ChemFOnt: Showing chemical card for Pteroyltriglutamic acid (CFc000001268)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:52 UTC

Chemfont ID

CFc000001268

Molecule Identification

Common Name

Pteroyltriglutamic acid

Definition

Pteroyltriglutamic acid is a crystalline conjugate of folic acid containing three molecules of glutamic acid instead of one and having the general properties of a polypeptide. As a measure of enterocyte function, the deconjugation of Pteroylpolyglutamic acid (pteroyl-L-glutamyl-gamma-L-glutamyl-gamma-L-glutamic acid) to folic acid and subsequent active absorption was measured in 19 patients with progressive systemic sclerosis and compared with 14 controls. The absorption step of folic acid was identical in the two groups, while deconjugation of pteroyl-L-glutamyl-gamma-L-glutamyl-gamma-L-glutamic acid was significantly decreased in the patients with progressive systemic sclerosis. This observation suggests a primary epithelial defect of the small intestine in patients with progressive systemic sclerosis. (PMID 3583071 ). Glutamyl hydrolase cleaves the poly-g-glutamate chain folate and antifolate poly-g-glutamates. Its cellular location is lysosomal with large amts. of the enzyme constitutively secreted. The highest levels of glutamyl hydrolase mRNA in humans is found in the liver and kidney (PMID:10598552 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Pteroyltriglutamate	Generator
N-[N-(N-Pteroyl-L-gamma-glutamyl)-L-gamma-glutamyl]-glutamic acid	HMDB
Folic acid diglutamate	HMDB
N-[4-[[(2-amino-1,4-dihydro-4-oxo-6-Pteridinyl)methyl]amino]benzoyl]-L-gamma-glutamyl-L-gamma-glutamyl-L-glutamic acid	HMDB
N-[N-[N-[4-[[(2-amino-1,4-dihydro-4-oxo-6-Pteridinyl)methyl]amino]benzoyl]-L-.gamma.-glutamyl]-L-.gamma.-glutamyl]- L-glutamic acid	HMDB
Pteropterin	HMDB, MeSH
Pteroyl-gamma-triglutamic acid	HMDB
Pteroyl-L-glutamyl-gamma-L-glutamyl-gamma-L-glutamic acid	HMDB
Pteroyltri-gamma-L-glutamic acid	HMDB
Teropterin	MeSH, HMDB
Pteropterin, sodium salt	MeSH, HMDB
Pteroyl-gamma-glutamyl-gamma-glutamylglutamic acid	MeSH, HMDB
2-{[4-carboxy-4-({4-carboxy-1-hydroxy-4-[(4-{[(4-hydroxy-2-imino-1,2-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]butylidene}amino)-1-hydroxybutylidene]amino}pentanedioate	Generator, HMDB
Pteroyltriglutamic acid	MeSH

Chemical Formula

C₂₉H₃₃N₉O₁₂

Average Molecular Weight

699.6254

Monoisotopic Molecular Weight

699.224867565

IUPAC Name

2-(4-{4-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]-4-carboxybutanamido}-4-carboxybutanamido)pentanedioic acid

Traditional Name

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

CAS Registry Number

89-38-3

SMILES

NC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)NC(CCC(=O)NC(CCC(=O)NC(CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)=CN=C2N1

InChI Identifier

InChI=1S/C29H33N9O12/c30-29-37-23-22(25(44)38-29)33-15(12-32-23)11-31-14-3-1-13(2-4-14)24(43)36-18(28(49)50)6-9-20(40)34-16(26(45)46)5-8-19(39)35-17(27(47)48)7-10-21(41)42/h1-4,12,16-18,31H,5-11H2,(H,34,40)(H,35,39)(H,36,43)(H,41,42)(H,45,46)(H,47,48)(H,49,50)(H3,30,32,37,38,44)

InChI Key

WOLQREOUPKZMEX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Gamma-glutamyl alpha-amino acid
Glutamic acid or derivatives
Glutamine or derivatives
Tetracarboxylic acid or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Hippuric acid
Hippuric acid or derivatives
Pterin
Alpha-amino acid or derivatives
Pteridine
Aminobenzamide
Aminobenzoic acid or derivatives
Benzoic acid or derivatives
Benzamide
Benzoyl
Phenylalkylamine
Aniline or substituted anilines
Pyrimidone
Aralkylamine
Secondary aliphatic/aromatic amine
Aminopyrimidine
Monocyclic benzene moiety
Fatty amide
Fatty acyl
N-acyl-amine
Benzenoid
Pyrazine
Pyrimidine
Vinylogous amide
Heteroaromatic compound
Secondary carboxylic acid amide
Amino acid
Amino acid or derivatives
Carboxamide group
Secondary amine
Organoheterocyclic compound
Azacycle
Carboxylic acid
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Organopnictogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0001902)

Source

Endogenous

Endogenous (HMDB: HMDB0001902)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.086 g/L	ALOGPS
logP	-0.55	ALOGPS
logP	-2.6	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	2.98	ChemAxon
pKa (Strongest Basic)	2.08	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	341.79 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	167.19 m³·mol⁻¹	ChemAxon
Polarizability	67.38 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0001902

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022730

KNApSAcK ID

Not Available

Chemspider ID

6702

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6381

PubChem Compound

6968

PDB ID

Not Available

ChEBI ID

554079

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Pteroyltriglutamic acid (CFc000001268)

MOL for CFc000001268 (Pteroyltriglutamic acid)

3D MOL for CFc000001268 (Pteroyltriglutamic acid)

3D SDF for CFc000001268 (Pteroyltriglutamic acid)

3D-SDF for CFc000001268 (Pteroyltriglutamic acid)

PDB for CFc000001268 (Pteroyltriglutamic acid)

3D PDB for CFc000001268 (Pteroyltriglutamic acid)

SMILES for CFc000001268 (Pteroyltriglutamic acid)

INCHI for CFc000001268 (Pteroyltriglutamic acid)

Structure for CFc000001268 (Pteroyltriglutamic acid)

3D Structure for CFc000001268 (Pteroyltriglutamic acid)