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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-23 11:37:50 UTC
Update Date2019-07-23 05:47:23 UTC
HMDB IDHMDB0006486
Secondary Accession Numbers
  • HMDB06486
Metabolite Identification
Common Name5-Methyldihydrofolic acid
Description5-Methyldihydrofolic acid is a biopterin derivative present in human body fluids and tissues. (PMID: 932231 ).
Structure
Data?1563860842
Synonyms
ValueSource
5-Methyl-5,8-dihydrofolic acidHMDB
N-[P-[[(2-aminodihydro-4-Hydroxy-5-methyl-6-pteridinyl)methyl]amino]benzoyl]- glutamic acidHMDB
Chemical FormulaC20H23N7O6
Average Molecular Weight457.4399
Monoisotopic Molecular Weight457.170981503
IUPAC Name(2S)-2-[(4-{[(2-amino-5-methyl-4-oxo-1,4,5,8-tetrahydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
Traditional Name(2S)-2-[(4-{[(2-amino-5-methyl-4-oxo-1,8-dihydropteridin-6-yl)methyl]amino}phenyl)formamido]pentanedioic acid
CAS Registry Number59904-24-4
SMILES
CN1C(CNC2=CC=C(C=C2)C(=O)N[C@@H](CCC(O)=O)C(O)=O)=CNC2=C1C(=O)N=C(N)N2
InChI Identifier
InChI=1S/C20H23N7O6/c1-27-12(9-23-16-15(27)18(31)26-20(21)25-16)8-22-11-4-2-10(3-5-11)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,9,13,22H,6-8H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H4,21,23,25,26,31)/t13-/m0/s1
InChI KeyVWNDXSYYCICZGD-ZDUSSCGKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dihydrofolic acids and derivatives. These are heterocyclic compounds based on the 5,6-dihydropteroic acid/7,8-dihydropteroic acid skeleton conjugated with one or more L-glutamic acid units (or derivative thereof).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentDihydrofolic acids and derivatives
Alternative Parents
Substituents
  • Dihydrofolic acid or derivatives
  • Glutamic acid or derivatives
  • Hippuric acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Hippuric acid
  • N-acyl-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Aminobenzamide
  • Aminobenzoic acid or derivatives
  • Benzamide
  • Benzoic acid or derivatives
  • Benzoyl
  • Tertiary aliphatic/aromatic amine
  • Aniline or substituted anilines
  • Phenylalkylamine
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyrimidine
  • Vinylogous amide
  • Heteroaromatic compound
  • Tertiary amine
  • Amino acid or derivatives
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Enamine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Secondary amine
  • Azacycle
  • Organic nitrogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP-0.43ALOGPS
logP-3.5ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)2.93ChemAxon
pKa (Strongest Basic)4.16ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area198.48 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity127.46 m³·mol⁻¹ChemAxon
Polarizability46.03 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-1444900000-3d359a64f380caa37e40JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-000i-4023390000-d0c5ce85f9ff7bf11058JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0302900000-858fd7ea200bd40564e3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0924300000-3bee881ebce2cd040c1aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0920000000-988f5acd079eb44b523dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-0000900000-facf36af51a3d5028489JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08g0-1245900000-c9a48033185f257663cfJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9751300000-6fb9d636c4cfbe8bf60fJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
  • Lysosome
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023936
KNApSAcK IDNot Available
Chemspider ID4956218
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2304240
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6453871
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Leeming RJ, Blair JA, Melikian V, O'Gorman DJ: Biopterin derivatives in human body fluids and tissues. J Clin Pathol. 1976 May;29(5):444-51. [PubMed:932231 ]