(2R,3R,4R,5S,6S)-6-[dimethyl({3-[(2Z)-tricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-ylidene]propyl})azaniumyl]-3,4,5-trihydroxyoxane-2-carboxylate

• ChemBase ID: 165162
• Molecular Formular: C26H29NO6
• Molecular Mass: 451.51156
• Monoisotopic Mass: 451.19948765
• SMILES: [C@H]1([C@H]([C@H](O[C@@H]([C@@H]1O)[N+](CC/C=C/1\c2c(C=Cc3c1cccc3)cccc2)(C)C)C(=O)[O-])O)O
• Canonical SMILES: [O-]C(=O)[C@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)O)O)[N+](CC/C=C/1\c2ccccc2C=Cc2c1cccc2)(C)C
• InChI: InChI=1S/C26H29NO6/c1-27(2,25-23(30)21(28)22(29)24(33-25)26(31)32)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-14,21-25,28-30H,7,15H2,1-2H3/t21-,22-,23+,24-,25+/m1/s1
• InChIKey: DJRZMHSVTCVTFB-RXFVIIJJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6S)-6-[dimethyl({3-[(2Z)-tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-ylidene]propyl})azaniumyl]-3,4,5-trihydroxyoxane-2-carboxylate
• IUPAC Traditional name: (2R,3R,4R,5S,6S)-6-[dimethyl({3-[(2Z)-tricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-2-ylidene]propyl})ammonio]-3,4,5-trihydroxyoxane-2-carboxylate
• Synonyms: 3-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-N-β-D-glucopyranuronosyl-N,N-dimethyl-1-propanaminium Inner Salt; Cyclobenzaprine N-Glucuronide; Cyclobenzaprine N-β-D-Glucuronide

Database IDs

• CAS Number: 67324-97-4
• PubChem SID: 162259295
• PubChem CID: 71315061

CALCULATED PROPERTIES

• Acid pKa: 3.4004073
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.87533313
• LogD (pH = 7.4): -0.87255734
• Log P: -1.643011
• Molar Refractivity: 156.904 cm^3
• Polarizability: 48.394558 Å^3
• Polar Surface Area: 110.05 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C987755

The major metabolite of Cyclobenzaprine.

REFERENCES

• Hucker, H. B., et al.: Drug Metab. Dispos., 6, 659 (1978)