3-[(1-methyl-1H-indol-3-yl)methylidene]-1H,2H,3H-pyrrolo[3,2-b]pyridin-2-one hydrochloride

• ChemBase ID: 154401
• Molecular Formular: C17H14ClN3O
• Molecular Mass: 311.76556
• Monoisotopic Mass: 311.08253976
• SMILES: Cn1cc(c2c1cccc2)/C=C/1\c2c(cccn2)NC1=O.Cl
• Canonical SMILES: O=C1Nc2c(/C/1=C\c1cn(c3c1cccc3)C)nccc2.Cl
• InChI: InChI=1S/C17H13N3O.ClH/c1-20-10-11(12-5-2-3-7-15(12)20)9-13-16-14(19-17(13)21)6-4-8-18-16;/h2-10H,1H3,(H,19,21);1H
• InChIKey: GXUJPQDCLCDKLU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(1-methyl-1H-indol-3-yl)methylidene]-1H,2H,3H-pyrrolo[3,2-b]pyridin-2-one hydrochloride
• IUPAC Traditional name: 3-[(1-methylindol-3-yl)methylidene]-1H-pyrrolo[3,2-b]pyridin-2-one hydrochloride
• Synonyms: 1,3-Dihydro-3-[(1-methyl-1H-indol-3-yl)methylene]-2H-pyrrolo[3,2-b]pyridin-2-one hydrochloride; GW441756 hydrochloride

Database IDs

• CAS Number: 504433-24-3(freebase)
• MDL Number: MFCD07370136
• PubChem SID: 162248540; 24895126
• PubChem CID: 71311857

CALCULATED PROPERTIES

• Acid pKa: 10.1827545
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.7552888
• LogD (pH = 7.4): 2.7551591
• Log P: 2.755846
• Molar Refractivity: 83.1856 cm^3
• Polarizability: 31.915184 Å^3
• Polar Surface Area: 46.92 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble10 mg/mL
• Apperance: powder, red
• Melting Point: ≥270 °C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C17H13N3O · HCl

DETAILS

Sigma Aldrich - G3420

Biochem/physiol Actions
Highly selective and potent TrkA kinase inhibitor. Orally active. IC50 = 2 nM
Legal Information
Sold for research purposes under agreement from Glaxo-Smith-Kline