U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of DIHYDROFOLIC ACID

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

Approval Year

PubMed

PubMed

TitleDatePubMed
Developing a dynamic pharmacophore model for HIV-1 integrase.
2000 Jun 1
Preliminary application of liquid chromatography-electrospray-ionization mass spectrometry to the detection of 5-methyltetrahydrofolic acid monoglutamate in human plasma.
2001 Dec 25
Molecular action of methotrexate in inflammatory diseases.
2002
Reaction-path energetics and kinetics of the hydride transfer reaction catalyzed by dihydrofolate reductase.
2003 Nov 25
Hydride transfer during catalysis by dihydrofolate reductase from Thermotoga maritima.
2003 Sep 1
Folate requirements of the 2-keto-L-gulonic acid-producing strain Ketogulonigenium vulgare LMP P-20356 in L-sorbose/CSL medium.
2004 Aug
Sodium-dependent methotrexate carrier-1 is expressed in rat kidney: cloning and functional characterization.
2004 Mar
Kinetics of the inhibition of bovine liver dihydrofolate reductase by tea catechins: origin of slow-binding inhibition and pH studies.
2005 May 24
Methotrexate enhances the anti-inflammatory effect of CF101 via up-regulation of the A3 adenosine receptor expression.
2006
Sulfonamides in the environment as veterinary drugs.
2006
Folic acid and its metabolites modulate IGF-I receptor gene expression in colon cancer cells in a p53-dependent manner.
2006 Jun
A functional 19-base pair deletion polymorphism of dihydrofolate reductase (DHFR) and risk of breast cancer in multivitamin users.
2007 Apr
Experimental characterization of Cis-acting elements important for translation and transcription in halophilic archaea.
2007 Dec
Role of airway lactoperoxidase in scavenging of hydrogen peroxide damage in asthma.
2007 Jul
Ligand binding and circular permutation modify residue interaction network in DHFR.
2007 Jun
Adenosine in inflammatory joint diseases.
2007 Mar
Metabolism of halophilic archaea.
2008 Mar
Novel triazine JPC-2067-B inhibits Toxoplasma gondii in vitro and in vivo.
2008 Mar 5
(E)-N'-(5-Chloro-2-hydroxy-benzyl-idene)-p-toluene-sulfonohydrazide.
2008 Nov 22
Regulation of translation in haloarchaea: 5'- and 3'-UTRs are essential and have to functionally interact in vivo.
2009
(E)-N'-(3,3-Diphenyl-allyl-idene)-p-toluene-sulfonohydrazide.
2009 Apr 18
(E)-N'-(4-Chloro-benzyl-idene)-p-toluene-sulfonohydrazide 0.15-hydrate.
2009 Apr 25
A mapping of drug space from the viewpoint of small molecule metabolism.
2009 Aug
QM/MM study of thymidylate synthase: enzymatic motions and the temperature dependence of the rate limiting step.
2009 Mar 12
Management of Pneumocystis Jirovecii pneumonia in HIV infected patients: current options, challenges and future directions.
2010
Antimicrobial evaluation of novel substituted pyrimidinopyrazoles and pyrimidinotriazoles.
2010 Apr
Dynamic subcellular localization of isoforms of the folate pathway enzyme serine hydroxymethyltransferase (SHMT) through the erythrocytic cycle of Plasmodium falciparum.
2010 Dec 3
Complete genomic sequence of bacteriophage felix o1.
2010 Mar
Cobalamin deficiency, hyperhomocysteinemia, and dementia.
2010 May 6
A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1α expression and mitochondrial biogenesis.
2012
Patents
Name Type Language
DIHYDROFOLIC ACID
Common 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
7,8-DIHYDROFOLIC ACID
DSC  
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
Created by admin on Sat Dec 16 01:35:08 UTC 2023 , Edited by admin on Sat Dec 16 01:35:08 UTC 2023
PRIMARY
CHEBI
23743
Created by admin on Sat Dec 16 01:35:08 UTC 2023 , Edited by admin on Sat Dec 16 01:35:08 UTC 2023
PRIMARY
DRUG BANK
DB02015
Created by admin on Sat Dec 16 01:35:08 UTC 2023 , Edited by admin on Sat Dec 16 01:35:08 UTC 2023
PRIMARY
EPA CompTox
DTXSID401027140
Created by admin on Sat Dec 16 01:35:08 UTC 2023 , Edited by admin on Sat Dec 16 01:35:08 UTC 2023
PRIMARY
NSC
165989
Created by admin on Sat Dec 16 01:35:08 UTC 2023 , Edited by admin on Sat Dec 16 01:35:08 UTC 2023
PRIMARY
CHEBI
15633
Created by admin on Sat Dec 16 01:35:08 UTC 2023 , Edited by admin on Sat Dec 16 01:35:08 UTC 2023
PRIMARY
FDA UNII
KXP0KNM559
Created by admin on Sat Dec 16 01:35:08 UTC 2023 , Edited by admin on Sat Dec 16 01:35:08 UTC 2023
PRIMARY
CAS
4033-27-6
Created by admin on Sat Dec 16 01:35:08 UTC 2023 , Edited by admin on Sat Dec 16 01:35:08 UTC 2023
PRIMARY
RXCUI
2267573
Created by admin on Sat Dec 16 01:35:08 UTC 2023 , Edited by admin on Sat Dec 16 01:35:08 UTC 2023
PRIMARY
DAILYMED
KXP0KNM559
Created by admin on Sat Dec 16 01:35:08 UTC 2023 , Edited by admin on Sat Dec 16 01:35:08 UTC 2023
PRIMARY
WIKIPEDIA
Dihydrofolic acid
Created by admin on Sat Dec 16 01:35:08 UTC 2023 , Edited by admin on Sat Dec 16 01:35:08 UTC 2023
PRIMARY