sodium (2S,3S,4S,5R,6R)-6-{[(9R)-2-carbamoyl-2-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-9-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate

• ChemBase ID: 174740
• Molecular Formular: C21H21N2NaO8
• Molecular Mass: 452.38981
• Monoisotopic Mass: 452.11955992
• SMILES: c12c(cccc1)N(c1c(cccc1)C[C@H]2O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)[O-])C(=O)N.[Na+]
• Canonical SMILES: O[C@@H]1[C@H](O)[C@@H](O[C@H]([C@H]1O)C(=O)[O-])O[C@@H]1Cc2ccccc2N(c2c1cccc2)C(=O)N.[Na+]
• InChI: InChI=1S/C21H22N2O8.Na/c22-21(29)23-12-7-3-1-5-10(12)9-14(11-6-2-4-8-13(11)23)30-20-17(26)15(24)16(25)18(31-20)19(27)28;/h1-8,14-18,20,24-26H,9H2,(H2,22,29)(H,27,28);/q;+1/p-1/t14-,15+,16+,17-,18+,20-;/m1./s1
• InChIKey: VLZQDUOKNQNYPV-GWHKFDRHSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,3S,4S,5R,6R)-6-{[(9R)-2-carbamoyl-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-9-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate
• IUPAC Traditional name: sodium (2S,3S,4S,5R,6R)-6-{[(9R)-2-carbamoyl-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-9-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate
• Synonyms: (10R)-5-(Aminocarbonyl)-10,11-dihydro-5H-dibenz[b,f]azepin-10-yl β-D-Glucopyranosiduronic Acid Sodium Salt; (R)-(Aminocarbonyl)-10,11-dihydro-5H-dibenz[b,f]azepin-10-yl β-D-Glucopyranosiduronic Acid Sodium Salt; R-Licarbazepine Glucuronide Sodium Salt; (R)-10-Monohydroxy-10,11-dihydro Carbamazepine O-β-D-Glucuronide Sodium Salt

Database IDs

• CAS Number: 104746-01-2
• PubChem SID: 164230650
• PubChem CID: 71750796

CALCULATED PROPERTIES

• Acid pKa: 3.2814193
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.9192936
• LogD (pH = 7.4): -3.1487968
• Log P: 0.28117988
• Molar Refractivity: 115.4047 cm^3
• Polarizability: 41.07768 Å^3
• Polar Surface Area: 165.61 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M546505

(R)-10-Monohydroxy-10,11-dihydro Carbamazepine O-β-D-Glucuronide is a metabolite of antiepileptic agent Oxcarbazepine, (OXC) (O869250) and Eslicarbazepine acetate, (BIA 2-093) (E659000).

REFERENCES

• Schuetz, H., et al.: Xenobiotica, 16, 769 (1986)
• Grant, S., et al.: Drugs, 43, 873 (1986)
• Volosov, A., et al.: Clin. Pharmacol. Ther., 66, 547 (1986)