(1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-10-[(1S,2R,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-10-yl]-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-11-ol

• ChemBase ID: 177089
• Molecular Formular: C58H80N2O8
• Molecular Mass: 933.2644
• Monoisotopic Mass: 932.59146753
• SMILES: c1(c2c3c(cc1c1c(c4c5c(c1)C[C@@H]1[C@]67[C@@]5([C@H]([C@]([C@H](C6)C(C(C)(C)C)(O)C)(CC7)OC)O4)CCN1CC1CC1)O)C[C@@H]1[C@]45[C@@]3([C@H]([C@]([C@H](C4)C(C(C)(C)C)(O)C)(CC5)OC)O2)CCN1CC1CC1)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]3N(CC1)CC1CC1)cc(c2O)c1cc2C[C@H]3N(CC[C@]45c2c(c1O)O[C@H]4[C@@]1(OC)CC[C@@]35C[C@@H]1C(C(C)(C)C)(O)C)CC1CC1
• InChI: InChI=1S/C58H80N2O8/c1-49(2,3)51(7,63)37-27-53-15-17-57(37,65-9)47-55(53)19-21-59(29-31-11-12-31)39(53)25-33-23-35(43(61)45(67-47)41(33)55)36-24-34-26-40-54-16-18-58(66-10,38(28-54)52(8,64)50(4,5)6)48-56(54,42(34)46(68-48)44(36)62)20-22-60(40)30-32-13-14-32/h23-24,31-32,37-40,47-48,61-64H,11-22,25-30H2,1-10H3/t37-,38-,39-,40-,47-,48-,51?,52?,53-,54-,55+,56+,57-,58-/m1/s1
• InChIKey: IIKJUPFUFVJKHV-BFVCJTJTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-10-[(1S,2R,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-10-yl]-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-11-ol
• IUPAC Traditional name: (1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-10-[(1S,2R,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-10-yl]-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-11-ol
• Synonyms: (αS,5α,7α)-(α'S,5'α,7'α)-17,17'-Bis(cyclopropylmethyl)-α,α'-bis(1,1-dimethylethyl)-4,5:4',5'-diepoxy-18,18',19,19'-tetrahydro-3,3'-dihydroxy-6,6'-dimethoxy-α,α'-dimethyl-[2,2'-bi-6,14-ethenomorphinan]-7,7'-dimethanol; Buprenorphine Impurity G; [5α,7α(S)]-[5'α,7'α(S)]-17,17'-Bis(cyclopropylmethyl)-α,α'-bis(1,1-dimethylethyl)-4,5:4',5'-diepoxy-18,18',19,19'-tetrahydro-3,3'-dihydroxy-6,6'-dimethoxy-α,α'-dimethyl-[2,2'-bi-6,14-ethenomorphinan]-7,7'-dimethanol; Pseudo Buprenorphine

Database IDs

• CAS Number: 163597-04-4
• PubChem SID: 164232999
• PubChem CID: 71751866

CALCULATED PROPERTIES

• Acid pKa: 9.113151
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): 0.8249498
• LogD (pH = 7.4): 2.7333724
• Log P: 6.3189626
• Molar Refractivity: 262.6028 cm^3
• Polarizability: 105.16672 Å^3
• Polar Surface Area: 124.32 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P839160

An impurity of Buprenorphine (B689570).

REFERENCES

• Debrabandere, L. et al.: J. Forensic Sci., 40, 250 (1995)