ChemFOnt: Showing chemical card for Heptaglutamyl folic acid (CFc000002809)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:46 UTC

Chemfont ID

CFc000002809

Molecule Identification

Common Name

Heptaglutamyl folic acid

Definition

Heptaglutamyl folic acid is a naturally occurring form of folate. In contrast to synthetic folic acid, natural food folates are predominantly polyglutamates with a variable number of glutamate residues. (PMID 15831124 ). Approximately two-thirds of total folate intake from a mixed unfortified diet is in the polyglutamyl form, derived mainly from vegetables. These polyglutamates need to be hydrolysed to the monoglutamate form for normal absorption in the proximal small intestine. This process is controlled by the intestinal brush-border enzyme glutamate carboxypeptidase II (GCPII). (PMID 12042451 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Heptaglutamyl folate	Generator
(3S,9S)-3,9-Diamino-5,6,6-tris[(2S)-2-amino-4-carboxybutanoyl]-7-{n-[(2S)-2-amino-4-carboxybutanoyl]-1-(4-{[(4-hydroxy-2-imino-1,2-dihydropteridin-6-yl)methyl]amino}phenyl)formamido}-7-({[(2S)-2-amino-4-carboxybutanoyl]oxy}carbonyl)-4,8-dioxoundecane-1,5,11-tricarboxylate	HMDB

Chemical Formula

C₅₄H₆₈N₁₄O₂₇

Average Molecular Weight

1345.1953

Monoisotopic Molecular Weight

1344.43783304

IUPAC Name

(3S,9S)-3,9-diamino-5,6,6-tris[(2S)-2-amino-4-carboxybutanoyl]-7-{N-[(2S)-2-amino-4-carboxybutanoyl]-1-(4-{[(2-amino-4-oxo-3,4-dihydropteridin-6-yl)methyl]amino}phenyl)formamido}-7-({[(2S)-2-amino-4-carboxybutanoyl]oxy}carbonyl)-4,8-dioxoundecane-1,5,11-tricarboxylic acid

Traditional Name

(3S,9S)-3,9-diamino-5,6,6-tris[(2S)-2-amino-4-carboxybutanoyl]-7-{N-[(2S)-2-amino-4-carboxybutanoyl]-1-(4-{[(2-amino-4-oxo-3H-pteridin-6-yl)methyl]amino}phenyl)formamido}-7-({[(2S)-2-amino-4-carboxybutanoyl]oxy}carbonyl)-4,8-dioxoundecane-1,5,11-tricarboxylic acid

CAS Registry Number

None

SMILES

N[C@@H](CCC(O)=O)C(=O)OC(=O)C(N(C(=O)[C@@H](N)CCC(O)=O)C(=O)C1=CC=C(NCC2=NC3=C(N=C2)N=C(N)NC3=O)C=C1)(C(=O)[C@@H](N)CCC(O)=O)C(C(=O)[C@@H](N)CCC(O)=O)(C(=O)[C@@H](N)CCC(O)=O)C(C(O)=O)(C(=O)[C@@H](N)CCC(O)=O)C(=O)[C@@H](N)CCC(O)=O

InChI Identifier

InChI=1S/C54H68N14O27/c55-24(5-12-31(69)70)39(83)52(49(92)93,40(84)25(56)6-13-32(71)72)53(41(85)26(57)7-14-33(73)74,42(86)27(58)8-15-34(75)76)54(43(87)28(59)9-16-35(77)78,50(94)95-48(91)30(61)11-18-37(81)82)68(47(90)29(60)10-17-36(79)80)46(89)21-1-3-22(4-2-21)63-19-23-20-64-44-38(65-23)45(88)67-51(62)66-44/h1-4,20,24-30,63H,5-19,55-61H2,(H,69,70)(H,71,72)(H,73,74)(H,75,76)(H,77,78)(H,79,80)(H,81,82)(H,92,93)(H3,62,64,66,67,88)/t24-,25-,26-,27-,28-,29-,30-,54?/m0/s1

InChI Key

KNLHIYYNBQALAI-IMYKNWLQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as peptides. Peptides 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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
Glutamic acid or derivatives
Hippuric acid or derivatives
Alpha-amino acid amide
Pterin
Gamma amino acid or derivatives
Alpha-amino acid or derivatives
Pteridine
Aminobenzamide
Aminobenzoic acid or derivatives
Benzoic acid or derivatives
Aniline or substituted anilines
Gamma-keto acid
Phenylalkylamine
Benzoyl
Beta-keto acid
Aralkylamine
Secondary aliphatic/aromatic amine
Pyrimidone
Amino fatty acid
Aminopyrimidine
Monocyclic benzene moiety
Fatty acyl
Beta-hydroxy ketone
Gamma-aminoketone
Benzenoid
Keto acid
N-acyl-amine
Carboxylic acid imide, n-substituted
Pyrimidine
Pyrazine
Vinylogous amide
Heteroaromatic compound
Dicarboximide
Alpha-aminoketone
Carboxylic acid imide
Carboxylic acid anhydride
Amino acid
Amino acid or derivatives
Ketone
Secondary amine
Organoheterocyclic compound
Azacycle
Carboxylic acid
Hydrocarbon derivative
Organic nitrogen compound
Amine
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Primary amine
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 2827456)

Source

Endogenous

Endogenous (HMDB: HMDB0006559)

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	0.56 g/L	ALOGPS
logP	-2.9	ALOGPS
logP	-5.9	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	2.24	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	38	ChemAxon
Hydrogen Donor Count	18	ChemAxon
Polar Surface Area	751.93 Å²	ChemAxon
Rotatable Bond Count	44	ChemAxon
Refractivity	309.73 m³·mol⁻¹	ChemAxon
Polarizability	126.39 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

HMDB0006559

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023971

KNApSAcK ID

Not Available

Chemspider ID

35016009

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2304198

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477856

PDB ID

Not Available

ChEBI ID

89846

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Heptaglutamyl folic acid (CFc000002809)

MOL for CFc000002809 (Heptaglutamyl folic acid)

3D MOL for CFc000002809 (Heptaglutamyl folic acid)

3D SDF for CFc000002809 (Heptaglutamyl folic acid)

3D-SDF for CFc000002809 (Heptaglutamyl folic acid)

PDB for CFc000002809 (Heptaglutamyl folic acid)

3D PDB for CFc000002809 (Heptaglutamyl folic acid)

SMILES for CFc000002809 (Heptaglutamyl folic acid)

INCHI for CFc000002809 (Heptaglutamyl folic acid)

Structure for CFc000002809 (Heptaglutamyl folic acid)

3D Structure for CFc000002809 (Heptaglutamyl folic acid)