7,8-dihydrofolate monoglutamate (PAMDB110253)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110253
Identification
Name: 7,8-dihydrofolate monoglutamate
Description:Dianion of dihydrofolic acid arising from deprotonation of both carboxylic acid functions.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 7,8-pteroylglutamic acid
  • 7,8-pteroylglutamate
  • 7,8-dihydropteroyl monoglutamate
  • H2PteGlu
  • H2PteGlu1
  • dihydrofolate
  • 7,8-dihydropteroylglutamate
  • 7,8-dihydrofolate
Chemical Formula: C19H19N7O6
Average Molecular Weight: 441.4
Monoisotopic Molecular Weight: 443.1553314431
InChI Key: OZRNSSUDZOLUSN-LBPRGKRZSA-L
InChI: 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)/p-2/t12-/m0/s1
CAS number: 4033-27-6
IUPAC Name:N-(4-{[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamate
Traditional IUPAC Name: dihydrofolic acid
SMILES:C(NC1(C=CC(C(=O)NC(C(=O)[O-])CCC([O-])=O)=CC=1))C3(CNC2(=C(C(=O)NC(N)=N2)N=3))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as glutamic acid and derivatives. These 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 Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassCarboxylic acids and derivatives
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
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 mg/mLALOGPS
logP-1.6ALOGPS
logP-2.1ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)3.16ChemAxon
pKa (Strongest Basic)3.68ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area207.6 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity121.19 m3·mol-1ChemAxon
Polarizability44.38 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0322900000-3bd8be8b6fc531102b49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0952200000-3a44b5c375b9b981244fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1930000000-71775fd6210c3e719dc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0113900000-62b9c33c60c2e2fd46c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xv-1349500000-3d3bae7b4497b96fc55dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9441000000-c0339a106358ca6d7221View in MoNA
References
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. [15781612 ]
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.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CAS4033-27-6
ChEBI57451
HMDBHMDB01056
IAF126034911
KEGGC00415
MetaboLightsMTBLC57451
PubChem40480038