(1S,10S,11S,14R,15R)-14-(cyanomethyl)-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-5-yl sulfamate

• ChemBase ID: 5238
• Molecular Formular: C21H28N2O4S
• Molecular Mass: 404.52302
• Monoisotopic Mass: 404.17697839
• SMILES: c1(c(cc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2CC#N)C)OC)OS(=O)(=O)N
• Canonical SMILES: N#CC[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1cc(OC)c(c2)OS(=O)(=O)N
• InChI: InChI=1S/C21H28N2O4S/c1-21-9-7-15-16(18(21)6-4-14(21)8-10-22)5-3-13-11-20(27-28(23,24)25)19(26-2)12-17(13)15/h11-12,14-16,18H,3-9H2,1-2H3,(H2,23,24,25)/t14-,15+,16-,18+,21-/m1/s1
• InChIKey: NTSPHKOMJMBWOU-NNKXXINSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10S,11S,14R,15R)-14-(cyanomethyl)-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-5-yl sulfamate
• IUPAC Traditional name: (1S,10S,11S,14R,15R)-14-(cyanomethyl)-4-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6-trien-5-yl sulfamate
• Synonyms: (17beta)-17-(cyanomethyl)-2-methoxyestra-1(10),2,4-trien-3-yl sulfamate

Database IDs

• PubChem SID: 160968667; 99444067
• PubChem CID: 11188898

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.497481
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.237743
• LogD (pH = 7.4): 3.2374394
• Log P: 3.2377467
• Molar Refractivity: 106.1739 cm^3
• Polarizability: 42.13624 Å^3
• Polar Surface Area: 102.41 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.9
• LOG S: -4.79
• Solubility (Water): 6.59e-03 g/l

DETAILS

DrugBank - DB07596

Drug information: experimental