Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2021-09-14 15:42:23 UTC
HMDB IDHMDB0014780
Secondary Accession Numbers
  • HMDB14780
Metabolite Identification
Common NamePemetrexed
DescriptionPemetrexed is only found in individuals that have used or taken this drug. It is a chemotherapy drug manufactured and marketed by Eli Lilly and Company. Its indications are the treatment of pleural mesothelioma as well as non-small cell lung cancer.Pemetrexed is an antifolate containing the pyrrolopyrimidine-based nucleus that exerts its antineoplastic activity by disrupting folate-dependent metabolic processes essential for cell replication. In vitro studies have shown that pemetrexed inhibits thymidylate synthase (TS), dihydrofolate reductase (DHFR), and glycinamide ribonucleotide formyltransferase (GARFT), all folate-dependent enzymes involved in the de novo biosynthesis of thymidine and purine nucleotides. Pemetrexed is transported into cells by both the reduced folate carrier and membrane folate binding protein transport systems. Once in the cell, pemetrexed is converted to polyglutamate forms by the enzyme folylpolyglutamate synthetase. The polyglutamate forms are retained in cells and are inhibitors of TS and GARFT. Polyglutamation is a time- and concentration-dependent process that occurs in tumor cells and, to a lesser extent, in normal tissues. Polyglutamated metabolites have an increased intracellular half-life resulting in prolonged drug action in malignant cells.
Structure
Data?1582753220
Synonyms
ValueSource
LY231514HMDB
Pemetrexed disodiumHMDB
MTAHMDB
N-(4-(2-(2-Amino-3,4-dihydro-4-oxo-7H-pyrrolo(2,3-D)pyrimdin-5-yl)ethyl)benzoyl)glutamic acidHMDB
Disodium, pemetrexedHMDB
ALIMTAHMDB
(2R)-2-{[4-(2-{4-hydroxy-2-imino-1H,2H,7H-pyrrolo[2,3-D]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioateGenerator
PemetrexedMeSH
Chemical FormulaC20H21N5O6
Average Molecular Weight427.4106
Monoisotopic Molecular Weight427.149183429
IUPAC Name(2R)-2-{[4-(2-{2-amino-4-oxo-1H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioic acid
Traditional Namepemetrexed
CAS Registry Number150399-23-8
SMILES
NC1=NC(=O)C2=C(NC=C2CCC2=CC=C(C=C2)C(=O)N[C@H](CCC(O)=O)C(O)=O)N1
InChI Identifier
InChI=1S/C20H21N5O6/c21-20-24-16-15(18(29)25-20)12(9-22-16)6-3-10-1-4-11(5-2-10)17(28)23-13(19(30)31)7-8-14(26)27/h1-2,4-5,9,13H,3,6-8H2,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29)/t13-/m1/s1
InChI KeyWBXPDJSOTKVWSJ-CYBMUJFWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • Hippuric acid or derivatives
  • Hippuric acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Benzamide
  • Benzoic acid or derivatives
  • Pyrrolo[2,3-d]pyrimidine
  • Pyrrolopyrimidine
  • Benzoyl
  • Hydroxypyrimidine
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • Substituted pyrrole
  • Pyrimidine
  • Heteroaromatic compound
  • Pyrrole
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.046 g/LNot Available
LogP-1.5Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.046 g/LALOGPS
logP10(0.11) g/LALOGPS
logP10(0.73) g/LChemAxon
logS10(-4) g/LALOGPS
pKa (Strongest Acidic)3.34ChemAxon
pKa (Strongest Basic)0.96ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area186.97 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity109.45 m³·mol⁻¹ChemAxon
Polarizability43.04 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+201.59231661259
DarkChem[M-H]-191.53631661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pemetrexed,1TMS,#1C[Si](C)(C)OC(=O)CC[C@@H](NC(=O)C1=CC=C(CCC2=C[NH]C3=C2C(=O)N=C(N)[NH]3)C=C1)C(=O)O4159.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,1TMS,#2C[Si](C)(C)OC(=O)[C@@H](CCC(=O)O)NC(=O)C1=CC=C(CCC2=C[NH]C3=C2C(=O)N=C(N)[NH]3)C=C14158.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,1TMS,#3C[Si](C)(C)NC1=NC(=O)C2=C([NH]C=C2CCC2=CC=C(C(=O)N[C@H](CCC(=O)O)C(=O)O)C=C2)[NH]14270.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,1TMS,#4C[Si](C)(C)N1C=C(CCC2=CC=C(C(=O)N[C@H](CCC(=O)O)C(=O)O)C=C2)C2=C1[NH]C(N)=NC2=O4259.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,1TMS,#5C[Si](C)(C)N(C(=O)C1=CC=C(CCC2=C[NH]C3=C2C(=O)N=C(N)[NH]3)C=C1)[C@H](CCC(=O)O)C(=O)O4161.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,1TMS,#6C[Si](C)(C)N1C(N)=NC(=O)C2=C1[NH]C=C2CCC1=CC=C(C(=O)N[C@H](CCC(=O)O)C(=O)O)C=C14238.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TMS,#1C[Si](C)(C)OC(=O)CC[C@@H](NC(=O)C1=CC=C(CCC2=C[NH]C3=C2C(=O)N=C(N)[NH]3)C=C1)C(=O)O[Si](C)(C)C3953.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TMS,#2C[Si](C)(C)NC1=NC(=O)C2=C([NH]C=C2CCC2=CC=C(C(=O)N[C@H](CCC(=O)O[Si](C)(C)C)C(=O)O)C=C2)[NH]14051.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TMS,#3C[Si](C)(C)OC(=O)CC[C@H](C(=O)O)N(C(=O)C1=CC=C(CCC2=C[NH]C3=C2C(=O)N=C(N)[NH]3)C=C1)[Si](C)(C)C3935.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TMS,#4C[Si](C)(C)OC(=O)CC[C@@H](NC(=O)C1=CC=C(CCC2=CN([Si](C)(C)C)C3=C2C(=O)N=C(N)[NH]3)C=C1)C(=O)O4032.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TMS,#5C[Si](C)(C)OC(=O)CC[C@@H](NC(=O)C1=CC=C(CCC2=C[NH]C3=C2C(=O)N=C(N)N3[Si](C)(C)C)C=C1)C(=O)O4029.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TMS,#6C[Si](C)(C)NC1=NC(=O)C2=C([NH]C=C2CCC2=CC=C(C(=O)N[C@H](CCC(=O)O)C(=O)O[Si](C)(C)C)C=C2)[NH]14052.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TMS,#7C[Si](C)(C)OC(=O)[C@@H](CCC(=O)O)N(C(=O)C1=CC=C(CCC2=C[NH]C3=C2C(=O)N=C(N)[NH]3)C=C1)[Si](C)(C)C3970.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TMS,#8C[Si](C)(C)OC(=O)[C@@H](CCC(=O)O)NC(=O)C1=CC=C(CCC2=CN([Si](C)(C)C)C3=C2C(=O)N=C(N)[NH]3)C=C14017.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TMS,#9C[Si](C)(C)OC(=O)[C@@H](CCC(=O)O)NC(=O)C1=CC=C(CCC2=C[NH]C3=C2C(=O)N=C(N)N3[Si](C)(C)C)C=C14035.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TMS,#10C[Si](C)(C)N(C1=NC(=O)C2=C([NH]C=C2CCC2=CC=C(C(=O)N[C@H](CCC(=O)O)C(=O)O)C=C2)[NH]1)[Si](C)(C)C4104.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TMS,#11C[Si](C)(C)NC1=NC(=O)C2=C([NH]C=C2CCC2=CC=C(C(=O)N([C@H](CCC(=O)O)C(=O)O)[Si](C)(C)C)C=C2)[NH]14066.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TMS,#12C[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C)C=C2CCC1=CC=C(C(=O)N[C@H](CCC(=O)O)C(=O)O)C=C14188.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TMS,#13C[Si](C)(C)NC1=NC(=O)C2=C([NH]C=C2CCC2=CC=C(C(=O)N[C@H](CCC(=O)O)C(=O)O)C=C2)N1[Si](C)(C)C4150.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TMS,#14C[Si](C)(C)N(C(=O)C1=CC=C(CCC2=CN([Si](C)(C)C)C3=C2C(=O)N=C(N)[NH]3)C=C1)[C@H](CCC(=O)O)C(=O)O4002.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TMS,#15C[Si](C)(C)N1C=C(CCC2=CC=C(C(=O)N[C@H](CCC(=O)O)C(=O)O)C=C2)C2=C1N([Si](C)(C)C)C(N)=NC2=O4170.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TMS,#16C[Si](C)(C)N(C(=O)C1=CC=C(CCC2=C[NH]C3=C2C(=O)N=C(N)N3[Si](C)(C)C)C=C1)[C@H](CCC(=O)O)C(=O)O4034.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,1TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](NC(=O)C1=CC=C(CCC2=C[NH]C3=C2C(=O)N=C(N)[NH]3)C=C1)C(=O)O4448.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,1TBDMS,#2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CCC(=O)O)NC(=O)C1=CC=C(CCC2=C[NH]C3=C2C(=O)N=C(N)[NH]3)C=C14444.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,1TBDMS,#3CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]C=C2CCC2=CC=C(C(=O)N[C@H](CCC(=O)O)C(=O)O)C=C2)[NH]14466.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,1TBDMS,#4CC(C)(C)[Si](C)(C)N1C=C(CCC2=CC=C(C(=O)N[C@H](CCC(=O)O)C(=O)O)C=C2)C2=C1[NH]C(N)=NC2=O4447.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,1TBDMS,#5CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C(CCC2=C[NH]C3=C2C(=O)N=C(N)[NH]3)C=C1)[C@H](CCC(=O)O)C(=O)O4400.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,1TBDMS,#6CC(C)(C)[Si](C)(C)N1C(N)=NC(=O)C2=C1[NH]C=C2CCC1=CC=C(C(=O)N[C@H](CCC(=O)O)C(=O)O)C=C14397.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](NC(=O)C1=CC=C(CCC2=C[NH]C3=C2C(=O)N=C(N)[NH]3)C=C1)C(=O)O[Si](C)(C)C(C)(C)C4491.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TBDMS,#2CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]C=C2CCC2=CC=C(C(=O)N[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)C=C2)[NH]14512.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TBDMS,#3CC(C)(C)[Si](C)(C)OC(=O)CC[C@H](C(=O)O)N(C(=O)C1=CC=C(CCC2=C[NH]C3=C2C(=O)N=C(N)[NH]3)C=C1)[Si](C)(C)C(C)(C)C4440.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TBDMS,#4CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](NC(=O)C1=CC=C(CCC2=CN([Si](C)(C)C(C)(C)C)C3=C2C(=O)N=C(N)[NH]3)C=C1)C(=O)O4485.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TBDMS,#5CC(C)(C)[Si](C)(C)OC(=O)CC[C@@H](NC(=O)C1=CC=C(CCC2=C[NH]C3=C2C(=O)N=C(N)N3[Si](C)(C)C(C)(C)C)C=C1)C(=O)O4479.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TBDMS,#6CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]C=C2CCC2=CC=C(C(=O)N[C@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)C=C2)[NH]14490.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TBDMS,#7CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CCC(=O)O)N(C(=O)C1=CC=C(CCC2=C[NH]C3=C2C(=O)N=C(N)[NH]3)C=C1)[Si](C)(C)C(C)(C)C4447.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TBDMS,#8CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CCC(=O)O)NC(=O)C1=CC=C(CCC2=CN([Si](C)(C)C(C)(C)C)C3=C2C(=O)N=C(N)[NH]3)C=C14480.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TBDMS,#9CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CCC(=O)O)NC(=O)C1=CC=C(CCC2=C[NH]C3=C2C(=O)N=C(N)N3[Si](C)(C)C(C)(C)C)C=C14476.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TBDMS,#10CC(C)(C)[Si](C)(C)N(C1=NC(=O)C2=C([NH]C=C2CCC2=CC=C(C(=O)N[C@H](CCC(=O)O)C(=O)O)C=C2)[NH]1)[Si](C)(C)C(C)(C)C4541.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TBDMS,#11CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]C=C2CCC2=CC=C(C(=O)N([C@H](CCC(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C)C=C2)[NH]14454.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TBDMS,#12CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]1)N([Si](C)(C)C(C)(C)C)C=C2CCC1=CC=C(C(=O)N[C@H](CCC(=O)O)C(=O)O)C=C14573.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TBDMS,#13CC(C)(C)[Si](C)(C)NC1=NC(=O)C2=C([NH]C=C2CCC2=CC=C(C(=O)N[C@H](CCC(=O)O)C(=O)O)C=C2)N1[Si](C)(C)C(C)(C)C4559.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TBDMS,#14CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C(CCC2=CN([Si](C)(C)C(C)(C)C)C3=C2C(=O)N=C(N)[NH]3)C=C1)[C@H](CCC(=O)O)C(=O)O4431.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TBDMS,#15CC(C)(C)[Si](C)(C)N1C=C(CCC2=CC=C(C(=O)N[C@H](CCC(=O)O)C(=O)O)C=C2)C2=C1N([Si](C)(C)C(C)(C)C)C(N)=NC2=O4556.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Pemetrexed,2TBDMS,#16CC(C)(C)[Si](C)(C)N(C(=O)C1=CC=C(CCC2=C[NH]C3=C2C(=O)N=C(N)N3[Si](C)(C)C(C)(C)C)C=C1)[C@H](CCC(=O)O)C(=O)O4458.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pemetrexed GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-4296100000-61f13aa328f04f2193462017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pemetrexed GC-MS (2 TMS) - 70eV, Positivesplash10-056r-1222390000-1922107d9a1510f7ea852017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pemetrexed GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pemetrexed GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Pemetrexed DI-ESI-qTof , Positive-QTOFsplash10-00di-0009300000-2b11923a816fae5694ac2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pemetrexed 10V, Positive-QTOFsplash10-03di-0124900000-823efc7fe28d46d36b1e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pemetrexed 20V, Positive-QTOFsplash10-01q9-0595200000-40f20d687bf52bf258502017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pemetrexed 40V, Positive-QTOFsplash10-0j59-2950000000-02b1adc8f50941ec66512017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pemetrexed 10V, Negative-QTOFsplash10-004i-0003900000-05ee3dff6a5cb9c0f0082017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pemetrexed 20V, Negative-QTOFsplash10-055f-7449700000-e8461ae1b25e058467dc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pemetrexed 40V, Negative-QTOFsplash10-0f6y-9581000000-1d564e2a04015586902a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pemetrexed 10V, Positive-QTOFsplash10-0059-0060900000-c08073e1cb9d840b7ae92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pemetrexed 20V, Positive-QTOFsplash10-001i-1980000000-905a773cb8f67a9df28e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pemetrexed 40V, Positive-QTOFsplash10-03e9-1940000000-d4ae1b2367ede6e4bc562021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pemetrexed 10V, Negative-QTOFsplash10-0bvi-0004900000-cfe04a4c69804bd48ab72021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pemetrexed 20V, Negative-QTOFsplash10-0pec-1907500000-a026b00353204e58661d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pemetrexed 40V, Negative-QTOFsplash10-0udi-2910000000-3d0cf7fa7cfd8b10c8812021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00642 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00642 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID54830
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPemetrexed
METLIN IDNot Available
PubChem Compound60843
PDB IDNot Available
ChEBI ID775209
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 References
  1. Adjei AA: Pemetrexed (Alimta): a novel multitargeted antifolate agent. Expert Rev Anticancer Ther. 2003 Apr;3(2):145-56. [PubMed:12722874 ]
  2. Rollins KD, Lindley C: Pemetrexed: a multitargeted antifolate. Clin Ther. 2005 Sep;27(9):1343-82. [PubMed:16291410 ]
  3. Lansiaux A, Lokiec F: [Pemetrexed: from preclinic to clinic]. Bull Cancer. 2007;94 Spec No Actualites:S134-8. [PubMed:17845983 ]
  4. Fuld AD, Dragnev KH, Rigas JR: Pemetrexed in advanced non-small-cell lung cancer. Expert Opin Pharmacother. 2010 Jun;11(8):1387-402. doi: 10.1517/14656566.2010.482560. [PubMed:20446853 ]

Enzymes

General function:
Involved in ATP binding
Specific function:
Required for the phosphorylation of the deoxyribonucleosides deoxycytidine (dC), deoxyguanosine (dG) and deoxyadenosine (dA). Has broad substrate specificity, and does not display selectivity based on the chirality of the substrate. It is also an essential enzyme for the phosphorylation of numerous nucleoside analogs widely employed as antiviral and chemotherapeutic agents.
Gene Name:
DCK
Uniprot ID:
P27707
Molecular weight:
30518.315
References
  1. De Pas TM, Toffalorio F, Giovannetti E, Radice D, Russo F, Angeli I, Calamai G, Spitaleri G, Catania C, Noberasco C, Milani A, Pelosi G, Danesi R, De Braud F: Optimizing pemetrexed-gemcitabine combination in patients with advanced non-small cell lung cancer: a pharmacogenetic approach. J Thorac Oncol. 2011 Apr;6(4):768-73. doi: 10.1097/JTO.0b013e31820d7818. [PubMed:21336182 ]
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GART
Uniprot ID:
P22102
Molecular weight:
107766.295
References
  1. Schultz RM, Dempsey JA: Sequence dependence of Alimta (LY231514, MTA) combined with doxorubicin in ZR-75-1 human breast carcinoma cells. Anticancer Res. 2001 Sep-Oct;21(5):3209-14. [PubMed:11848474 ]
  2. Hanauske AR, Chen V, Paoletti P, Niyikiza C: Pemetrexed disodium: a novel antifolate clinically active against multiple solid tumors. Oncologist. 2001;6(4):363-73. [PubMed:11524555 ]
  3. Molina JR, Adjei AA: The role of Pemetrexed (Alimta , LY231514) in lung cancer therapy. Clin Lung Cancer. 2003 Jul;5(1):21-7. [PubMed:14596699 ]
  4. Giovannetti E, Mey V, Nannizzi S, Pasqualetti G, Marini L, Del Tacca M, Danesi R: Cellular and pharmacogenetics foundation of synergistic interaction of pemetrexed and gemcitabine in human non-small-cell lung cancer cells. Mol Pharmacol. 2005 Jul;68(1):110-8. Epub 2005 Mar 28. [PubMed:15795320 ]
  5. Kindler HL: Pemetrexed in pancreatic cancer. Semin Oncol. 2002 Dec;29(6 Suppl 18):49-53. [PubMed:12571811 ]
  6. Adjei AA: Gemcitabine and Pemetrexed disodium in treating breast cancer. Oncology (Williston Park). 2001 Feb;15(2 Suppl 3):34-7. [PubMed:11252887 ]
  7. Pivot X, Raymond E, Laguerre B, Degardin M, Cals L, Armand JP, Lefebvre JL, Gedouin D, Ripoche V, Kayitalire L, Niyikiza C, Johnson R, Latz J, Schneider M: Pemetrexed disodium in recurrent locally advanced or metastatic squamous cell carcinoma of the head and neck. Br J Cancer. 2001 Sep 1;85(5):649-55. [PubMed:11531245 ]
  8. Adjei AA: Gemcitabine and pemetrexed disodium combinations in vitro and in vivo. Lung Cancer. 2001 Dec;34 Suppl 4:S103-5. [PubMed:11742712 ]
  9. Adjei AA: Pemetrexed in the treatment of selected solid tumors. Semin Oncol. 2002 Apr;29(2 Suppl 5):50-3. [PubMed:12023793 ]
  10. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
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. Hanauske AR, Chen V, Paoletti P, Niyikiza C: Pemetrexed disodium: a novel antifolate clinically active against multiple solid tumors. Oncologist. 2001;6(4):363-73. [PubMed:11524555 ]
  2. Norman P: Pemetrexed disodium (Eli Lilly). Curr Opin Investig Drugs. 2001 Nov;2(11):1611-22. [PubMed:11763166 ]
  3. Mauritz R, Peters GJ, Priest DG, Assaraf YG, Drori S, Kathmann I, Noordhuis P, Bunni MA, Rosowsky A, Schornagel JH, Pinedo HM, Jansen G: Multiple mechanisms of resistance to methotrexate and novel antifolates in human CCRF-CEM leukemia cells and their implications for folate homeostasis. Biochem Pharmacol. 2002 Jan 15;63(2):105-15. [PubMed:11841783 ]
  4. Schultz RM, Dempsey JA: Sequence dependence of Alimta (LY231514, MTA) combined with doxorubicin in ZR-75-1 human breast carcinoma cells. Anticancer Res. 2001 Sep-Oct;21(5):3209-14. [PubMed:11848474 ]
  5. Adjei AA: Pemetrexed in the treatment of selected solid tumors. Semin Oncol. 2002 Apr;29(2 Suppl 5):50-3. [PubMed:12023793 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  7. Adjei AA: Gemcitabine and Pemetrexed disodium in treating breast cancer. Oncology (Williston Park). 2001 Feb;15(2 Suppl 3):34-7. [PubMed:11252887 ]
  8. Pivot X, Raymond E, Laguerre B, Degardin M, Cals L, Armand JP, Lefebvre JL, Gedouin D, Ripoche V, Kayitalire L, Niyikiza C, Johnson R, Latz J, Schneider M: Pemetrexed disodium in recurrent locally advanced or metastatic squamous cell carcinoma of the head and neck. Br J Cancer. 2001 Sep 1;85(5):649-55. [PubMed:11531245 ]
  9. Adjei AA: Gemcitabine and pemetrexed disodium combinations in vitro and in vivo. Lung Cancer. 2001 Dec;34 Suppl 4:S103-5. [PubMed:11742712 ]
  10. Molina JR, Adjei AA: The role of Pemetrexed (Alimta , LY231514) in lung cancer therapy. Clin Lung Cancer. 2003 Jul;5(1):21-7. [PubMed:14596699 ]
  11. Giovannetti E, Mey V, Nannizzi S, Pasqualetti G, Marini L, Del Tacca M, Danesi R: Cellular and pharmacogenetics foundation of synergistic interaction of pemetrexed and gemcitabine in human non-small-cell lung cancer cells. Mol Pharmacol. 2005 Jul;68(1):110-8. Epub 2005 Mar 28. [PubMed:15795320 ]
  12. Kindler HL: Pemetrexed in pancreatic cancer. Semin Oncol. 2002 Dec;29(6 Suppl 18):49-53. [PubMed:12571811 ]
General function:
Involved in IMP cyclohydrolase activity
Specific function:
Bifunctional enzyme that catalyzes 2 steps in purine biosynthesis.
Gene Name:
ATIC
Uniprot ID:
P31939
Molecular weight:
64615.255
References
  1. Kindler HL: Pemetrexed in pancreatic cancer. Semin Oncol. 2002 Dec;29(6 Suppl 18):49-53. [PubMed:12571811 ]
  2. Hanauske AR, Chen V, Paoletti P, Niyikiza C: Pemetrexed disodium: a novel antifolate clinically active against multiple solid tumors. Oncologist. 2001;6(4):363-73. [PubMed:11524555 ]
  3. Racanelli AC, Rothbart SB, Heyer CL, Moran RG: Therapeutics by cytotoxic metabolite accumulation: pemetrexed causes ZMP accumulation, AMPK activation, and mammalian target of rapamycin inhibition. Cancer Res. 2009 Jul 1;69(13):5467-74. doi: 10.1158/0008-5472.CAN-08-4979. Epub 2009 Jun 23. [PubMed:19549896 ]
General function:
Involved in thymidylate synthase activity
Specific function:
Contributes to the de novo mitochondrial thymidylate biosynthesis pathway.
Gene Name:
TYMS
Uniprot ID:
P04818
Molecular weight:
35715.65
References
  1. Adjei AA: Gemcitabine and Pemetrexed disodium in treating breast cancer. Oncology (Williston Park). 2001 Feb;15(2 Suppl 3):34-7. [PubMed:11252887 ]
  2. Hanauske AR, Chen V, Paoletti P, Niyikiza C: Pemetrexed disodium: a novel antifolate clinically active against multiple solid tumors. Oncologist. 2001;6(4):363-73. [PubMed:11524555 ]
  3. Pivot X, Raymond E, Laguerre B, Degardin M, Cals L, Armand JP, Lefebvre JL, Gedouin D, Ripoche V, Kayitalire L, Niyikiza C, Johnson R, Latz J, Schneider M: Pemetrexed disodium in recurrent locally advanced or metastatic squamous cell carcinoma of the head and neck. Br J Cancer. 2001 Sep 1;85(5):649-55. [PubMed:11531245 ]
  4. Adjei AA: Gemcitabine and pemetrexed disodium combinations in vitro and in vivo. Lung Cancer. 2001 Dec;34 Suppl 4:S103-5. [PubMed:11742712 ]
  5. Norman P: Pemetrexed disodium (Eli Lilly). Curr Opin Investig Drugs. 2001 Nov;2(11):1611-22. [PubMed:11763166 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  7. Schultz RM, Dempsey JA: Sequence dependence of Alimta (LY231514, MTA) combined with doxorubicin in ZR-75-1 human breast carcinoma cells. Anticancer Res. 2001 Sep-Oct;21(5):3209-14. [PubMed:11848474 ]
  8. Adjei AA: Pemetrexed in the treatment of selected solid tumors. Semin Oncol. 2002 Apr;29(2 Suppl 5):50-3. [PubMed:12023793 ]
  9. Molina JR, Adjei AA: The role of Pemetrexed (Alimta , LY231514) in lung cancer therapy. Clin Lung Cancer. 2003 Jul;5(1):21-7. [PubMed:14596699 ]
  10. Giovannetti E, Mey V, Nannizzi S, Pasqualetti G, Marini L, Del Tacca M, Danesi R: Cellular and pharmacogenetics foundation of synergistic interaction of pemetrexed and gemcitabine in human non-small-cell lung cancer cells. Mol Pharmacol. 2005 Jul;68(1):110-8. Epub 2005 Mar 28. [PubMed:15795320 ]
  11. Kindler HL: Pemetrexed in pancreatic cancer. Semin Oncol. 2002 Dec;29(6 Suppl 18):49-53. [PubMed:12571811 ]

Transporters

General function:
Involved in nucleoside transmembrane transporter activity
Specific function:
Mediates both influx and efflux of nucleosides across the membrane (equilibrative transporter). It is sensitive (ES) to low concentrations of the inhibitor nitrobenzylmercaptopurine riboside (NBMPR) and is sodium-independent. It has a higher affinity for adenosine. Inhibited by dipyridamole and dilazep (anticancer chemotherapeutics drugs)
Gene Name:
SLC29A1
Uniprot ID:
Q99808
Molecular weight:
50218.8
References
  1. De Pas TM, Toffalorio F, Giovannetti E, Radice D, Russo F, Angeli I, Calamai G, Spitaleri G, Catania C, Noberasco C, Milani A, Pelosi G, Danesi R, De Braud F: Optimizing pemetrexed-gemcitabine combination in patients with advanced non-small cell lung cancer: a pharmacogenetic approach. J Thorac Oncol. 2011 Apr;6(4):768-73. doi: 10.1097/JTO.0b013e31820d7818. [PubMed:21336182 ]