(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(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-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 175584
• Molecular Formular: C31H43NO10
• Molecular Mass: 589.67382
• Monoisotopic Mass: 589.28869658
• SMILES: [C@H]1(O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)Oc1c2c3c(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
• 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[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C31H43NO10/c1-27(2,3)28(4,38)16-13-29-8-9-31(16,39-5)26-30(29)10-11-32-17(29)12-14-6-7-15(22(42-26)18(14)30)40-25-21(35)19(33)20(34)23(41-25)24(36)37/h6-7,16-17,19-21,23,25-26,32-35,38H,8-13H2,1-5H3,(H,36,37)/t16-,17-,19+,20+,21-,23+,25-,26-,28?,29-,30+,31-/m1/s1
• InChIKey: OOLGGESLZHGXGC-JMMNWFMBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(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-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(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-yl]oxy}oxane-2-carboxylic acid
• Synonyms: Norbuprenorphine Glucuronide; Norbuprenorphine 3-β-D-Glucuronide; (5α,7α)-4,5-Epoxy-18,19-dihydro-7-[(1S)-1-hydroxy-1,2,2-trimethylpropyl]-6-methoxy-6,14-ethenomorphinan-3-yl β-D-Glucopyranosiduronic Acid

Database IDs

• CAS Number: 469887-29-4
• PubChem SID: 164231494
• PubChem CID: 71751172

CALCULATED PROPERTIES

• Acid pKa: 2.6743338
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -1.5513722
• LogD (pH = 7.4): -1.5516284
• Log P: -1.5510259
• Molar Refractivity: 146.5374 cm^3
• Polarizability: 59.23535 Å^3
• Polar Surface Area: 167.17 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: >150°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - N661310

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)