(2S,3S,5R,6S)-6-{[(1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-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}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 163098
• Molecular Formular: C35H49NO10
• Molecular Mass: 643.76426
• Monoisotopic Mass: 643.33564677
• SMILES: c1(c2c3c(cc1)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[C@H]1[C@H](C([C@@H]([C@@H](O1)C(=O)O)O)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]3N(CC1)CC1CC1)ccc2O[C@@H]1O[C@@H](C(=O)O)[C@H](C([C@@H]1O)O)O
• InChI: InChI=1S/C35H49NO10/c1-31(2,3)32(4,42)20-15-33-10-11-35(20,43-5)30-34(33)12-13-36(16-17-6-7-17)21(33)14-18-8-9-19(26(46-30)22(18)34)44-29-25(39)23(37)24(38)27(45-29)28(40)41/h8-9,17,20-21,23-25,27,29-30,37-39,42H,6-7,10-16H2,1-5H3,(H,40,41)/t20-,21-,23?,24+,25-,27+,29-,30-,32?,33-,34+,35-/m1/s1
• InChIKey: CZULHKGIAJASAA-SXIZQGHHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,5R,6S)-6-{[(1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-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}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,5R,6S)-6-{[(1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-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}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (5α,7α)-17-(Cyclopropylmethyl)-4,5-epoxy-18,19-dihydro-7-[(1S)-1-hydroxy-1,2,2,-trimethylpropyl]-6-methoxy-6,14-ethenomorphinan-3-yl β-D-Glucuronide; Buprenorphine 3-Glucuronide; Buprenorphine 3-β-D-Glucuronide; Buprenorphine Glucuronide; Buprenorphine β-D-Glucuronide

Database IDs

• CAS Number: 101224-22-0
• PubChem SID: 162257233
• PubChem CID: 71314296

CALCULATED PROPERTIES

• Acid pKa: 2.674239
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -0.6471143
• LogD (pH = 7.4): -0.64788723
• Log P: -0.64678246
• Molar Refractivity: 163.7741 cm^3
• Polarizability: 65.84219 Å^3
• Polar Surface Area: 158.38 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol (warm); Water
• Apperance: White Solid

Safety Information

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

DETAILS

Toronto Research Chemicals - B689580

A metabolite of Buprenorphine (B689570). Controlled substance.

REFERENCES

• Rolleri, E., et al.: Clin. Chim. Acta, 66, 319 (1976)
• Moore, R.A., et al.: Ann. Clin. Biochem., 21, 318 (1976)