ChemFOnt: Showing chemical card for Pentaglutamyl folate (CFc000002768)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:43 UTC

Chemfont ID

CFc000002768

Molecule Identification

Common Name

Pentaglutamyl folate

Definition

Pentaglutamyl folate is a naturally occurring form of folic acid. Naturally occurring folates exist in multiple forms, differing in pteridine ring structure and number of glutamate residues. (PMID: 10702529 ). Low methionine synthase activity for whatever reason (metabolic or dietary) may lead to an increase in the relative abundance of Pentaglutamyl folate. (PMID: 10329020 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Pentaglutamyl folic acid	Generator
Pte-penta-glu	HMDB
Pteroylpentaglutamate	HMDB
Pteroylpentaglutamic acid	HMDB
(2S)-2-{[(4S)-4-carboxy-4-{[(4S)-4-carboxy-4-{[(4S)-4-carboxy-4-{[(4S)-4-carboxy-1-hydroxy-4-[(4-{[(4-hydroxy-2-imino-1,2-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]butylidene]amino}-1-hydroxybutylidene]amino}-1-hydroxybutylidene]amino}-1-hydroxybutylidene]amino}pentanedioate	Generator, HMDB

Chemical Formula

C₃₉H₄₇N₁₁O₁₈

Average Molecular Weight

957.8534

Monoisotopic Molecular Weight

957.310053755

IUPAC Name

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

Traditional Name

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

CAS Registry Number

33611-85-7

SMILES

NC1=NC(=O)C2=NC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(O)=O)C(O)=O)C(O)=O)C(O)=O)C(O)=O)C(O)=O)=CN=C2N1

InChI Identifier

InChI=1S/C39H47N11O18/c40-39-49-31-30(33(58)50-39)43-19(16-42-31)15-41-18-3-1-17(2-4-18)32(57)48-24(38(67)68)8-13-28(54)46-22(36(63)64)6-11-26(52)44-20(34(59)60)5-10-25(51)45-21(35(61)62)7-12-27(53)47-23(37(65)66)9-14-29(55)56/h1-4,16,20-24,41H,5-15H2,(H,44,52)(H,45,51)(H,46,54)(H,47,53)(H,48,57)(H,55,56)(H,59,60)(H,61,62)(H,63,64)(H,65,66)(H,67,68)(H3,40,42,49,50,58)/t20-,21-,22-,23-,24-/m0/s1

InChI Key

IVSPPVMFGMVDLI-LSBAASHUSA-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
Hexacarboxylic acid or derivatives
Gamma-glutamyl alpha-amino acid
Glutamic acid or derivatives
Glutamine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Hippuric acid
Hippuric acid or derivatives
N-acyl-l-alpha-amino acid
Pterin
Alpha-amino acid or derivatives
Pteridine
Aminobenzamide
Aminobenzoic acid or derivatives
Benzoic acid or derivatives
Benzamide
Benzoyl
Phenylalkylamine
Aniline or substituted anilines
Secondary aliphatic/aromatic amine
Pyrimidone
Aminopyrimidine
Aralkylamine
Benzenoid
Pyrimidine
Pyrazine
Monocyclic benzene moiety
Fatty amide
N-acyl-amine
Fatty acyl
Vinylogous amide
Heteroaromatic compound
Amino acid or derivatives
Secondary carboxylic acid amide
Amino acid
Carboxamide group
Azacycle
Organoheterocyclic compound
Secondary amine
Carboxylic acid
Organic nitrogen compound
Amine
Primary amine
Organic oxide
Organonitrogen compound
Organopnictogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
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: HMDB0006487)
Extracellular (HMDB: HMDB0006487)

Organelle

Lysosome (HMDB: HMDB0006487)
Mitochondrion (HMDB: HMDB0006487)

Source

Endogenous

Endogenous (HMDB: HMDB0006487)

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	0.12 g/L	ALOGPS
logP	-0.85	ALOGPS
logP	-4	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	2.72	ChemAxon
pKa (Strongest Basic)	-7.7	ChemAxon
Physiological Charge	-6	ChemAxon
Hydrogen Acceptor Count	24	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	474.59 Å²	ChemAxon
Rotatable Bond Count	29	ChemAxon
Refractivity	223.36 m³·mol⁻¹	ChemAxon
Polarizability	91.54 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

HMDB0006487

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023937

KNApSAcK ID

Not Available

Chemspider ID

66096

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2304239

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73374

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Pentaglutamyl folate (CFc000002768)

MOL for CFc000002768 (Pentaglutamyl folate)

3D MOL for CFc000002768 (Pentaglutamyl folate)

3D SDF for CFc000002768 (Pentaglutamyl folate)

3D-SDF for CFc000002768 (Pentaglutamyl folate)

PDB for CFc000002768 (Pentaglutamyl folate)

3D PDB for CFc000002768 (Pentaglutamyl folate)

SMILES for CFc000002768 (Pentaglutamyl folate)

INCHI for CFc000002768 (Pentaglutamyl folate)

Structure for CFc000002768 (Pentaglutamyl folate)

3D Structure for CFc000002768 (Pentaglutamyl folate)