(2R,3S,9R)-5-acetyl-6-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0^{2,9}.0^{3,7}.0^{15,18}]octadeca-1(17),5,11(18),12,14-pentaen-4-one

• ChemBase ID: 5245
• Molecular Formular: C20H20N2O3
• Molecular Mass: 336.3844
• Monoisotopic Mass: 336.14739251
• SMILES: O=C1C(=C(N2[C@H]1[C@H]1c3c[nH]c4c3c(ccc4)C[C@H]1C2(C)C)O)C(=O)C
• Canonical SMILES: CC(=O)C1=C(O)N2[C@H](C1=O)[C@H]1c3c[nH]c4c3c(C[C@H]1C2(C)C)ccc4
• InChI: InChI=1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,25H,7H2,1-3H3/t12-,16+,17+/m1/s1
• InChIKey: RLOAZVAJNNPPDI-DQYPLSBCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,9R)-5-acetyl-6-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0^{2,9}.0^{3,7}.0^{15,18}]octadeca-1(17),5,11(18),12,14-pentaen-4-one
• IUPAC Traditional name: (2R,3S,9R)-5-acetyl-6-hydroxy-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0^{2,9}.0^{3,7}.0^{15,18}]octadeca-1(17),5,11(18),12,14-pentaen-4-one
• Synonyms: (6AR,11AS,11BR)-10-ACETYL-9-HYDROXY-7,7-DIMETHYL-2,6,6A,7,11A,11B-HEXAHYDRO-11H-PYRROLO[1',2':2,3]ISOINDOLO[4,5,6-CD]INDOL-11-ONE

Database IDs

• PubChem SID: 160968674; 99444075
• PubChem CID: 54682463; 65261

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.560514
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.239259
• LogD (pH = 7.4): -0.9651673
• Log P: 3.0807009
• Molar Refractivity: 103.9978 cm^3
• Polarizability: 37.018154 Å^3
• Polar Surface Area: 73.4 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.47
• LOG S: -3.3
• Solubility (Water): 1.69e-01 g/l

DETAILS

DrugBank - DB07604

Drug information: experimental