(1S,2R,3S,6S,14R,15R,16R)-3-(cyclopropylmethyl)-11-hydroxy-16-(2-hydroxy-3,3-dimethylbutan-2-yl)-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7,9,11-trien-3-ium-3-olate

• ChemBase ID: 163097
• Molecular Formular: C29H41NO5
• Molecular Mass: 483.63954
• Monoisotopic Mass: 483.29847342
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]45[C@@]3([C@H]([C@]([C@H](C4)C(C(C)(C)C)(C)O)(CC5)OC)O2)CC[N@@+]1(CC1CC1)[O-])O
• Canonical SMILES: CO[C@]12CC[C@]3(C[C@@H]1C(C(C)(C)C)(O)C)[C@@]14[C@H]2Oc2c4c(C[C@H]3[N@@+](CC1)([O-])CC1CC1)ccc2O
• InChI: InChI=1S/C29H41NO5/c1-25(2,3)26(4,32)20-15-27-10-11-29(20,34-5)24-28(27)12-13-30(33,16-17-6-7-17)21(27)14-18-8-9-19(31)23(35-24)22(18)28/h8-9,17,20-21,24,31-32H,6-7,10-16H2,1-5H3/t20-,21-,24-,26?,27-,28+,29-,30+/m1/s1
• InChIKey: UHSWHHMBOWNLKN-OJHOSZFKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,3S,6S,14R,15R,16R)-3-(cyclopropylmethyl)-11-hydroxy-16-(2-hydroxy-3,3-dimethylbutan-2-yl)-15-methoxy-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-trien-3-ium-3-olate
• IUPAC Traditional name: (1S,2R,3S,6S,14R,15R,16R)-3-(cyclopropylmethyl)-11-hydroxy-16-(2-hydroxy-3,3-dimethylbutan-2-yl)-15-methoxy-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-trien-3-ium-3-olate
• Synonyms: [5α,7α(S)]-17-(Cyclopropylmethyl)-α-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-α-methyl-6,14-ethenomorphinan-7-methanol 17-Oxide; Buprenorphine N-oxide

Database IDs

• CAS Number: 112242-17-8
• PubChem SID: 162257232
• PubChem CID: 71314295

CALCULATED PROPERTIES

• Acid pKa: 9.808115
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.907646
• LogD (pH = 7.4): 2.9060214
• Log P: 2.907704
• Molar Refractivity: 133.8072 cm^3
• Polarizability: 52.56774 Å^3
• Polar Surface Area: 85.8 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Yellow Solid
• Melting Point: 206-209°C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

DETAILS

Toronto Research Chemicals - B689575

Prodrug of Buprenorphine, exhibits improved bioavailability