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Record Information
Version3.6
Creation Date2013-07-09 16:18:43 UTC
Update Date2017-03-02 22:05:44 UTC
HMDB IDHMDB61104
Secondary Accession NumbersNone
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
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity138.08 m3·mol-1ChemAxon
Polarizability46.48 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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
NuGOwiki LinkHMDB61104
Metagene LinkHMDB61104
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