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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:55 UTC
HMDB IDHMDB0015288
Secondary Accession Numbers
  • HMDB15288
Metabolite Identification
Common NameTrimetrexate
DescriptionTrimetrexate, also known as trimetrexic acid or neutrexin, belongs to the class of organic compounds known as quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups. Trimetrexate is a drug which is used for use, with concurrent leucovorin administration (leucovorin protection), as an alternative therapy for the treatment of moderate-to-severe pneumocystis carinii pneumonia (pcp) in immunocompromised patients, including patients with the acquired immunodeficiency syndrome (aids). also used to treat several types of cancer including colon cancer. It has been investigated for use in treating leiomyosarcoma.It is a methotrexate (MTX) analog that is active against transport-deficient MTX-resistant tumor cells that overcome the acquired and natural resistance to methotrexate. Trimetrexate is a very strong basic compound (based on its pKa). Trimetrexate is a potentially toxic compound. It is a dihydrofolate reductase inhibitor. It has been used with leucovorin in treating pneumocystis pneumonia. Other uses include skin lymphoma. Trimetrexate is a quinazoline derivative.
Structure
Data?1582753279
Synonyms
ValueSource
Trimetrexic acidGenerator
NeutrexinHMDB
TMQHMDB
TMXHMDB
Monohydrate, monoacetate trimetrexateHMDB
Trimetrexate ipsen brandHMDB
Trimetrexate monohydrate, monoacetateHMDB
JB 11HMDB
Hydrate, trimetrexateHMDB
Ipsen brand OF trimetrexateHMDB
JB-11HMDB
Trimetrexate hydrateHMDB
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 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
Description Belongs to the class of organic compounds known as quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassBenzodiazines
Direct ParentQuinazolinamines
Alternative Parents
Substituents
  • Quinazolinamine
  • Methoxyaniline
  • Aminophenyl ether
  • Aniline or substituted anilines
  • Phenylalkylamine
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Secondary aliphatic/aromatic amine
  • Alkyl aryl ether
  • Aralkylamine
  • Aminopyrimidine
  • Pyrimidine
  • Benzenoid
  • Imidolactam
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Ether
  • Azacycle
  • Secondary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Primary amine
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point215 - 217 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.031 g/LNot Available
LogP2Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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 Area117.54 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity107.7 m³·mol⁻¹ChemAxon
Polarizability40.24 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+189.09931661259
DarkChem[M-H]-191.48431661259
DeepCCS[M+H]+188.60330932474
DeepCCS[M-H]-186.24530932474
DeepCCS[M-2H]-220.3530932474
DeepCCS[M+Na]+195.57830932474
AllCCS[M+H]+190.732859911
AllCCS[M+H-H2O]+187.932859911
AllCCS[M+NH4]+193.332859911
AllCCS[M+Na]+194.032859911
AllCCS[M-H]-192.132859911
AllCCS[M+Na-2H]-192.132859911
AllCCS[M+HCOO]-192.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TrimetrexateCOC1=CC(NCC2=C(C)C3=C(C=C2)N=C(N)N=C3N)=CC(OC)=C1OC4771.5Standard polar33892256
TrimetrexateCOC1=CC(NCC2=C(C)C3=C(C=C2)N=C(N)N=C3N)=CC(OC)=C1OC3432.8Standard non polar33892256
TrimetrexateCOC1=CC(NCC2=C(C)C3=C(C=C2)N=C(N)N=C3N)=CC(OC)=C1OC3703.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Trimetrexate,1TMS,isomer #1COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC3661.3Semi standard non polar33892256
Trimetrexate,1TMS,isomer #1COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC3368.0Standard non polar33892256
Trimetrexate,1TMS,isomer #1COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC5134.2Standard polar33892256
Trimetrexate,1TMS,isomer #2COC1=CC(NCC2=CC=C3N=C(N)N=C(N[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC3706.8Semi standard non polar33892256
Trimetrexate,1TMS,isomer #2COC1=CC(NCC2=CC=C3N=C(N)N=C(N[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC3375.3Standard non polar33892256
Trimetrexate,1TMS,isomer #2COC1=CC(NCC2=CC=C3N=C(N)N=C(N[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC5112.1Standard polar33892256
Trimetrexate,1TMS,isomer #3COC1=CC(N(CC2=CC=C3N=C(N)N=C(N)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC3604.7Semi standard non polar33892256
Trimetrexate,1TMS,isomer #3COC1=CC(N(CC2=CC=C3N=C(N)N=C(N)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC3356.9Standard non polar33892256
Trimetrexate,1TMS,isomer #3COC1=CC(N(CC2=CC=C3N=C(N)N=C(N)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC5209.0Standard polar33892256
Trimetrexate,2TMS,isomer #1COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC3663.4Semi standard non polar33892256
Trimetrexate,2TMS,isomer #1COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC3399.4Standard non polar33892256
Trimetrexate,2TMS,isomer #1COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC4854.6Standard polar33892256
Trimetrexate,2TMS,isomer #2COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC3505.5Semi standard non polar33892256
Trimetrexate,2TMS,isomer #2COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC3307.7Standard non polar33892256
Trimetrexate,2TMS,isomer #2COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC4707.8Standard polar33892256
Trimetrexate,2TMS,isomer #3COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC3562.7Semi standard non polar33892256
Trimetrexate,2TMS,isomer #3COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC3458.6Standard non polar33892256
Trimetrexate,2TMS,isomer #3COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC4780.1Standard polar33892256
Trimetrexate,2TMS,isomer #4COC1=CC(N(CC2=CC=C3N=C(N)N=C(N[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC3528.1Semi standard non polar33892256
Trimetrexate,2TMS,isomer #4COC1=CC(N(CC2=CC=C3N=C(N)N=C(N[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC3333.8Standard non polar33892256
Trimetrexate,2TMS,isomer #4COC1=CC(N(CC2=CC=C3N=C(N)N=C(N[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC4688.1Standard polar33892256
Trimetrexate,2TMS,isomer #5COC1=CC(NCC2=CC=C3N=C(N)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC3568.5Semi standard non polar33892256
Trimetrexate,2TMS,isomer #5COC1=CC(NCC2=CC=C3N=C(N)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC3467.5Standard non polar33892256
Trimetrexate,2TMS,isomer #5COC1=CC(NCC2=CC=C3N=C(N)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC4811.2Standard polar33892256
Trimetrexate,3TMS,isomer #1COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC3454.0Semi standard non polar33892256
Trimetrexate,3TMS,isomer #1COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC3268.8Standard non polar33892256
Trimetrexate,3TMS,isomer #1COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC4483.7Standard polar33892256
Trimetrexate,3TMS,isomer #2COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC3553.3Semi standard non polar33892256
Trimetrexate,3TMS,isomer #2COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC3487.8Standard non polar33892256
Trimetrexate,3TMS,isomer #2COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC4429.4Standard polar33892256
Trimetrexate,3TMS,isomer #3COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC3558.5Semi standard non polar33892256
Trimetrexate,3TMS,isomer #3COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC3466.0Standard non polar33892256
Trimetrexate,3TMS,isomer #3COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC4485.3Standard polar33892256
Trimetrexate,3TMS,isomer #4COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC3417.0Semi standard non polar33892256
Trimetrexate,3TMS,isomer #4COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC3386.1Standard non polar33892256
Trimetrexate,3TMS,isomer #4COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC4432.4Standard polar33892256
Trimetrexate,3TMS,isomer #5COC1=CC(N(CC2=CC=C3N=C(N)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC3412.7Semi standard non polar33892256
Trimetrexate,3TMS,isomer #5COC1=CC(N(CC2=CC=C3N=C(N)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC3397.5Standard non polar33892256
Trimetrexate,3TMS,isomer #5COC1=CC(N(CC2=CC=C3N=C(N)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC4472.5Standard polar33892256
Trimetrexate,4TMS,isomer #1COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC3410.2Semi standard non polar33892256
Trimetrexate,4TMS,isomer #1COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC3360.5Standard non polar33892256
Trimetrexate,4TMS,isomer #1COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC4143.7Standard polar33892256
Trimetrexate,4TMS,isomer #2COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC3408.9Semi standard non polar33892256
Trimetrexate,4TMS,isomer #2COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC3337.4Standard non polar33892256
Trimetrexate,4TMS,isomer #2COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC4191.7Standard polar33892256
Trimetrexate,4TMS,isomer #3COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC3485.8Semi standard non polar33892256
Trimetrexate,4TMS,isomer #3COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC3554.9Standard non polar33892256
Trimetrexate,4TMS,isomer #3COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)=CC(OC)=C1OC4138.1Standard polar33892256
Trimetrexate,5TMS,isomer #1COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC3416.5Semi standard non polar33892256
Trimetrexate,5TMS,isomer #1COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC3440.4Standard non polar33892256
Trimetrexate,5TMS,isomer #1COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(N([Si](C)(C)C)[Si](C)(C)C)C3=C2C)[Si](C)(C)C)=CC(OC)=C1OC3890.8Standard polar33892256
Trimetrexate,1TBDMS,isomer #1COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC3818.1Semi standard non polar33892256
Trimetrexate,1TBDMS,isomer #1COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC3570.1Standard non polar33892256
Trimetrexate,1TBDMS,isomer #1COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC5025.9Standard polar33892256
Trimetrexate,1TBDMS,isomer #2COC1=CC(NCC2=CC=C3N=C(N)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC3884.1Semi standard non polar33892256
Trimetrexate,1TBDMS,isomer #2COC1=CC(NCC2=CC=C3N=C(N)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC3570.0Standard non polar33892256
Trimetrexate,1TBDMS,isomer #2COC1=CC(NCC2=CC=C3N=C(N)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC5029.1Standard polar33892256
Trimetrexate,1TBDMS,isomer #3COC1=CC(N(CC2=CC=C3N=C(N)N=C(N)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3836.9Semi standard non polar33892256
Trimetrexate,1TBDMS,isomer #3COC1=CC(N(CC2=CC=C3N=C(N)N=C(N)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3514.4Standard non polar33892256
Trimetrexate,1TBDMS,isomer #3COC1=CC(N(CC2=CC=C3N=C(N)N=C(N)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC5158.2Standard polar33892256
Trimetrexate,2TBDMS,isomer #1COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC4021.6Semi standard non polar33892256
Trimetrexate,2TBDMS,isomer #1COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC3796.1Standard non polar33892256
Trimetrexate,2TBDMS,isomer #1COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC4767.0Standard polar33892256
Trimetrexate,2TBDMS,isomer #2COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3830.2Semi standard non polar33892256
Trimetrexate,2TBDMS,isomer #2COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3665.1Standard non polar33892256
Trimetrexate,2TBDMS,isomer #2COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC4679.3Standard polar33892256
Trimetrexate,2TBDMS,isomer #3COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC3937.8Semi standard non polar33892256
Trimetrexate,2TBDMS,isomer #3COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC3769.1Standard non polar33892256
Trimetrexate,2TBDMS,isomer #3COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)=CC(OC)=C1OC4672.8Standard polar33892256
Trimetrexate,2TBDMS,isomer #4COC1=CC(N(CC2=CC=C3N=C(N)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3849.8Semi standard non polar33892256
Trimetrexate,2TBDMS,isomer #4COC1=CC(N(CC2=CC=C3N=C(N)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3685.6Standard non polar33892256
Trimetrexate,2TBDMS,isomer #4COC1=CC(N(CC2=CC=C3N=C(N)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC4678.6Standard polar33892256
Trimetrexate,2TBDMS,isomer #5COC1=CC(NCC2=CC=C3N=C(N)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC3959.3Semi standard non polar33892256
Trimetrexate,2TBDMS,isomer #5COC1=CC(NCC2=CC=C3N=C(N)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC3783.3Standard non polar33892256
Trimetrexate,2TBDMS,isomer #5COC1=CC(NCC2=CC=C3N=C(N)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC4728.1Standard polar33892256
Trimetrexate,3TBDMS,isomer #1COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3904.1Semi standard non polar33892256
Trimetrexate,3TBDMS,isomer #1COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3824.9Standard non polar33892256
Trimetrexate,3TBDMS,isomer #1COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC4549.4Standard polar33892256
Trimetrexate,3TBDMS,isomer #2COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC4068.7Semi standard non polar33892256
Trimetrexate,3TBDMS,isomer #2COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC3991.9Standard non polar33892256
Trimetrexate,3TBDMS,isomer #2COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC4469.4Standard polar33892256
Trimetrexate,3TBDMS,isomer #3COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC4064.4Semi standard non polar33892256
Trimetrexate,3TBDMS,isomer #3COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC3975.7Standard non polar33892256
Trimetrexate,3TBDMS,isomer #3COC1=CC(NCC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC4518.2Standard polar33892256
Trimetrexate,3TBDMS,isomer #4COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3960.8Semi standard non polar33892256
Trimetrexate,3TBDMS,isomer #4COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3836.3Standard non polar33892256
Trimetrexate,3TBDMS,isomer #4COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC4477.6Standard polar33892256
Trimetrexate,3TBDMS,isomer #5COC1=CC(N(CC2=CC=C3N=C(N)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3948.1Semi standard non polar33892256
Trimetrexate,3TBDMS,isomer #5COC1=CC(N(CC2=CC=C3N=C(N)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC3851.7Standard non polar33892256
Trimetrexate,3TBDMS,isomer #5COC1=CC(N(CC2=CC=C3N=C(N)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC4526.1Standard polar33892256
Trimetrexate,4TBDMS,isomer #1COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC4032.2Semi standard non polar33892256
Trimetrexate,4TBDMS,isomer #1COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC4032.6Standard non polar33892256
Trimetrexate,4TBDMS,isomer #1COC1=CC(N(CC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC4338.8Standard polar33892256
Trimetrexate,4TBDMS,isomer #2COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC4031.3Semi standard non polar33892256
Trimetrexate,4TBDMS,isomer #2COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC4017.8Standard non polar33892256
Trimetrexate,4TBDMS,isomer #2COC1=CC(N(CC2=CC=C3N=C(N[Si](C)(C)C(C)(C)C)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC4383.2Standard polar33892256
Trimetrexate,4TBDMS,isomer #3COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC4129.9Semi standard non polar33892256
Trimetrexate,4TBDMS,isomer #3COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC4173.1Standard non polar33892256
Trimetrexate,4TBDMS,isomer #3COC1=CC(NCC2=CC=C3N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C3=C2C)=CC(OC)=C1OC4293.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Trimetrexate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ugj-0409000000-97a2080cda5a334649532017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trimetrexate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimetrexate 10V, Positive-QTOFsplash10-00dr-0409000000-a9fcda741827d39a85bc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimetrexate 20V, Positive-QTOFsplash10-000i-0903000000-d3e9f90709b809eb4f3d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimetrexate 40V, Positive-QTOFsplash10-000i-2911000000-97342eb0d2ab1fad8f132016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimetrexate 10V, Negative-QTOFsplash10-014i-0209000000-e610f7928dd8d57d924c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimetrexate 20V, Negative-QTOFsplash10-014i-0209000000-c28a10a57fcb7298832a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimetrexate 40V, Negative-QTOFsplash10-00kf-9431000000-249d2de16520a29665852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimetrexate 10V, Positive-QTOFsplash10-00di-0109000000-a0632a23538eb5952dd12021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimetrexate 20V, Positive-QTOFsplash10-00di-0309000000-95e446c0693d174b1b3e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimetrexate 40V, Positive-QTOFsplash10-000i-0930000000-a03a19d017251496a0fb2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimetrexate 10V, Negative-QTOFsplash10-014i-0009000000-f667390d4352ff65f24d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimetrexate 20V, Negative-QTOFsplash10-0gbi-0129000000-24c353e7a0c027954a2a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trimetrexate 40V, Negative-QTOFsplash10-00vj-2493000000-41a8bf8d77660b776bda2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01157 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01157 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01157
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5381
KEGG Compound IDC11154
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTrimetrexate
METLIN IDNot Available
PubChem Compound5583
PDB IDNot Available
ChEBI ID119101
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in dihydrofolate reductase activity
Specific function:
Key enzyme in folate metabolism. Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis. Binds its own mRNA and that of DHFRL1.
Gene Name:
DHFR
Uniprot ID:
P00374
Molecular weight:
21452.61
References
  1. Bertino JR, Zhao SC, Mineishi S, Ercikan-Abali EA, Banerjee D: Use of variants of dihydrofolate reductase in gene transfer to produce resistance to methotrexate and trimetrexate. Prog Exp Tumor Res. 1999;36:82-94. [PubMed:10386066 ]
  2. Graffner-Nordberg M, Kolmodin K, Aqvist J, Queener SF, Hallberg A: Design, synthesis, computational prediction, and biological evaluation of ester soft drugs as inhibitors of dihydrofolate reductase from Pneumocystis carinii. J Med Chem. 2001 Jul 19;44(15):2391-402. [PubMed:11448221 ]
  3. Warlick CA, Diers MD, Wagner JE, McIvor RS: In vivo selection of antifolate-resistant transgenic hematopoietic stem cells in a murine bone marrow transplant model. J Pharmacol Exp Ther. 2002 Jan;300(1):50-6. [PubMed:11752096 ]
  4. Zhu WY, Bunni M, Priest DG, DiCapua JL, Dressler JM, Chen Z, Melera PW: Severe folate restriction results in depletion of and alteration in the composition of the intracellular folate pool, moderate sensitization to methotrexate and trimetrexate, upregulation of endogenous DHFR activity, and overexpression of metallothionein II and folate receptor alpha that, upon folate repletion, confer drug resistance to CHL cells. J Exp Ther Oncol. 2002 Sep-Oct;2(5):264-77. [PubMed:12416030 ]
  5. Sweeney CL, Frandsen JL, Verfaillie CM, McIvor RS: Trimetrexate inhibits progression of the murine 32Dp210 model of chronic myeloid leukemia in animals expressing drug-resistant dihydrofolate reductase. Cancer Res. 2003 Mar 15;63(6):1304-10. [PubMed:12649191 ]
  6. Polshakov VI, Birdsall B, Frenkiel TA, Gargaro AR, Feeney J: Structure and dynamics in solution of the complex of Lactobacillus casei dihydrofolate reductase with the new lipophilic antifolate drug trimetrexate. Protein Sci. 1999 Mar;8(3):467-81. [PubMed:10091649 ]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]