ChemFOnt: Showing chemical card for 5-Methyldihydrofolic acid (CFc000002767)

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

CFc000002767

Molecule Identification

Common Name

5-Methyldihydrofolic acid

Definition

5-Methyldihydrofolic acid is a biopterin derivative present in human body fluids and tissues. (PMID: 932231 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-2-[(4-{[(2-amino-5-methyl-4-oxo-1,4,5,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid	ChEBI
5-Methyl-5,8-dihydrofolic acid	ChEBI
5-Methyldihydrofolate	ChEBI
(2S)-2-[(4-{[(2-amino-5-methyl-4-oxo-1,4,5,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioate	Generator
5-Methyl-5,8-dihydrofolate	Generator
N-[P-[[(2-aminodihydro-4-Hydroxy-5-methyl-6-pteridinyl)methyl]amino]benzoyl]- glutamic acid	HMDB

Chemical Formula

C₂₀H₂₃N₇O₆

Average Molecular Weight

457.4399

Monoisotopic Molecular Weight

457.170981503

IUPAC Name

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

Traditional Name

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

CAS Registry Number

59904-24-4

SMILES

CN1C(CNC2=CC=C(C=C2)C(=O)N[C@@H](CCC(O)=O)C(O)=O)=CNC2=C1C(=O)N=C(N)N2

InChI Identifier

InChI=1S/C20H23N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,9,13,22H,6-8H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t13-/m0/s1

InChI Key

VWNDXSYYCICZGD-ZDUSSCGKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydrofolic acids and derivatives. These are heterocyclic compounds based on the 5,6-dihydropteroic acid/7,8-dihydropteroic acid skeleton conjugated with one or more L-glutamic acid units (or derivative thereof).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Pterins and derivatives

Direct Parent

Dihydrofolic acids and derivatives

Alternative Parents

Substituents

Dihydrofolic acid or derivatives
Glutamic acid or derivatives
Hippuric acid or derivatives
N-acyl-alpha amino acid or derivatives
Hippuric acid
N-acyl-alpha-amino acid
Alpha-amino acid or derivatives
Aminobenzamide
Aminobenzoic acid or derivatives
Benzamide
Benzoic acid or derivatives
Benzoyl
Tertiary aliphatic/aromatic amine
Aniline or substituted anilines
Phenylalkylamine
Aminopyrimidine
Pyrimidone
Secondary aliphatic/aromatic amine
Dicarboxylic acid or derivatives
Benzenoid
Monocyclic benzene moiety
Pyrimidine
Vinylogous amide
Heteroaromatic compound
Tertiary amine
Amino acid or derivatives
Amino acid
Secondary carboxylic acid amide
Carboxamide group
Enamine
Carboxylic acid
Carboxylic acid derivative
Secondary amine
Azacycle
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen 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: HMDB0006486)
Extracellular (HMDB: HMDB0006486)

Organelle

Lysosome (HMDB: HMDB0006486)
Mitochondrion (HMDB: HMDB0006486)

Source

Endogenous

Endogenous (HMDB: HMDB0006486)

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	0.25 g/L	ALOGPS
logP	-0.43	ALOGPS
logP	-3.5	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	2.93	ChemAxon
pKa (Strongest Basic)	4.16	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	198.48 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	127.46 m³·mol⁻¹	ChemAxon
Polarizability	46.03 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

HMDB0006486

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023936

KNApSAcK ID

Not Available

Chemspider ID

4956218

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2304240

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6453871

PDB ID

Not Available

ChEBI ID

134470

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 5-Methyldihydrofolic acid (CFc000002767)

MOL for CFc000002767 (5-Methyldihydrofolic acid)

3D MOL for CFc000002767 (5-Methyldihydrofolic acid)

3D SDF for CFc000002767 (5-Methyldihydrofolic acid)

3D-SDF for CFc000002767 (5-Methyldihydrofolic acid)

PDB for CFc000002767 (5-Methyldihydrofolic acid)

3D PDB for CFc000002767 (5-Methyldihydrofolic acid)

SMILES for CFc000002767 (5-Methyldihydrofolic acid)

INCHI for CFc000002767 (5-Methyldihydrofolic acid)

Structure for CFc000002767 (5-Methyldihydrofolic acid)

3D Structure for CFc000002767 (5-Methyldihydrofolic acid)