DIHYDROFOLIC ACID

First approved in 2024

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H21N7O6
Molecular Weight	443.4133
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

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

InChIKey=OZRNSSUDZOLUSN-LBPRGKRZSA-N

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

HIDE SMILES / InChI

Molecular Formula	C19H21N7O6
Molecular Weight	443.4133
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1α expression and mitochondrial biogenesis.	2012	23056435
Dynamic subcellular localization of isoforms of the folate pathway enzyme serine hydroxymethyltransferase (SHMT) through the erythrocytic cycle of Plasmodium falciparum.	2010-12-03	21129192
[Photobiochemistry of folates: a photochemical reduction of folic acid].	2010-07-01	20586292
Characterisation of the bifunctional dihydrofolate synthase-folylpolyglutamate synthase from Plasmodium falciparum; a potential novel target for antimalarial antifolate inhibition.	2010-07	20350571
Cobalamin deficiency, hyperhomocysteinemia, and dementia.	2010-05-06	20505848
Antimicrobial evaluation of novel substituted pyrimidinopyrazoles and pyrimidinotriazoles.	2010-04	22247851
Complete genomic sequence of bacteriophage felix o1.	2010-03	21994654
Management of Pneumocystis Jirovecii pneumonia in HIV infected patients: current options, challenges and future directions.	2010	22096390
Binding of natural and synthetic polyphenols to human dihydrofolate reductase.	2009-12-18	20054477
Mechanistic insights into folic acid-dependent vascular protection: dihydrofolate reductase (DHFR)-mediated reduction in oxidant stress in endothelial cells and angiotensin II-infused mice: a novel HPLC-based fluorescent assay for DHFR activity.	2009-12	19660467
A mapping of drug space from the viewpoint of small molecule metabolism.	2009-08	19701464
Voltammetric determination of sulfamethoxazole at a multiwalled carbon nanotube modified glassy carbon sensor and its application studies.	2009-07	20355213
(E)-N'-(4-Chloro-benzyl-idene)-p-toluene-sulfonohydrazide 0.15-hydrate.	2009-04-25	21583931
(E)-N'-(3,3-Diphenyl-allyl-idene)-p-toluene-sulfonohydrazide.	2009-04-18	21583873
(E)-N'-(4-Bromo-benzyl-idene)-p-toluene-sulfonohydrazide.	2009-03-25	21582542
QM/MM study of thymidylate synthase: enzymatic motions and the temperature dependence of the rate limiting step.	2009-03-12	19182971
Regulation of translation in haloarchaea: 5'- and 3'-UTRs are essential and have to functionally interact in vivo.	2009	19214227
(E)-N'-(5-Chloro-2-hydroxy-benzyl-idene)-p-toluene-sulfonohydrazide.	2008-11-22	21581392
(E)-N'-(5-Bromo-2-hydroxy-benzyl-idene)-p-toluene-sulfonohydrazide.	2008-11-13	21581316
(E)-N'-Benzyl-idene-p-toluene-sulfono-hydrazide.	2008-08-30	21201816
Novel triazine JPC-2067-B inhibits Toxoplasma gondii in vitro and in vivo.	2008-03-05	18320016
Metabolism of halophilic archaea.	2008-03	18278431
catena-Poly[bis-(sulfamethoxazolium) [[trichloridocadmate(II)]-μ-chlorido] monohydrate].	2007-12-21	21200590
Experimental characterization of Cis-acting elements important for translation and transcription in halophilic archaea.	2007-12	18159946
Role of airway lactoperoxidase in scavenging of hydrogen peroxide damage in asthma.	2007-07	19727356
Ligand binding and circular permutation modify residue interaction network in DHFR.	2007-06	17571919
A functional 19-base pair deletion polymorphism of dihydrofolate reductase (DHFR) and risk of breast cancer in multivitamin users.	2007-04	17413111
A quantum mechanics/molecular mechanics study of the catalytic mechanism of the thymidylate synthase.	2007-03-27	17328531
Adenosine in inflammatory joint diseases.	2007-03	18404428
Protein motions during catalysis by dihydrofolate reductases.	2006-08-29	16873119
Folic acid and its metabolites modulate IGF-I receptor gene expression in colon cancer cells in a p53-dependent manner.	2006-06	16728583
Methotrexate enhances the anti-inflammatory effect of CF101 via up-regulation of the A3 adenosine receptor expression.	2006	17101059
Sulfonamides in the environment as veterinary drugs.	2006	16802579
Kinetics of the inhibition of bovine liver dihydrofolate reductase by tea catechins: origin of slow-binding inhibition and pH studies.	2005-05-24	15895994
The antifolate activity of tea catechins.	2005-03-15	15781612
Over-expression, purification, and characterization of recombinant human arylamine N-acetyltransferase 1.	2005-02	16003948
Folate requirements of the 2-keto-L-gulonic acid-producing strain Ketogulonigenium vulgare LMP P-20356 in L-sorbose/CSL medium.	2004-08	15293031
Microscale synthesis of isotopically labeled R-[6-xH]N5,N10-methylene-5,6,7,8-tetrahydrofolate as a cofactor for thymidylate synthase.	2004-05-01	15081906
Sodium-dependent methotrexate carrier-1 is expressed in rat kidney: cloning and functional characterization.	2004-03	14612385
Inhibition of the rat breast cytosolic bioactivation of ethanol to acetaldehyde by some plant polyphenols and folic acid.	2004	15456641
Reaction-path energetics and kinetics of the hydride transfer reaction catalyzed by dihydrofolate reductase.	2003-11-25	14622003
Hydride transfer during catalysis by dihydrofolate reductase from Thermotoga maritima.	2003-09-01	12765545
Role of water in the catalytic cycle of E. coli dihydrofolate reductase.	2002-06	12021443
Molecular action of methotrexate in inflammatory diseases.	2002	12106498
Preliminary application of liquid chromatography-electrospray-ionization mass spectrometry to the detection of 5-methyltetrahydrofolic acid monoglutamate in human plasma.	2001-12-25	11767307
Developing a dynamic pharmacophore model for HIV-1 integrase.	2000-06-01	10841789

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:54:24 GMT 2025` Edited by `admin` on `Mon Mar 31 20:54:24 GMT 2025`
Record UNII	KXP0KNM559
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIHYDROFOLIC ACID

Common Name

English

7,8-DIHYDROFOLIC ACID

Preferred Name

English

NSC-165989

Code

English

7,8-DIHYDROFOLIC ACID [DSC]

Common Name

English

(2S)-2-((4-(((2-AMINO-4-OXO-1,4,7,8-TETRAHYDROPTERIDIN-6-YL)METHYL)AMINO)BENZOYL)AMINO)PENTANEDIOIC ACID

Systematic Name

English

CALCIUM FOLINATE IMPURITY G [EP IMPURITY]

Common Name

English

L-GLUTAMIC ACID, N-(4-(((2-AMINO-3,4,7,8-TETRAHYDRO-4-OXO-6-PTERIDINYL)METHYL)AMINO)BENZOYL)-

Systematic Name

English

7,8-DIHYDRO-L-FOLIC ACID

Common Name

English

Code System Code Type Description

PUBCHEM

135398604