Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2013-02-09 00:33:23 UTC
HMDB IDHMDB15288
Secondary Accession NumbersNone
Metabolite Identification
Common NameTrimetrexate
DescriptionA nonclassical folic acid inhibitor through its inhibition of the enzyme dihydrofolate reductase. It is being tested for efficacy as an antineoplastic agent and as an antiparasitic agent against pneumocystis pneumonia in AIDS patients. Myelosuppression is its dose-limiting toxic effect. [PubChem]
Structure
Thumb
Synonyms
  1. TMQ
  2. TMX
  3. Trimetrexato [INN-Spanish]
  4. Trimetrexatum [INN-Latin]
Chemical FormulaC19H23N5O3
Average Molecular Weight369.4176
Monoisotopic Molecular Weight369.180089627
IUPAC Name5-methyl-6-{[(3,4,5-trimethoxyphenyl)amino]methyl}quinazoline-2,4-diamine
Traditional IUPAC Nametrimetrexate
CAS Registry Number52128-35-5
SMILES
COC1=CC(NCC2=C(C)C3=C(C=C2)N=C(N)N=C3N)=CC(OC)=C1OC
InChI Identifier
InChI=1S/C19H23N5O3/c1-10-11(5-6-13-16(10)18(20)24-19(21)23-13)9-22-12-7-14(25-2)17(27-4)15(8-12)26-3/h5-8,22H,9H2,1-4H3,(H4,20,21,23,24)
InChI KeyNOYPYLRCIDNJJB-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassQuinazolines
Sub ClassN/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Pyrogallols and Derivatives
Substituents
  • Alkyl Aryl Ether
  • Aminopyrimidine
  • Anisole
  • Phenylmethylamine
  • Polyamine
  • Pyrimidine
  • Toluene
Direct ParentQuinazolines
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
Biofunction
  • Antibiotics
  • Antifungal Agents
  • Antimetabolites, Antineoplastic
  • Antiprotozoals
  • Folic Acid Antagonists
Application
  • Pharmaceutical
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point215 - 217 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.09e-02 g/LNot Available
LogP2Not Available
Predicted Properties
PropertyValueSource
water solubility0.031 g/LALOGPS
logP2.36ALOGPS
logP2.28ChemAxon
logS-4.1ALOGPS
pKa (strongest acidic)17.04ChemAxon
pKa (strongest basic)7.54ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count8ChemAxon
hydrogen donor count3ChemAxon
polar surface area117.54ChemAxon
rotatable bond count6ChemAxon
refractivity107.7ChemAxon
polarizability40.24ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01157
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01157
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01157
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5381
KEGG Compound IDC11154
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTrimetrexate
NuGOwiki LinkHMDB15288
Metagene LinkHMDB15288
METLIN IDNot Available
PubChem Compound5583
PDB IDNot Available
ChEBI ID119101
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
DHFR
Uniprot ID:
P00374