ChemFOnt: Showing chemical card for Dihydrofolic acid (CFc000000831)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:20 UTC

Chemfont ID

CFc000000831

Molecule Identification

Common Name

Dihydrofolic acid

Definition

Dihydrofolic acid is a folic acid derivative acted upon by dihydrofolate reductase to produce tetrahydrofolic acid. It interacts with bacteria during cell division. It can be targeted with drug analogs to prevent nucleic acid synthesis. Dihydrofolic acid is also known by the name Dihydrofolate - more commonly Vitamin B9.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
7,8-Dihydrofolate	ChEBI
7,8-Dihydrofolic acid	ChEBI
7,8-Dihydropteroylglutamate	ChEBI
Dihydrofolate	ChEBI
N-(7,8-Dihydropteroyl)-L-glutamic acid	ChEBI
7,8-Dihydropteroylglutamic acid	Generator
N-(7,8-Dihydropteroyl)-L-glutamate	Generator
7,8-Dihydro-L-folic acid	HMDB
H2PteGlu	HMDB
H2PteGlu1	HMDB
L-N-[p-[[(2-Amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]benzoyl]-glutamic acid	HMDB
N-(4-(((2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-glutamic acid	HMDB
N-(4-{[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acid	HMDB
N-[4-[[(2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid	HMDB
N-[4-[[(2-Amino-3,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acid	HMDB
Vitamin b9	HMDB
Dihydrofolate, (D)-isomer	HMDB

Chemical Formula

C₁₉H₂₁N₇O₆

Average Molecular Weight

443.4133

Monoisotopic Molecular Weight

443.155331439

IUPAC Name

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

Traditional Name

dihydrofolic acid

CAS Registry Number

4033-27-6

SMILES

NC1=NC(=O)C2=C(NCC(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)=N2)N1

InChI Identifier

InChI=1S/C19H21N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,12,21H,5-8H2,(H,24,29)(H,27,28)(H,31,32)(H4,20,22,25,26,30)/t12-/m0/s1

InChI Key

OZRNSSUDZOLUSN-LBPRGKRZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
Hippuric acid or derivatives
Hippuric acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Pterin
Aminobenzamide
Aminobenzoic acid or derivatives
Pteridine
Benzamide
Benzoic acid or derivatives
Benzoyl
Phenylalkylamine
Aniline or substituted anilines
Hydroxypyrimidine
Secondary aliphatic/aromatic amine
Dicarboxylic acid or derivatives
Benzenoid
Pyrimidine
Monocyclic benzene moiety
Heteroaromatic compound
Amino acid
Secondary carboxylic acid amide
Ketimine
Carboxamide group
Carboxylic acid
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Organoheterocyclic compound
Organic 1,3-dipolar compound
Azacycle
Organic oxygen compound
Imine
Hydrocarbon derivative
Carbonyl group
Amine
Organic oxide
Organonitrogen compound
Organopnictogen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydrofolic acids (CHEBI:15633 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 7226494)

Organ

Liver (HMDB: HMDB0001056)

Cellular substructure

Extracellular (HMDB: HMDB0001056)

Organelle

Lysosome (HMDB: HMDB0001056)
Mitochondrion (HMDB: HMDB0001056)

Source

Exogenous

Exogenous (HMDB: HMDB0001056)

Food

Animal origin

Poultry

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)

Endogenous

Endogenous (HMDB: HMDB0001056)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Folate Malabsorption, Hereditary (HMDB: HMDB0001056)
Methylenetetrahydrofolate Reductase Deficiency (MTHFRD) (PathBank: SMP0120522)
Beta-Ureidopropionase Deficiency (PathBank: SMP0120678)
UMP Synthase Deficiency (Orotic Aciduria) (PathBank: SMP0120507)
Dihydropyrimidinase Deficiency (PathBank: SMP0120473)
MNGIE (Mitochondrial Neurogastrointestinal Encephalopathy) (PathBank: SMP0120530)
Folate Malabsorption, Hereditary (PathBank: SMP0120656)

Drug action pathway

Methotrexate Action Pathway (HMDB: HMDB0001056)
Methotrexate Action Pathway (PathBank: SMP0000432)

Metabolic pathway

Folate Metabolism (PathBank: SMP0000801)
Pyrimidine Metabolism (PathBank: SMP0087340)
Folate Metabolism (HMDB: HMDB0001056)
Pyrimidine Metabolism (PathBank: SMP0002370)
One Carbon Pool by Folate (PathBank: SMP0122040)
Pterine Biosynthesis (HMDB: HMDB0001056)
One Carbon Pool by Folate I (PathBank: SMP0002369)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001056)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	-0.93	ALOGPS
logP	-1.8	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	2.09	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	207.6 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	120.99 m³·mol⁻¹	ChemAxon
Polarizability	44.31 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

HMDB0001056

DrugBank ID

DB02015

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15633

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Smith, Karin; Scrimgeour, K. G.; Huennekens, F. M. Folic acid coenzymes and one-carbon metabolism. XV. Synthesis of a new form of dihydrofolate. Biochemical and Biophysical Research Communications (1963), 11(5), 388-92.

Showing chemical card for Dihydrofolic acid (CFc000000831)

MOL for CFc000000831 (Dihydrofolic acid)

3D MOL for CFc000000831 (Dihydrofolic acid)

3D SDF for CFc000000831 (Dihydrofolic acid)

3D-SDF for CFc000000831 (Dihydrofolic acid)

PDB for CFc000000831 (Dihydrofolic acid)

3D PDB for CFc000000831 (Dihydrofolic acid)

SMILES for CFc000000831 (Dihydrofolic acid)

INCHI for CFc000000831 (Dihydrofolic acid)

Structure for CFc000000831 (Dihydrofolic acid)

3D Structure for CFc000000831 (Dihydrofolic acid)