MiMeDB: Showing metabocard for Dihydrofolic acid (MMDBc0029538)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:31:29 UTC

Update Date

2024-10-15 17:17:32 UTC

Metabolite ID

MMDBc0029538

Metabolite Identification

Common Name

Dihydrofolic acid

Description

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

Molecular Formula

C₁₉H₂₁N₇O₆

Average Mass

443.4133

Monoisotopic Mass

443.155331439

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

4033-27-6

SMILES

Not Available

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

Not Available

Physical Properties

State

Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Lysosome
Mitochondria

Biospecimen Locations

Blood
Feces
Liver

Tissue Locations

Liver

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192410	Dihydrofolate reductase	Enzyme	P00374	Homo sapiens
MMDBp0192469	Folylpolyglutamate synthase, mitochondrial	Enzyme	Q05932	Homo sapiens
MMDBp0193968	Thymidylate synthase	Enzyme	P04818	Homo sapiens
MMDBp0194161	Dihydrofolate reductase	Enzyme	B0YJ76	Homo sapiens
MMDBp0196796	Dihydrofolate reductase, mitochondrial	Unknown	Q86XF0

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001217	Folic acid	Dihydrofolic acid	dihydrofolate reductase	VMH; KEGG	30371894
MMDBr0001227	Dihydrofolic acid	Pentaglutamyl Folate (Dhf)	folylpolyglutamate synthase	VMH	10777604
MMDBr0001228	Dihydrofolic acid	Pentaglutamyl Folate (Dhf)	folylpolyglutamate synthase	VMH	10777604
MMDBr0001288	Pentaglutamyl Folate (Dhf)	Dihydrofolic acid	gamma-glutamyl hydrolase (conjugase, folylpolygammaglutamyl hydrolase)	VMH	11375437 2867095 9614206
MMDBr0001289	Pentaglutamyl Folate (Dhf)	Dihydrofolic acid	gamma-glutamyl hydrolase (conjugase, folylpolygammaglutamyl hydrolase)	VMH	11375437 2867095 9614206
MMDBr0002489	Dihydrofolic acid	Tetrahydrofolic acid	dihydrofolate reductase	VMH	15153070 1631094 6882460
MMDBr0002490	Dihydrofolic acid	Tetrahydrofolic acid	dihydrofolate reductase	VMH	15153070 16171773 1631094 6882460 962851
MMDBr0002578	Dihydrofolic acid	Folic acid	dihydrofolate reductase	VMH; KEGG	30371894
MMDBr0002579	Folic acid	Dihydrofolic acid	dihydrofolate reductase	VMH; KEGG	30371894
MMDBr0007308	Dihydrofolic acid	Folic acid	Not Available	VMH	30371894
MMDBr0007309	Dihydrofolic acid	Tetrahydrofolic acid	Not Available	VMH; KEGG	30371894
MMDBr0007310	Dihydropteroate	Dihydrofolic acid	Not Available	VMH	30371894
MMDBr0007980	dUMP	Dihydrofolic acid	Not Available	VMH; KEGG	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	182	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	388	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool	Metabolic reconstruction
Bacteria	Actinobacteria	126	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	126	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Bacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	3	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	0.005	0.001	uM	Adult (>18 years old)	Both	Normal	HMDB	7226494
Human Liver	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597

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

Not Available

General References

Navarro-Peran E, Cabezas-Herrera J, Garcia-Canovas F, Durrant MC, Thorneley RN, Rodriguez-Lopez JN: The antifolate activity of tea catechins. Cancer Res. 2005 Mar 15;65(6):2059-64. doi: 10.1158/0008-5472.CAN-04-3469. [PubMed:15781612 ]

Showing metabocard for Dihydrofolic acid (MMDBc0029538)

MOL for #<Metabolite:0x0000562ee48f3068>

3D MOL for #<Metabolite:0x0000562ee48f3068>

3D SDF for #<Metabolite:0x0000562ee48f3068>

3D-SDF for #<Metabolite:0x0000562ee48f3068>

PDB for #<Metabolite:0x0000562ee48f3068>

3D PDB for #<Metabolite:0x0000562ee48f3068>

SMILES for #<Metabolite:0x0000562ee48f3068>

INCHI for #<Metabolite:0x0000562ee48f3068>

Structure for #<Metabolite:0x0000562ee48f3068>

3D Structure for #<Metabolite:0x0000562ee48f3068>