(1R,9R,10S,13R)-3,4-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene-10,13-diol

• ChemBase ID: 1332
• Molecular Formular: C19H27NO4
• Molecular Mass: 333.42198
• Monoisotopic Mass: 333.19400835
• SMILES: O[C@@]12[C@]3(C[C@H](O)CC2)CCN([C@H]1Cc1c3c(OC)c(OC)cc1)C
• Canonical SMILES: COc1c(OC)ccc2c1[C@]13CCN([C@@H](C2)[C@]3(O)CC[C@H](C1)O)C
• InChI: InChI=1S/C19H27NO4/c1-20-9-8-18-11-13(21)6-7-19(18,22)15(20)10-12-4-5-14(23-2)17(24-3)16(12)18/h4-5,13,15,21-22H,6-11H2,1-3H3/t13-,15-,18+,19-/m1/s1
• InChIKey: LCAHPIFLPICNRW-OYYCAODRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,9R,10S,13R)-3,4-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2(7),3,5-triene-10,13-diol
• IUPAC Traditional name: @drotebanol
• Synonyms: Drotebanol

Database IDs

• CAS Number: 3176-03-2
• PubChem SID: 160964792; 46508971
• PubChem CID: 45029744; 6916258

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.643597
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -2.12219
• LogD (pH = 7.4): -0.48397934
• Log P: 1.0239459
• Molar Refractivity: 91.993 cm^3
• Polarizability: 36.04947 Å^3
• Polar Surface Area: 62.16 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.61
• LOG S: -2.19
• Solubility (Water): 2.15e+00 g/l

DETAILS

DrugBank - DB01547

Drug information: illicit; experimental