(2R,10S,14R)-13-(cyclopropylmethyl)-18,18,19,19-tetramethyl-3,20-dioxa-13-azaheptacyclo[13.5.2.18,14.01,17.02,10.04,9.010,15]tricosa-4,6,8-trien-5-ol

• ChemBase ID: 163101
• Molecular Formular: C28H37NO3
• Molecular Mass: 435.59828
• Monoisotopic Mass: 435.27734405
• SMILES: c1(c2c3c(cc1)C[C@@H]1C45[C@@]3([C@H](C3(C(C4)C(C(O3)(C)C)(C)C)CC5)O2)CCN1CC1CC1)O
• Canonical SMILES: Oc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)C24CCC31OC(C(C3C2)(C)C)(C)C)CC1CC1
• InChI: InChI=1S/C28H37NO3/c1-24(2)19-14-26-9-10-28(19,32-25(24,3)4)23-27(26)11-12-29(15-16-5-6-16)20(26)13-17-7-8-18(30)22(31-23)21(17)27/h7-8,16,19-20,23,30H,5-6,9-15H2,1-4H3/t19?,20-,23-,26?,27+,28?/m1/s1
• InChIKey: MFRSJMQUIFQWSF-JOMVMCAMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,10S,14R)-13-(cyclopropylmethyl)-18,18,19,19-tetramethyl-3,20-dioxa-13-azaheptacyclo[13.5.2.1^8,^1^4.0^1,^1^7.0^2,^1^0.0^4,^9.0^1^0,^1^5]tricosa-4,6,8-trien-5-ol
• IUPAC Traditional name: (2R,10S,14R)-13-(cyclopropylmethyl)-18,18,19,19-tetramethyl-3,20-dioxa-13-azaheptacyclo[13.5.2.1^8,^1^4.0^1,^1^7.0^2,^1^0.0^4,^9.0^1^0,^1^5]tricosa-4,6,8-trien-5-ol
• Synonyms: [8R-(4bS*,8α,8aα,9aβ,12aα,12bβ)]-7-(Cyclopropylmethyl)-5,6,7,8,9,9a,10,11-octahydro-10,10,11,11-tetramethyl-8a,12a-ethano-4,8-methano-12bH-benzofuro[3,2-e]furo[2,3-g]isoquinolin-1-ol; (4bS,8R,8aS,9aR,12aR,12bR)-7-(Cyclopropylmethyl)-5,6,7,8,9,9a,10,11-octahydro-10,10,11,11-tetramethyl-8a,12a-ethano-4,8-methano-12bH-benzofuro[3,2-e]furo[2,3-g]isoquinolin-1-ol; Buprenorphine Impurity I; Buprenorphine Furanyl Impurity (Buprenorphine Impurity I)

Database IDs

• CAS Number: 89663-73-0
• PubChem SID: 162257236
• PubChem CID: 71314299

CALCULATED PROPERTIES

• Acid pKa: 10.459329
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.97590864
• LogD (pH = 7.4): 1.9236971
• Log P: 3.9035852
• Molar Refractivity: 123.6768 cm^3
• Polarizability: 49.08199 Å^3
• Polar Surface Area: 41.93 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B689595

A metabolite of Buprenorphine (B689570).

REFERENCES

• Cone, E. et al.: J. Chrom. Biomed. Appl., 337, 291 (1985)
• Garrett, E. et al.: J. Pharmac. Sci., 74, 515 (1985)