(14S,19R)-19-[(2R)-2-hydroxypentan-2-yl]-15-methoxy-3-methyl-13-oxa-3-azahexacyclo[13.2.2.1^{2,8}.0^{1,6}.0^{6,14}.0^{7,12}]icosa-7,9,11,16-tetraen-11-yl acetate

• ChemBase ID: 1268
• Molecular Formular: C27H35NO5
• Molecular Mass: 453.5705
• Monoisotopic Mass: 453.25152323
• SMILES: O1[C@H]2C34C5(C(N(CC3)C)Cc3c4c1c(OC(=O)C)cc3)C[C@@H](C2(OC)C=C5)[C@](O)(CCC)C
• Canonical SMILES: CCC[C@]([C@H]1CC23C=CC1(OC)[C@@H]1C43CCN(C2Cc2c4c(O1)c(cc2)OC(=O)C)C)(O)C
• InChI: InChI=1S/C27H35NO5/c1-6-9-24(3,30)19-15-25-10-11-27(19,31-5)23-26(25)12-13-28(4)20(25)14-17-7-8-18(32-16(2)29)22(33-23)21(17)26/h7-8,10-11,19-20,23,30H,6,9,12-15H2,1-5H3/t19-,20?,23+,24-,25?,26?,27?/m1/s1
• InChIKey: LFYBMMHFJIAKFE-XRACTLHESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (14S,19R)-19-[(2R)-2-hydroxypentan-2-yl]-15-methoxy-3-methyl-13-oxa-3-azahexacyclo[13.2.2.1^{2,8}.0^{1,6}.0^{6,14}.0^{7,12}]icosa-7,9,11,16-tetraen-11-yl acetate
• IUPAC Traditional name: acetorphine
• Synonyms: Acetorphine

Database IDs

• CAS Number: 25333-77-1
• PubChem SID: 46506577; 160964728
• PubChem CID: 62795

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.683273
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.52695745
• LogD (pH = 7.4): 1.0808058
• Log P: 2.6579092
• Molar Refractivity: 125.6657 cm^3
• Polarizability: 49.22155 Å^3
• Polar Surface Area: 68.23 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.59
• LOG S: -4.36
• Solubility (Water): 1.97e-02 g/l

DETAILS

DrugBank - DB01469

Drug information: illicit; experimental