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Record Information
Version4.0
Creation Date2013-07-09 16:18:43 UTC
Update Date2017-09-27 08:44:01 UTC
HMDB IDHMDB0061104
Secondary Accession Numbers
  • HMDB61104
Metabolite Identification
Common Name7-hydroxymethotrexate
Description7-hydroxymethotrexate is a metabolite of methotrexate. Methotrexate, abbreviated MTX and formerly known as amethopterin, is an antimetabolite and antifolate drug. It is used in treatment of cancer, autoimmune diseases, ectopic pregnancy, and for the induction of medical abortions. It acts by inhibiting the metabolism of folic acid. Methotrexate began to replace the more toxic antifolate aminopterin starting in the 1950s. The drug was developed by Yellapragada Subbarao. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
7-OH-MethotrexateMeSH
Chemical FormulaC20H22N8O6
Average Molecular Weight470.4387
Monoisotopic Molecular Weight470.166230476
IUPAC Name(2S)-2-[(4-{[(4-amino-2-imino-7-oxo-1,2,3,7-tetrahydropteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioic acid
Traditional Name(2S)-2-[(4-{[(4-amino-2-imino-7-oxo-1,3-dihydropteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioic acid
CAS Registry NumberNot Available
SMILES
CN(CC1=NC2=C(N)NC(=N)NC2=NC1=O)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C20H22N8O6/c1-28(8-12-18(32)26-16-14(23-12)15(21)25-20(22)27-16)10-4-2-9(3-5-10)17(31)24-11(19(33)34)6-7-13(29)30/h2-5,11H,6-8H2,1H3,(H,24,31)(H,29,30)(H,33,34)(H5,21,22,25,26,27,32)/t11-/m0/s1
InChI KeyHODZDDDNGRLGSI-NSHDSACASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as folic acids. These are heterocyclic compounds based on the 4-[(pteridin-6-ylmethyl)amino]benzoic acid skeleton conjugated with one or more L-glutamate units.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPteridines and derivatives
Direct ParentFolic acids
Alternative Parents
Substituents
  • Folic acid
  • Glutamic acid or derivatives
  • Hippuric acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Hippuric acid or derivatives
  • Aminobenzamide
  • Aminobenzoic acid or derivatives
  • Alpha-amino acid or derivatives
  • Benzoic acid or derivatives
  • Benzamide
  • Aniline or substituted anilines
  • Dialkylarylamine
  • Tertiary aliphatic/aromatic amine
  • Benzoyl
  • Aminopyrimidine
  • Aralkylamine
  • Dicarboxylic acid or derivatives
  • Pyrimidine
  • Pyrazine
  • Primary aromatic amine
  • Benzenoid
  • Monocyclic benzene moiety
  • Imidolactam
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Lactam
  • Secondary carboxylic acid amide
  • Tertiary amine
  • Carboxylic acid
  • Carboxylic acid derivative
  • 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

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP-0.23ALOGPS
logP-2.9ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)3.25ChemAxon
pKa (Strongest Basic)15.22ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area222.66 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity138.08 m³·mol⁻¹ChemAxon
Polarizability46.48 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00b9-1233900000-8bc5376eafbe1eb8f28fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006t-7235892000-4b2cad533312d909fe68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0201900000-db11246c2c99e5718b9fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0007-0593400000-9c664fb6486a11b7ec23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-2910000000-1490508aa6dee6e2b790View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gdi-0000900000-de9131e1636ca2c1a8ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufr-1242900000-bf6d7f96598831eda2ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-6942100000-f5ffd40b5028aa548f52View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00467
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available