3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-2,3-dihydro-1H-indol-2-one

• ChemBase ID: 153756
• Molecular Formular: C15H14N2O
• Molecular Mass: 238.28446
• Monoisotopic Mass: 238.11061308
• SMILES: Cc1cc([nH]c1/C=C\1/c2ccccc2NC1=O)C
• Canonical SMILES: O=C1Nc2c(/C/1=C/c1[nH]c(cc1C)C)cccc2
• InChI: InChI=1S/C15H14N2O/c1-9-7-10(2)16-14(9)8-12-11-5-3-4-6-13(11)17-15(12)18/h3-8,16H,1-2H3,(H,17,18)
• InChIKey: WUWDLXZGHZSWQZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-2,3-dihydro-1H-indol-2-one; (3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-2,3-dihydro-1H-indol-2-one
• IUPAC Traditional name: 3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-1H-indol-2-one; semaxanib
• Synonyms: 1,3-Dihydro-3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylene]-2H-indol-2-one; SU 5416; Semaxanib (SU5416)

Database IDs

• CAS Number: 204005-46-9; 194413-58-6
• MDL Number: MFCD01940922
• PubChem SID: 24278606; 162247895
• PubChem CID: 5329098

CALCULATED PROPERTIES

• Acid pKa: 11.290427
• H Acceptors: 1
• H Donor: 2
• LogD (pH = 5.5): 2.9780974
• LogD (pH = 7.4): 2.978045
• Log P: 2.9780982
• Molar Refractivity: 74.5585 cm^3
• Polarizability: 27.052265 Å^3
• Polar Surface Area: 44.89 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: insoluble
• Apperance: yellow to yellow orange

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: -20°C

Pharmacology Properties

• Target: VEGFR
• Gene Information: human ... EGFR(1956), FLT1(2321), IGFBP1(3484), IL2(3558), KDR(3791), PDGFRB(5159)mouse ... Flt1(14254), Kdr(16542)

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C15H14N2O

DETAILS

Sigma Aldrich - S8442

Biochem/physiol Actions
SU 5416 is a vascular endothelial growth factor (VEGF) receptor protein tyrosine kinase 1/2 inhibitor.