Classification Term: 200

Tetrahydrofolic acids and derivatives (ontology term: CHEMONTID:0002618)

Heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit (or a derivative thereof) ." []

found 7 associated metabolites at family metabolite taxonomy ontology rank level.

Ancestor: Tetrahydropteroic acids and derivatives

Child Taxonomies: Tetrahydrofolic acids

Tetrahydropteroyltri-L-glutamic acid

(2S)-2-[(4S)-4-[(4S)-4-{[4-({[(6S)-2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl]methyl}amino)phenyl]formamido}-4-carboxybutanamido]-4-carboxybutanamido]pentanedioic acid

C29H37N9O12 (703.2561562000001)


Tetrahydropteroyltri-L-glutamic acid (CAS: 4227-85-4), also known as (6S)-H4pteglu3, belongs to the class of organic compounds known as tetrahydrofolic acids and derivatives. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit (or a derivative thereof). Tetrahydropteroyltri-L-glutamic acid is a strong basic compound (based on its pKa). In humans, this compound is produced by the bacteria in the gut and may be found in feces or urine. Tetrahydropteroyltri-L-glutamica cid exists in all living species, ranging from bacteria to humans. Tetrahydropteroyltri-L-glutamic acid is an intermediate in the synthesis of methionine by bacteria. It is a substrate for the enzyme 5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase which catalyzes the reaction 5-methyltetrahydropteroyltri-L-glutamic acid + L-homocysteine = tetrahydropteroyltri-L-glutamic acid + L-methionine. A human metabolite taken as a putative food compound of mammalian origin [HMDB]

   

5-Methyltetrahydropteroyltri-L-glutamic acid

(2S)-2-[(4S)-4-[(4S)-4-{[4-({[(6S)-2-amino-5-methyl-4-oxo-1,4,5,6,7,8-hexahydropteridin-6-yl]methyl}amino)phenyl]formamido}-4-carboxybutanamido]-4-carboxybutanamido]pentanedioic acid

C30H39N9O12 (717.2718054)


5-Methyltetrahydropteroyltri-L-glutamic acid (CAS: 13061-55-7) is formed during the reaction between the carbonyl group of 5-methyltetrahydropteroate and the amine group on one end of three replicates of glutamate. It is involved in several pathways as a product of enzymatic reduction such as in tetrahydrofolate biosynthesis II and methionine biosynthesis I, II, and III. It is also involved in several pathways as a product of enzymatic oxidation such as in the pathways folate polyglutamylation I and carbon tetrachloride degradation II. In humans, this compound is produced by the bacteria in the gut and may be found in feces or urine. 5-Methyltetrahydropteroyltri-L-glutamate is formed under reaction between carbonyl group of 5-Methyltetrahydropteroate and amine group on one end of three replicates of glutamate. It is involved in several pathways such as tetrahydrofolate biosynthesis II, methionine biosynthesis I,II,III as a product of enzymatic reduction; while in pathways folate polyglutamylation I and carbon tetrachloride degradation II as a product of enzymatic oxidation. [HMDB]. 5-Methyltetrahydropteroyltri-L-glutamate is found in many foods, some of which are common cabbage, chives, lime, and garden rhubarb.

   

Tetrahydrofolyl-[Glu](2)

2-{4-[(4-{[(2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}pentanedioic acid

C24H30N8O9 (574.213565)


Tetrahydrofolyl-[Glu](n) is involved in the folate biosynthesis pathway. Tetrahydrofolyl-[Glu](n) can be reversibly converted into Tetrahydrofolyl-[Glu](2) by folylpolyglutamate synthase [EC:6.3.2.17]. Tetrahydrofolyl-[Glu](n) can be irreversibly converted into tetrahydrofolate by gamma-glutamyl hydrolase [EC:3.4.19.9]. [HMDB] Tetrahydrofolyl-[Glu](n) is involved in the folate biosynthesis pathway. Tetrahydrofolyl-[Glu](n) can be reversibly converted into Tetrahydrofolyl-[Glu](2) by folylpolyglutamate synthase [EC:6.3.2.17]. Tetrahydrofolyl-[Glu](n) can be irreversibly converted into tetrahydrofolate by gamma-glutamyl hydrolase [EC:3.4.19.9].

   

Tetrahydrofolyl-[Glu](n)

2-(4-{4-[(4-{[(2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}-4-carboxybutanamido)pentanedioic acid

C29H37N9O12 (703.2561562000001)


Tetrahydrofolyl-[Glu](n) is involved in the folate biosynthesis pathway. Tetrahydrofolyl-[Glu](n) can be reversibly converted into Tetrahydrofolyl-[Glu](2) by folylpolyglutamate synthase [EC:6.3.2.17]. Tetrahydrofolyl-[Glu](n) can be irreversibly converted into tetrahydrofolate by gamma-glutamyl hydrolase [EC:3.4.19.9]. Sample structure image shows the case when n=3. Tetrahydrofolyl-[Glu](n) is involved in the folate biosynthesis pathway. Tetrahydrofolyl-[Glu](n) can be reversibly converted into Tetrahydrofolyl-[Glu](2) by folylpolyglutamate synthase [EC:6.3.2.17]. Tetrahydrofolyl-[Glu](n) can be irreversibly converted into tetrahydrofolate by gamma-glutamyl hydrolase [EC:3.4.19.9].

   

4,4-Dimethyl-5a-cholesta-8-en-3b-ol

(2S,5S,7R,14R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-5-ol

C29H50O (414.386145)


4,4-Dimethyl-5alpha-cholesta-8-en-3beta-ol is involved in the biosynthesis of steriods. 4,4-Dimethyl-5alpha-cholesta-8-en-3beta-ol is reversibly converted into 14-Demethyllanosterol by delta24-sterol reductase [EC:1.3.1.72].

   

5-Methyltetrahydropteroylpentaglutamate

(2S,6R,11S)-2,11-Diamino-6-{n-[(4S)-4-amino-4-carboxybutanoyl]-1-(4-{[(4-hydroxy-2-imino-5-methyl-1,2,5,6,7,8-hexahydropteridin-6-yl)methyl]amino}phenyl)formamido}-6-({[(4S)-4-amino-4-carboxybutanoyl]oxy}carbonyl)-7-(carboxymethyl)-5,8-dioxododecanedioate

C40H53N11O18 (975.3569878000001)


5-Methyltetrahydropteroylpentaglutamate is a naturally occurring folate coenzyme; binds to an inhibits glyxine N-methyltransferase to regulate the availability of methyl groups in the liver (Journal of Biological Chemistry 264 (16): 9638-9642 JUN 5 1989 ). A naturally occurring folate coenzyme; binds to an inhibits glyxine N-methyltransferase to regulate the availability of methyl groups in the liver; (Journal of Biological Chemistry 264 (16): 9638-9642 JUN 5 1989 ) [HMDB]

   

Methyltetrahydrofolate

2-[(4-{[(2-amino-4-oxo-5,6,7,8-tetrahydro-3H-pteridin-6-yl)methyl]amino}phenyl)formamido]-5-methoxy-5-oxopentanoic acid

C20H25N7O6 (459.186623)