methyl (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-carboxylate

• ChemBase ID: 163100
• Molecular Formular: C36H51NO10
• Molecular Mass: 657.79084
• Monoisotopic Mass: 657.35129684
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]45[C@@]3([C@H]([C@]([C@H](C4)C(O)(C(C)(C)C)C)(CC5)OC)O2)CCN1CC1CC1)O[C@H]1[C@H](C([C@@H]([C@@H](O1)C(=O)OC)O)O)O
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2ccc3c4c2O[C@@H]2[C@@]54CCN([C@H](C3)[C@@]35CC[C@@]2(OC)[C@H](C3)C(C(C)(C)C)(O)C)CC2CC2)[C@H](C([C@@H]1O)O)O
• InChI: InChI=1S/C36H51NO10/c1-32(2,3)33(4,42)21-16-34-11-12-36(21,44-6)31-35(34)13-14-37(17-18-7-8-18)22(34)15-19-9-10-20(27(47-31)23(19)35)45-30-26(40)24(38)25(39)28(46-30)29(41)43-5/h9-10,18,21-22,24-26,28,30-31,38-40,42H,7-8,11-17H2,1-6H3/t21-,22-,24?,25+,26-,28+,30-,31-,33?,34-,35+,36-/m1/s1
• InChIKey: VZKKTXYWMBSYAV-PZXCHJTFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (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-carboxylate
• IUPAC Traditional name: methyl (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-carboxylate
• 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-Glucuronic Acid Methyl Ester; Buprenorphine β-D-Glucuronide Methyl Ester

Database IDs

• PubChem SID: 162257235
• PubChem CID: 71314298

CALCULATED PROPERTIES

• Acid pKa: 12.164206
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -1.2127969
• LogD (pH = 7.4): -0.17794576
• Log P: 2.2301798
• Molar Refractivity: 168.5432 cm^3
• Polarizability: 67.91898 Å^3
• Polar Surface Area: 147.38 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMSO; Methanol
• Apperance: Pale-Yellow Foam

DETAILS

Toronto Research Chemicals - B689590

Intermediate in the preparation of Buprenorphine metabolites.