Record Information
Version1.0
Creation date2011-09-21 00:13:21 UTC
Update date2015-07-21 06:57:11 UTC
Primary IDFDB022395
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDihydrofolic acid
DescriptionDihydrofolic acid, also known as 7,8-dihydrofolate or H2PTEGLU, 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. Dihydrofolic acid is a moderately basic compound (based on its pKa). Dihydrofolic acid exists in all eukaryotes, ranging from yeast to humans.
CAS Number4033-27-6
Structure
Thumb
Synonyms
SynonymSource
7,8-DihydrofolateChEBI
7,8-Dihydrofolic acidChEBI
7,8-DihydropteroylglutamateChEBI
DihydrofolateChEBI
N-(7,8-Dihydropteroyl)-L-glutamic acidChEBI
7,8-Dihydropteroylglutamic acidGenerator
N-(7,8-Dihydropteroyl)-L-glutamateGenerator
7,8-Dihydro-L-folic acidHMDB
H2PteGluHMDB
H2PteGlu1HMDB
L-N-[p-[[(2-Amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]benzoyl]-glutamic acidHMDB
N-(4-(((2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-glutamic acidHMDB
N-(4-{[(2-amino-4-oxo-3,4,7,8-tetrahydropteridin-6-yl)methyl]amino}benzoyl)-L-glutamic acidHMDB
N-[4-[[(2-Amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acidHMDB
N-[4-[[(2-Amino-3,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-glutamic acidHMDB
Vitamin b9HMDB
Dihydrofolate, (D)-isomerHMDB
7,8-dihydrofolatehmdb
dihydrofolatehmdb
L-N-[p-[[(2-amino-7,8-dihydro-4-hydroxy-6-pteridinyl)methyl]amino]benzoyl]-Glutamic acidhmdb
N-(4-(((2-amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl)amino)benzoyl)-L-Glutamic acidhmdb
N-(7,8-dihydropteroyl)-L-glutamic acidhmdb
N-[4-[[(2-amino-1,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-Glutamic acidhmdb
N-[4-[[(2-amino-3,4,7,8-tetrahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-L-Glutamic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP-0.93ALOGPS
logP-1.8ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)3.37ChemAxon
pKa (Strongest Basic)2.09ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area207.6 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity120.99 m³·mol⁻¹ChemAxon
Polarizability44.31 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC19H21N7O6
IUPAC name(2S)-2-[(4-{[(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
InChI IdentifierInChI=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 KeyOZRNSSUDZOLUSN-LBPRGKRZSA-N
Isomeric SMILESNC1=NC2=C(N=C(CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)CN2)C(=O)N1
Average Molecular Weight443.4133
Monoisotopic Molecular Weight443.155331439
Classification
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamic 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-2469100000-dfb9d32424c0c60215dcJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-3320390000-c5791f4954b5cefa68e1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0322900000-3bd8be8b6fc531102b49JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0952200000-3a44b5c375b9b981244fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-1930000000-71775fd6210c3e719dc1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0113900000-62b9c33c60c2e2fd46c6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xv-1349500000-3d3bae7b4497b96fc55dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9441000000-c0339a106358ca6d7221JSpectraViewer
ChemSpider ID89228
ChEMBL IDCHEMBL46294
KEGG Compound IDC00415
Pubchem Compound ID98792
Pubchem Substance IDNot Available
ChEBI ID15633
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01056
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34911
KNApSAcK IDNot Available
HET IDDHF
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDihydrofolate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Folylpolyglutamate synthase, mitochondrialFPGSQ05932
Dihydrofolate reductaseDHFRP00374
Thymidylate synthaseTYMSP04818
Pathways
NameSMPDB LinkKEGG Link
Folate MetabolismSMP00053 map00670
Pterine BiosynthesisSMP00005 map00790
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference