Pemetrexed disodium (CHEM019158)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:52:09 UTC
Update Date2016-11-09 01:15:56 UTC
Accession NumberCHEM019158
Identification
Common NamePemetrexed disodium
ClassSmall Molecule
DescriptionAn organic sodium salt that is the disodium salt of N-{4-pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid. Inhibits thymidylate synthase (TS), 421 dihydrofolate reductase (DHFR), and glycinamide ribonucleotide formyltransferase (GARFT).
Contaminant Sources
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Disodium (2S)-2-({4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-D]pyrimidin-5-yl)ethyl]benzoyl}amino)pentanedioateChEBI
AlimtaKegg
Disodium (2S)-2-({4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-D]pyrimidin-5-yl)ethyl]benzoyl}amino)pentanedioic acidGenerator
Disodium;(2S)-2-[[4-[2-(2-amino-4-oxo-1,7-dihydropyrrolo[2,3-D]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acidGenerator
Disodium, pemetrexedMeSH
MTAMeSH
N-(4-(2-(2-amino-3,4-dihydro-4-oxo-7H-pyrrolo(2,3-D)Pyrimdin-5-yl)ethyl)benzoyl)glutamic acidMeSH
PemetrexedMeSH
Pemetrexed disodiumMeSH
Chemical FormulaC20H19N5Na2O6
Average Molecular Mass471.381 g/mol
Monoisotopic Mass471.113 g/mol
CAS Registry Number150399-23-8
IUPAC Namedisodium (2S)-2-{[4-(2-{2-amino-4-oxo-1H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioate
Traditional Namedisodium pemetrexed(2-)
SMILES[Na+].[Na+].NC1=NC(=O)C2=C(NC=C2CCC2=CC=C(C=C2)C(=O)N[C@@H](CCC([O-])=O)C([O-])=O)N1
InChI IdentifierInChI=1S/C20H21N5O6.2Na/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);;/q;2*+1/p-2/t13-;;/m0../s1
InChI KeyNYDXNILOWQXUOF-GXKRWWSZSA-L
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
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Hippuric acid
  • Hippuric acid or derivatives
  • Benzamide
  • Pyrrolo[2,3-d]pyrimidine
  • Benzoic acid or derivatives
  • Pyrrolopyrimidine
  • Benzoyl
  • Aminopyrimidine
  • Pyrimidone
  • Monocyclic benzene moiety
  • Pyrimidine
  • Substituted pyrrole
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Pyrrole
  • Vinylogous amide
  • Heteroaromatic compound
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid salt
  • Azacycle
  • Organic alkali metal salt
  • Carboxylic acid
  • Organoheterocyclic compound
  • Organic salt
  • Organic oxygen compound
  • Organic sodium salt
  • Organic nitrogen compound
  • Amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic zwitterion
  • Primary amine
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP1.54ALOGPS
logP1.49ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.34ChemAxon
pKa (Strongest Basic)0.81ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area192.63 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity131.12 m³·mol⁻¹ChemAxon
Polarizability42.43 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0089-0331900000-441ac22c4f283172cde3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0952400000-7fcec9d6f5416716cabeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0213-2941100000-393c77eebc82561ef87eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-bd1111b18314bb02ad4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0000900000-bd1111b18314bb02ad4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0000900000-bd1111b18314bb02ad4fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT000846
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPemetrexed
Chemspider IDNot Available
ChEBI ID63722
PubChem Compound ID6918197
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19137122
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20209614