Pralatrexate (CHEM019821)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:32:46 UTC
Update Date2016-11-09 01:16:04 UTC
Accession NumberCHEM019821
Identification
Common NamePralatrexate
ClassSmall Molecule
DescriptionA pteridine that is the N-4-benzoyl derivative of L-glutamic acid. Used for treatment of Peripheral T-Cell Lymphoma, an aggressive form of non-Hodgkins lymphoma.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S)-2-((4-((1Rs)-1-((2,4-Diaminopteridin-6-yl)methyl)but-3-ynyl)benzoyl)amino)pentanedioic acidChEBI
(2S)-2-({4-[1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl]benzoyl}amino)pentanedioic acidChEBI
10-Propargyl-10-deazaaminopterinChEBI
FolotynChEBI
HSDB 7786ChEBI
N-(4-(1-((2,4-Diamino-6-pteridinyl)methyl)-3-butynyl)benzoyl)-L-glutamic acidChEBI
PralatrexatoChEBI
PralatrexatumChEBI
(2S)-2-((4-((1Rs)-1-((2,4-Diaminopteridin-6-yl)methyl)but-3-ynyl)benzoyl)amino)pentanedioateGenerator
(2S)-2-({4-[1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl]benzoyl}amino)pentanedioateGenerator
N-(4-(1-((2,4-Diamino-6-pteridinyl)methyl)-3-butynyl)benzoyl)-L-glutamateGenerator
Pralatrexic acidGenerator
Chemical FormulaC23H23N7O5
Average Molecular Mass477.473 g/mol
Monoisotopic Mass477.176 g/mol
CAS Registry Number146464-95-1
IUPAC Name(2S)-2-({4-[1-(2,4-diaminopteridin-6-yl)pent-4-yn-2-yl]phenyl}formamido)pentanedioic acid
Traditional Namepralatrexate
SMILESNC1=NC2=NC=C(CC(CC#C)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(O)=O)C(O)=O)N=C2C(N)=N1
InChI IdentifierInChI=1S/C23H23N7O5/c1-2-3-14(10-15-11-26-20-18(27-15)19(24)29-23(25)30-20)12-4-6-13(7-5-12)21(33)28-16(22(34)35)8-9-17(31)32/h1,4-7,11,14,16H,3,8-10H2,(H,28,33)(H,31,32)(H,34,35)(H4,24,25,26,29,30)/t14?,16-/m0/s1
InChI KeyOGSBUKJUDHAQEA-WMCAAGNKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzothiadiazoles. These are heterocyclic aromatic compounds containing a benzene ring fused to a thiadiazole ring. Thiadiazole is a five-membered aromatic heterocycle made up of one sulfur atom and two nitrogen atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiadiazoles
Sub ClassNot Available
Direct ParentBenzothiadiazoles
Alternative Parents
Substituents
  • 1,2,3-benzothiadiazole
  • Thiobenzoic acid or derivatives
  • Benzenoid
  • Azole
  • Thiadiazole
  • Heteroaromatic compound
  • Carbothioic s-ester
  • Thiocarboxylic acid ester
  • Azacycle
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Solubility0.018 g/LALOGPS
logP0.1ALOGPS
logP0.33ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)3.44ChemAxon
pKa (Strongest Basic)2.86ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area207.3 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity126.82 m³·mol⁻¹ChemAxon
Polarizability47.31 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-1513900000-5596beb52832aa3566ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01si-0002900000-6fc75eff8254786e9df5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0106900000-5ac9be915593c90e1ce4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0059-2698000000-a5acf2f9d1da2432962aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0000900000-b353523bc14906b8a722Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-1203900000-e69e51466057378426a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9425000000-129bfd939baa92b07749Spectrum
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 IDDB06813
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 LinkPralatrexate
Chemspider IDNot Available
ChEBI ID71223
PubChem Compound ID148121
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=20622807
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20669794
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20702104
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=20739433
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21179031
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21245435
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21417858
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21591544
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21726160
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21841501
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21939422
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21956523
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22076116
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22343388
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=22362328
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=22394596
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=22457602
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=22534814
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=22542448
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=22789917
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=22921318
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=23008944
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=23032692
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=23040436
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=23115213