphenyl)-, methyl ester


glycopentaosylceramide

An oligoglycosylceramide consisting of a glycopentaosyl moiety attached to the ceramide oxygen with an unspecified N-acyl substituent attached to the ceramide nitrogen.


name: 1alpha,25-dihydroxy-19-norvitamin d3 / 1alpha,25-dihydroxy-19-norcholecalciferol


glycotetraosylceramide

An oligoglycosylceramide consisting of a glycotetraosyl moiety attached to the ceramide oxygen with an unspecified N-acyl substituent attached to the ceramide nitrogen.


name: 26,27-diethyl-1alpha,25-dihydroxy-22-thiavitamin d3 / 26,27-diethyl-1alpha,25-dihydroxy-22-thiacholecalciferol


cerebroside

Any member of a group of glycosphingolipids, also known as monoglycosylceramides, which are important components in animal muscle and nerve cell membranes.


chalcones

A ketone that is 1,3-diphenylpropenone (benzylideneacetophenone), ArCH=CH(=O)Ar, and its derivatives formed by substitution.


N,N'-diacetylchitobioses

Any of the chitobioses acetylated on both amino nitrogens.


chlorate salt

Any salt that has chlorate, [ClO3](-), as the anionic component.


chlorohydrocarbon

A compound derived from a hydrocarbon by replacing at least one hydrogen atom with a chlorine atom.


chlorine molecular entity

A halogen molecular entity containing one or more atoms of chlorine.


chlorite salt

Any salt that has chlorite, [ClO2](-), as the anionic component.


name: 5-alpha-Cholestane-3-beta,5,6-beta-triol, 6-acetate 3-(hydrogen succinate)


name: Palmitoyl 3-carbacyclic Phosphatidic Acid


An  organochlorine compound that is propane-1,2-diol substituted by a chlorine atom at unspecified position.


chloroacetate

A haloacetate(1-) resulting from the deprotonation of the carboxy group of chloroacetic acid.


name: 9-Octadecenoic acid (9Z)-, (2-hydroxy-2-oxido-1,2-oxaphospholan-4-yl)methyl ester


chloroalanine

Any  chloroamino acid in which the the amino acid specified is alanine.


Major microspecies at pH 7.3.


A guanidinium ion resulting from the protonation of both the primary amino and guanidino groups and deprotonation of the carboxy group of 5-hydroxy-L-arginine; Major microspecies at pH 7.3.


chloroalkane

Any haloalkane that consists of an alkane substituted by at least one chloro group.


chloroamino acid

A  haloamino acid that is an amino acid carrying at least one halogen atom.


name: 2-Propenoic acid, 3-(2,4-dimethoxyphenyl)-, (E)-


chloroaniline

Any  substituted aniline carrying at least one chloro group.


name: Carbamic acid, N-[2-(2-naphthalenyl)ethyl]-, 2-(1-methylethyl)phenyl ester


NK13650 B

Major microspecies at pH 7.3.


NK13650 D

Major microspecies at pH 7.3.


NK13650 C

Major microspecies at pH 7.3.


chlorobenzenes

Any organochlorine compound containing a benzene ring which is substituted by one or more chlorines.


NK13650 A

Major microspecies at pH 7.3.


alpelisib

Alpelisib is a phosphatidylinositol 3-kinase (PI3K) inhibitor with potent antitumor activity.


TCPMOH

Tris(4-chlorophenyl)methanol (TCPMOH) is a water contaminant with unknown etiology, but is believed to be a byproduct of DDT manufacturing. It is highly persistent in the environment, and bioaccumulates in marine species.


TCPM

TCPM is structurally related to the organochlorine pesticide Dichlorodiphenyltrichloroethane (DDT), and evidence suggests they are likely manufacturing byproducts of this legacy contaminant


O-(arachidonyl)-beta-D-glucuronate

Major species at pH 7.3


Major species at pH 7.3.


chlorobenzoate

Any member of the class of benzoates in which the benzene ring is substituted by at least one chloro group.


name: (E)-ferulic acid beta-D-glucuronate ester

description: Major species at pH 7.3.


A tertiary ammonium ion that is the conjugate acid of givinostat resulting from the protonation of the tertiary amino group; Major species at pH 7.3.


A hydroxy-L-arginine that is L-arginine substituted by a hydroxy group at position 5.


A member of the class of chalcones that is trans-chalcone hydroxylated at C-2' and -4'.


A member of the class of chalcones that is trans-chalcone hydroxylated at C-2' and C-4.


NP-313 is a specific small molecule inhibitor of ubiquitin-like protein UHRF1, binds with the SRA domain groove of UHRF1.


chlorobenzoic acid

Any member of the class of benzoic acids in which the benzene ring is substituted by at least one chloro group.


GSK503 is a potent and specific inhibitor of EZH2 methyltransferase.


ceralasertib

Ceralasertib is an orally available morpholino-pyrimidine-based inhibitor of ataxia telangiectasia and rad3 related (ATR) kinase, with potential antineoplastic activity. Upon oral administration, Ceralasertib selectively inhibits ATR activity by blocking the downstream phosphorylation of the serine/threonine protein kinase CHK1. This prevents ATR-mediated signaling, and results in the inhibition of DNA damage checkpoint activation, disruption of DNA damage repair, and the induction of tumor cell apoptosis.


7DG (7-Desacetoxy-6,7-dehydrogedunin) is a protein kinase R (PKR) inhibitor. 7DG protects macrophages from lethal toxin-induced pyroptosis.


talazoparib tosylate

Talazoparib is an orally available small molecule inhibitor of the DNA repair enzyme poly ADP-ribose polymerase (PARP) which is used as an antineoplastic agent in the treatment of selected cases of breast cancer. Talazoparib is associated with a moderate rate of serum aminotransferase elevations during therapy and is suspected to cause rare instances of clinically apparent acute liver injury.


TRIAPINE

Triapine is a synthetic heterocyclic carboxaldehyde thiosemicarbazone with potential antineoplastic activity. Triapine inhibits the enzyme ribonucleotide reductase, resulting in the inhibition of the conversion of ribonucleoside diphosphates to deoxyribonucleotides necessary for DNA synthesis. This agent has been shown to inhibit tumor growth in vitro.


IPAG

IPAG is a potent sigma-receptor antagonist.


chlorobenzophenone

A member of the class of benzophenones that is any substituted benzophenone in which at least one of the substituents is a chlorine.


pacritinib

An azamacrocycle with formula C28H32N4O3. It is a Janus kinase inhibitor and its citrate salt is approved for the treatment of intermediate or high risk, primary or secondary myelofibrosis.


telatinib

A member of the class of furopyridazines that is furo[2,3-d]pyridazine substituted by (4-chlorophenyl)amino and [2-(methylcarbamoyl)pyridin-4-yl]methoxy groups at positions 4 and 7, respectively. It is a potent inhibitor of VEGFR2/3, c-Kit and PDGFRalpha.


resminostat

An enamide resulting from the formal condensation of the carboxy group of (2E)-3-[1-({4-[(dimethylamino)methyl]phenyl}sulfonyl)-1H-pyrrol-3-yl]prop-2-enoic acid with the amino group of hydroxylamine. It is an orally bioavailable inhibitor of histone deacetylases with potential antineoplastic activity.


ORTERONEL

A member of the class of pyrroloimidazoles that is 6,7-dihydro-5H-pyrrolo[1,2-c]imidazole substituted by hydroxy and 6-(methylcarbamoyl)naphthalen-2-yl groups at position 7 (the 7S-stereoisomer). It is a non-steroidal 17,20-lyase inhibitor that suppresses androgen synthesis. It was previously in clinical development for the treatment of castration-resistant prostate cancer -- trial now discontinued.


tasquinimod

Tasquinimod is a quinoline-3-carboxamide linomide analogue with antiangiogenic and potential antineoplastic activities. Tasquinimod has been shown to decrease blood vessel density but the exact mechanism of action is not known. This agent has also been shown to augment the antineoplastic effects of docetaxel and androgen ablation in a murine model of prostate cancer involving human prostate cancer xenografts.


varlitinib

A member of the class of quinazolines that is quinazoline substituted by {3-chloro-4-[(1,3-thiazol-2-yl)methoxy]phenyl}amino and [(4R)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl]amino groups at positions 4 and 6, respectively. It is a tyrosine kinase inhibitor of both ErbB-2 (Her-2/neu) and EGFR and has shown significant anti-tumour activity in preclinical models of human breast, lung, and epidermal carcinoma tumours.


PI3K/mTOR Kinase Inhibitor PF-04691502 is an agent targeting the phosphatidylinositol 3 kinase (PI3K) and mammalian target of rapamycin (mTOR) in the PI3K/mTOR signaling pathway, with potential antineoplastic activity.


volasertib

A member of the class of pteridines that is (7R)-7-ethyl-5-methyl-8-(propan-2-yl)-7,8-dihydropteridin-6(5H)-one substituted by a [4-({trans-4-[4-(cyclopropylmethyl)piperazin-1-yl]cyclohexyl}carbamoyl)-2-methoxyphenyl]amino group at position 2. It is as polo-like kinase 1 inhibitor (IC50 = 0.87 nM) with potential antineoplastic activity.


chlorobenzoyl-CoA

A member of the class of  benzoyl-CoAs in which the acyl group specified is chlorobenzoyl.


riviciclib

A synthetic dihydroxyflavone that is 5,7-dihydroxyflavone which is substituted by a (2R,3S)-2-(hydroxymethyl)-1-methylpyrrolidin-3-yl group at position 8 and by a chlorine at the 2' position. A cyclin-dependent kinase inhibitor that exhibits anti-cancer properties.


A member of the class of pyridopyrimidines that is pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione substituted by (2R)-2,3-dihydroxypropyl, (2-fluoro-4-iodophenyl)amino, fluoro, and methyl groups at positions 3, 5, 6, and 8, respectively. It is a non-ATP competitive allosteric inhibitor of MEK1/2.


savolitinib

A member of the class of triazolopyrazines that is 1H-[1,2,3]triazolo[4,5-b]pyrazine substituted by (1S)-1-(imidazo[1,2-a]pyridin-6-yl)ethyl and 1-methyl-1H-pyrazol-4-yl groups at positions 1 and 6, respectively. It is a highly selective MET tyrosine kinase inhibitor that is approved in China for advanced NSCLC with MET exon 14 skipping mutations.


A diterpene that is produced by a diterpene synthase from Cephalotaxus sinensis.


chlorocatechol

Any member of the class of catechols that is catechol substituted by at least one chloro group.


A member of the class of chromenes that is 2H-chromene substituted by a phenyl group at position 2. It is a metabolite of flavanone found in rat urine.


chlorocyclohexene

A chlorohydrocarbon that is cyclohexene in which one or more hydrogens have been replaced by chlorines.


chloroethanol

An organochlorine compound that is ethanol substituted by at least one chloro group.


furopyridazine

Any organic heterobicyclic compound containing ortho-fused furan and pyridazine rings.


A tertiary ammonium ion that is the conjugate acid of pacritinib resulting from the protonation of the pyrrolidine nitrogen; Major species at pH 7.3.


sulfopin

A sulfone that is thiolane substituted by two oxo groups at position 1 and by a (chloroacetyl)(2,2-dimethylpropyl)amino group at position 3. It is a covalent inhibitor of Pin1 (Ki = 17 nM) that inhibits Myc-driven tumors in vivo.


BIS(ETHYL)NORSPERMINE

N(1),N(11)-bis(ethyl)norspermine (DENSPM), a N-terminally alkylated tetraamine and polyamine mimetics, disrupts polyamine pool homeostasis by modulating the activities of the biosynthetic enzymes, ornithine decarboxylase (ODC), and S-adenosylmethionine decarboxylase (AdoMetDC).


chloroethenes

A chloroalkene that is ethene in which one or more of the hydrogens has been replaced by chlorine.


avenalumate

Major microspecies at pH 7.3.


A hexadecenal that carries a double bond at position 2.


(S)-tolvaptan

The (S)-enantiomer of tolvaptan.


tolvaptan

A member of the class of benzazepines that is 2,3,4,5-tetrahydro-1H-1-benzazepine substituted by 2-methyl-4-(2-methylbenzamido)benzoyl, hydroxy, and chloro groups at positions 1, 5, and 7, respectively.


(R)-tolvaptan

The (R)-enantiomer of tolvaptan.


Major species at pH 7.3.


C6 WDR5 inhibitor


A 3-hydroxy fatty acyl-CoA(4-) oxanion arising from deprotonation of the phosphate and diphosphate OH groups of 3-hydroxypentanoyl-CoA; major species at pH 7.3.


Sesterviridene A

A sesterterpene that is produced by a sesterterpene synthase from Kitasatospora viridis.


BAY 73-6691

A member of the class of pyrazolopyrimidines that is 4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine substituted by 2-chlorophenyl, oxo, and (2R)-3,3,3-trifluoro-2-methylpropyl groups at positions 1, 4 and 6, respectively. It is a potent and selective inhibitor of phosphodiesterase 9 (PDE9), currently in pre-clinical development for the treatment of Alzheimer's disease.


Sesterviolene A

A sesterterpene that is produced by a sesterterpene synthase from Streptomyces violens


motiol

A fernane-type skeleton with a Delta7 double bond.


4beta-carboxyl motiol

Major microspecies at pH 7.3.


2alpha-hydroxyl, 4beta-carboxyl motiol

Major microspecies at pH 7.3.


chlorohydroquinones

Any member of the class of  hydroquinones that is  hydroquinone carrying at least one chloro substituent at unspecified position.


chloromethanes

A halomethane that is methane in which one or more hydrogens has been replaced by chlorine.


chlorophenol

A halophenol that is any phenol containing one or more covalently bonded chlorine atoms.


chlorophenoxyacetate anion

A monocarboxylic acid anion obtained by deprotonation of the carboxy group of any chlorophenoxyacetic acid.


chlorophenoxyacetic acid

A monocarboxylic acid that is phenoxyacetic acid in which at least one of the phenyl hydrogens is replaced by chlorine.


chlorophenylethane

Any  chlorohydrocarbon that is phenylethane substituted by at least one chloro group at unspecified position.


chlorophenylethylene

A chlorohydrocarbon that is consists of ethylene in which one or more hydrogens are replaced by chlorophenyl groups.


chlorophenylmethane

A chlorohydrocarbon that is phenylmethane substituted by a chloro group at unspecified position.


chloropropene

Any chloroalkene that is propene substituted by at least one chloro group at unspecified position.


cholate salt

A bile acid salt having cholate as the anionic component.


8-epiiridodial lactol

A lactol that is (+)-iridodial lactol in which the configuration of the carbon at position 7 is inverted from S to R.


glycerol 1-phosphate(2-)

An  organophosphate oxoanion that is the dianion of glycerol 1-phosphate arising from deprotonation of the phosphate OH groups; major species at pH 7.3.


cholestanoyl-CoA

A steroidal acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of any cholestan-26-oic acid.


(+)-cis-carveol

The (1S,5S)-stereoisomer of carveol.


cholestenoyl-CoA

A steroidal acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of any cholestenoic acid.


A dihydroxyflavone that is  chrysin substituted by a geranyl group at position 8.


cholines

A quaternary ammonium ion based on the choline ion and its substituted derivatives thereof.


choloyl-CoAs

A steroidal acyl-CoA formed by thioester formation between coenzyme A and any cholic acid.


bile acid taurine conjugate

A bile acid conjugate resulting from the formal condensation of a bile acid with the amino group of taurine.


chromanol

Any member of the class of chromanes that is chromane substituted by one or more hydroxy groups.


4-hydroxy-8-methoxyquinaldic acid

A quinolinemonocarboxylic acid that is kynurenic acid which is substituted by a methoxy group at position 8.


chromones

A chromenone that consists of a 1,4-benzopyrone skeleton and its substituted derivatives thereof.


cinnamaldehydes

An  enal based on a cinnamaldehyde skeleton and its substituted derivatives.


cinnamamide

The simplest member of the class of cinnamamides that consists of acrylamide bearing a phenyl substituent at the 3-position.


cinnamamides

An enamide which is cinnamamide or a derivative of cinnamamide obtained by replacement of one or more of its hydrogens.


cinnamate

A member of the class of cinnamates that results from the deprotonation of the carboxy group of cinnamic acid.


cinnamic acids

Any alpha,beta-unsaturated monocarboxylic acid based on the cinnamic acid skeleton and its substituted derivatives.


name: cis-14-hydroxy-10,13-dioxo-7-heptadecenoic acid L-aspartate ester


A 2,6-dimethyl-5-methylenehept-2-enoic acid having Z-configuration.


The cis-isomer of 3-hexenal.


A 4-(3-hydroxy-1-benzothiophen-2-yl)-2-oxobut-3-enoate in which the acyclic double bond has Z-geometry.


The (4S,7R)-stereoisomer of 4-isopropenyl-7-methyloxepan-2-one.


A cyclohexadienediol in which the two hydroxy groups are ortho and cis to one another, with chlorine atoms on each of the other four ring carbons.


citral

An enal that consists of octa-2,6-dienal bearing methyl substituents at positions 3 and 7. A mixture of the two geometric isomers geranial and neral, it is the major constituent (75-85%) of oil of lemon grass, the volatile oil of Cymbopogon citratus, or of C. flexuosus. It also occurs in oils of verbena, lemon, and orange.


coenzyme

A low-molecular-weight, non-protein organic compound participating in enzymatic reactions as dissociable acceptor or donor of chemical groups or electrons.


colchicine

An  alkaloid that is a carbotricyclic compound comprising 5,6,7,9-tetrahydrobenzo[a]heptalene having four methoxy substituents at the 1-, 2-, 3- and 10-positions as well as an oxo group at the 9-position and an acetamido group at the 7-position. It has been isolated from the plants belonging to genus Colchicum.


molecular entity

Any constitutionally or isotopically distinct atom, molecule, ion, ion pair, radical, radical ion, complex, conformer etc., identifiable as a separately distinguishable entity.


copper-sulfur cluster

A copper-sulfur cluster is a unit comprising two or more copper atoms and bridging sulfur ligand(s).


coproporphyrin

A member of the class of porphyrins obtained during the heme biosynthesis in humans.


coumarate

A member of the class of cinnamates obtained by the deprotonation of the carboxy group of coumaric acid.


DOCEBENONE

A member of the class of benzoquinones that is p-benzoquinone in which the hydrogens are substituted by three methyl groups and a 12-hydroxydodeca-5,10-diyn-1-yl group.


coumaric acid

A monohydroxycinnamic acid that is prop-2-enoic acid substituted by a hydroxyphenyl group at position 3.


arachidonyl trifluoromethyl ketone

A fatty acid derivative that is arachidonic acid in which the OH part of the carboxy group has been replaced by a trifluoromethyl group


cumate

A member of the class of benzoates obtained by the deprotonation of the carboxy group of cumic acid.


cumic acid

A member of the class of  benzoic acids that is cumene substituted by at least one carboxy group.


cutins

Polyester macromolecules consisting of omega-hydroxy acid monomers connected via ester linkages.


cyanates

Salts and esters of cyanic acid, HOC#N; compounds carrying the cyanate functional group -O-C#N.


cyanides

Salts and C-organyl derivatives of hydrogen cyanide, HC#N.


cyanogenic glycoside

A glycoside in which the aglycone contains a cyanide group. A cyanogenic glycoside can release poisonous hydrogen cyanide if acted upon by some enzyme.


cyanohydrin

An alpha-hydroxynitrile resulting from the formal addition of hydrogen cyanide to the C=O bond of an aldehyde or ketone.


cyanopyridine

Any pyridine carrying at least one cyano substituent.


cyclic hydroxamic acid

A lactam having a hydroxy substituent on the amide nitrogen.


cyclic monoterpene ketone

A cyclic terpene ketone in which the terpene specified is monoterpene.


cyclitol

A polyol consisting of a cycloalkane containing at least three hydroxy groups, each attached to a different ring carbon atom.


cycloalkane

Saturated monocyclic hydrocarbons (with or without side chains).


cyclodextrin

A macrocycle composed of five or more D-glucopyranose units bonded via (1->4)-linkages.


cyclodiene organochlorine insecticide

A sub-category of organochlorine insecticides, the members of which are all derived from hexachlorocyclopentadiene. They possess a structure based on two 3-dimensional carbon ring units, one of which is heavily chlorinated.


cyclohexadienecarboxylic acid

Any cyclohexadiene substituted by a carboxylic group at unspecified position.


cyclohexadienediol

Any cyclohexadiene in which two hydroxy groups are located on the cyclohexadiene ring.


cyclohexadienol

A cyclohexadiene carrying at least one hydroxy substituent.


cyclohexanedione

Cyclohexanones carrying two oxo substituents.


cyclohexanols

An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton.


cyclohexanones

Any alicyclic ketone based on a cyclohexane skeleton and its substituted derivatives thereof.


CYCLOPENTANE

A cycloalkane that consists of five carbons each bonded with two hydrogens above and below the plane. The parent of the class of cyclopentanes.


cyclopentanes

Cyclopentane and its derivatives formed by substitution.


cyclopentanols

An alcohol in which one or more hydroxy groups are attached to a cyclopentane skeleton.


cyclopentenyl fatty acid

A carbocyclic, unsaturated fatty acid containing a cyclopentene ring at any point in the carbon chain.


cyclopropenyl fatty acid

Any fatty acid containing a three-membered carbocyclic unit which includes a double bond.


A member of the class of oxazolidines that is isoxazoldin-3-one which is substituted at position 4 by an amino group.


cysteine derivative

An amino acid derivative resulting from reaction of cysteine at the amino group, carboxy group, or thiol group, or from the replacement of any hydrogen of cysteine by a heteroatom. The definition normally excludes peptides containing cysteine residues.


cytidyl group

Group formed by loss of a 2'-, 3'- or 5'-hydroxy group from the ribose moiety of cytidine.


cytochalasin B

An organic heterotricyclic compound, that is a mycotoxin which is cell permeable an an inhibitor of cytoplasmic division by blocking the formation of contractile microfilaments.


cytokinin

A phytohormone that promote cell division, or cytokinesis, in plant roots and shoots.


dehydroamino acid

An amino acid derivative that is an amino acid whose side-chain has undergone formal dehydrogenation.


(Z)-dehydrotyrosine

A 2,3-dehydroamino acid resulting from the formal elimination of a molecule of hydrogen from the side-chain of tyrosine.


A multi-methyl-branched fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of 3,4,4-trimethylhepta-2,5-dienoic acid.


deoxycortisol

A 3,20-dioxo steroid having the structure of cortisol but lacking one or more of its hydroxy groups.


deoxyglucose

A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.


deoxyhexose

Any C6 deoxy sugar having at least one hydroxy group replaced by hydrogen.


deoxy sugar

Any sugar having a hydroxy group replaced with a hydrogen atom.


ABRUSOSIDE A

A triterpenoid saponin that is (22S,24Z)-3beta-hydroxy-26-oxo-22,26-epoxy-9beta,19-cyclolanost-24-en-28-oic acid having a beta-D-glucosyl residue attached at position 3 via a glycosidic bond.


(+)-ABSCISIC ACID

The naturally occurring (1'S)-(+) enantiomer of abscisic acid. It is an important sesquiterpenoid plant hormone which acts as a regulator of plant responses to environmental stresses such as drought and cold.


absinthin

A dimeric sesquiterpene lactone that is produced by the plant Artemisia absinthium (Wormwood). The bitter tasting constituent of Absinthe.


diamine

Any polyamine that contains two amino groups.


ABYSSINONE I

A monohydroxyflavanone that is (2S)-2',2'-dimethyl-2,3-dihydro-2'H,4H-2,6'-bichromen-4-one carrying a hydroxy substituent at position 7.


A dicarboxylic acid dianion that is the conjugate base of 2,6-diaminopimelic acid.


diazole

An azole that is either one of a pair of heterocyclic organic compounds comprising three carbon atoms and two nitrogen atoms arranged in a ring.


ABYSSINONE V

A trihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7 and 4' and prenyl groups at positions 3' and 5' respectively.


DIBENZOTHIOPHENE

A mancude organic heterotricyclic parent that consists of a thiophene ring flanked by two benzene rings ortho-fused across the 2,3- and 4,5-positions.


dibenzothiophene 5-oxide

A member of the class of dibenzothiophenes that is the 5-oxo derivative of dibenzothiophene.


dibromobisphenol

A bromobisphenol substituted by two bromo groups at unspecified positions.


ABYSSINONE VI

A member of the class of chalcones that is isolated from the stem of Erythrina abyssinica.


dichlorobenzene

Any member of the class of chlorobenzenes carrying two chloro groups at unspecified positions.


dichlorobenzoyl-CoA

Any  chlorobenzoyl-CoA having dichlorobenzoyl as the aroyl substituent.


dichlorocatechol

A chlorocatechol carrying two chloro groups at unspecified positions.


dichlorohydroquinone

A member of the class of  chlorohydroquinones carrying two chloro substituents at unspecified positions.


dichlorophenol

Any chlorophenol carrying chloro substituents.


difluoroacetate

A monocarboxylic acid anion that is obtained by removal of a proton from the carboxylic acid group of difluoroacetic acid.


difluoroacetic acid

A monocarboxylic acid that is acetic acid in which two of the methyl hydrogens are substituted by fluorines.


acalyphin

A member of the class of tetrahydropyridines that is 2,3-dihydroxy-4-methoxy-1-methyl-6-oxo-1,2,3,6-tetrahydropyridine-3-carbonitrile having a beta-D-glucosyl residue attached at position 3 via a glycosidic bond.


acamelin

A member of the class of 1-benzofurans that is 1-benzofuran-4,7-dione bearing additional methyl and methoxy substituents at positions 2 and 7 respectively.


5-oxo-2-furylacetic acid

An oxo monocarboxylic acid that is 2,5-dihydrofuran-2-ylacetic acid substituted by an oxo group at position 5.


dihydrocarvone

A dihydrocarvone resulting from reduction of the endocyclic cyclohexene double bond.


A 3-oxo steroid that is cortisone in which the double bond between positions 4 and 5 has been reduced to a single bond.


acanthicifoline

A 2,7-naphthyridine derivative that is 1,4-dihydro-2,7-naphthyridin-3(2H)-one which is substituted at positions 1 and 5 by methyl and methoxy groups, respectively.


dihydrodipicolinic acid

A dicarboxylic acid in which the carboxylic acid groups are at the 2 and 6 positions of a dihydropyridine.


dihydrofolic acids

A group of heterocyclic compounds based on the 7,8-dihydropteroic acid skeleton conjugated with one or more L-glutamic acid units.


The simplest member of the class of dihydroisocoumarins that is the 3,4-dihydro derivative of isocoumarin.


dihydrojasmonic acid

Any oxo monocarboxylic acid that is the dihydro derivative of  jasmonic acid.


A beta-D-glucoside that is the 4,4'-bis(beta-D-glucosyl) derivative of (-)-syringaresinol.


S-substituted dihydrolipoamide

A monocarboxylic acid amide consisting of dihydrolipoamide carrying substituents on at least one of the sulfanyl groups.


dihydrophaseic acid

An apo carotenoid sesquiterpenoid that is phaseic acid in which the keto group has been reduced to the corresponding alcohol such that the two hydroxy groups are on opposite sides of the 6-membered ring.


dihydrophenanthrene

Any member of the class of  phenanthrenes that is the dihydrogenated derivative of phenanthrene and its substituted derivatives.


acarbose

A tetrasaccharide derivative consisting of a dideoxy-4-{[4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl C7 cyclitol moiety [called valienol (or valienamine)] linked via nitrogen to isomaltotriose.


pyrroline

Any organic heteromonocyclic compound with a structure based on a dihydropyrrole.


dihydrouridine

The uridine derivative obtained by formal hydrogenation of the endocyclic double bond in the uracil ring.


dihydroxy-5beta-cholanic acid

A hydroxy-5beta-cholanic acid carrying two hydroxy groups at unspecified positions.


dihydroxyacetophenone

A hydroxyacetophenone carrying two hydroxy substituents.


dihydroxybenzoic acid

Any member of the class of  hydroxybenzoic acids carrying  two phenolic hydroxy groups on the benzene ring and its derivatives.


dihydroxyindole

Any member of the class of  hydroxyindoles carrying two hydroxy groups.


naphthalenediols

Any hydroxynaphthalene derivative that has two hydroxy substituents.


acebutolol

An ether that is the 2-acetyl-4-(butanoylamino)phenyl ether of the primary hydroxy group of 3-(propan-2-ylamino)propane-1,2-diol.


dihydroxyproline

A hydroxyproline that is proline substituted by two hydroxy substituents.


diiodotyrosine

A dihalogenated L-tyrosine which has two iodo-substituents on the benzyl moiety.


dimethoxyflavone

Any methoxyflavone with two methoxy substituents.


dimethylaniline

A methylaniline carrying at least two methyl groups.


dimethylmaleic acid

A dicarboxylic acid that is maleic acid in which each of the hydrogens that is attached to a carbon atom is substituted by a methyl group.


acerosin

A trihydroxyflavone that is 5,7,3'-trihydroxyflavone with methoxy substituents at positions 6, 8 and 4' respectively.


dinitroglycerol

A nitroglycerol carrying two nitro groups at unspecified positions.


dinitrotoluene

Any  nitrotoluene carrying two nitro substituents.


diol

A compound that contains two hydroxy groups, generally assumed to be, but not necessarily, alcoholic. Aliphatic diols are also called glycols.


dibenzodioxine

Oxanthrene (formerly dibenzo[b,e][1,4]dioxine) and its derivatives.


A dicarboxylic acid dianion obtained by deprotonation of both carboxy groups of diphenic acid.


An alpha-amino-acid residue that is an L-cysteine residue in which the hydrogen attached to the sulfur is substituted by a [4-(2-carboxyethyl)-5-{[4-(2-carboxyethyl)-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl}-3-(carboxymethyl)-1H-pyrrol-2-yl]methyl group.


diterpenoid

Any terpenoid derived from a diterpene. The term includes compounds in which the C20 skeleton of the parent diterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl groups).


divalent carboacyl group

A divalent carboacyl group is a group formed by loss of OH from two carboxy groups of a polycarboxylic acid.


behenate

A straight-chain saturated fatty acid anion that is the conjugate base of behenic acid, arising from deprotonation of the carboxylic acid group.


dodecanol

A fatty alcohol consisting of a hydroxy function at any position of an unbranched saturated chain of twelve carbon atoms.


dodecenoic acid

A C12, straight-chain fatty acid carrying a double bond at any position.


dodecenoyl-CoA

A monounsaturated fatty acyl-CoA in which the S-acyl moiety contains 12 carbons and 1 double bond.


bevantolol

A propanolamine that is 3-aminopropane-1,2-diol in which the hydrogen of the primary hydroxy group is substituted by 3-methylphenyl and one of the hydrogens attached to the nitrogen is substituted by 2-(3,4-dimethoxyphenyl)ethyl. A beta1 adrenoceptor antagonist, it has been shown to be as effective as other beta-blockers for the treatment of angina pectoris and hypertension.


dodecyl palmitate

A palmitate ester resulting from the formal condensation of palmitic acid with dodecan-1-ol. It is A wax ester synthesised by retinal pigment epithelial membranes.


dolichol phosphate

An  isoprenoid phosphate in which the isoprenoid specified is dolichol.


ecdysteroid

A class of steroids that include insect moulting and sex hormones.


icosanoid

Any member of the group of signalling molecules arising from oxidation of the three C20 essential fatty acids (EFAs) icosapentaenoic acid (EPA), arachidonic acid (AA) and dihomo-gamma-linolenic acid (DGLA).


icosenoic acid

An icosanoid comprising icosanoic acid having one C=C bond at any position.


ellagitannin

A form of hydrolysable tannin produced from ellagic acid. Ellagitannins are glucosides which are readily hydrolysed by water to regenerate ellagic acid when the plants are eaten.


salicylanilide

An amide of salicylic acid and of aniline; it is therefore both a salicylamide and an anilide.


enoyl group

Acyl groups derived from alkenoic acids.


enzyme inhibitor

A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.


A sesquiterpene that is 1,2,3,4,4a,5,6,7-octahydronaphthalene substituted by methyl groups at positions 4 and 4a and a prop-1-en-2-yl group at position 6 (the 4R,4aR,6R-stereoisomer).


epi-dihydrophaseic acid

A cyclic ether that is phaseic acid in which the keto group has been reduced to the corresponding alcohol such that the two hydroxy groups are on the same side of the 6-membered ring.


epoxy monocarboxylic acid

Monocarboxylic acids containing at least one epoxy group.


ACETOCHLOR

A monocarboxylic acid amide that is N-phenylacetamide carrying an ethyl and a methyl group at positions 2 and 6 respectively on the benzene ring while one of the methyl hydrogens as well as the hydrogen attached to the nitrogen atom have been replaced by a chloro and an ethoxymethyl group respectively.


estradiol

A 3-hydroxy steroid that is estra-1,3,5(10)-triene substituted by hydroxy groups at positions 3 and 17.


ethanediol

Any diol that is ethane or substituted ethane carrying two hydroxy groups.


ethanols

Any primary alcohol based on an ethanol skeleton.


ethyl ester

Any carboxylic ester resulting from the formal condensation of the carboxy group of a carboxylic acid with ethanol.


METHANESULFONIC ACID ETHYL ESTER

A methanesulfonate ester resulting from the formal condensation of methanesulfonic acid with ethanol.


ETHYL NITROSOUREA

A member of the class of N-nitrosoureas that is urea in which one of the nitrogens is substituted by ethyl and nitroso groups.


ethyl sulfide

An aliphatic sulfide in which the sulfur atom is bonded to at least one ethyl group.


ethyl 3-hydroxyhexanoate

A fatty acid ester that is the ethyl ester of 3-hydroxyhexanoic acid.


acetophenazine

A member of the class of  phenothiazines that is 10H-phenothiazine substituted by a 3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl group at the nitogen atom and an acetyl group at position 2.


bromfenac

Amfenac in which the the hydrogen at the 4 position of the benzoyl group is substituted by bromine. It is used for the management of ocular pain and treatment of postoperative inflammation in patients who have undergone cataract extraction. It was withdrawn from the US market in 1998, following concerns over off-label abuse and hepatic failure.


fatty alcohol

An aliphatic alcohol consisting of a chain of 3 to greater than 27 carbon atoms. Fatty alcohols may be saturated or unsaturated and may be branched or unbranched.


fatty-acyl group

A fatty-acyl group is a group formed by loss of OH from the carboxy group of a fatty acid.


ACETOSYRINGONE

A member of the class of  acetophenones that is 1-phenylethanone substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5.


flavones

A member of the class of flavonoid with a 2-aryl-1-benzopyran-4-one (2-arylchromen-4-one) skeleton and its substituted derivatives.


A member of the class of  fluorenes carrying an oxo substituent at position 9.


fluorenes

An ortho-fused polycyclic arene in which the skeleton is composed of two benzene rings ortho-fused to cyclopentane.


fluoroalkane

A haloalkane that is an alkane in which at least one hydrogen atom has been replaced by a fluorine atom.


fluoroamino acid

An organofluorine compound that consists of an amino acid substituted by a fluoro group.


fluoroaniline

A substituted aniline carrying an additional fluoro substituent on the benzene ring.


fluorobenzoic acid

Any benzoic acid carrying at least one fluoro substituent on the benzene ring. Fluorobenzoic acids are important intermediates in the synthesis of antibacterial drugs.


fluorobenzoyl-CoA

Any member of the class of benzoyl-CoAs having fluorobenzoyl as the aroyl substituent.


formamides

Amides with the general formula R(1)R(2)NCHO (R(1) and R(2) can be H).


formylindanone

Any member of the class of indanones in which a hydrogen attached to carbon in the indanone skeleton has been replaced by a formyl group.


fructosyllysine

A glyco-amino acid consisting of a D-fructosyl residue attached to the epsilon-amino group of L-lysine.


A 1-O-acetylmaltose in which the anomeric centre at the reducing end has alpha-configuration.


acetylagmatine

A member of the class of guanidines that is agmatine acetylated at the N4-position.


furanocoumarin

Any furochromene that consists of a furan ring fused with a coumarin. The fusion may occur in different ways in give several isomers.


furans

Compounds containing at least one furan ring.


acetylblasticidin S

A member of the class of blasticidins that is blasticidin S in which the side-chain amino group is acetylated.


dimyristoylphosphatidylcholine

A phosphatidylcholine where the phosphatidyl acyl groups are specified as tetradecanoyl (myristoyl).


galactaric acid derivative

A hexaric acid derivative that is formally obtained from galactaric acid.


An acetate ester obtained by acetylation of the O-14 position of browniine.


galactoglucomannan

A heteroglycan that consists of a backbone of randomly distributed (1->4)-linked mannose and glucose units with (1->6)-linked galactose units attached to mannose units.


galactoglycerolipid

Any glycoglycerolipid having galactosyl as the glyco component.


galactonic acid

A hexonic acid that has been found to increase in red blood cells of galactosemic patients.


ACETYLCARANINE

An organic heteropentacyclic compound that is caranine in which the hydroxy group is acetylated.


galactooligosaccharide

An oligosaccharide comprised of galactose residues.


galactosaminyl group

A glycosaminyl group obtained by removing the hydroxy group from the hemiacetal function of a galactosamine and, by extension, of a lower oligosaccharide having a galactosamine at the reducing end.


galactosyl group

A glycosyl group obtained by removing the hydroxy group from the hemiacetal function of a galactose and, by extension, of a lower oligosaccharide having galactose at the reducing end.


galactosylglycerol

A glycosylglycerol in which the glycosyl residue specified is galactose.


galactosiduronic acid

Any substance produced by linking galacturonic acid to another substance via a glycosidic bond.


gallotannin

A class of hydrolysable tannins obtained by condensation of the carboxy group of gallic acid (and its polymeric derivatives) with the hydroxy groups of a monosaccharide (most commonly glucose).


galloyl beta-D-glucose

A class of beta-D-glucose compounds having an unspecified number of O-galloyl groups in undeined positions.


acetohydrazide

A carbohydrazide that is hydrazine in which one of the hydrogens is replaced by an acetyl group.


geranylgeraniol

A diterpenoid that is hexadeca-2,6,10,14-tetraene substituted by methyl groups at positions 3, 7, 11 and 15 and a hydroxy group at position 1.


A tripeptide composed of N-acetylleucyl, leucyl and norleucinal residues joined in sequence.


GEROQUINOL

A polyprenylhydroquinone consisting of hydroquinone in which the hydrogen at position 2 is substituted by a (2E)-3,7-dimethylocta-2,6-dien-1-yl group.


acetylpyruvic acid

A dioxo monocarboxylic acid that is pentanoic acid carrying two oxo groups at positions 2 and 4.


achillin

A sesquiterpene lactone that is (3R,3aS,9aS,9bS)-3,3a,4,5,9a,9b-hexahydroazuleno[4,5-b]furan-2,7-dione carrying three additional methyl substituents at positions 3, 6 and 9.


glucocorticoid

Glucocorticoids are a class of steroid hormones that regulate a variety of physiological processes, in particular control of the concentration of glucose in blood.


glucooligosaccharide

An oligosaccharide comprised of glucose residues.


glucosamine phosphate

A hexosamine phosphate having glucosamine as the amino sugar component.


glucosamines

Any  hexosamine that is glucose in which at least one of the hydroxy groups has been replaced by an amino group.


glucosaminyl group

A glycosaminyl group obtained by removing the hydroxy group from the hemiacetal function of a glucosamine and, by extension, of a lower oligosaccharide having a glucosamine at the reducing end.


glucosaminylamine

A member of the class of  glucosamines that is 2-amino-2-deoxyglucose  in which the anomeric hydroxy group has been replaced by an additional amino group.


glucosaminylphosphodolichol

A polyprenyl glycosyl phosphate consisting of a glucosaminyl residue attached to dolichol phosphate.


glucosinolate

Water-soluble anionic substituted thioglucosides. Glucosinolates have a central C atom which is bonded via an S atom to a glycone group and via an N atom to a sulfonated oxime group, and which also carries a side-group. The side-chain and sulfate group have an anti stereochemical configuration across the C=N double bond.


D-glucosyl group

The glucosyl group formed from D-glucopyranose.


glucosyl group

A glycosyl group obtained by removing the hydroxy group from the hemiacetal function of a glucose and, by extension, of a lower oligosaccharide having glucose at the reducing end.


aconifine

A diterpenoid that is aconitine bearing a 10-hydroxy substituent.


glucosyloxyanthraquinone

A monosaccharide derivative that is anthracene-9,10-dione substituted by a beta-D-glucopyranosyloxy group at position 1.


aconitine

A diterpenoid that is 20-ethyl-3alpha,13,15alpha-trihydroxy-1alpha,6alpha,16beta-trimethoxy-4-(methoxymethyl)aconitane-8,14alpha-diol having acetate and benzoate groups at the 8- and 14-positions respectively.


glucosiduronic acid

Any substance produced by linking glucuronic acid to another substance via a glycosidic bond.


glutaconic acid

A pentenedioic acid that is pent-2-ene substituted by carboxy groups at positions 1 and 5.


acremoauxin A

An indolyl carboxylate ester obtained by formal condensation of one of the primary hydroxy groups of D-arabinitol with the carboxy group of (2R)-2-(indol-3-yl)propanoic acid.


glutaconyl-CoA

A  2-enoyl-CoA that is the glutaconyl derivative of CoA.


glutamic semialdehyde

An  aldehydic acid derived from the  formal reduction of one of the carboxy groups glutamic acid to a formyl group.


glutamic acid derivative

An amino acid derivative resulting from reaction of glutamic acid at the amino group or either of the carboxy groups, or from the replacement of any hydrogen by a heteroatom. The definition normally excludes peptides containing glutamic acid residues.


L-glutamine derivative

A proteinogenic amino acid derivative resulting from reaction of L-glutamine at the amino group, the carboxy group, or the carboxamide, or from the replacement of any hydrogen of L-glutamine by a heteroatom.


glutamine family amino acid

An L-alpha-amino acid which is L-glutamic acid or any of the essential amino acids biosynthesised from it (glutamine, proline and arginine). A closed class.


glutaramic acid

A dicarboxylic acid monoamide that is formally derived from glutaric acid by conversion of one of the two carboxylic acid groups to the corresponding amide.


glutarate

A dicarboxylic acid anion obtained by deprotonation of at least one of the carboxy groups of glutaric acid.


acrifoline

A quinolizidine alkaloid that is lycopodine having a C=C double bond at the 11-position, a keto substituent at the 8-position and the keto group at position 5 replaced by a beta-hydroxy group.


glutaryl-CoAs

Any  omega-carboxyacyl-CoA in which the acyl group specified is glutaryl or its substituted derivative.


glutathione conjugate

Any bioconjugate in which glutathione is one of the components


glutathione derivative

Any organonitrogen compound derived from the Glu-Cys-Gly tripeptide glutathione.


2-phosphoglyceric acid

A monophosphoglyceric acid having the phospho group at the 2-position.


phosphoglyceric acid

An aldonic acid phosphate where the aldonic acid component is glyceric acid.


acronidine

An organic heterotetracyclic compound that is 3H-furo[2,3-b]pyrano[3,2-f]quinoline carrying a gem-dimethyl group at position 3 as well as two methoxy substituents at positions 5 and 11.


glycerol ether

Any ether having glyceryl as at least one of the O-substituents.


acronycidine

A quinoline alkaloid that is furo[2,3-b]quinoline bearing four methoxy substituents at positions 4, 5, 7 and 8.


ACRONINE

An alkaloid antineoplastic agent isolated from Acronychia baueri.


glycine derivative

A proteinogenic amino acid derivative resulting from reaction of glycine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.


ACROPHYLLINE

A quinoline alkaloid that is furo[2,3-b]quinolin-4-one bearing additional 3,3-dimethylallyl and methoxy substituents at positions 9 and 7 respectively.


glycolaldehydes

An aldehyde derived from a glycol by reduction of one of the hydroxy groups.


acroptilin

A sesquiterpene lactone that is isolated from Acroptilon repens and displays anti-allergic properties.


glycophospholipid

Any phospholipid that contain both phosphate and carbohydrate as integral structural components.


glycosaminyl group

A glycosyl group obtained by removing the hydroxy group from the hemiacetal function of a glycosamine and, by extension, of a lower oligosaccharide having a glycosamine at the reducing end.


acrovestone

A polyphenol that is isolated from Acronychia pedunculata and exhibits moderate antioxidant and antityrosinase activities.


glycoside

A glycosyl compound resulting from the attachment of a glycosyl group to a non-acyl group RO-, RS-, RSe-, etc. The bond between the glycosyl group and the non-acyl group is called a glycosidic bond. By extension, the terms N-glycosides and C-glycosides are used as class names for glycosylamines and for compounds having a glycosyl group attached to a hydrocarbyl group respectively. These terms are misnomers and should not be used. The preferred terms are glycosylamines and C-glycosyl compounds, respectively.


glycosinolate

An sulfur oxoanion resulting from the deprotonation of the hydroxy group attached to the sulfur of a glycosinolic acid.


glycosphingolipid

A glycosphingolipid is a glycolipid that is a carbohydrate-containing derivative of a sphingoid or ceramide. It is understood that the carbohydrate residue is attached by a glycosidic linkage to O-1 of the sphingoid.


glycosyl group

An organic group obtained by removing the hydroxy group from the hemiacetal function of a monosaccharide or monosaccharide derivative and, by extension, of a lower oligosaccharide or oligosaccharide derivative.


glycosylglycerol

A glycoside resulting from the condensation of one of the hydroxy groups of glycerol with a glycosyl group.


glycosyl glycoside

Any disaccharide in which the two monosaccharide components are connected by a glycosidic linkage between their anomeric centres.


glycosyloxy group

An organic group obtained by removing the proton from the hemiacetal function of a monosaccharide or monosaccharide derivative and, by extension, of a lower oligosaccharide or oligosaccharide derivative.


actinidine

A member of the class of cyclopentapyridines that is 6,7-dihydrocyclopenta[c]pyridine bearing two methyl substituents at positions 4 and 7.


chemical entity

A chemical entity is a physical entity of interest in chemistry including molecular entities, parts thereof, and chemical substances.


group

A defined linked collection of atoms or a single atom within a molecular entity.


guanidines

Any organonitrogen compound containing a carbamimidamido (guanidino) group. Guanidines have the general structure (R(1)R(2)N)(R(3)R(4)N)C=N-R(5) and are related structurally to amidines and ureas.


ACTINODAPHNINE

An organic heteropentacyclic compound 6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]quinoline bering additional hydroxy and methoxy substituents at positions 10 and 11 respectively.


DEHYDROCOSTUSLACTONE

An organic heterotricyclic compound and guaianolide sesquiterpene lactone that is acrylic acid which is substituted at position 2 by a 4-hydroxy-3,8-bis(methylene)decahydoazulen-5-yl group and in which the hydroxy group and the carboxy group have undergone formal condensation to afford the corresponding gamma-lactone.


guanosines

Any purine ribonucleoside that is a derivative of guanosine.


guanosyl group

A group formed by loss of a 2'-, 3'- or 5'-hydroxy group from the ribose moiety of guanosine.


gulonic acid

A hexonic acid formed by oxidising the aldehyde group of gulose to a carboxylic acid group.


haloalkane

A halohydrocarbon that is an alkane in which at least one hydrogen atom has been replaced by with a halogen atom.


haloamino acid

Any non-proteinogenic amino acid carrying at least one halo group.


halohydrocarbon

A compound derived from a hydrocarbon by replacing a hydrogen atom with a halogen atom.


2,2':6',3''-Terpyridine carrying a phenyl substituent at the 4-position of the central pyridine ring.


name: hemediol-L-aspartate ester-L-glutamate ester-L-methionine sulfonium


aculeacin A

A lipopeptide that is isolated from Aspergillus aculeatus and exhibits antifungal activity.


name: heptakis-L-histidino tetracopper mu4-sulfide hydroxide


TERPYRIDINE

A tridentate heterocyclic ligand that binds metals at three meridional sites giving two adjacent 5-membered MN2C2 chelate rings.


heptenedioic acid

A dicarboxylic acid that is heptene carrying two carboxy groups.


heptenone

Any ketone that ia heptane substituted by an oxo group at unspecified position.


herbicide

A substance used to destroy plant pests.


aciclovir

An oxopurine that is  guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.


organic heterocyclic compound

A cyclic compound having as ring members atoms of carbon and at least of one other element.


hexadecatrienoic acid

Any trienoic fatty acid having sixteen carbons.


A long-chain primary fatty alcohol that is hexadecanol containing a double bond at unspecified position.


hexadecenal

A monounsaturated fatty acid aldehyde that is hexadecanal which has undergone formal dehydrogenation to introduce a double bond at unspecified position.


hexadecenoic acid

A C16 straight-chain monounsaturated fatty acid having one C=C double bond.


hexadecenoyl-CoA

A monounsaturated fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of any hexadecenoic acid.


hexadienal

An  enal that is hexadiene carrying an oxo group at position 1.


An N-nitro compound that is 1,3,5-triazinane in which all three of the hydrogens attached to the nitrogens have been replaced by nitro groups. It is widely used in both industrial and military explosives.


hexahydroxyflavone

Members of the class of hydroxyflavone that is  flavone substituted by 6 hydroxy groups.


name: hexakis-L-cysteinyl L-serinyl octairon heptasulfide


A diol that consists of a cyclohexane skeleton carrying two hydroxy substituents.


hexanone

A ketone that is a hexane carrying an oxo substituent at unspecified position.


hexenal

A monounsaturated fatty acid aldehyde that is hexene having an oxo group at position 1.


An alkene that is hexane carrying a double bond at position 1.


hexenoic acid

A C6, medium-chain fatty acid carrying a double bond at any position along the main chain.


monosaccharide sulfate

Any carbohydrate sulfate that is a monosaccharide carrying at least one O-sulfo substituent.


hexuronate

A uronate obtained via deprotonation of the carboxy group of any hexuronic acid.


histidine derivative

An amino acid derivative resulting from reaction of histidine at the amino group or the carboxy group, or from the replacement of any hydrogen of histidine by a heteroatom. The definition normally excludes peptides containing alanine residues.


homocystines

A non-proteinogenic alpha-amino acid obtained by oxidative dimerisation of homocysteine and its derivatives.


hormone

Originally referring to an endogenous compound that is formed in specialized organ or group of cells and carried to another organ or group of cells, in the same organism, upon which it has a specific regulatory function, the term is now commonly used to include non-endogenous, semi-synthetic and fully synthetic analogues of such compounds.


HYDANTOIN

An imidazolidinone with oxo groups at position 2 and 4.


hydrazines

Hydrazine (diazane) and its substituted derivatives.


hydrocarbon

A compound consisting of carbon and hydrogen only.


proton

Nuclear particle of charge number +1, spin 1/2 and rest mass of 1.007276470(12) u.


A 2'-deoxyribonucleoside 5'-monophosphate(2-) obtained by deprotonation of the phosphate OH groups of 2'-deoxyuridine 5'-monophosphate (dUMP); major species at pH 7.3.


HPETE

Mono-hydroperoxy (e)icosatetraenoic acids (HPETEs) are the primary products of lipoxygenase-catalysed oxygenation of arachidonic acid.


hydroquinones

Benzenediols that have the hydroxy substituents in the 1- and 4-positions.


hydroxamic acid anion

An oxoanion resulting from the removal of a proton from the hydroxy group of any hydroxamic acid.


hydroxamic acid

A compound, RkE(=O)lNHOH, derived from an oxoacid RkE(=O)l(OH) (l =/= 0) by replacing -OH with -NHOH, and derivatives thereof. Specific examples of hydroxamic acids are preferably named as N-hydroxy amides.


hydroxides

Hydroxides are chemical compounds containing a hydroxy group or salts containing hydroxide (OH(-)).


hydroxy fatty acid

Any fatty acid carrying one or more hydroxy substituents.


hydroxy-L-arginine

A hydroxy-amino acid that is L-arginine substituted by at least one hydroxy group.


hydroxy-L-glutamic acid

A hydroxy-amino acid  that is L-glutamic acid substituted by at least one hydroxy group.


hydroxy-L-lysine

A hydroxy-amino acid that is L-lysine substituted by hydroxy groups.


hydroxy-amino acid

A non-proteinogenic alpha-amino acid bearing one or more hydroxy groups at unspecified positions.


hydroxy-5beta-cholanic acid

Any member of the class of 5beta-cholanic acids carrying at least one hydroxy group at unspecified position.


hydroxyacetophenone

Any member of the class of  acetophenones carrying at least one hydroxy substituent.


hydroxy carboxylic acid

Any carboxylic acid with at least one hydroxy group.


hydroxybenzoate

Any benzoate derivative carrying a single carboxylate group and at least one hydroxy substituent.


hydroxybenzoic acid

Any benzoic acid carrying one or more phenolic hydroxy groups on the benzene ring.


hydroxybenzophenone

Any benzophenone into which is substituted one or more hydroxy groups.


hydroxybenzoyl-CoA

Any member of the class of  benzoyl-CoAs having hydroxybenzoyl as the aroyl substituent.


hydroxybenzyl alcohol

Any member of the class of benzyl alcohols that is a benzyl alcohol substituted by at least one hydroxy group on the benzene ring.


secondary alpha-hydroxy ketone

An alpha-hydroxy ketone in which the carbonyl group and the hydroxy group are linked by a carbon bearing one hydrogen and one organyl group. Secondary alpha-hydroxy ketones are also known as acyloins, and are formally derived from reductive coupling of two carboxylic acid groups.


hydroxybiphenyls

Any member of the class of biphenyls that has one or more hydroxy groups attached to the benzenoid ring system.


hydroxybutyric acid

Any compound comprising a butyric acid core carrying at least one hydroxy substituent.


hydroxybutanoyl-CoA

Any member of the class of  butanoyl-CoAs having hydroxybutanoyl as the acyl substituent.


hydroxycinnamic acid

Any member of the class of  cinnamic acids carrying one or more hydroxy substituents.


ADEFOVIR

A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens has been replaced by a 2-(6-amino-9H-purin-9-yl)ethoxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(t-butoxycarbonyloxymethyl) ester (dipivoxil ester) prodrug is used to treat chronic hepatitis B viral infection.


hydroxycyclohexanone

Any member of the class of cyclohexanones carrying one or more hydroxy substituents.


hydroxyflavanone

A member of the class of flavanones that consists of flavanone with one or more hydroxy substituents.


hydroxyflavone

Any flavone in which one or more ring hydrogens are replaced by hydroxy groups.


hydroxyfluorenes

Any member of the class of  fluorenes containing a mono- or poly-substituted  fluorene ring in which at least one of the substituents is a hydroxy group.


A member of the class of  hydroxyindoles that is 1H-indole substituted by a hydroxy group at position 4.


hydroxykynurenamine

Any kynurenamine carrying a hydroxy substituent.


hydroxylamines

Hydroxylamine, H2N-OH, and its hydrocarbyl derivatives.


hydroxymalonate

A dicarboxylic acid anion obtained by deprotonation of at least one of the carboxy groups of hydroxymalonic acid.


hydroxynaphthalene

Any member of the class of  naphthalenes that is naphthalene carrying one or more hydroxy groups.


hydroxynitrile

Any nitrile compound which also contains a hydroxy group.


hydroxyphenylacetaldehyde oxime

An  aldoxime that is acetaldehyde oxime in which one of the methyl hydrogens has been replaced by a hydroxyphenyl group.


hydroxyproline

A proline derivative that is proline substituted by at least one hydroxy group.


hydroxypyridine

Any member of the class of pyridines with at least one hydroxy substituent.


hydroxyoctadecanoic acid

A hydroxy fatty acid that is ocatadecanoic acid (stearic acid) in which the aliphatic chain has been substituted by one or more hydroxy groups.


A streptomycin bearing an additional hydroxy substituent at the 5'-position (on the furanose ring)


hydroxytoluene

Any member of the class of  toluenes carrying one or more hydroxy substituents.


HYPOCHLOROUS ACID

A chlorine oxoacid with formula HOCl; a weak, unstable acid, it is the active form of chlorine in water.


iduronic acid

A member of the class of  iduronic acids that is the major uronic acid component of the dermatan sulfate and heparin.


The hydroxy monocarboxylic acid anion that is the conjugate base of 3-(imidazol-5-yl)lactic acid.


imidazoles

A five-membered organic heterocycle containing two nitrogen atoms at positions 1 and 3, or any of its derivatives; compounds containing an imidazole skeleton.


imide

A dicarboximide that is 3,4,5,6-tetrahydrophthalimide in which the hydrogen attached to the nitrogen is replaced by a p-bromophenyl group.


imine

Compounds having the structure RN=CR2 (R = H, hydrocarbyl). Thus analogues of aldehydes or ketones, having NR doubly bonded to carbon; aldimines have the structure RCH=NR, ketimines have the structure R'2C=NR (where R' is not H). Imines include azomethines and Schiff bases. Imine is used as a suffix in systematic nomenclature to denote the C=NH group excluding the carbon atom.


iminodiacetate

A dicarboxylic acid dianion resulting from the removal of a proton from both of the carboxy groups of iminodiacetic acid.


iminodiacetic acid

An amino dicarboxylic acid that is glycine in which one of the hydrogens attached to the nitrogen is substituted by a carboxymethyl group.


dibucaine

A monocarboxylic acid amide that is the 2-(diethylamino)ethyl amide of 2-butoxyquinoline-4-carboxylic acid. One of the most potent and toxic of the long-acting local anesthetics, its parenteral use was restricted to spinal anesthesia. It is now generally only used (usually as the hydrochloride) in creams and ointments and in suppositories for temporary relief of pain and itching associated with skin and anorectal conditions.


indolylmethylglucosinolate

A glucosinolate that is the conjugate base of indolylmethylglucosinolic acid.


indole-3-acetic acids

An  indol-3-yl carboxylic acid in which the carboxylic acid specified is acetic acid.


indole-3-carboxylic acid

An indole-3-carboxylic acid carrying a carboxy group at position 3.


indol-3-yl carboxylic acid

Any indolyl carboxylic acid carrying an indol-3-yl or substituted indol-3-yl group.


3-(indol-3-yl)lactic acid

A hydroxy monocarboxylic acid that is lactic acid substituted by a 1H-indol-3-yl group at position 3. It is a metabolite of tryptophan.


An indolyl alcohol carrying a hydroxymethyl group at position 3. It is a constituent of the cruciferous vegetables and had anticancer activity.


adenosylcob(III)yrinic acid a,c-diamide

A cobalt corrinoid that is cob(III)yrinic acid a,c-diamide having a 5'-adenosyl group attached to the central cobalt atom.


indoleacetaldehyde

An aldehyde that is acetaldehyde substituted by an indolyl group.


oxoacid

A compound which contains oxygen, at least one other element, and at least one hydrogen bound to oxygen, and which produces a conjugate base by loss of positive hydrogen ion(s) (hydrons).


inorganic molecular entity

A molecular entity that contains no carbon.


inorganic peroxide

Compounds of structure ROOR' in which R and R' are inorganic groups.


inorganic phosphate

Any  phosphate that contains no carbon atom.


inosines

Any purine ribonucleoside that is a derivative of inosine.


inositol

Any cyclohexane-1,2,3,4,5,6-hexol.


inosyl group

An inosyl group is a group formed by loss of a 2'-, 3'- or 5'-hydroxy group from the ribose moiety of inosine.


adenylyl selenate

The 5'-selenonooxyphosphate ester of adenosine.


insecticide

Strictly, a substance intended to kill members of the class Insecta.  In common usage, any substance used for preventing, destroying, repelling or controlling insects.


intercalator

A role played by a chemical agent which exhibits the capability of occupying space between DNA base pairs due to particular properties in size, shape and charge. Intercalation of chemical compounds in DNA helix can result in replication errors (shift, mutation) or DNA damages.


iodate salt

Any salt that has chlorate, [IO3](-), as the anionic component.


iodoamino acid

An amino acid containing at least one iodo substituent.


iodothyronine

An  iodoamino acid in which the amino acid specified is  thyronine.


iodotyrosine

A tyrosine derivative which has at least one iodo-substituent on the benzyl moiety.


salt

A salt is an assembly of cations and anions.


ionophore

A compound which can carry specific ions through membranes of cells or organelles.


ion

A molecular entity having a net electric charge.


isoleucine derivative

An amino acid derivative resulting from reaction of isoleucine at the amino group or the carboxy group, or from the replacement of any hydrogen of isoleucine by a heteroatom. The definition normally excludes peptides containing isoleucine residues.


6-oxohexanoic acid

A medium-chain fatty acid comprising hexanoic acid carrying an oxo group at position 6.


isoprenoid

Any lipid formally derived from isoprene (2-methylbuta-1,3-diene), the skeleton of which can generally be discerned in repeated occurrence in the molecule. The skeleton of isoprenoids may differ from strict additivity of isoprene units by loss or shift of a fragment, commonly a methyl group. The class includes both hydrocarbons and oxygenated derivatives.


isoquinoline alkaloid

Any alkaloid that has a structure based on an isoquinoline nucleus. They are derived from the amino acids like tyrosine and phenylalanine.


isoquinolines

A class of organic heteropolycyclic compound consisting of isoquinoline and its substitution derivatives.


juvenile hormone

A family of farnesane sesquiterpenoids that regulate many aspects of insect physiology.


ADRENOTERONE

A 3-oxo Delta(4)-steroid that is androst-4-ene carrying three oxo-substituents at positions 3, 11 and 17.


keto-disaccharide

Any disaccharide that contains a keto group within its structure.


ketoaldehyde

Any compound that has an aldehydic and ketonic group in the same molecule.


ketoaldonic acid

Oxo carboxylic acids formally derived from aldonic acids by replacement of a secondary CHOH group by a carbonyl group.


deoxyketohexose

Any ketohexose having at least one hydroxy group replaced by hydrogen.


keto-D-gluconate

A ketogluconate of D-configuration


ketogluconic acid

A gluconic acid that contains a ketonic carbonyl group.


ketohexose

Any hexose containing a single ketone group.


ketooctose

A ketooctose is a ketone-containing octose.


ketopentose

A pentose having a single ketone group at the 2-position.


ketose

Ketonic parent sugars (polyhydroxy ketones H[CH(OH)]nC(=O)[CH(OH)]mH) and their intramolecular hemiketals.


ketotetrose

A tetrose having a single ketone group at the 2-position.


ketotriose

Any ketone-containing triose.


ketoxime

Oximes of ketones R2C=NOH (where R =/= H).


laballenic acid

A C18, 5,6-allenic fatty acid.


lactam

Cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.


lactate

A hydroxy monocarboxylic acid anion that is the conjugate base of lactic acid, arising from deprotonation of the carboxy group.


lactate salt

Any organic salt that has lactate as the cation.


1H-Pyrrole substituted at C-2 and -5 by methyl groups, at C-3 by methoxycarbonyl and at C-4 by a 2-benzylbenzoyl group.


(+)-iridodial

An  iridodial that is (1R,2R)-2-[(2R)-1-oxopropan-2-yl]cyclopentanecarbaldehyde substituted by a methyl group at position 2 (2S-stereoisomer).


lactone

Any cyclic carboxylic ester containing a 1-oxacycloalkan-2-one structure, or an analogue having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.


lactosamine

A disaccharide that consists of D-glucosamine having a beta-D-galactosyl residue attached at position 4.


aethusin

A polyene that is tridecane carrying trans double bonds at positions 2, 8, and 10 and triple bonds at positions 4 and 6. It is a phytotoxin isolated from the plant, Aethusa cynapium.


lanthionine

An alanine derivative in which two alanine residues are linked on their beta-carbons by a thioether linkage.


leucine

A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.


L-leucine derivative

A proteinogenic amino acid derivative resulting from reaction of L-leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of L-leucine by a heteroatom.


leukotriene

Any icosanoid from that family of C20 polyunsaturated fatty acids and their derivatives generated by leukocytes from arachidonic acid, each member having four double bonds of which three are conjugated.


lignan

Any phenylpropanoid  derived from phenylalanine via dimerization of substituted cinnamic alcohols, known as monolignols, to a dibenzylbutane skeleton. Note that while individual members of the class have names ending ...lignane, ...lignene, ...lignadiene, etc., the class names lignan, neolignan, etc., do not end with an "e".


AFLATOXIN

An aflatoxin having a tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromene skeleton with oxygen functionality at positions 1, 4 and 11.


linolenic acid

A two-membered subclass of octadecatrienoic acid comprising the (9Z,12Z,15Z)- and (6Z,9Z,12Z)-isomers. Linolenic acids are nutrients essential to the formation of prostaglandins and are also used in making paints and synthetic resins.


A member of the class of aflatoxins that is 8,9-dihydro-9-hydroxyaflatoxin B1 having an S-glutathionyl moiety attached at position 8.


CASTANIN

A  4'-methoxyisoflavone that is isoflavone substituted by methoxy groups at positions 6 and 4' and a hydroxy group at position 7.


lipoyl group

A univalent carboacyl group that is derived from 5-(1,2-dithiolan-3-yl)pentanoic acid.


afzelechin

A tetrahydroxyflavan that is  (2S)-flavan substituted by hydroxy groups at positions 3, 5, 7 and 4' respectively.


lombricine

A serine derivative that is serine in which the hydrogen of the hydroxy group has been replaced by a (2-carbamimidamidoethoxy)(hydroxy)phosphoryl group.


A biflavonoid consisting of two molecules of afzelechin joined by a (4alpha->8) linkage.


agar

A complex mixture of polysaccharides extracted from species of red algae. Its two main components are agarose and agaropectin. Agarose is the component responsible for the high-strength gelling properties of agar, while agaropectin provides the viscous properties.


luteolin O-glucuronoside

A glycosyloxyflavone that is an O-glucuronidated derivative of luteolin.


lysine

A diamino acid that is caproic (hexanoic) acid bearing two amino substituents at positions 2 and 6.


L-lysine derivative

A proteinogenic amino acid derivative resulting from reaction of L-lysine at the amino group or the carboxy group, or from the replacement of any hydrogen of L-lysine by a heteroatom.


lyxose

An aldopentose that occurs only rarely in nature.


macrolide antibiotic

A macrocyclic lactone with a ring of twelve or more members which exhibits antibiotic activity.


macrolide

A macrocyclic lactone with a ring of twelve or more members derived from a polyketide.


agarose

A linear polysaccharide made up from alternating D-galactose and 3,6-anhydro-alpha-L-galactopyranose residues joined by alpha-(1->3)- and beta-(1->4)-linkages.


malate

A dicarboxylic acid anion obtained by deprotonation of at least one of the carboxy groups of malic acid.


AGATHISFLAVONE

A biflavonoid that is obtained by oxidative coupling of two molecules of apigenin resulting in a bond between positions C-6 and C-8 of the two chromene rings.


agavoside A

A steroid saponin that consists of (25R)-5alpha-spirostan-3beta-ol substituted by an oxo group at position 12 and a  beta-D-galactopyranosyl moiety at position 3 via a glycosidic linkage.


malonyl-CoAs

Any short-chain fatty acyl-CoA in which the the fatty acid specified is malonic acid or its derivatives.


maltodextrin

A dextrin in which the D-glucose units are linked by alpha-(1->4) glycosidic bonds.


edrophonium

A quaternary ammonium ion that is N-ethyl-N,N-dimethylanilinium in which one of the meta positions is substituted by a hydroxy group. It is a reversible inhibitor of cholinesterase, with a rapid onset (30-60 seconds after injection) but a short duration of action (5-15 minutes). The chloride salt is used in myasthenia gravis both diagnostically and to distinguish between under- or over-treatment with other anticholinesterases. It has also been used for the reversal of neuromuscular blockade in anaesthesia, and for the management of poisoning due to tetrodotoxin, a neuromuscular blocking toxin found in puffer fish and other marine animals.


adinazolam

A triazolo[4,3-a][1,4]benzodiazepine having a dimethylaminomethyl group at the 1-position, a phenyl group at the 6-position and a chloro substituent at the 8-position.


AGNUSIDE

A benzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with the primary hydroxy group of aucubin. It is an iridoid glycoside found in several Vitex plants including Vitex agnus-castus.


manganate

A divalent inorganic anion obtained by removal of both protons from manganic acid.


A manganese cation that is monoatomic and has a formal charge of +4.


mannaric acid

A hexaric acid obtained by the oxidation of mannose.


mannobiose

A glycosylmannose that is D-mannopyranose attached to a beta-D-mannopyranosyl group at position 4 via a glycosidic linkage.


mannosylinositol phosphorylceramide

A class of complex phosphoglycosphingolipids with a mannose-inositol-P head group. As with other ceramide derivatives, substituents R(1) and R(2) vary with different sphingoid bases and fatty acyl moieties.


mannosyl group

The simplest member of the class of mannosyl groups obtained by removing the hydroxy group from the hemiacetal function of a mannose.


mannosyl groups

A glycosyl group obtained by removing the hydroxy group from the hemiacetal function of a mannose and, by extension, of a lower oligosaccharide having mannose at the reducing end.


mannooligosaccharide

An oligosaccharide comprised of mannose residues.


menaquinones

Any prenylnaphthoquinone having a prenyl or polyprenyl group at position 3 and a methyl group at position 2 on the naphthoquinone ring.


MENTHOL

Any secondary alcohol that is one of the eight possible diastereoisomers of 5-methyl-2-(propan-2-yl)cyclohexan-1-ol.


A glycol that is butane-2,3-diol in which a hydrogen from each of the methyl groups is replaced by a thiol group.


AGROCLAVINE

An ergot alkaloid that is ergoline which contains a double bond between positions 8 and 9, and which is substituted by methyl groups at positions 6 and 8.


meso-lanthionine

The meso-isomer of lanthionine. It is a key constituent of bacterial peptidoglycan type A51 and A3delta.


mesobilirubin IXalpha

A biladiene that is a homologue of bilirubin IXalpha (vinyl groups reduced to ethyl), a natural product of heme catabolism and the primary pigment of bile acid.


metal-sulfur cluster

A metal-sulfur cluster is a unit comprising two or more metal atoms and bridging sulfur ligand(s).


methacrylate

A monocarboxylic acid anion that is obtained by removal of a proton from the carboxylic acid group of methacrylic acid.


METHACRYLIC ACID

An alpha,beta-unsaturated monocarboxylic acid that is acrylic acid in which the hydrogen at position 2 is substituted by a methyl group.


methanediols

A  diol that is methane in which two of the hydrogens have been replaced by hydroxy groups respectively.


methanesulfonate ester

An organosulfonic ester resulting from the formal condensation of methanesulfonic acid with the hydroxy group of an alcohol, phenol, heteroarenol, or enol.


methanesulfonate

A 1,1-diunsubstituted alkanesulfonate that is the conjugate base of methanesulfonic acid.


methionine derivative

An amino acid derivative resulting from reaction of methionine at the amino group or the carboxy group, or from the replacement of any hydrogen of methionine  by a heteroatom. The definition normally excludes peptides containing methionine residues.


monomethoxybenzene

Compounds containing a benzene skeleton substituted with one methoxy group.


methoxybenzoic acid

Any benzoic acid carrying one or more methoxy substituents.


ajmalicine

A monoterpenoid indole alkaloid with formula C21H24N2O3, isolated from several Rauvolfia and Catharanthus species. It is a selective alpha1-adrenoceptor antagonist used for the treatment of high blood pressure.


methoxyflavanone

A member of the class of flavanones that consists of flavanone with one or more methoxy substituents.


methoxyflavone

Any member of the class of flavones with at least one methoxy substituent.


methyl ester

Any carboxylic ester resulting from the formal condensation of a carboxy group with methanol.


methyl halides

A haloalkane that is methane in which one of the hydrogens is substituted by a halide atom.


METHANESULFONIC ACID METHYL ESTER

A methanesulfonate ester resulting from the formal condensation of methanesulfonic acid with methanol.


methyl-L-alanine

Any alanine derivative that is L-alanine having one or more methyl groups attached to the amino group.


methyl-L-methionine

A L-methionine derivative carrying methyl substituents at the N or S atom.


methyl myo-inositols

A cyclitol that is myo-inositol in which one of the alcoholic hydrogens is substituted by a methyl group.


methyl-branched fatty acyl-CoA

A branched-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of any methyl-branched fatty acid.


methyladenine

Any member of the class of 6-aminopurines that is adenine bearing a single methyl substituent.


methylaniline

A substituted aniline carrying one or more methyl groups at unspecified positions.


methylbenzyl alcohol

Members of the class of benzyl alcohols substituted by at least one methyl group.


methylbutanal

Any member of the class of  butanals carrying a methyl substituent at an unspecified position.


methylbutanoyl-CoA

Any member of the class of  butanoyl-CoAs having methylbutanoyl as the acyl substituent.


methylcatechol

Any member of the class of catechols carrying one or more methyl substituents.


methylcytidine

Any member of the class of cytidines that is cytidine substituted by at least one methyl group.


methylguanine

A 2-aminopurine that is guanine bearing a single methyl substituent.


methylguanosine

Any guanosine carrying one or more methyl substituents.


methylisocitric acid

A tricarboxylic acid that is isocitric acid substituted by a methyl group alpha- to one of the carboxylic acid groups.


3-methylmalic acid

A dicarboxylic acid that is succinic acid carrying hydroxy and methyl substituents at positions 2 and 3 respectively.


methylmercury compound

An  alkylmercury compound in which the  alkyl group specified is methyl.


methylnaphthalenes

Any naphthalene carrying one or more methyl substituents.


ALACHLOR

An aromatic amide that is N-(2,6-diethylphenyl)acetamide substituted by a methoxymethyl group at at the nitrogen atom while one of the hydrogens of the methyl group has been replaced by a chlorine atom.


alosetron

A pyrido[4,3-b]indole compound having a 5-methyl-1H-imidazol-4-ylmethyl group at the 2-position.


methylpropanoyl-CoA

A propanoyl-CoA substituted by a methyl group on the propanoyl side chain.


methylpseudouridine

A member of the class of  pseudouridines that is pseudouridine substituted by a methyl group at unspecified position.


alamarine

A member of the class of isoquinolinonaphthyridines that is 5,6-dihydroisoquinolino[2,1-b][2,7]naphthyridin-8-one bearing additional hydroxy, methoxy and 1-hydroxyethyl substituents at positions 2, 3 and 12.


methylpyridines

Any member of the class of pyridines that carries at least one methyl substituent.


methyltetrahydrofolate

A group of heterocyclic compounds based on the N-methylated 5,6,7,8-tetrahydropteroic acid skeleton conjugated with one or more L-glutamic acid or L-glutamate units.


methyluridine

A uridine bearing one or more methyl substituents.


alangicine

An isoquinoline alkaloid that is 1',2'-didehydroemetan bearing two hydroxy substituents at positions 6' and 9 as well as three methoxy substituents at positions 7', 10 and 11.


mevalonate

A racemate composed of equimolar amounts of (R)- and (S)-mevalonate.


mevalonic acid

A racemate composed of equimolar amounts of (R)- and (S)-mevalonic acid.


mineralocorticoid

Mineralocorticoids are a class of steroid hormones that regulate water and electrolyte metabolism.


mitomycin

A family of aziridine-containing natural products isolated from Streptomyces caespitosus or Streptomyces lavendulae.


alangimarckine

A member of the class of beta-carbolines that is tubulosan bearing methoxy groups at positions 10 and 11 as well as a hydroxy group at position 9.


elemental molecule

A molecule all atoms of which have the same atomic number.


molecular ion

In mass spectrometry, a molecular ion is an ion formed by the removal from (positive ions) or addition to (negative ions) a molecule of one or more electrons without fragmentation of the molecular structure.


molecule

Any polyatomic entity that is an electrically neutral entity consisting of more than one atom.


alangimarine

A member of the class of isoquinolinonaphthyridines that is 5,6-dihydroisoquinolino[2,1-b][2,7]naphthyridin-8-one bearing additional hydroxy, methoxy and vinyl substituents at positions 2, 3 and 12 respectively.


molybdopterin cofactor

A molybdopterin to which a metal or metal oxide is coordinated, and that acts as a prosthetic group.


monoamine molecular messenger

A group of neurotransmitters and neuromodulators that contain one amino group that is connected to an aromatic ring by ethylene group  (-CH2-CH2-). Monoamines are derived from the aromatic amino acids phenylalanine, tyrosine, histidine and tryptophan.


alangiside

An organic heterotetracyclic compound that is an alkaloidal glycoside isolated from Alangium salviifolium.


acetylenic fatty acid

Any  unsaturated fatty acid containing at least one triple bond in the carbon chain framework.


monocarboxylic acid

An oxoacid containing a single carboxy group.


monohydroxyacetophenone

A hydroxyacetophenone carrying at least one hydroxy substituent.


monohydroxybenzoate

A hydroxybenzoate carrying a single hydroxy substituent at unspecified position.


monohydroxybenzoic acid

Any hydroxybenzoic acid having a single phenolic hydroxy substituent on the benzene ring.


naphthols

Any hydroxynaphthalene derivative that has a single hydroxy substituent.


cresol

A hydroxytoluene that consists of toluene carrying a single hydroxy substituent at any position. A 'closed class'.


HELENINE

A sesquiterpene lactone that is 3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2-one bearing two methyl substituents at positions 5 and 8a as well as a methylidene substituent at position 3.


monoiodotyrosine

An  iodotyrosine carrying a single iodo substituent.


monomethoxyflavone

Any methoxyflavone with a single methoxy substituent.


mononitroglycerol

A nitroglycerol that is glycerol in which one nitro group replaces the hydrogen(s) attached to one of the hydroxy groups.


monophosphoglyceric acid

A glyceric acid phosphate in which only one of the hydroxy groups has been phosphorylated.


monoterpene ketone

A terpene ketone derived from a monoterpene.


monoterpenoid

Any terpenoid derived from a monoterpene. The term includes compounds in which the C10 skeleton of the parent monoterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl groups).


monounsaturated fatty acid

Any fatty acid with one double or triple bond in the fatty acid chain and singly bonded carbon atoms in the rest of the chain. MUFAs have positive effects on the cardiovascular system, and in diabetes treatment.


morphinane alkaloid

An  isoquinoline alkaloid based on a morphinan skeleton and its substituted derivatives.


alatolide

A germacrane sesquiterpenoid laactone obtained by formal condensation of the carboxy group of isobutyric acid with the secondary hydroxy group of trihydroxygermaeranolide.


mugineic acid

An azetidinecarboxylic acid that is the parent of the class of mugineic acids.


ALBAFURAN A

A member of the class of 1-benzofurans that is 1-benzofuran substituted by a hydroxy group at position 6 and a 2-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-3,5-dihydroxyphenyl group at position 2.


bis(2-chloroethyl) sulfide

An ethyl sulfide that is diethyl sulfide in which a hydrogen from each of the terminal methyl groups is replaced by a chlorine. It is a powerful vesicant regulated under the Chemical Weapons Convention.


mutagen

An agent that increases the frequency of mutations above the normal background level, usually by interacting directly with DNA and causing it damage, including base substitution.


mycolic acid

Mycolic acids are alpha-branched, beta-hydroxy long-chain fatty acids found in the cell walls of the mycolata taxon, a group of bacteria that includes Mycobacterium tuberculosis, the causative agent of the disease tuberculosis.


mycotoxin

Poisonous substance produced by fungi.


myo-inositol monophosphate

A myo-inositol phosphate that is myo-inositol in which one of the hydroxy groups is replaced by a phosphate group. A 'closed class'.


myo-inositol phosphate

An inositol phosphate in which the inositol component has myo-configuration.


A tetraphene having methyl substituents at the 7- and 12-positions. It is a potent carcinogen and is present in tobacco smoke.


myrtenic acid

A monoterpenoid that is 6,6-dimethylbicyclo[3.1.1]hept-2-ene substituted by a carboxy group at position 2.


MYXOTHIAZOL

A 2,4'-bi-1,3-thiazole substituted at the 4-position with a (1E,3S,4R,5E)-7-amino-3,5-dimethoxy-4-methyl-7-oxohepta-1,5-dien-1-yl] group and at the 2'-position with a (2S,3E,5E)-7-methylocta-3,5-dien-2-yl group. It is an inhibitor of coenzyme Q - cytochrome c reductase.


naphthaldehydes

An  arenecarbaldehyde that is a mono or poly-substituted naphthalene in which at least one of the substituents is a formyl group.


naphthalenes

Any benzenoid aromatic compound having a skeleton composed of two ortho-fused benzene rings.


naphthalenone

Any naphthalene that is carrying at least one oxo substituent.


naphthoquinone

A polycyclic aromatic ketone metabolite of naphthalene.


naphthoic acid

An aromatic carboxylic acid that consists of a naphthalene skeleton substituted by one or more carboxy groups.


salbutamol

A member of the class of phenylethanolamines that is 4-(2-amino-1-hydroxyethyl)-2-(hydroxymethyl)phenol having a tert-butyl group attached to the nirogen atom. It acts as a beta-adrenergic agonist used in the treatment of asthma and chronic obstructive pulmonary disease (COPD).


neohesperidoside

A glycoside containing alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranosyl residue as the sugar unit.


neolignan

A phenylpropanoid that includes plant products formed primarily from oxidative coupling of two para-propylphenol moities. Unlike lignan, the units are coupled at  positions other than their beta-carbon atoms.


neoxanthin

An epoxycarotenoid that is 6,7-didehydro-5,5',6,6'-tetrahydro-5',6'-epoxy-beta,beta-carotene which is substituted by hydroxy groups at the 3, 3', and 5 positions.


neuraminate

A member of the class of neuraminates obtained by deprotonation of the carboxy group of keto-neuraminic acid.


neutral glycosphingolipid

Any glycosphingolipid containing unsubstituted glycosyl moieties.


NADP

Abbreviation for nicotinamide-adenine dinucleotide phosphate when its oxidation state is unknown or unspecified.


NAD(P)

A coenzyme that may be NAD or NADP.


pyridinecarboxamide

A member of the class of pyridines that is a substituted pyridine in which at least one of the substituents is a carboxamide or N-substituted caraboxamide group.


nitramine

Amines substituted at N with a nitro group (a contracted form of N-nitroamines); they are thus amides of nitric acid, and the class is composed of nitramide, O2NNH2, and its derivatives formed by substitution.


A tricarboxylic acid trianion resulting from the deprotonation of all three hydroxy groups of nitrilotriacetic acid.


aldicarb

The oxime carbamate resulting from the addition of 2-methyl-2-(methylsulfanyl)propanaldoxime to methyl isocyanate. A member of the class of oxime carbamate insecticides, aldicarb is a mixture of E and Z isomers; it is not known which isomer is more active.


nitroaniline

A substituted aniline that carries one or more nitro groups.


nitrobenzoic acid

Any member of the class of benzoic acids with at least one nitro substituent attached to the benzene ring.


nitroglycerol

A nitrate ester that is glycerol in which nitro group(s) replace the hydrogen(s) attached to one or more of the hydroxy groups.


nitrotoluene

Any member of the class of  toluenes bearing one or more nitro substituents on the benzene ring.


nonanone

Any ketone that is nonane substituted by an oxo group at unspecified position.


nonaprenol

Any polyprenol composed of at least nine isoprene units.


norcoclaurine

A benzylisoquinoline alkaloid based on a  benzyltetrahydroisoquinoline skeleton.