(2R,6S,14R,15S,16R)-3-(cyclopropylmethyl)-16-(2-hydroxy-3,3-dimethylbutan-2-yl)-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7,9,11-triene-11,15-diol

• ChemBase ID: 166404
• Molecular Formular: C28H39NO4
• Molecular Mass: 453.61356
• Monoisotopic Mass: 453.28790873
• SMILES: c1(c2c3c(cc1)C[C@@H]1C45[C@@]3([C@H]([C@]([C@H](C4)C(C(C)(C)C)(C)O)(O)CC5)O2)CCN1CC1CC1)O
• Canonical SMILES: Oc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)C24CC[C@]1(O)[C@H](C2)C(C(C)(C)C)(O)C)CC1CC1
• InChI: InChI=1S/C28H39NO4/c1-24(2,3)25(4,31)19-14-26-9-10-28(19,32)23-27(26)11-12-29(15-16-5-6-16)20(26)13-17-7-8-18(30)22(33-23)21(17)27/h7-8,16,19-20,23,30-32H,5-6,9-15H2,1-4H3/t19-,20-,23-,25?,26?,27+,28+/m1/s1
• InChIKey: PVQDTNRTSUTFFF-AAAVBUIWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,6S,14R,15S,16R)-3-(cyclopropylmethyl)-16-(2-hydroxy-3,3-dimethylbutan-2-yl)-13-oxa-3-azahexacyclo[13.2.2.1^2,^8.0^1,^6.0^6,^1^4.0^7,^1^2]icosa-7,9,11-triene-11,15-diol
• IUPAC Traditional name: (2R,6S,14R,15S,16R)-3-(cyclopropylmethyl)-16-(2-hydroxy-3,3-dimethylbutan-2-yl)-13-oxa-3-azahexacyclo[13.2.2.1^2,^8.0^1,^6.0^6,^1^4.0^7,^1^2]icosa-7,9,11-triene-11,15-diol
• Synonyms: [5α,7α(S)]-17-(Cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-7-(1-hydroxy-1,2,2-trimethylpropyl)-6,14-ethenomorphinan-3,6-diol; 6-O-Desmethyl Buprenorphine

Database IDs

• CAS Number: 130668-48-3
• PubChem SID: 162260537
• PubChem CID: 71315723

CALCULATED PROPERTIES

• Acid pKa: 10.4151325
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.05577726
• LogD (pH = 7.4): 0.9669743
• Log P: 2.906632
• Molar Refractivity: 127.0111 cm^3
• Polarizability: 50.358246 Å^3
• Polar Surface Area: 73.16 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethylformamide; Methanol
• Apperance: Off-White Solid
• Melting Point: 139-142°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D291290

An intermediate in the production of Buprenorphine.