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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-24 21:13:23 UTC
Update Date2021-09-24 21:13:23 UTC
HMDB IDHMDB0304896
Secondary Accession NumbersNone
Metabolite Identification
Common NameLarotrectinib
Description(3S)-N-{5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl}-3-hydroxypyrrolidine-1-carboximidic acid belongs to the class of organic compounds known as phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. Based on a literature review very few articles have been published on (3S)-N-{5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl}-3-hydroxypyrrolidine-1-carboximidic acid.
Structure
Thumb
Synonyms
ValueSource
(3S)-N-{5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl}-3-hydroxypyrrolidine-1-carboximidateGenerator
ARRY-470MeSH
LOXO-101MeSH
N-(5-(2-(2,5-Difluorophenyl)pyrrolidin-1-yl)pyrazolo(1,5-a)pyrimidin-3-yl)-3-hydroxypyrrolidine-1-carboxamideMeSH
VitrakviMeSH
Chemical FormulaC21H22F2N6O2
Average Molecular Weight428.444
Monoisotopic Molecular Weight428.177230298
IUPAC Name(3S)-N-{5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl}-3-hydroxypyrrolidine-1-carboxamide
Traditional Name(3S)-N-{5-[(2R)-2-(2,5-difluorophenyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-3-yl}-3-hydroxypyrrolidine-1-carboxamide
CAS Registry NumberNot Available
SMILES
O[C@H]1CCN(C1)C(=O)NC1=C2N=C(C=CN2N=C1)N1CCC[C@@H]1C1=C(F)C=CC(F)=C1
InChI Identifier
InChI=1S/C21H22F2N6O2/c22-13-3-4-16(23)15(10-13)18-2-1-7-28(18)19-6-9-29-20(26-19)17(11-24-29)25-21(31)27-8-5-14(30)12-27/h3-4,6,9-11,14,18,30H,1-2,5,7-8,12H2,(H,25,31)/t14-,18+/m0/s1
InChI KeyNYNZQNWKBKUAII-KBXCAEBGSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrrolidines
Sub ClassPhenylpyrrolidines
Direct ParentPhenylpyrrolidines
Alternative Parents
Substituents
  • 2-phenylpyrrolidine
  • Pyrazolo[1,5-a]pyrimidine
  • Pyrazolopyrimidine
  • Pyrrolidine carboxylic acid or derivatives
  • Dialkylarylamine
  • Pyrrolidine-1-carboxamide
  • Aminopyrimidine
  • Fluorobenzene
  • Halobenzene
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Pyrimidine
  • Imidolactam
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Pyrazole
  • Azole
  • Urea
  • Tertiary amine
  • Secondary alcohol
  • Azacycle
  • Amine
  • Organohalogen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organofluoride
  • Organonitrogen compound
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.07ALOGPS
logP2.44ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)10.44ChemAxon
pKa (Strongest Basic)1.17ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity122.96 m³·mol⁻¹ChemAxon
Polarizability41.45 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+198.52432859911
AllCCS[M+H-H2O]+196.18232859911
AllCCS[M+Na]+201.2932859911
AllCCS[M+NH4]+200.67532859911
AllCCS[M-H]-196.30232859911
AllCCS[M+Na-2H]-196.4232859911
AllCCS[M+HCOO]-196.732859911
DeepCCS[M+H]+198.92530932474
DeepCCS[M-H]-196.5330932474
DeepCCS[M-2H]-229.41330932474
DeepCCS[M+Na]+204.83830932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Larotrectinib,2TMS,isomer #1C[Si](C)(C)O[C@H]1CCN(C(=O)N(C2=C3N=C(N4CCC[C@@H]4C4=CC(F)=CC=C4F)C=CN3N=C2)[Si](C)(C)C)C13550.7Semi standard non polar33892256
Larotrectinib,2TMS,isomer #1C[Si](C)(C)O[C@H]1CCN(C(=O)N(C2=C3N=C(N4CCC[C@@H]4C4=CC(F)=CC=C4F)C=CN3N=C2)[Si](C)(C)C)C13480.5Standard non polar33892256
Larotrectinib,2TMS,isomer #1C[Si](C)(C)O[C@H]1CCN(C(=O)N(C2=C3N=C(N4CCC[C@@H]4C4=CC(F)=CC=C4F)C=CN3N=C2)[Si](C)(C)C)C14650.3Standard polar33892256
Larotrectinib,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CCN(C(=O)N(C2=C3N=C(N4CCC[C@@H]4C4=CC(F)=CC=C4F)C=CN3N=C2)[Si](C)(C)C(C)(C)C)C13934.4Semi standard non polar33892256
Larotrectinib,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CCN(C(=O)N(C2=C3N=C(N4CCC[C@@H]4C4=CC(F)=CC=C4F)C=CN3N=C2)[Si](C)(C)C(C)(C)C)C13934.8Standard non polar33892256
Larotrectinib,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CCN(C(=O)N(C2=C3N=C(N4CCC[C@@H]4C4=CC(F)=CC=C4F)C=CN3N=C2)[Si](C)(C)C(C)(C)C)C14670.8Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Larotrectinib 10V, Positive-QTOFsplash10-004i-0000900000-e2a6bbe5d45ba2eff4592021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Larotrectinib 20V, Positive-QTOFsplash10-004i-0003900000-c8eb341681ccf7895c9d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Larotrectinib 40V, Positive-QTOFsplash10-0frt-0198200000-e4ddadbeaf7a22f130482021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Larotrectinib 10V, Negative-QTOFsplash10-004i-0000900000-12e16b56afd7cc3639ad2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Larotrectinib 20V, Negative-QTOFsplash10-004i-1114900000-ea5893716e003fe283df2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Larotrectinib 40V, Negative-QTOFsplash10-0w2d-3793200000-acae1e1d5e4a7e0456b62021-10-11Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
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 ID44210503
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
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