Human Metabolome Database Version 3.5

Showing metabocard for Trimetrexate (HMDB15288)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:51 -0600
Update Date 2013-02-08 17:33:23 -0700
HMDB ID HMDB15288
Secondary Accession Numbers None
Metabolite Identification
Common Name Trimetrexate
Description A 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
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Display: 2D Structure | 3D Structure
Synonyms
  1. TMQ
  2. TMX
  3. Trimetrexato [INN-Spanish]
  4. Trimetrexatum [INN-Latin]
Chemical Formula C19H23N5O3
Average Molecular Weight 369.4176
Monoisotopic Molecular Weight 369.180089627
IUPAC Name 5-methyl-6-{[(3,4,5-trimethoxyphenyl)amino]methyl}quinazoline-2,4-diamine
Traditional IUPAC Name trimetrexate
CAS Registry Number 52128-35-5
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 Key NOYPYLRCIDNJJB-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Quinazolines
Sub Class N/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Pyrogallols and Derivatives
Substituents
  • Alkyl Aryl Ether
  • Aminopyrimidine
  • Anisole
  • Phenylmethylamine
  • Polyamine
  • Pyrimidine
  • Toluene
Direct Parent Quinazolines
Ontology
Status Expected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point 215 - 217 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 3.09e-02 g/L Not Available
LogP 2 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.031 g/L ALOGPS
LogP 2.36 ALOGPS
LogP 2.28 ChemAxon
LogS -4.08 ALOGPS
pKa (strongest acidic) 17.04 ChemAxon
pKa (strongest basic) 7.54 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 117.54 A2 ChemAxon
Rotatable Bond Count 6 ChemAxon
Refractivity 107.7 ChemAxon
Polarizability 40.24 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB01157
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB01157
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB01157 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID 5381 Link_out
KEGG Compound ID C11154 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Trimetrexate Link_out
NuGOwiki Link HMDB15288 Link_out
Metagene Link HMDB15288 Link_out
METLIN ID Not Available
PubChem Compound 5583 Link_out
PDB ID Not Available
ChEBI ID 119101 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: Dihydrofolate reductase
Reactions: Not Available
Gene Name: DHFR
Uniprot ID: P00374 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA