Anthranilate

2-Aminobenzoic acid, also known as anthranilate or vitamin L1, belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. 2-Aminobenzoic acid exists as a solid, slightly soluble (in water), and a weakly acidic compound (based on its pKa). 2-Aminobenzoic acid has been found in human epidermis tissue, and has also been primarily detected in feces, urine, blood, and cerebrospinal fluid. Within the cell, 2-aminobenzoic acid is primarily located in the cytoplasm and mitochondria. 2-Aminobenzoic acid exists in all living organisms, ranging from bacteria to humans. 2-Aminobenzoic acid participates in a number of enzymatic reactions. In particular, L-Glutamic acid, pyruvic acid, and 2-aminobenzoic acid can be biosynthesized from chorismate and L-glutamine; which is mediated by the enzyme anthranilate synthase. Furthermore, 2-Aminobenzoic acid and phosphoribosyl pyrophosphate can be converted into N-(5-phosphoribosyl)-anthranilate through its interaction with the enzyme anthranilate synthase component ii. Furthermore, L-Glutamic acid, pyruvic acid, and 2-aminobenzoic acid can be biosynthesized from chorismate and L-glutamine; which is mediated by the enzyme anthranilate synthase. Finally, 2-Aminobenzoic acid and phosphoribosyl pyrophosphate can be converted into N-(5-phosphoribosyl)-anthranilate; which is mediated by the enzyme anthranilate synthase component ii. In humans, 2-aminobenzoic acid is involved in the tryptophan metabolism pathway. Outside of the human body, 2-aminobenzoic acid can be found in a number of food items such as climbing bean, ginseng, black mulberry, and rambutan. This makes 2-aminobenzoic acid a potential biomarker for the consumption of these food products. 2-Aminobenzoic acid is a potentially toxic compound. 2-Aminobenzoic acid is an organic compound. It is a substrate of enzyme anthranilate hydroxylase [EC 1.14.13.35] in benzoate degradation via hydroxylation pathway (KEGG).

1-amino-2-carboxybenzene
2-amino-benzoate
2-amino-benzoic acid
2-aminobenzoate
2-aminobenzoic acid
2-aminophenylacetate
2-aminophenylacetic acid
2-carboxyaniline
Anthranate
Anthranic acid
Anthranilate
Anthranilic acid
Anthranilic acid gr
Carboxyaniline
H-2-abz-oh
Kyselina o-aminobenzoova
Kyselina anthranilova
O-amino-benzoate
O-amino-benzoic acid
O-aminobenzoate
O-aminobenzoic acid
O-anthranilate
O-anthranilic acid
O-carboxyaniline
Ortho-amidobenzoate
Ortho-amidobenzoic acid
Ortho-aminobenzoate
Ortho-aminobenzoic acid
Vitamin l
Vitamin l1
2-aminobenzoesaeure
O-aminobenzoesaeure


4-(2-Aminophenyl)-2,4-dioxobutanoic acid belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 4-(2-Aminophenyl)-2,4-dioxobutanoic acid is considered to be a practically insoluble (in water) and relatively neutral molecule. 4-(2-Aminophenyl)-2,4-dioxobutanoic acid has been primarily detected in feces. Within the cell, 4-(2-aminophenyl)-2,4-dioxobutanoic acid is primarily located in the cytoplasm and mitochondria. 4-(2-Aminophenyl)-2,4-dioxobutanoic acid exists in all living organisms, ranging from bacteria to humans. In humans, 4-(2-aminophenyl)-2,4-dioxobutanoic acid is involved in the tryptophan metabolism pathway. 4-(2-Aminophenyl)-2,4-dioxobutanoic acid is a substrate for Kynurenine/alpha-aminoadipate aminotransferase mitochondrial.


Kynurenic Acid

Kynurenic acid (KYNA) is a well-known endogenous antagonist of the glutamate ionotropic excitatory amino acid receptors N-methyl-D-aspartate (NMDA), alphaamino-3-hydroxy-5-methylisoxazole-4-propionic acid and kainate receptors and of the nicotine cholinergic subtype alpha 7 receptors. KYNA neuroprotective and anticonvulsive activities have been demonstrated in animal models of neurodegenerative diseases. Because of KYNA's neuromodulatory character, its involvement has been speculatively linked to the pathogenesis of a number of neurological conditions including those in the ageing process. Different patterns of abnormalities in various stages of KYNA metabolism in the CNS have been reported in Alzheimer's disease, Parkinson's disease and Huntington's disease. In HIV-1-infected patients and in patients with Lyme neuroborreliosis a marked rise of KYNA metabolism was seen. In the ageing process KYNA metabolism in the CNS of rats shows a characteristic pattern of changes throughout the life span. A marked increase of the KYNA content in the CNS occurs before the birth, followed by a dramatic decline on the day of birth. A low activity was seen during ontogenesis, and a slow and progressive enhancement occurs during maturation and ageing. This remarkable profile of KYNA metabolism alterations in the mammalian brain has been suggested to result from the development of the organisation of neuronal connections and synaptic plasticity, development of receptor recognition sites, maturation and ageing. There is significant evidence that KYNA can improve cognition and memory, but it has also been demonstrated that it interferes with working memory. Impairment of cognitive function in various neurodegenerative disorders is accompanied by profound reduction and/or elevation of KYNA metabolism. The view that enhancement of CNS KYNA levels could underlie cognitive decline is supported by the increased KYNA metabolism in Alzheimer's disease, by the increased KYNA metabolism in down's syndrome and the enhancement of KYNA function during the early stage of Huntington's disease. Kynurenic acid is the only endogenous N-methyl-D-aspartate (NMDA) receptor antagonist identified up to now, that mediates glutamatergic hypofunction. Schizophrenia is a disorder of dopaminergic neurotransmission, but modulation of the dopaminergic system by glutamatergic neurotransmission seems to play a key role. Despite the NMDA receptor antagonism, kynurenic acid also blocks, in lower doses, the nicotinergic acetycholine receptor, i.e., increased kynurenic acid levels can explain psychotic symptoms and cognitive deterioration. Kynurenic acid levels are described to be higher in the cerebrospinal fluid (CSF) and in critical central nervous system (CNS) regions of schizophrenics as compared to controls. (PMID: 17062375, 16088227).


L-3-Hydroxykynurenine (L-3-HK) is a metabolite in the kynurenine pathway, the major route of tryptophan degradation in mammals. Kynurenine 3-monooxygenase, an NADPH-dependent flavin monooxygenase, catalyses the hydroxylation of L-kynurenine to L-3-hydroxykynurenine. 3-hydroxykynurenine can be converted to 3-hydroxyanthranilate by the enzyme 3-hydroxykinureninase. It may also be converted to 4-(2-amino-3-hydroxphenyl)-2,4-dioxobutanoate by the enzyme kynurenine-oxoglutarate transaminase. L-3-Hydroxykynurenine (L-3-HK) is a known generator of highly reactive free radicals. An elevation of L-3-HK levels has been shown to constitute a significant hazard in situations of excitotoxic injury. In particular, L-3-HK may contribute to the neuronal deficits underlying HIV-associated dementia (PMID: 7830088). Pharmacological interventions aimed at decreasing L-3-HK formation may therefore be particularly useful for the treatment of neurological diseases which are associated with an abnormally enhanced flux through the kynurenine pathway (PMID: 10583474).


3-hydroxyanthranilic acid

3-Hydroxyanthranilic acid, also known as 2-amino-3-hydroxy-benzoate or 3-ohaa, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3-Hydroxyanthranilic acid exists as a solid, soluble (in water), and a moderately acidic compound (based on its pKa). 3-Hydroxyanthranilic acid has been found in human epidermis and bladder tissues, and has also been detected in multiple biofluids, such as urine and blood. Within the cell, 3-hydroxyanthranilic acid is primarily located in the cytoplasm. 3-Hydroxyanthranilic acid exists in all living organisms, ranging from bacteria to humans. In humans, 3-hydroxyanthranilic acid is involved in the tryptophan metabolism pathway. 3-Hydroxyanthranilic acid is an oxidation product of tryptophan metabolism. It may be a free radical scavenger and a carcinogen.


Cinnavalininate

Cinnavalininate, also known as cinnabarinic acid or cinnabarinate, belongs to the class of organic compounds known as phenoxazines. These are polycyclic aromatic compounds containing a phenoxazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a 1,4-oxazine ring. Cinnavalininate is considered to be a practically insoluble (in water) and relatively neutral molecule. Cinnavalininate exists in all living organisms, ranging from bacteria to humans. In humans, cinnavalininate is involved in the tryptophan metabolism pathway. Cinnavalininate is an intermediate in the tryptophan metabolic pathway [Kegg: C05640]. It is generated from 3-hydroxyanthranilate via the enzyme catalase (EC:1.11.1.6).


4-(2 Amino-3-hydroxyphenyl)-2,4-dioxobutanoate is found in the tryptophan metabolic pathway and is an intermediate in tryptophan degradation [Kegg: C05645]. More specifically it is an intermediate in the conversion of 3-hydroxy-L-kynurenine to xanthurenate. The conversion is catalyzed by kynurenine aminotransferase (EC 2.6.1.7).


Youssoufene B3

Xanthurenic acid, also known as xanthurenate or 8-hydroxykynurenate, belongs to the class of organic compounds known as quinoline carboxylic acids. These are quinolines in which the quinoline ring system is substituted by a carboxyl group at one or more positions. Xanthurenic acid exists as a solid, slightly soluble (in water), and a moderately acidic compound (based on its pKa). Xanthurenic acid has been found in human epidermis tissue, and has also been detected in multiple biofluids, such as feces, urine, and blood. In humans, xanthurenic acid is involved in the tryptophan metabolism pathway. Xanthurenic acid has been found to be associated with several diseases known as colorectal cancer, eosinophilic esophagitis, and hemodialysis; xanthurenic acid has also been linked to the inborn metabolic disorders including kynureninase deficiency. Xanthurenic acid is a metabolite from tryptophan catabolism. It is a substrate of the enzyme methyltransferases [EC 2.1.1.-] in pathway tryptophan metabolism (KEGG).


2-amino-3-carboxymuconic acid semialdehyde is an intermediate metabolite of the tryptophan-niacin catabolic pathway. Current interest in the degradation of tryptophan is mostly due to the role of quinolinate and other metabolites in several neuropathological conditions. Quinolinate is a neurotoxin formed nonenzymatically from 2-amino-3-carboxymuconic semialdehyde in mammalian tissues. 2-Amino-3-carboxymuconic semialdehyde is enzymatically converted to 2-aminomuconate via 2-aminomuconic semialdehyde. (PMID: 10510494, 16267312, 14275129).


2-aminomuconic 6-semialdehyde

2-aminomuconic semialdehyde is an intermediate in the oxidative metabolism of tryptophan in mammals, and takes place via the kynurenine pathway, which is also used for NAD biosynthesis in all eukaryotic organisms. 2-Aminomuconic semialdehyde is reported to be unstable and spontaneously converted to picolinic acid (regarded as metabolically inert and is excreted in the urine as a glycine conjugate), and enzymatically converted to 2-aminomuconic acid through the action of 2-aminomuconic semialdehyde dehydrogenase. (PMID: 10510494, 16267312, 14275129).

2-aminomuconate 6-semialdehyde
2-aminomuconate semialdehyde
2-aminomuconic semialdehyde
2-aminomuconic acid 6-semialdehyde
(2e,4z)-2-amino-6-oxohexa-2,4-dienoate
2-aminomuconic acid semialdehyde


Oxitriptan

5-Hydroxy-L-tryptophan is an aromatic amino acid naturally produced by the body from the essential amino acid L-tryptophan. 5-Hydroxy-L-tryptophan is the immediate precursor of the neurotransmitter serotonin. The conversion to serotonin is catalyzed by the enzyme aromatic L-amino acid decarboxylase (EC 4.1.1.28) (AADC1 also known as DOPA decarboxylase), an essential enzyme in the metabolism of the monoamine neurotransmitters. An accumulation of 5-hydroxy-L-tryptophan in cerebrospinal fluid occurs in aromatic L-amino acid decarboxylase deficiency (AADC deficiency) (OMIM: 608643) accompanied by an increased excretion in the urine of the patients, which are indicative of the disorder but not specific. 5-Hydroxy-L-tryptophan is also increased in other disorders such as in Parkinson's patients with severe postural instability and gait disorders. The amount of endogenous 5-hydroxy-L-tryptophan available for serotonin synthesis depends on the availability of tryptophan and on the activity of various enzymes, especially tryptophan hydroxylase (EC 1.14.16.4), indoleamine 2,3-dioxygenase (EC 1.13.11.52), and tryptophan 2,3-dioxygenase (TDO) (EC 1.13.11.11). 5-Hydroxy-L-tryptophan has been used clinically for over 30 years. In addition to its use in the treatment of depression, the therapeutic administration of 5-hydroxy-L-tryptophan has been shown to be effective in treating a wide variety of conditions, including fibromyalgia, insomnia, binge eating associated with obesity, cerebellar ataxia, and chronic headaches. 5-Hydroxy-L-tryptophan easily crosses the blood-brain barrier and effectively increases central nervous system (CNS) synthesis of serotonin. Supplementation with 5-hydroxy-L-tryptophan is hypothesized to normalize serotonin synthesis, which is putatively related to its antidepressant properties (PMID: 9295177, 17240182, 16023217). When present in sufficiently high levels, 5-hydroxytryptophan can be a neurotoxin and a metabotoxin. A neurotoxin is a compound that disrupts or attacks neural cells or tissue. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Signs and symptoms of AADC deficiency generally appear in the first year of life. Affected infants may have severe developmental delay, weak muscle tone (hypotonia), muscle stiffness, difficulty moving, and involuntary writhing movements of the limbs (athetosis). They may be lacking in energy (lethargic), feed poorly, startle easily, and have sleep disturbances. Since 5-hydroxytryptophan is a precursor to serotonin, altered levels of serotonin can accumulate in the brain, which leads to abnormal neural signalling. Infants with AADC deficiency have very low levels of neural signalling molecules while individuals who consume high levels of 5-hydroxytryptophan will have very high levels of neural signalling molecules. Both conditions can lead to vomiting, nausea, extreme drowsiness, and lethargy. 5-Hydroxytryptophan (5-HTP), also known as oxitriptan (INN) is sold over-the-counter in the United Kingdom, the United States, and Canada as a dietary supplement for use as an antidepressant, appetite suppressant, and sleep aid. It is also marketed in many European countries for the indication of major depression under trade names such as Cincofarm, Levothym, Levotonine, Oxyfan, Telesol, Tript-OH, and Triptum. Several double-blind placebo-controlled clinical trials have demonstrated the effectiveness of 5-HTP in the treatment of depression, though a lack of high-quality studies has been noted. More and larger studies are needed to determine if 5-HTP is truly effective in treating depression.


Serotonin

Serotonin is a biochemical messenger and regulator, synthesized from the essential amino acid L-Tryptophan. Serotonin in the nervous system acts as a local transmitter at synapses, and as a paracrine or hormonal modulator of circuits upon diffusion, allowing a wide variety of "state-dependent" behavioral responses to different stimuli. Serotonin is widely distributed in the nervous system of vertebrates and invertebrates and some of its behavioral effects have been preserved along evolution. Such is the case of aggressive behavior and rhythmic motor patterns , including those responsible for feeding. In vertebrates, which display a wider and much more sophisticated behavioral repertoire, serotonin also modulates sleep, the arousal state , sexual behavior, and others, and deficiencies of the serotonergic system causes disorders such as depression, obsessive-compulsive disorder, phobias, posttraumatic stress disorder, epilepsy, and generalized anxiety disorder. Serotonin has three different modes of action in the nervous system: as transmitter, acting locally at synaptic boutons; upon diffusion at a distance from its release sites, producing paracrine (also called volume) effects, and by circulating in the blood stream, producing hormonal effects. The three modes can affect a single neuronal circuit. (PMID: 16047543).


5-Hydroxyindoleacetaldehyde, also known as 5-hial, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. 5-Hydroxyindoleacetaldehyde is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 5-Hydroxyindoleacetaldehyde has been found in human liver and kidney tissues, and has also been detected in multiple biofluids, such as feces, urine, and blood. Within the cell, 5-hydroxyindoleacetaldehyde is primarily located in the cytoplasm and mitochondria. In humans, 5-hydroxyindoleacetaldehyde is involved in the tryptophan metabolism pathway. Outside of the human body, 5-hydroxyindoleacetaldehyde can be found in a number of food items such as sweet rowanberry, rose hip, summer savory, and gram bean. This makes 5-hydroxyindoleacetaldehyde a potential biomarker for the consumption of these food products. 5-Hydroxyindoleacetaldehyde is a biogenic aldehyde of serotonin derived from the action of monoamine oxidase (MAO). (PMIDs 11306106, 2470392).


(5-hydroxyindol-3-yl)acetic acid

5-hydroxyindoleacetic acid (5HIAA) is a breakdown product of serotonin that is excreted in the urine. Serotonin is a hormone found at high levels in many body tissues. Serotonin and 5HIAA are produced in excess amounts by carcinoid tumors, and levels of these substances may be measured in the urine to test for carcinoid tumors. (NCI).


5-methoxyindole-3-acetic acid

5-Methoxyindoleacetic acid (5-MIAA) is formed through oxidative deamination. It is identified in the urine, and the concentration is determined to be 1.3 µg/mL using GC-MS (PMID: 12908946). An increase in urinary 5-MIAA excretion was shown in patients with cancer of the stomach, rectum, and lung (PMID: 2446428).


5-Hydroxy-N-formylkynurenine belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 5-Hydroxy-N-formylkynurenine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). In humans, 5-hydroxy-N-formylkynurenine is involved in the tryptophan metabolism pathway. 5-Hydroxy-N-formylkynurenine is an intermediate in tryptophan metabolism. 5-Hydroxy-N-formylkynurenine is converted from 5-Hydroxy-L-tryptophan via the enzyme, indoleamine 2,3-dioxygenase [EC:1.13.11.52].


5-Hydroxykynurenine is found in the tryptophan metabolism pathway. It is created from 5-Hydroxy-N-formylkynurenine through the action of arylformamidase [EC:3.5.1.9]. 5-Hydroxykynurenine is then converted to 5-Hydroxykynurenamine by the action of dopa decarboxylase [EC:4.1.1.28].


5-Hydroxykynurenamine, also known as mausamine, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 5-Hydroxykynurenamine is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). In humans, 5-hydroxykynurenamine is involved in the tryptophan metabolism pathway. 5-Hydroxykynurenamine is an intermediate in the tryptophan metabolic pathway [Kegg: C05638]. It is generated from 5-hydroxykynurenine via the enzyme DOPA decarboxylase.


4,6-Dihydroxyquinoline, also known as quinoline-4,6-diol, belongs to the class of organic compounds known as hydroxyquinolones. Hydroxyquinolones are compounds containing a quinoline moiety bearing a hydroxyl group and a ketone. Quinoline or benzo[b]pyridine is a bicyclic compound that consists of benzene fused to a pyridine. 4,6-Dihydroxyquinoline is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 4,6-Dihydroxyquinoline has been primarily detected in feces. Within the cell, 4,6-dihydroxyquinoline is primarily located in the cytoplasm. In humans, 4,6-dihydroxyquinoline is involved in the tryptophan metabolism pathway. 4,6-Dihydroxyquinoline is the product of the conversion of 5-hydroxykynurenamine by the enzyme monoamine oxidase, both metabolites from the 5-hydroxytryptophan metabolism. (PMIDs 7160021, 312499).


ACETYLSEROTONIN

N-Acetylserotonin is an intermediate in the metabolic pathway of melatonin and indoleamine in the pineal gland of mammalians. Serotonin-N-acetyltransferase (SNAT), which regulates the rate of melatonin biosynthesis in the pineal gland, catalyzes the acetylation of 5HT to N-acetylserotonin (NAS). A methyl group from S-adenosylmethionine is transferred to NAS by hydroxyindole-O-methyltransferase (HIOMT), and finally NAS is converted to 5-methoxy-N-acetyltryptamine, or melatonin. In most mammalian species the content of NAS (and melatonin) in the pineal gland shows clear circadian changes with the highest level occurring during the dark period. This elevation of the contents of NAS (and melatonin) in the dark period is due to the increase of SNAT activity and the elevation of SNAT gene expression. Experimental studies show that N-acetylserotonin possess free radical scavenging activity. Acute administration of irreversible and reversible selective MAO-A inhibitors and high doses (or chronic administration of low doses) of relatively selective MAO-B inhibitors (but not of highly selective MAO-B inhibitors) suppressed MAO-A activity and stimulated N-acetylation of pineal serotonin into N-acetylserotonin, the immediate precursor of melatonin. N-acetylserotonin increase after MAO-A inhibitors might mediate their antidepressive and antihypertensive effects. N-Acetylserotonin is the product of the O-demethylation of melatonin mediated by cytochrome P-450 isoforms: Cytochrome p450, subfamily IIc, polypeptide 19 (CYP2C19, a clinically important enzyme that metabolizes a wide variety of drugs), with a minor contribution from Cytochrome p450, subfamily I, polypeptide (2CYP1A2, involved in O-deethylation of phenacetin). (PMID 15616152, 11103901, 10721079, 10591054).


Melatonin

Melatonin is a biogenic amine that is found in animals, plants and microbes. Aaron B.Lerner of Yale University is credited for naming the hormone and for defining its chemical structure in 1958. In mammals, melatonin is produced by the pineal gland. The pineal gland is small endocrine gland, about the size of a rice grain and shaped like a pine cone (hence the name), that is located in the center of the brain (rostro-dorsal to the superior colliculus) but outside the blood-brain barrier. The secretion of melatonin increases in darkness and decreases during exposure to light, thereby regulating the circadian rhythms of several biological functions, including the sleep-wake cycle. In particular, melatonin regulates the sleep-wake cycle by chemically causing drowsiness and. lowering the body temperature. Melatonin is also implicated in the regulation of mood,learning and memory, immune activity, dreaming, fertility and reproduction. Melatonin is also an effective antioxidant. Most of the actions of melatonin are mediated through the binding and activation of melatonin receptors. Individuals with autism spectrum disorders(ASD) may have lower than normal levels of melatonin. A 2008 study found that unaffected parents of individuals with ASD also have lower melatonin levels, and that the deficits. were associated with low activity of the ASMT gene, which encodes the last enzyme of melatonin synthesis. Reduced melatonin production has also been proposed as a likely factor in the significantly higher cancer rates in night workers.


Acetyl-N-formyl-5-methoxykynurenamine (AFMK) results from the oxidative cleavage of the pyrrole ring during melatonin oxidation by myeloperoxidase (MPO), a superoxide anion (O)-dependent reaction. AFMK is also expected to be formed from oxidation catalyzed by the unspecific enzyme indoleamine-2,3-dioxygenase (IDO), found in a variety of cell types including monocyte/macrophage lineages. MPO- and IDO-catalyzed melatonin oxidation has the requirement of O in common, a species formed in large amounts in inflammatory conditions. The non-enzymatic formation of AFMK can also be expected by its direct reaction with highly reactive oxygen species, such as hydroxyl radical and singlet oxygen. Thus, we assume that AFMK is a product formed in a route of melatonin metabolism, especially active in inflammation. As AFMK is biologically more active on leukocytes than melatonin, the metabolizing of melatonin to AFMK at inflammatory sites possibly plays a role in immunomodulation. AFMK is found in the CSF of patients with meningitis, and in some samples at a remarkably high concentration. AFMK was also found in some patients to exceed the concentration of melatonin normally found in serum (PMID: 16150112).


N-methylserotonin

N-Methylserotonin belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5. N-Methylserotonin is considered to be a practically insoluble (in water) and relatively neutral molecule. N-Methylserotonin has been primarily detected in blood. Within the cell, N-methylserotonin is primarily located in the cytoplasm. In humans, N-methylserotonin is involved in the tryptophan metabolism pathway. Outside of the human body, N-methylserotonin can be found in citrus. This makes N-methylserotonin a potential biomarker for the consumption of this food product. N-methylserotonin is a product of the serotonin-degradative pathway, found in urine specimens of patients with psychiatric disorders (PubMed ID 8747157 ).


Formyl-5-hydroxykynurenamine belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group and a phenyl group. Formyl-5-hydroxykynurenamine is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Formyl-5-hydroxykynurenamine can be biosynthesized from serotonin; which is mediated by the enzyme indoleamine 2,3-dioxygenase 1 [EC 1.13.11.52]. In humans, formyl-5-hydroxykynurenamine is involved in the tryptophan metabolism pathway.


Tryptamine

Tryptamine is a monoamine compound that is common precursor molecule to many hormones and neurotransmitters. Biosynthesis generally proceeds from the amino acid tryptophan, with tryptamine in turn acting as a precursor for other compounds. Substitutions to the tryptamine molecule give rise to a group of compounds collectively known as tryptamines. The most well-known tryptamines are serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle.


Indoleacetaldehyde is a substrate for Retina-specific copper amine oxidase, Aldehyde dehydrogenase X (mitochondrial), Amine oxidase B, Amiloride-sensitive amine oxidase, Aldehyde dehydrogenase (mitochondrial), Fatty aldehyde dehydrogenase, 4-trimethylaminobutyraldehyde dehydrogenase, Aldehyde dehydrogenase (dimeric NADP-preferring), Aldehyde dehydrogenase family 7 member A1, Amine oxidase A, Aldehyde dehydrogenase 1A3 and Membrane copper amine oxidase.


Indoleacetic acid

Indoleacetic acid (IAA) is a breakdown product of tryptophan metabolism and is often produced by the action of bacteria in the mammalian gut. Some endogenous production of IAA in mammalian tissues also occurs. It may be produced by the decarboxylation of tryptamine or the oxidative deamination of tryptophan. IAA frequently occurs at low levels in urine and has been found in elevated levels in the urine of patients with phenylketonuria ((PMID: 13610897). Using material extracted from human urine, it was discovered by Kogl in 1933 that Indoleacetic acid is also an important plant hormone (PMID: 13610897). Specifically IAA is a member of the group of phytohormones called auxins. IAA is generally considered to be the most important native auxin. Plant cells synthesize IAA from tryptophan. (wikipedia) IAA and some derivatives can be oxidised by horseradish peroxidase (HRP) to cytotoxic species. IAA is only toxic after oxidative decarboxylation; the effect of IAA/HRP is thought to be due in part to the formation of methylene-oxindole, which may conjugate with DNA bases and protein thiols. IAA/HRP could be used as the basis for targeted cancer, a potential new role for plant auxins in cancer therapy. (PMID: 11163327).

(1h-indol-3-yl)-acetate
(1h-indol-3-yl)-acetic acid
1h-indol-3-ylacetate
1h-indol-3-ylacetic acid
1h-indole-3-acetate
1h-indole-3-acetic acid
2-(1h-indol-3-yl)acetate
2-(1h-indol-3-yl)acetic acid
2-(3-indolyl)acetate
2-(3-indolyl)acetic acid
3-(carboxymethyl)indole
3-iaa
3-indole-acetic acid
3-indoleacetate
3-indoleacetic acid
3-indolylacetate
3-indolylacetic acid
Heteroauxin
Indol-3-ylacetate
Indol-3-ylacetic acid
Indole-3-acetate
Indole-3-acetic acid
Indoleacetate
Indoleacetic acid
Indolyl-3-acetate
Indolyl-3-acetic acid
Indolylacetate
Indolylacetic acid
Kyselina 3-indolyloctova
Rhizopin
Rhizopon a
Skatole carboxylate
Skatole carboxylic acid
Alpha-indol-3-yl-acetic acid
B-indoleacetate
B-indoleacetic acid
B-indolylacetate
B-indolylacetic acid
Beta-indole-3-acetic acid
Beta-indoleacetate
Beta-indoleacetic acid
Beta-indolylacetate
Beta-indolylacetic acid
(indol-3-yl)acetate
(indol-3-yl)acetic acid
2-(indol-3-yl)ethanoic acid
3-indolylessigsaeure
Iaa
Ies
2-(indol-3-yl)ethanoate


N-methyltryptamine

N-Methyltryptamine (NMT), or monomethyltryptamine, is a tryptamine alkaloid that has been found in the bark, shoots and leaves of numerous plants. (wikipedia). N-Methyltryptamine was detected in urine from all autistic patients with mental retardation and epilepsy and many autistic patients (32/47) with mental retardation (PubMed ID 8747157 ).


RETINAL

Vitamin A (all-trans retinol) is converted in the retina to the 11-cis-isomer of retinaldehyde or 11-cis-retinal. 11-cis-retinal functions in the retina in the transduction of light into the neural signals necessary for vision. 11-cis-retinal, while attached to opsin in rhodopsin is isomerized to all-trans-retinal by light. This is the event that triggers the nerve impulse to the brain which allows for the perception of light. All-trans-retinal is then released from opsin and reduced to all-trans-retinol. All-trans-retinol is isomerized to 11-cis-retinol in the dark, and then oxidized to 11-cis-retinal. 11-cis-retinal recombines with opsin to re-form rhodopsin. Night blindness or defective vision at low illumination results from a failure to resynthesize 11-cis retinal rapidly (http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/vit_0260.shtml).


Cis-11-retinol is produce from vitamin A cycle driven by interphotoreceptor retinoid binding protein(IRBP). cis-11-retinol is released from retinal pigment epithelium(RPE) membranes. (PMID: 10655150). Retinoid metabolism of RPE cells freshly isolated by trypsinization showed no 11- cis -retinal and little 11- cis -retinol formation. Nondamaged cells cultured on thermally responsive surfaces detached in sheets upon temperature change. They showed metabolism similar to that of cells freshly isolated by nonenzymatic means. After trypsinization, confluent cultures dissociated into individual cells, but these cells showed poor retinoid metabolism, including no detectable retinyl esters or 11- cis -retinoid isomers. (PMID: 10375454).


Vitamin A

Retinyl palmitate, or vitamin A palmitate, is a common vitamin supplement, with formula C36H60O2. It is available in both oral and injectable forms for treatment of vitamin A deficiency, under the brand names Aquasol and Palmitate. Retinyl palmitate is an alternate for retinyl acetate in vitamin A supplements, and is available in oily or dry forms. It is a pre-formed version of vitamin A, and can thus be realistically over-dosed, unlike beta-carotene.

All-trans-retinol palmitate
All-trans-retinyl palmitate
All-trans-vitamin a palmitate
Aquapalm
Aquasol a
Arovit
Axerophthol palmitate
Dispatabs tabs
Ester found in fish liver oils
Lutavit a 500 plus
Myvak
Myvax
Optovit a
Optovit-a
Retinol palmitate
Retinyl hexadecanoate
Retinyl hexadecanoic acid
Retinyl palmitate
Retinyl palmitic acid
Testavol s
Vitamin a palmitate
Vitazyme a
Trans-retinol palmitate
Trans-retinyl palmitate
All-trans-retinyl hexadecanoate
All-trans-retinyl hexadecanoic acid
All-trans-retinyl palmitic acid
Retinol palmitic acid
Vitamin a palmitic acid


diglyceride

DG(16:1(9Z)/22:0/0:0) belongs to the family of Diacylglycerols. These are glycerolipids lipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. DG(16:1(9Z)/22:0/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway.


9-cis-retinol is a retinoid. Retinoids (vitamin A and its analogs) are essential dietary substances that are needed by mammals for reproduction, normal embryogenesis, growth, vision, and maintaining normal cellular differentiation and the integrity of the immune system. Within cells, retinoids regulate gene transcription acting through ligand-dependent transcription factors, the retinoic acid receptors (RARs), and the retinoid X receptors (RXRs). All-trans-retinoic acid binds only to RARs with high affinity, whereas its 9-cis isomer binds with high affinity to both RARs and RXRs. The actions of all-trans- and 9-cis-retinoic acid in regulating cellular responses are distinct and not interchangeable. (PMID: 9115228).


Beta carotene

B-Carotene is a carotenoid that is a precursor of vitamin A. It is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (porphyria, erythropoietic). (From Reynolds JEF(Ed): Martindale: The Extra Pharmacopoeia (electronic version). Micromedex, Inc, Engewood, CO, 1995.) -- Pubchem; Carotene is an orange photosynthetic pigment important for photosynthesis. It is responsible for the orange colour of the carrot and many other fruits and vegetables. It contributes to photosynthesis by transmitting the light energy it absorbs to chlorophyll. Chemically, carotene is a terpene. It is the dimer of retinol (vitamin A) and comes in two primary forms: alpha- and beta-carotene. gamma-, delta- and epsilon-carotene also exist. Carotene can be stored in the liver and converted to vitamin A as needed. Beta-carotene is an anti-oxidant and such can be useful for curbing the excess of damaging free radicals in the body. However, the usefulness of beta-carotene as a dietary supplement (i.e. taken as a pill) is still subject to debate. Beta-carotene is fat-soluble, so a small amount of fat is needed to absorb it into the body. -- Wikipedia.


In vivo, 9-cis-retinal is formed through oxidation of 9-cis-retinol by cis-retinol dehydrogenase (cRDH). (PMID: 15572038). The generation of retinoic acid from retinol is a two-step reaction, with the rate-limiting step being the oxidation of retinol into the intermediate retinaldehyde. Two classes of. unrelated enzymes have been implicated in the oxidation of retinol, the classical cytosolic medium chain alcohol dehydrogenases and recently identified microsomal members of the short chain alcohol dehydrogenase reductase (SDR) superfamily. Further oxidation of the retinaldehyde to the retinoic acid is believed to be catalyzed by several cytosolic aldehyde dehydrogenases. Retinoids are micronutrients required to maintain and promote health of vertebrates. They act physiologically by participating in the visual cycle, in regulating cell differentiation, in embryonic development (PMID: 10893430), in maintaining normal reproduction, and in the immune response (PMID: 8882153). In non-ocular tissues, the effects of retinoids within the body are mediated through retinoic acid receptors (RARs) and retinoid X receptors (RXRs), which act to regulate gene expression as ligand-dependent transcription factors. The naturally occurring ligands for these nuclear receptors are thought to be all-trans-retinoic acid for RARs and 9-cis-retinoic acid for RXRs (PMID: 10322133). While many details of the molecular actions of the RARs and RXRs in regulating gene transcription are understood (PMID: 10418975), tissue-specific synthetic pathway(s) of their ligands has not been adequately defined. Nevertheless, the therapeutic efficacy of retinoids, including 9-cis-retinoic acid, is well established in both tissue culture and animal models of breast cancer (PMID: 8825126, PMID: 12743994).


Alitretinoin

9-cis-Retinoic acid is an active retinoid that regulates expression of retinoid responsive genes, serving as a ligand for two classes of ligand-dependent transcription factors: the retinoic acid receptors and retinoid X receptors. Retinoids (vitamin A and its analogs) are essential dietary substances that are needed by mammals for reproduction, normal embryogenesis, growth, vision, and maintaining normal cellular differentiation and the integrity of the immune system. Within cells, retinoids regulate gene transcription acting through ligand-dependent transcription factors, the retinoic acid receptors (RARs), and the retinoid X receptors (RXRs). all-trans-Retinoic acid binds only to RARs with high affinity, whereas its 9-cis isomer binds with high affinity to both RARs and RXRs. The actions of all-trans- and 9-cis-retinoic acid in regulating cellular responses are distinct and not interchangeable (PMID: 9115228).


Tretinoin

all-trans-Retinoic acid (ATRA) is an isomer of retinoic acid, the oxidized form of vitamin A. Retinoic acid functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately controls anterior/posterior patterning in early developmental stages (PMID: 17495912). It is an important regulator of gene expression during growth and development, and in neoplasms. As a drug, all-trans-retinoic acid is known as tretinoin. Tretinoin is derived from maternal vitamin A and is essential for normal growth and embryonic development. An excess of tretinoin can be teratogenic. Tretinoin is used in the treatment of psoriasis, acne vulgaris, and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute).


4-oxo-retinol, a metabolite of retinol synthesized in mouse embryonal carcinoma F9 cells,is active in inducing differentiation of these cells. It also functions as a ligand of retinoic acid receptors and a transcriptional activator of reporter. genes.[PMID: 9110564]. 4-Oxoretinol is a metabolite of retinol in the human promyelocytic leukemia cell line NB4 which induces cell growth arrest and granulocytic differentiation.[PMID: 9581846].


All-trans-13,14-dihydroretinol is involved in the retinol metabolism pathway. In this pathway, all-trans-13,14-dihydroretinol and an acceptor molecule is reversibly converted to retinol (vitamin A) plus reduced acceptor via the enzyme all-trans-retinol 13,14-reductase (EC 1.3.99.23). (KEGG).


Retinoyl beta-glucuronide is a naturally occurring, biologically active metabolite of vitamin A. Although retinoyl beta-glucuronide is regarded as a detoxification product of retinoic acid, it plays several roles in the functions of vitamin A. It can serve as a source of retinoic acid, and it may be a vehicle for transport of retinoic acid to target tissues. Topically applied retinoyl beta-glucuronide is comparable in efficacy to retinoic acid in the treatment of acne in humans, without the same side effects. Retinoyl beta-glucuronide may or may not be teratogenic, depending on the mode of administration and the species in which it is used. It may be a valuable therapeutic compound for the treatment of skin disorders and certain types of cancers.

13-cis-retinoic acid acyl beta-d-glucuronide

13-cis-retinoic acid acyl beta-delta-glucuronide


all-trans-4-hydroxyretinoic acid

4-Hydroxyretinoic acid is an NADPH-dependent hydroxylation metabolite of retinoic acid in the microsomes, via the cytochrome P-450 system. Retinoic acid is an activated metabolite of retinol that supports the systemic functions of vitamin A in vivo. (PMID: 1538719, 1932598, 2851384).


all-trans-18-hydroxyretinoic acid

all-trans-18-Hydroxyretinoic acid, also known as 18-hydroxy-all-trans-retinoic acid or 18-hydroxyretinoate, belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. all-trans-18-Hydroxyretinoic acid is considered to be a practically insoluble (in water) and relatively neutral molecule. Within the cell, all-trans-18-hydroxyretinoic acid is primarily located in the membrane (predicted from logP) and cytoplasm. In humans, all-trans-18-hydroxyretinoic acid is involved in the retinol metabolism pathway. all-trans-18-Hydroxyretinoic acid is also involved in the metabolic disorder called vitamin a deficiency.


Ubiquinol 8 is a ubiquinol in which the polyprenyl substituent is octaprenyl. Ubiquinol-8 is the reduced form of ubiquinone-8. Ubiquinone (also known as coenzyme Q) is an isoprenoid quinone that functions as an electron carrier in membranes. In eukaryotes, ubiquinone is found mostly within the inner mitochondrial membrane where it functions in respiratory electron transport, transferring two electrons from either complex I (NADH dehydrogenase) or complex II (succinate-ubiquinone reductase) to complex III (bc1 complex). The quinone nucleus of ubiquinone is derived directly from 4-hydroxybenzoate, while the isoprenoid subunits of the polyisoprenoid tail are synthesized via the methylerythritol phosphate pathway, which feeds isoprene units into the polyprenyl biosynthesis pathways. The number of isoprenoid subunits in the ubiquinone side chain varies in different species. For example, Saccharomyces cerevisiae has 6 such subunits, Escherichia coli K-12 has 8, rat and mouse have 9, and Homo sapiens has 10. Ubiquinol-8 is effective as an anti-oxidant. By donating one of its hydrogen atoms to become the free-radical semiquinone (.Q-), it can neutralize a lipid peroxyl radical. The free-radical semiquinone is then restored to a non-free-radical state by the respiratory chain Q cycle. Ubiquinol or the free-radical semiquinone can also regenerate the Vitamin E tocopheroxyl radical by electron donation (http://www.benbest.com/nutrceut/CoEnzymeQ.html).


Threonine

Threonine is an essential amino acid in humans. It is abundant in human plasma, particularly in newborns. Severe deficiency of threonine causes neurological dysfunction and lameness in experimental animals. Threonine is an immunostimulant which promotes the growth of thymus gland. It also can probably promote cell immune defense function. This amino acid has been useful in the treatment of genetic spasticity disorders and multiple sclerosis at a dose of 1 gram daily. It is highly concentrated in meat products, cottage cheese and wheat germ. (http://www.dcnutrition.com/AminoAcids/) The threonine content of most of the infant formulas currently on the market is approximately 20% higher than the threonine concentration in human milk. Due to this high threonine content the plasma threonine concentrations are up to twice as high in premature infants fed these formulas than in infants fed human milk. The whey proteins which are used for infant formulas are sweet whey proteins. Sweet whey results from cheese production. Threonine catabolism in mammals appears to be due primarily (70-80%) to the activity of threonine dehydrogenase (EC 1.1.1.103) that oxidizes threonine to 2-amino-3-oxobutyrate, which forms glycine and acetyl CoA, whereas threonine dehydratase (EC 4.2.1.16) that catabolizes threonine into 2-oxobutyrate and ammonia, is significantly less active. Increasing the threonine plasma concentrations leads to accumulation of threonine and glycine in the brain. Such accumulation affects the neurotransmitter balance which may have consequences for the brain development during early postnatal life. Thus, excessive threonine intake during infant feeding should be avoided. (PMID 9853925).


Malonic acid

Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2. The ionised form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's ethyl ester. The name originates from Latin malum, meaning apple. Malonic acid is the archetypal example of a competitive inhibitor: it acts against succinate dehydrogenase (complex II) in the respiratory electron transport chain.

Carboxyacetic acid
Dicarboxylate
Dicarboxylic acid
Dicarboxymethane
Kyselina malonova
Kyselina malonova [czech]
Malonate
Malonate dicarboxylic acid
Malonic acid
Metahnedicarboxylic acid
Methanedicarbonic acid
Methanedicarboxylic acid
Propanedioate
Propanedioic acid
Propanedioic acid dithallium salt
Propanediolic acid
Thallium malonate
Alpha,omega-dicarboxylic acid


beta-Hydroxybutyric acid

3-Hydroxybutyric acid (or beta-hydroxybutyrate) is a ketone body. Like the other ketone bodies (acetoacetate and acetone), levels of 3-hydroxybutyrate in blood and urine are raised in ketosis. In humans, 3-hydroxybutyrate is synthesized in the liver from acetyl-CoA and can be used as an energy source by the brain when blood glucose is low. Blood levels of 3-hydroxybutyric acid levels may be monitored in diabetic patients to look for diabetic ketoacidosis. Persistent mild hyperketonemia is a common finding in newborns. Ketone bodies serve as an indispensable source of energy for extrahepatic tissues, especially the brain and lung of developing mammals. Another important function of ketone bodies is to provide acetoacetyl-CoA and acetyl-CoA for the synthesis of cholesterol, fatty acids, and complex lipids. During the early postnatal period, acetoacetate (AcAc) and beta-hydroxybutyrate are preferred over glucose as substrates for synthesis of phospholipids and sphingolipids in accord with requirements for brain growth and myelination. Thus, during the first 2 weeks of postnatal development, when the accumulation of cholesterol and phospholipids accelerates, the proportion of ketone bodies incorporated into these lipids increases. On the other hand, an increased proportion of ketone bodies is utilized for cerebroside synthesis during the period of active myelination. In the lung, AcAc serves better than glucose as a precursor for the synthesis of lung phospholipids. The synthesized lipids, particularly dipalmitoylphosphatidylcholine, are incorporated into surfactant, and thus have a potential role in supplying adequate surfactant lipids to maintain lung function during the early days of life (PMID: 3884391). 3-Hydroxybutyric acid is found to be associated with fumarase deficiency and medium-chain acyl-CoA dehydrogenase deficiency, which are inborn errors of metabolism.

3-hydroxy-butanoate
3-hydroxy-butanoic acid
3-hydroxy-butyrate
3-hydroxy-butyric acid
3-hydroxybutanoate
3-hydroxybutanoic acid
3-hydroxybutyrate
3-hydroxybutyric acid
3-oh-butyric acid
Biopol
Dl-3-hydroxybutyrate
Dl-3-hydroxybutyric acid
Dl-b-hydroxybutyric acid
Dl-beta-hydroxybutyric acid
B-hydroxy-n-butyrate
B-hydroxy-n-butyric acid
B-hydroxybutanoate
B-hydroxybutanoic acid
B-hydroxybutyrate
B-hydroxybutyric acid
Beta-hydroxy-n-butyrate
Beta-hydroxy-n-butyric acid
Beta-hydroxybutanoate
Beta-hydroxybutanoic acid
Beta-hydroxybuttersaeure
Beta-hydroxybutyrate
Beta-hydroxybutyric acid
(1)-3-hydroxybutyric acid
3 hba
3-hydroxybuttersaeure
Bhba
(1)-3-hydroxybutyrate
3-oh-butyrate
β-hydroxy-n-butyrate
β-hydroxy-n-butyric acid
β-hydroxybutanoate
β-hydroxybutanoic acid
B-hydroxybuttersaeure
β-hydroxybuttersaeure
β-hydroxybutyrate
β-hydroxybutyric acid
Dl-b-hydroxybutyrate
Dl-beta-hydroxybutyrate
Dl-β-hydroxybutyrate
Dl-β-hydroxybutyric acid


Butenoic Acid

But-2-enoic acid is fatty acid formed by the action of fatty acid synthases from acetyl-CoA and malonyl-CoA precursors. It is involved in the fatty acid biosynthesis. Specifically, it is the product of reaction between (R)-3-Hydroxybutyric acid and fatty acid synthase.

(2e)-2-butenoate
(2e)-2-butenoic acid
(2e)-but-2-enoate
(2e)-but-2-enoic acid
(e)-2-butenoate
(e)-2-butenoic acid
(e)-but-2-enoate
(e)-but-2-enoic acid
(e)-crotonic acid
2-butenoate
2-butenoic acid
3-methyl-acrylic acid
3-methylacrylic acid
Beo
Butenoate
Butenoic acid
Crotonic acid
Kyselina krotonova
Solid crotonic acid
Trans-crotonic acid
A-butenoate
A-butenoic acid
A-crotonic acid
Alpha-butenoate
Alpha-butenoic acid
Alpha-crotonic acid
B-methylacrylic acid
Beta-methacrylic acid
Beta-methylacrylic acid
Trans-2-butenoate
Trans-2-butenoic acid
But-2-enoate
Crotonate
3-methylacrylate


3-oxohexanoic acid

3-Oxohexanoic acid is fatty acid formed by the action of Fatty acid synthases from acetyl-CoA and malonyl-CoA precursors. This fatty acid is involved in fatty acid biosynthesis. Specifically, it is the product of reaction between malonic acid and three enznymes; beta-ketoacyl -acyl-carrier- protein synthase, fatty-acid Synthase, and beta- ketoacyl -acyl-carrier- protein synthase II.


hexanoic acid

Caproic acid is a colourless oily liquid that smells like cheese. It is a fatty acid found naturally in various animal fats and oils. Caproic acid is a medium chain triglyceride (MCT). MCTs are widely used for parenteral nutrition in individuals requiring supplemental nutrition, and are being more widely used in foods, drugs, and cosmetics (MCTs are essentially non-toxic). It is safe for human dietary consumption up to levels of 1g/kg (PMID: 10685018). Caproic acid is found to be associated with medium chain acyl-CoA dehydrogenase deficiency, which is an inborn error of metabolism.

1-hexanoate
1-hexanoic acid
1-pentanecarboxylate
1-pentanecarboxylic acid
Butylacetate
Butylacetic acid
Caproate
Caproic acid
Capronate
Capronic acid
Hexanoate
Hexanoic acid
Hexoate
Hexoic acid
Hexylate
Hexylic acid
N-caproate
N-caproic acid
N-hexanoate
N-hexanoic acid
N-hexoate
N-hexoic acid
N-hexylate
N-hexylic acid
Pentylformate
Pentylformic acid
6:0
C6:0
Ch3-[ch2]4-cooh
Pentanecarboxylic acid
Pentiformic acid
Pentanecarboxylate
Pentiformate
FA(6:0)


3-oxooctanoic acid

3-Oxo-Octanoic acid is fatty acid formed by the action of acid synthases from acetyl-CoA and malonyl-CoA precursors. It is involved in the fatty acid biosynthesis. Specifically, it is the product of reaction between malonic acid and three enzymes; beta-ketoacyl-acyl-carrier- protein synthase, fatty-acid Synthase and beta-ketoacyl -acyl-carrier- protein synthase II.

3-oxo-octanoate
3-oxo-octanoic acid
3-oxooctanoate
3-oxooctanoic acid
3-keto-n-caprylic acid
3-ketooctanoic acid
Beta-ketocaprylic acid
Beta-ketooctanoic acid
Beta-oxocaprylic acid
Beta-oxooctanoic acid
3-keto-n-caprylate
3-ketooctanoate
B-ketocaprylate
B-ketocaprylic acid
Beta-ketocaprylate
β-ketocaprylate
β-ketocaprylic acid
B-ketooctanoate
B-ketooctanoic acid
Beta-ketooctanoate
β-ketooctanoate
β-ketooctanoic acid
B-oxocaprylate
B-oxocaprylic acid
Beta-oxocaprylate
β-oxocaprylate
β-oxocaprylic acid
B-oxooctanoate
B-oxooctanoic acid
Beta-oxooctanoate
β-oxooctanoate
β-oxooctanoic acid


(R)-3-hydroxyoctanoic acid

In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. (R)-3-Hydroxyoctanoic acid is an intermediate in fatty acid biosynthesis. Specifically, (R)-3-Hydroxyoctanoic acid is converted from 3-Oxo-Octanoic acid via enzymes; fatty-acid Synthase and 3-oxoacyl- [acyl-carrier-protein] reductase. (E.C: 2.3.1.85 and E.C: 1.1.1.100).

(3r)-3-hydroxy-octanoic acid
(r)-3-hydroxycaprylic acid
(r)-3-oh octanoic acid
(r)-3-oh-caprylic acid
(r)-beta-hydroxycaprylic acid
(r)-beta-hydroxyoctanoic acid
(r)-beta-oh-caprylic acid
(r)-beta-oh-octanoic acid
(3r)-3-hydroxy-octanoate
(r)-3-hydroxyoctanoate
(r)-3-hydroxycaprylate
(r)-3-oh octanoate
(r)-3-oh-caprylate
(r)-b-hydroxycaprylate
(r)-b-hydroxycaprylic acid
(r)-beta-hydroxycaprylate
(r)-β-hydroxycaprylate
(r)-β-hydroxycaprylic acid
(r)-b-hydroxyoctanoate
(r)-b-hydroxyoctanoic acid
(r)-beta-hydroxyoctanoate
(r)-β-hydroxyoctanoate
(r)-β-hydroxyoctanoic acid
(r)-b-oh-caprylate
(r)-b-oh-caprylic acid
(r)-beta-oh-caprylate
(r)-β-oh-caprylate
(r)-β-oh-caprylic acid
(r)-b-oh-octanoate
(r)-b-oh-octanoic acid
(r)-beta-oh-octanoate
(r)-β-oh-octanoate
(r)-β-oh-octanoic acid


(2E)-oct-2-enoic acid

As to unsaturated acids, those with eight carbon atoms, 2-octenoic acid (trans-8: 1[2]) and 2-octynoic acid (8:::1[2]), increase the susceptibility to infection and fluidity while low concentrations of monounsaturated acids with 14 and 18 carbon atoms, myristoleic acid (cis-14:1[9]) and oleic acid (cis-18:1[9]), reduce both the susceptibility to infection and the fluidity of the membrane (PMID: 1963884).


Caprylic acid

Caprylic acid is the common name for the eight-carbon straight-chain fatty acid known by the systematic name octanoic acid. It is found naturally in coconuts and breast milk. It is an oily liquid with a slightly unpleasant rancid taste that is minimally soluble in water. Caprylic acid is used commercially in the production of esters used in perfumery and also in the manufacture of dyes (Wikipedia).

1-heptanecarboxylate
1-heptanecarboxylic acid
Caprylate
Caprylic acid
Emery 657
Kortacid 0899
Lunac 8-95
Lunac 8-98
N-caprylate
N-caprylic acid
N-octanoate
N-octanoic acid
N-octoate
N-octoic acid
N-octylate
N-octylic acid
Neo-fat 8
Neo-fat 8s
Octylate
Octylic acid
Prifac 2901
8:0
Acide octanoique
Acido octanoico
Acidum octanocium
C8:0
Ch3-[ch2]6-cooh
Kaprylsaeure
Octanoic acid
Octanoic acid (caprylic acid)
Octansaeure
Octoic acid
Octanoate
Octanoate (caprylate)
Octoate
FA(8:0)


3-oxodecanoic acid

In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. 3-Oxodecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, 3-Oxodecanoic acid is converted from Malonic acid via three enzymes; 3-oxoacyl-[acyl-carrier-protein] synthase, fatty-acid Synthase and beta-ketoacyl -acyl-carrier-protein synthase II. (EC:2.3.1.41, E.C: 2.3.1.85, 2.3.1.179).

3-ketodecanoic acid
3-oxocapric acid
Beta-ketocapric acid
Beta-ketodecanoic acid
Beta-oxodecanoic acid
3-ketodecanoate
3-oxodecanoate
3-oxocaprate
B-ketocaprate
B-ketocapric acid
Beta-ketocaprate
β-ketocaprate
β-ketocapric acid
B-ketodecanoate
B-ketodecanoic acid
Beta-ketodecanoate
β-ketodecanoate
β-ketodecanoic acid
B-oxodecanoate
B-oxodecanoic acid
Beta-oxodecanoate
β-oxodecanoate
β-oxodecanoic acid


trans-2-decenoic acid

In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. trans-Dec-2-enoic acid is an intermediate in fatty acid biosynthesis. Specifically, trans-Dec-2-enoic is converted from (R)-3-Hydroxydecanoic acid via enzyme, fatty-acid Synthase (EC:2.3.1.85).


Capric acid

Capric acid is a member of the series of fatty acids found in oils and animal fats. The names of caproic, caprylic, and capric acids are all derived from the word caper (Latin for goat). These fatty acids are light yellowish transparent oily liquids with uncomfortable smells. They are used in organic synthesis, perfume manufacturing, medicine, lubricating grease, rubber, and dye (Chemicalland21).

1-nonanecarboxylate
1-nonanecarboxylic acid
Caprate
Capric acid
Caprinate
Caprinic acid
Caprynate
Caprynic acid
Decoate
Decoic acid
Decylate
Decylic acid
Emery 659
Lunac 10-95
Lunac 10-98
N-caprate
N-capric acid
N-decanoate
N-decanoic acid
N-decoate
N-decoic acid
N-decylate
N-decylic acid
Prifac 2906
Prifac 296
10:0
C10:0
Ch3-[ch2]8-cooh
Decanoate
Dekansaeure
Kaprinsaeure
FA(10:0)


3-oxolauric acid

In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. 3-Oxo-Dodecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, 3-Oxo-Dodecanoic acid is converted form Malonic acid via three enzymes; 3-oxoacyl-[acyl-carrier-protein] synthase, fatty-acid Synthase and beta-ketoacyl -acyl-carrier-protein synthase II. (EC:2.3.1.41, E.C: 2.3.1.85, 2.3.1.179).


(3R)-3-HYDROXYDODECANOIC ACID

In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation.(R)-3-Hydroxydodecanoic acid is an intermediate in fatty acid biosynthesis. Specifically,(R)-3-Hydroxydodecanoic acid is converted from 3-Oxo-Dodecanoic acid via two enzymes; fatty-acid Synthase and 3-oxoacyl-[acyl-carrier-protein] reductase (EC: 2.3.1.85 and EC: 1.1.1.100).

(3r)-3-hydroxydodecanoic acid
(r)-3-oh dodecanoic acid
(r)-3-oh lauric acid
(r)-beta-hydroxydodecanoic acid
(r)-beta-hydroxylauric acid
(r)-beta-oh dodecanoic acid
(r)-beta-oh lauric aci
(3r)-3-hydroxydodecanoate
(r)-3-hydroxydodecanoate
(r)-3-oh dodecanoate
(r)-3-oh laate
(r)-3-oh laic acid
(r)-b-hydroxydodecanoate
(r)-b-hydroxydodecanoic acid
(r)-beta-hydroxydodecanoate
(r)-β-hydroxydodecanoate
(r)-β-hydroxydodecanoic acid
(r)-b-hydroxylaate
(r)-b-hydroxylaic acid
(r)-beta-hydroxylaate
(r)-beta-hydroxylaic acid
(r)-β-hydroxylaate
(r)-β-hydroxylaic acid
(r)-b-oh dodecanoate
(r)-b-oh dodecanoic acid
(r)-beta-oh dodecanoate
(r)-β-oh dodecanoate
(r)-β-oh dodecanoic acid
(r)-b-oh lauric aci
(r)-β-oh lauric aci


trans-2-dodecenoic acid

In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. trans-Dodec-2-enoic acid is an intermediate in fatty acid biosynthesis. Specifically, trans-Dodec-2-enoic acid is converted from (R)-3-Hydroxydodecanoic acid via two enzymes; fatty-acid Synthase and 3-Hydroxypalmitoyl- [acyl-carrier-protein] dehydratase (EC: 2.3.1.85 and EC: 4.2.1.61).


3-oxotetradecanoic acid

3-Oxo-tetradecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, 3-Oxo-tetradecanoic acid is converted from Malonic acid via three enzymes; 3-oxoacyl-[acyl-carrier-protein] synthase, fatty-acid Synthase and beta-ketoacyl -acyl-carrier-protein synthase II. (EC:2.3.1.41, E.C: 2.3.1.85, 2.3.1.179). In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation.


(R)-3-hydroxytetradecanoic acid

In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. (R)-3-Hydroxy-tetradecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, (R)-3-Hydroxy-tetradecanoic acid is converted from 3-Oxo-tetradecanoic acid via fatty-acid Synthase and 3-oxoacyl- [acyl-carrier-protein] reductase. (EC: 2.3.1.85 and EC:2.3.1.41).


trans-2-tetradecenoic acid

In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. trans-tetra-dec-2-enoic acid is an intermediate in fatty acid biosynthesis. Specifically, trans-tetra-dec-2-enoic acid converted from (R)-3-Hydroxy-tetradecanoic acid via two enzymes; fatty-acid Synthase and 3- Hydroxypalmitoyl- [acyl-carrier-protein] dehydratase (EC: 2.3.1.85 and EC: 4.2.1.61).


Myristic acid

Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed). Myristic acid is also commonly added to a penultimate nitrogen terminus glycine in receptor-associated kinases to confer the membrane localisation of the enzyme. this is achieved by the myristic acid having a high enough hydrophobicity to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of the eukaryotic cell.(wikipedia).

1-tridecanecarboxylate
1-tridecanecarboxylic acid
Crodacid
Myristate
Myristic acid
Myristic acid pure
Myristoate
Myristoic acid
N-tetradecan-1-oate
N-tetradecan-1-oic acid
N-tetradecanoate
N-tetradecanoic acid
Tetradecanoate
Tetradecanoic (myristic) acid
Tetradecanoic acid
1-tetradecanecarboxylic acid
14:0
Acide tetradecanoique
Ch3-[ch2]12-cooh
Myristinsaeure
N-tetradecoic acid
Tetradecoic acid
1-tetradecanecarboxylate
N-tetradecoate
Tetradecoate
FA(14:0)


3-oxopalmitic acid

In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. 3-Oxo-hexadecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, 3-Oxo-hexadecanoic acid is converted from Malonic acid via three enzymes; 3-oxoacyl-[acyl-carrier-protein] synthase, fatty-acid Synthase and beta-ketoacyl -acyl-carrier-protein synthase II. (EC:2.3.1.41, E.C: 2.3.1.85, 2.3.1.179).

3-oxo-hexadecanoate
3-oxo-hexadecanoic acid
3-oxohexadecanoate
3-oxohexadecanoic acid
3-keto palmitic acid
3-keto palmitate


(R)-3-hydroxypalmitic acid

In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. (R)-3-Hydroxy-hexadecanoic acid is an intermediate in fatty acid biosynthesis. Specifically, (R)-3-Hydroxy-hexadecanoic acid is converted from 3-Oxo-tetradecanoic acid via fatty-acid Synthase and 3-oxoacyl- [acyl-carrier-protein] reductase. (EC: 2.3.1.85 and EC: 2.3.1.41).

(r)-beta-hydroxypalmitic acid
(r)-b-hydroxypalmitate
(r)-b-hydroxypalmitic acid
(r)-beta-hydroxypalmitate
(r)-β-hydroxypalmitate
(r)-β-hydroxypalmitic acid
(r)-3-hydroxy-hexadecanoate


(E)-hexadec-2-enoic acid

In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. Trans-hexa-dec-2-enoic acid is an intermediate in fatty acid biosynthesis. Specifically, trans-hexa-dec-2-enoic acid converted from (R)-3-Hydroxy-hexadecanoic acid via two enzymes; fatty-acid Synthase and 3- Hydroxypalmitoyl- [acyl-carrier-protein] dehydratase (EC: 2.3.1.85 and EC: 4.2.1.61).


DG(16:0/18:1(9Z)/0:0) belongs to the family of Diacylglycerols. These are glycerolipids lipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. DG(16:0/18:1(9Z)/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway.


Trehalose

Trehalose, also known as mycose, is a 1-alpha (disaccharide) sugar found extensively but not abundantly in nature. It is thought to be implicated in anhydrobiosis - the ability of plants and animals to withstand prolonged periods of desiccation. The sugar is thought to form a gel phase as cells dehydrate, which prevents disruption of internal cell organelles by effectively splinting them in position. Rehydration then allows normal cellular activity to be resumed without the major, generally lethal damage that would normally follow a dehydration/reyhdration cycle. Trehalose is a non-reducing sugar formed from two glucose units joined by a 1-1 alpha bond giving it the name of alpha-D-glucopyranoglucopyranosyl-1,1-alpha-D-glucopyranoside. The bonding makes trehalose very resistant to acid hydrolysis, and therefore stable in solution at high temperatures even under acidic conditions. The bonding also keeps non-reducing sugars in closed-ring form, such that the aldehyde or ketone end-groups do not bind to the lysine or arginine residues of proteins (a process called glycation). The enzyme trehalase, present but not abundant in most people, breaks it into two glucose molecules, which can then be readily absorbed in the gut. Trehalose is an important components of insects circulating fluid.It acts as a storage form of insect circulating fluid and it is important in respiration.


icosanoyl-CoA

Eicosanoyl-CoA is an intermediate metabolite in the synthesis of phosphatidic acid, a substrate of lysophosphatidic acid acyltransferase with high specificity as an acyl donor. Cells and membranes of mammalian cells synthesize their glycerophospholipids and triglycerides to maintain the cellular integrity and to provide energy for cellular functions. The phospholipids are synthesized de novo in cells through an evolutionary conserved process involving serial acylations of glycerol-3-phosphate. Several isoforms of the enzyme 1-acylglycerol-3-phosphate-O-acyltransferase (EC 2.3.1.51, AGPAT) acylate lysophosphatidic acid at the sn-2 position to produce phosphatidic acid. Bile acid-CoA:amino acid N-acyltransferase (EC 2.3.1.65, BACAT) catalyzes the conjugation of bile acids to glycine and taurine for excretion into bile and can utilize Eicosanoyl-CoA as an acyl donor as well; this may play important roles in protection against toxicity by accumulation of unconjugated bile acids and non-esterified very long-chain fatty acids. (PMID: 17535882, 12810727).

Eicosanethioic acid s-ester with coenzyme a


DHAP(18:0) is the octadecanoyl derivative of dihydroxyacetone phosphate. It is also known as an alkyl-DHAP. This compound is formed by octadecanoic acid reacting with DHAP. Alkyl-DHAPs are intermediates in the synthesis of ether phospholipids. The initial steps of ether phospholipid biosynthesis take place in peroxisomes. Alkyl-dihydroxyacetonephosphate synthase is the peroxisomal enzyme that actually introduces the ether linkage. Levels of Alkyl-DHAP have been found to be strongly reduced in human fibroblasts derived from Zellweger syndrome and rhizomelic chondrodysplasia punctata patients. Four other enzymes are known to be involved in the metabolism of acyl-DHAP and alkyl-DHAP. These include: acyl-DHAP/alkyl-DHAP oxidoreductase, DHAP acyltransferase, alkyl-DHAP phosphohydrolase, and a dinitrofluorobenzene-insensitive acyl-DHAP acylhydrolase. Dihydroxyacetone phosphate (DHAP) is a biochemical compound primarily involved in the glycolysis metabolic pathway. DHAP is also the product of the dehydrogenation of L-glycerol-3-phosphate which is part of the entry of glycerol (sourced from triglycerides) into the glycolytic pathway. Conversely, reduction of glycolysis-derived DHAP to L-glycerol-3-phosphate provides adipose cells with the activated glycerol backbone they require to synthesize new triglycerides. Both reactions are catalyzed by the enzyme glycerol 3-phosphate dehydrogenase with NAD+/NADH as cofactor. DHAP may be referred to as glycerone phosphate in older texts. 1-Octadecyl-glycerone-3-phosphate is an intermediate in Ether lipid metabolism. DHAP(18:0) or 1-Octadecanoyl-glycerone-3-phosphate is the precursor to 1-Octadecyl-glycerone-3-phosphate DHAP(18:0e) which is generated via alkylglycerone phosphate synthase (EC: 2.5.1.26). Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. Ether lipids are called plasmalogens (1-O-1'-alkenyl-2-acylglycerophospholipids) if these are glycerol-containing phospholipids with an unsaturated O-(1-alkenyl) (vinyl ether) group at the first position on the glycerol chain. Plasmalogens as well as some 1-O-alkyl lipids are ubiquitous and sometimes major parts of the cell membranes in mammals and anaerobic bacteria. In archaea, ether lipids are the major polar lipids in the cell envelope and their abundance is one of the major characteristics that separate this group of prokaryotes from the bacteria. In these cells, diphytanylglycerolipids or bipolar macrocyclic tetraethers can form covalently linked 'bilayers'. (Wikipedia)


Stearyl alcohol

Octadenol is a fatty alcohol present in human and is normally incorporated into plasmalogen lipids. Patients with the autosomal recessive form of rhizomelic chondrodysplasia punctata (AR-RCDP) have elevated octadenol levels, but tended to be normal in other generalized peroxisomal disorders such as neonatal adrenoleukodystrophy and Zellweger syndrome (peroxisomal disorders are deficient in the incorporation of fatty alcohol into plasmalogen lipids). (PMID: 8373640). Sjogren-Larsson syndrome is defined by the triad of ichthyosis, mental retardation, and spasticity, and patients accumulate fatty alcohols such as Octadenol in the plasma and cultured fibroblasts. (PMID: 2241202). Sjogren-Larsson syndrome (SLS) is an autosomal recessive disorder associated with reduced activity of the fatty alcohol: NAD+ oxidoreductase complex (FAO). SLS patients are specifically deficient in the fatty aldehyde dehydrogenase (FALDH) component of FAO. Measurement of FAO and FALDH detection for SLS, FAO and FALDH activities in cultured skin fibroblasts using the 18-carbon substrate Octadenol is useful for SLS carrier detection. (PMID: 1583866). Patients with Sjogren-Larsson syndrome accumulate long-chain fatty alcohol in plasma, with a greater relative accumulation of Octadenol. (PMID: 2666627).

1-hydroxyoctadecane
Alcohol stearylicus
Alfol 18
Atalco s
N-1-octadecanol
N-octadecanol
N-octadecyl alcohol
Octadecan-1-ol
Octadecanol nf
Octadecyl alcohol
Stearal
Stearic alcohol
Stearol
Stearyl alcohol
Stearyl alcohol pure
1-octadecanol
Octadecanol
Stearylalkohol


DHAP(18:0e) is the octadecanoyl derivative of Dihydroxyacetone phosphate. It is also known as an alkyl-DHAP. This compound is formed by octadecanoic acid reacting with DHAP. Alkyl-DHAPs are intermediates in the synthesis of ether phospholipids. The initial steps of ether phospholipid biosynthesis take place in peroxisomes. Alkyl-dihydroxyacetonephosphate synthase is the peroxisomal enzyme that actually introduces the ether linkage. Levels of Alkyl-DHAP have been found to be strongly reduced in human fibroblasts derived from Zellweger syndrome and rhizomelic chondrodysplasia punctata patients. Four other enzymes are known to be involved in the metabolism of acyl-DHAP and alkyl-DHAP. These include: acyl-DHAP/alkyl-DHAP oxidoreductase, DHAP acyltransferase, alkyl-DHAP phosphohydrolase, and a dinitrofluorobenzene-insensitive acyl-DHAP acylhydrolase. Dihydroxyacetone phosphate (DHAP) is a biochemical compound primarily involved in the glycolysis metabolic pathway. DHAP is also the product of the dehydrogenation of L-glycerol-3-phosphate which is part of the entry of glycerol (sourced from triglycerides) into the glycolytic pathway. Conversely, reduction of glycolysis-derived DHAP to L-glycerol-3-phosphate provides adipose cells with the activated glycerol backbone they require to synthesize new triglycerides. Both reactions are catalyzed by the enzyme glycerol 3-phosphate dehydrogenase with NAD+/NADH as cofactor. DHAP may be referred to as glycerone phosphate in older texts. 1-Octadecyl-glycerone-3-phosphate is an intermediate in Ether lipid metabolism. DHAP(18:0e) or 1-Octadecyl-glycerone-3-phosphate is converted from 1-Octadecanoyl-glycerone-3-phosphate via alkylglycerone phosphate synthase (EC: 2.5.1.26). Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. Ether lipids are called plasmalogens (1-O-1'-alkenyl-2-acylglycerophospholipids) if these are glycerol-containing phospholipids with an unsaturated O-(1-alkenyl) (vinyl ether) group at the first position on the glycerol chain. Plasmalogens as well as some 1-O-alkyl lipids are ubiquitous and sometimes major parts of the cell membranes in mammals and anaerobic bacteria. In archaea, ether lipids are the major polar lipids in the cell envelope and their abundance is one of the major characteristics that separate this group of prokaryotes from the bacteria. In these cells, diphytanylglycerolipids or bipolar macrocyclic tetraethers can form covalently linked 'bilayers'. (Wikipedia).

1-octadecyl dhap
1-octadecyl dihdroxyacetone phosphate
1-octadecyl-glycerone-3-phosphate


Stearic acid

Stearic acid, also called octadecanoic acid, is one of the useful types of saturated fatty acids that comes from many animal and vegetable fats and oils. It is a waxy solid, and its chemical formula is CH3(CH2)16COOH. Its name comes from the Greek word stear, which means tallow. Its IUPAC name is octadecanoic acid. -- Wikipedia.

1-heptadecanecarboxylate
1-heptadecanecarboxylic acid
N-octadecanoate
N-octadecanoic acid
Octadecanoate
Octadecanoic acid
Stearate
Stearex beads
Stearic acid
Stearic acid cherry
Stearophanate
Stearophanic acid
FA(18:0)


arachidonoyl-CoA

Arachidonyl-CoA is an intermediate in Biosynthesis of unsaturated fatty acids. Arachidonyl-CoA is produced from 8,11,14-Eicosatrienoyl-CoA via the enzyme fatty acid desaturase 1 (EC 1.14.19.-). It is then converted to Arachidonic acid via the enzymepalmitoyl-CoA hydrolase (EC 3.1.2.2).


CDP-ethanolamine

Cytidine is a molecule (known as a nucleoside) that is formed when cytosine is attached to a ribose ring (also known as a ribofuranose) via a beta-N1-glycosidic bond. CDP-Ethanolamine has the chemical formula C11H20N4O11P2, and an average molecular weight of 446.2442. CDP-Ethanolamine is involved in multiple pathways, some of which are Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)) Pathway, Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)) Pathway, Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:0) Pathway, and Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) Pathway.

Cytidine 5'-(trihydrogen diphosphate), p'-(2-aminoethyl) ester


stearoyl-CoA

Stearoyl-CoA is a long-chain acyl CoA ester that acts as an intermediate metabolite in the biosynthesis of monounsaturated fatty acids; a critical committed step in the reaction is the introduction of the cis-configuration double bond into acyl-CoAs (between carbons 9 and 10). This oxidative reaction is catalyzed by the iron-containing, microsomal enzyme, stearoyl-CoA desaturase (SCD, EC 1.14.19.1). NADH supplies the reducing equivalents for the reaction, the flavoprotein is cytochrome b5-reductase and the electron carrier is the heme protein cytochrome b5. Stearoyl-CoA is converted into oleoyl-CoA and then used as a major substrate for the synthesis of various kinds of lipids including phospholipids, triglycerides, cholesteryl esters and wax esters. Oleic acid is the preferred substrate for acyl-CoA cholesterol acyltransferase (ACAT, EC 2.3.1.26) and diacylglycerol acyltransferase (DGAT, EC 2.3.1.20), the enzymes responsible for cholesteryl esters and triglycerides synthesis, respectively. In addition oleate is the major monounsaturated fatty acid in human adipose tissue and in the phospholipid of the red-blood-cell membrane. In the biosynthesis of sphinganine, stearoyl-CoA proceeds through the acyl-CoA + serine -> 3-keto-sphinganine -> sphinganine pathway, with the key enzyme being acyl-CoA serine acyltransferase (EC 2.3.1.50) to yield C20-(3-ketosphinganine) long-chain base. There is growing recognition that acyl-CoA esters could act as signaling molecules in cellular metabolism. (PMID: 12538075, 10998569, Prostaglandins Leukot Essent Fatty Acids. 2003 Feb;68(2):113-21.).

Octadecanoyl-coa
Octadecanoyl-coenzyme a
S-octadecanoate
S-octadecanoate coa
S-octadecanoate coenzyme a
S-octadecanoic acid
S-stearate coa
S-stearate coenzyme a
S-stearoylcoenzyme a
Stearoyl coenzyme a
Stearoyl coenzyme a ester
Stearoyl-coa
Stearoyl-coenzyme a
Stearyl coenzyme a
Stearyl-coa
Stearyl-coenzyme a
CoA(18:0)


O-octadecanoyl-L-carnitine

Stearoylcarnitine, also known as acylcarnitine C18:0, is a fatty ester lipid molecule. It is found in significantly greater amounts of patients with carnitine palmitoyltransferase (CPT) II deficiency when compared to controls (PMID: 15653102). Stearoylcarnitine is also found to be associated with celiac disease, another inborn error of metabolism. The carnitine palmitoyltransferase (CPT; EC 2.3.1.21) enzyme system, in conjunction with acyl-CoA synthetase and carnitine/acylcarnitine translocase, provides the mechanism whereby long-chain fatty acids are transferred from the cytosol to the mitochondrial matrix to undergo beta-oxidation (OMIM: 600650 ). Stearoylcarnitine is considered to be practically insoluble (in water) and acidic.

L-(3-carboxy-2-hydroxypropyl)trimethyl-ammonium stearate hydroxide inner salt

L-stearic acid ester with (3-carboxy-2-hydroxypropyl)trimethylammonium hydroxide inner salt


trans-Octadec-2-enoyl-CoA, also known as (2e)-octadecenoyl-coa, belongs to the class of organic compounds known as long-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a long-chain 2-enoyl chain of 13 to 21 carbon atoms. trans-Octadec-2-enoyl-CoA is considered to be a practically insoluble (in water) and relatively neutral molecule. trans-Octadec-2-enoyl-CoA has been primarily detected in urine. Within the cell, trans-octadec-2-enoyl-CoA is primarily located in the cytoplasm, membrane (predicted from logP) and mitochondria. In humans, trans-octadec-2-enoyl-CoA is involved in the metabolic disorder called the mitochondrial Beta-oxidation OF long chain saturated fatty acids pathway. trans-Octadec-2-enoyl-CoA is an intermediate in Biosynthesis of unsaturated fatty acids. trans-Octadec-2-enoyl-CoA is produced from 3-Hydroxyoctadecanoyl-CoA and then converted to Stearoyl-CoA via enzymatic reaction.


3-Oxooctadecanoyl-CoA is a metabolite intermediate in the microsomal fatty acid chain elongation system. Microsomal electron-transport components NADPH-cytochrome P450 reductase (EC 1.6.2.4) and cytochrome b5 (EC 1.6.2.2) participate in the conversion from 3-Oxooctadecanoyl-CoA to beta-hydroxystearoyl-CoA, the first reductive step of the microsomal chain elongating system initiated by NADPH. (PMID: 6404652).

3-ketostearoyl-coa
3-ketostearoyl-coenzyme a
3-oxostearoyl-coa
3-oxostearoyl-coenzyme a
Beta-ketostearoyl-coa
Beta-ketostearoyl-coenzyme a


apical plasma membrane

biolink:CellularComponent biolink:AnatomicalEntity biolink:PhysicalEssence biolink:OrganismalEntity biolink:SubjectOfInvestigation biolink:BiologicalEntity biolink:ThingWithTaxon biolink:NamedThing biolink:PhysicalEssenceOrOccurrent


Benazepril

Benazepril, brand name Lotensin, is a medication used to treat high blood pressure (hypertension), congestive heart failure, and chronic renal failure. Upon cleavage of its ester group by the liver, benazepril is converted into its active form benazeprilat, a non-sulfhydryl angiotensin-converting enzyme (ACE) inhibitor.

Benazeprilum [latin]
Benazepril sandoz
Forteekor


angiotensin I

Angiotensin I appears to have no biological activity and exists solely as a precursor to angiotensin 2. Angiotensin I is formed by the action of renin on angiotensinogen. Renin cleaves the peptide bond between the leucine (Leu) and valine (Val) residues on angiotensinogen, creating the ten-amino acid peptide (des-Asp) angiotensin I. Renin is produced in the kidneys in response to renal sympathetic activity, decreased intrarenal blood pressure at the juxtaglomerular cells, or decreased delivery of Na+ and Cl- to the macula densa.[3] If less Na+ is sensed by the macula densa, renin release by juxtaglomerular cells is increased. (Wikipedia)


Angiotensin II

Angiotensin II is a hormone that may act on the central nervous system to regulate renal sympathetic nerve activity, renal function, and, therefore, blood pressure. Angiotensin II is produced locally within the kidney and mediates tissue injury through a series of nonhemodynamic effects. angiotensin II is not only involved in the regulation of blood pressure, water and sodium homeostasis, and control of other neurohumoral systems, but also leads to excessive production of reactive oxygen species and to hypertrophy, proliferation, migration, and apoptosis of vascular cells. Angiotensin II is one of the main factors involved in hypertension-induced tissue damage. This peptide regulates the inflammatory process. Angiotensin II activates circulating cells, and participates in their adhesion to the activated endothelium and subsequent transmigration through the synthesis of adhesion molecules, chemokines and cytokines. Among the intracellular signals involved in angiotensin II-induced inflammation, the production of reactive oxygen species and the activation of nuclear factor-kappaB are the best known. Classical, well-defined actions of Angiotensin II in the brain include the regulation of hormone formation and release, the control of the central and peripheral sympathoadrenal systems, and the regulation of water and sodium intake. As a consequence of changes in the hormone, sympathetic and electrolyte systems, feedback mechanisms in turn modulate the activity of the brain Angiotensin II systems. There are two Angiotensin II systems in the brain. The discovery of brain Angiotensin II receptors located in neurons inside the blood brain barrier confirmed the existence of an endogenous brain Angiotensin II system, responding to Angiotensin II generated in and/or transported into the brain. In addition, Angiotensin II receptors in circumventricular organs and in cerebrovascular endothelial cells respond to circulating Angiotensin II of peripheral origin. Thus, the brain responds to both circulating and tissue Angiotensin II, and the two systems are integrated. (PMID: 17147923, 16672146, 16601568, 16481883, 16075377).


vasopressin

Antidiuretic hormone, also known commonly as vasopressin, is a nine amino acid peptide secreted from the posterior pituitary. Within hypothalamic neurons, the hormone is packaged in secretory vesicles with a carrier protein called neurophysin, and both are released upon hormone secretion.

3-(phenylalanine)-8-lysine oxytocin
8-l-lysine vasopressin
Adh
Antidiuretic hormone
Diapid
Pitressin
Pitressin tannate
Pressyn


Captopril

Captopril is a potent, competitive inhibitor of angiotensin-converting enzyme (ACE), the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Captopril may be used in the treatment of hypertension.


Cilazaprilat

Cilazaprilat belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Cilazaprilat is slightly soluble (in water) and a weakly acidic compound (based on its pKa).


Enalaprilat

Enalaprilat belongs to the family of Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. Enalaprilat is the active drug form of the ACE inhibitor Enalapril.


Enalapril

Enalapril is a prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is rapidly metabolized in the liver to enalaprilat following oral administration. Enalaprilat is a potent, competitive inhibitor of ACE, the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Enalapril may be used to treat essential or renovascular hypertension and symptomatic congestive heart failure.


fosinopril

Fosinopril is a phosphinic acid-containing ester prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is rapidly hydrolyzed to fosinoprilat, its principle active metabolite. Fosinoprilat inhibits ACE, the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Fosinopril may be used to treat mild to moderate hypertension, as an adjunct in the treatment of congestive heart failure, and to slow the rate of progression of renal disease in hypertensive individuals with diabetes mellitus and microalbuminuria or overt nephropathy.


Fosinoprilat

Fosinoprilat, also known as fosinoprilic acid or fosfenopril, belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Fosinoprilat is considered to be a practically insoluble (in water) and relatively neutral molecule. Fosinoprilat can be converted into fosinopril..


Lisinopril

One of the Angiotensin-converting enzyme inhibitors (ACE inhibitors), orally active, that has been used in the treatment of hypertension and congestive heart failure. -- Pubchem; Lisinopril is a drug of the angiotensin converting enzyme (ACE) inhibitor class that is primarily used in treatment of hypertension, congestive heart failure and heart attacks. Historically, lisinopril was the third ACE inhibitor, after captopril and enalapril that was introduced into therapy in early 1990s. Lisinopril has a number of properties that distinguish it from other ACE inhibitors: it is hydrophilic, has long half life and tissue penetration and is not metabolized by the liver. -- Wikipedia; Lisinopril is solely excreted in urine in the unchanged form. Elimination of the drug depends on glomerular filtration and tubular excretion. Rate of lisinopril elimination decreases with old age and kidney or heart failure. There is a relation between creatinine and lisinopril clearance. With prolonged therapy dose reduction can be necessary to avoid accumulation. -- Wikipedia.


Perindopril

Perindopril is a nonsulfhydryl prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is rapidly metabolized in the liver to perindoprilat, its active metabolite, following oral administration. Perindoprilat is a potent, competitive inhibitor of ACE, the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Perindopril may be used to treat mild to moderate essential hypertension, mild to moderate congestive heart failure, and to reduce the cardiovascular risk of individuals with hypertension or post-myocardial infarction and stable coronary disease.


Quinapril

Quinapril is a prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is metabolized to quinaprilat (quinapril diacid) following oral administration. Quinaprilat is a competitive inhibitor of ACE, the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Quinapril may be used to treat essential hypertension and congestive heart failure.


Ramiprilat

Ramiprilat, also known as ramiprilic acid, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Ramiprilat is considered to be a practically insoluble (in water) and relatively neutral molecule. Ramiprilat has been found in human liver and kidney tissues, and has also been detected in multiple biofluids, such as urine and blood. Within the cell, ramiprilat is primarily located in the cytoplasm. In humans, ramiprilat is involved in the ramipril metabolism pathway and the ramipril action pathway. Ramiprilat is a metabolite of ramipril. Ramipril is an angiotensin-converting enzyme (ACE) inhibitor, used to treat high blood pressure and congestive heart failure. (Wikipedia)

Ramiprilate
Ramiprilatum
Ramiprilic acid


Ramipril

Ramipril is a prodrug belonging to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is metabolized to ramiprilat in the liver and, to a lesser extent, kidneys. Ramiprilat is a potent, competitive inhibitor of ACE, the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Ramipril may be used in the treatment of hypertension, congestive heart failure, nephropathy, and to reduce the rate of death, myocardial infarction and stroke in individuals at high risk of cardiovascular events.


rescinnamine

Rescinnamine is only found in individuals that have used or taken this drug. It is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug. It is an alkaloid obtained from Rauwolfia serpentina and other species of Rauwolfia. [Wikipedia]Rescinnamine Binds to and inhibits the angiotensin converting enzyme. Rescinnamine competes with angiotensin I for binding at the angiotensin-converting enzyme, blocking the conversion of angiotensin I to angiotensin II. Inhibition of ACE results in decreased plasma angiotensin II. As angiotensin II is a vasoconstrictor and a negative-feedback mediator for renin activity, lower concentrations result in a decrease in blood pressure and stimulation of baroreceptor reflex mechanisms, which leads to decreased vasopressor activity and to decreased aldosterone secretion.

Methyl trimethoxycinnamoylreserpate
Trimethoxycinnamoyl methyl reserpate
Recinnamine
Rescinnamin
Reserpinene
Reserpinin
Reserpinine


Spirapril is an ACE inhibitor antihypertensive drug used to treat hypertension. Like many ACE inhibitors, this is a prodrug which is converted to the active metabolite spiraprilat following oral administration. ACE inhibitors are used primarily in treatment of hypertension and congestive heart failure.


Vatalanib

Vatalanib, also known as PTK 787 or CGP 79787, belongs to the class of organic compounds known as phthalazines. Phthalazines are compounds containing a phthalazine moiety, which consists of a benzene ring fused to a pyridazine, forming a 2,3-benzodiazine skeleton. Vatalanib is a drug which is used in combination with first- and second-line chemotherapy for the treatment of metastatic colorectal cancer and non-small cell lung cancer (nsclc). Vatalanib is considered to be a practically insoluble (in water) and relatively neutral molecule. Vatalanib (PTK787/ZK-222584) is a new oral antiangiogenic molecule that inhibits all known vascular endothelial growth factor receptors. Vatalanib is under investigation for the treatment of solid tumors.


Cys-Glu-Gly

7-Ethyl-10-hydroxycamptothecin (SN38) is the active metabolite of irinotecan (an analog of camptothecin - a topoisomerase I inhibitor); it is 1000 times more active than irinotecan itself. In vitro cytotoxicity assays show that the potency of SN-38 relative to irinotecan varies from 2- to 2000-fold. SN38 is metabolized via glucoronidation by UGT1A1. (Wikipedia) 7-Ethyl-10-hydroxycamptothecin (SN38), the active metabolite of irinotecan, exerts a 100-fold to 1000-fold higher effect than irinotecan itself against several tumor cell lines. (PMID: 23233044) Among five chemotherapeutic agents commonly used for breast cancer treatment, only an irinotecan metabolite SN38 showed additive antitumor activity with olaparib. (PMID: 22454224) Metabolism of irinotecan to SN38 is inefficient and subject to considerable patient-to-patient variability. One approach to more controlled administration of the anticancer agent is direct administration of the active SN38. (PMID: 23299391)


Irinotecan is an antineoplastic enzyme inhibitor primarily used in the treatment of colorectal cancer. It is a derivative of camptothecin that inhibits the action of topoisomerase I. Irinotecan prevents religation of the DNA strand by binding to topoisomerase I-DNA complex, and causes double-strand DNA breakage and cell death.

Irinotecan hydrochloride trihydrate
Irinotecanum [inn-latin]
Biotecan


NPC

Npc belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring). Npc is considered to be a practically insoluble (in water) and relatively neutral molecule. Npc has been found in human liver and kidney tissues, and has also been detected in multiple biofluids, such as urine and blood. In humans, Npc is involved in the irinotecan metabolism pathway and the irinotecan action pathway.


APC

Apc, also known as apc CPD, belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring). Apc is considered to be a practically insoluble (in water) and relatively neutral molecule. Apc has been found in human liver and kidney tissues, and has also been detected in multiple biofluids, such as urine and blood. In humans, Apc is involved in the irinotecan action pathway and the irinotecan metabolism pathway.


sn38 Glucuronide, also known as sn-38g, belongs to the class of organic compounds known as camptothecins. These are heterocyclic compounds comprising a planar pentacyclic ring structure, that includes a pyrrolo[3,4-beta]-quinoline moiety (rings A, B and C), conjugated pyridone moiety (ring D) and one chiral center at position 20 within the alpha-hydroxy lactone ring with (S) configuration (the E-ring). sn38 Glucuronide is slightly soluble (in water) and a weakly acidic compound (based on its pKa). sn38 Glucuronide has been found in human liver and kidney tissues, and has also been detected in multiple biofluids, such as urine and blood. In humans, SN38 glucuronide is involved in the irinotecan action pathway and the irinotecan metabolism pathway.


Paclitaxel

A cyclodecane isolated from the bark of the Pacific yew tree, TAXUS brevifolia. It stabilizes microtubules in their polymerized form leading to cell death. [PubChem] ABI-007 (Abraxane) is the latest attempt to improve upon paclitaxel, one of the leading chemotherapy treatments. Both drugs contain the same active agent, but Abraxane is delivered by a nanoparticle technology that binds to albumin, a natural protein, rather than the toxic solvent known as Cremophor. It is thought that delivering paclitaxel with this technology will cause fewer hypersensitivity reactions and possibly lead to greater drug uptake in tumors.

5beta,20-epoxy-1,2-alpha,4,7beta,10beta,13alpha-hexahydroxytax-11-en-9-one 4,10-diacetate 2-benzoate 13-ester with (2r,3s)-n-benzoyl-3-phenylisoserine

5b,20-epoxy-1,2-a,4,7b,10b,13a-hexahydroxytax-11-en-9-one 4,10-diacetate 2-benzoate 13-ester with (2r,3s)-n-benzoyl-3-phenylisoserine

5b,20-epoxy-1,2-a,4,7b,10b,13a-hexahydroxytax-11-en-9-one 4,10-diacetic acid 2-benzoic acid 13-ester with (2r,3s)-n-benzoyl-3-phenylisoserine

5beta,20-epoxy-1,2-alpha,4,7beta,10beta,13alpha-hexahydroxytax-11-en-9-one 4,10-diacetic acid 2-benzoic acid 13-ester with (2r,3s)-n-benzoyl-3-phenylisoserine

5β,20-epoxy-1,2-α,4,7β,10β,13α-hexahydroxytax-11-en-9-one 4,10-diacetate 2-benzoate 13-ester with (2r,3s)-n-benzoyl-3-phenylisoserine

5β,20-epoxy-1,2-α,4,7β,10β,13α-hexahydroxytax-11-en-9-one 4,10-diacetic acid 2-benzoic acid 13-ester with (2r,3s)-n-benzoyl-3-phenylisoserine


Phosphorus

Phosphorus, in its common form, is a waxy white (or yellowish) solid that has a characteristically disagreeable smell similar to that of garlic. Pure forms of the element are colourless and transparent. This nonmetal is not soluble in water, but is soluble in carbon disulfide. The white allotrope ignites spontaneously in air; however, both white and red phosphorus burn in air to produce phosphorus pentoxide. Phosphorus is a key element in all known forms of life. Physiologically, it exists as an ion in the body. Inorganic phosphorus in the form of the phosphate PO43- plays a major role in biological molecules such as DNA and RNA where it forms part of the structural framework of these molecules. Living cells also utilize phosphate to transport cellular energy via adenosine triphosphate (ATP). Nearly every cellular process that uses energy gets it in the form of ATP. ATP is also important for phosphorylation, a key regulatory event in cells. Phospholipids are the main structural components of all cellular membranes. Calcium phosphate salts are used by animals to stiffen their bones. An average person contains a little less than 1 kg of phosphorus, about three quarters of which is present in bones and teeth in the form of apatite. A well-fed adult in the industrialized world consumes and excretes about 1-3 g of phosphorus per day in the form of phosphate. Phosphorus is an essential mineral macronutrient, which is studied extensively in soil conservation in order to understand plant uptake from soil systems. Due to its reactivity to air and many other oxygen containing substances, phosphorus is not found free in nature, but it is widely distributed in many different minerals. Phosphorus is found to be associated with glycerol intolerance syndrome, which is an inborn error of metabolism.

Hittorf's phosphorus
Phosphorous
Phosphorus-30
Red phosphorus
Violet phosphorus
White phosphorus
15p
Fosforo
P
Phosphor
Phosphore
Phosphorus