(3S,6S,9S,15aR)-9-[(2S)-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: 312910
• Molecular Formular: C34H49N5O6
• Molecular Mass: 623.78276
• Monoisotopic Mass: 623.36828431
• SMILES: c1(c2c(n(c1)OC)cccc2)C[C@H]1C(=O)N[C@H](C(=O)N2[C@@H](C(=O)N[C@H](C(=O)N1)CCCCCC(=O)CC)CCCC2)[C@H](CC)C
• 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-/m0/s1
• InChIKey: JWOGUUIOCYMBPV-GMFLJSBRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,6S,9S,15aR)-9-[(2S)-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-[(2S)-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: Apicidin (OSI-2040)

Database IDs

• CAS Number: 183506-66-3

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

PROPERTIES

Pharmacology Properties

• Target: HDAC

Product Information

• Salt Data: Free Base