(1S,2R,6S,14R,15R,16R)-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: 175582
• Molecular Formular: C25H35NO4
• Molecular Mass: 413.5497
• Monoisotopic Mass: 413.25660861
• 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)CCN1)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]3NCC1)ccc2O
• InChI: InChI=1S/C25H35NO4/c1-21(2,3)22(4,28)16-13-23-8-9-25(16,29-5)20-24(23)10-11-26-17(23)12-14-6-7-15(27)19(30-20)18(14)24/h6-7,16-17,20,26-28H,8-13H2,1-5H3/t16-,17-,20-,22?,23-,24+,25-/m1/s1
• InChIKey: YOYLLRBMGQRFTN-SMCOLXIQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,6S,14R,15R,16R)-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)-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-(1,1-Dimethylethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-α-methyl-6,14-ethenomorphinan-7-methanol; N-De(cyclopropylmethyl)buprenorphine; N-Dealkylbuprenorphine; N-Desalkylbuprenorphine; Norbuprenorphine

Database IDs

• CAS Number: 78715-23-8
• PubChem SID: 164231492
• PubChem CID: 10001793

CALCULATED PROPERTIES

• Acid pKa: 9.796366
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.35394773
• LogD (pH = 7.4): 0.2944721
• Log P: 2.3001823
• Molar Refractivity: 114.5256 cm^3
• Polarizability: 45.635803 Å^3
• Polar Surface Area: 70.95 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Light Brown Solid
• Melting Point: 221-224°C

Safety Information

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

DETAILS

Toronto Research Chemicals - N661300

A metabolite of Buprenorphine.

REFERENCES

• Cone, E., et al.: Drug Metab. Dispos., 12, 577 (1984)
• Chauvin, M., et al.: Anesthesiology, 66, 327 (1984)
• Ceccato, A., et al.: J. Pharm. Biomed. Anal., 32, 619 (1984)
• Sittl, R., et al.: Clin. Ther., 27, 225 (1984)