(3S,6S,9S,15aR)-9-[(2R)-butan-2-yl]-6-[(1-methoxy-1H-indol-3-yl)methyl]-3-(6-oxooctyl)-tetradecahydro-1H-pyrido[1,2-a]1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrone

• ChemBase ID: 160752
• Molecular Formular: C34H49N5O6
• Molecular Mass: 623.78276
• Monoisotopic Mass: 623.36828431
• SMILES: c1ccc2c(c1)c(cn2OC)C[C@@H]1NC(=O)[C@@H](NC(=O)[C@@H]2N(C(=O)[C@H](NC1=O)[C@H](C)CC)CCCC2)CCCCCC(=O)CC
• Canonical SMILES: CCC(=O)CCCCC[C@@H]1NC(=O)[C@H]2CCCCN2C(=O)[C@H](NC(=O)[C@@H](NC1=O)Cc1cn(c2c1cccc2)OC)[C@@H](CC)C
• InChI: InChI=1S/C34H49N5O6/c1-5-22(3)30-34(44)38-19-13-12-18-29(38)33(43)35-26(16-9-7-8-14-24(40)6-2)31(41)36-27(32(42)37-30)20-23-21-39(45-4)28-17-11-10-15-25(23)28/h10-11,15,17,21-22,26-27,29-30H,5-9,12-14,16,18-20H2,1-4H3,(H,35,43)(H,36,41)(H,37,42)/t22-,26+,27+,29-,30+/m1/s1
• InChIKey: JWOGUUIOCYMBPV-VWIQTCEGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,6S,9S,15aR)-9-[(2R)-butan-2-yl]-6-[(1-methoxy-1H-indol-3-yl)methyl]-3-(6-oxooctyl)-tetradecahydro-1H-pyrido[1,2-a]1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrone
• IUPAC Traditional name: (3S,6S,9S,15aR)-9-[(2R)-butan-2-yl]-6-[(1-methoxyindol-3-yl)methyl]-3-(6-oxooctyl)-decahydro-2H-pyrido[1,2-a]1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrone
• Synonyms: N-[4-(1-Cyanocyclopentyl)phenyl]-2-[(4-pyridinylmethyl)amino]-3-pyridinecarboxamide; YN968D1 Hydrochloride; Apatinib Hydrochloride

Database IDs

• CAS Number: 1218779-89-5
• PubChem SID: 162254887
• PubChem CID: 44593387

CALCULATED PROPERTIES

• Acid pKa: 10.834099
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 3.374681
• LogD (pH = 7.4): 3.3745413
• Log P: 3.374683
• Molar Refractivity: 171.2108 cm^3
• Polarizability: 67.55282 Å^3
• Polar Surface Area: 138.84 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A726150

Apatinib is an orally available, small molecule multitargeted tyrosine kinase inhibitor. Apatinib selectively inhibits the vascular endothelial growth factor receptor-2 (VEGFR2). Apatinib functions by inhibiting VEGF-mediated endothelial cell migration an

REFERENCES

• Mi, Y. et al.: Cancer Res., 70, 7981 (2010)
• Tong, X.Z. et al.: Biochem. Pharmacol., 83, 586 (2010)
• Ding, J, et al.: J. Chrom B Anal. Technol. Biomed. Life Sci., 895, 108 (2010)