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

• ChemBase ID: 170322
• Molecular Formular: C21H20N2O8
• Molecular Mass: 428.3921
• Monoisotopic Mass: 428.12196561
• SMILES: c12c(cc(cc1)O[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)C(=O)O)O)O)O)N(c1c(cccc1)C=C2)C(=O)N
• Canonical SMILES: OC(=O)[C@H]1O[C@@H](Oc2ccc3c(c2)N(C(=O)N)c2ccccc2C=C3)[C@@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H20N2O8/c22-21(29)23-13-4-2-1-3-10(13)5-6-11-7-8-12(9-14(11)23)30-20-17(26)15(24)16(25)18(31-20)19(27)28/h1-9,15-18,20,24-26H,(H2,22,29)(H,27,28)/t15-,16-,17+,18-,20+/m0/s1
• InChIKey: NAXZOCXVDWEFKO-HBWRTXEVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-({2-carbamoyl-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-({2-carbamoyl-2-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,9,12,14-heptaen-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 3-Hydroxy-5H-dibenz[b,f]azepine-5-carboxamide β-D-Glucuronide; 3-Hydroxy Carbamazepine Glucuronide; 3-Hydroxy Carbamazepine β-D-Glucuronide

Database IDs

• PubChem SID: 164226232
• PubChem CID: 71748921

CALCULATED PROPERTIES

• Acid pKa: 3.0507824
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -1.9014074
• LogD (pH = 7.4): -2.9535797
• Log P: 0.5146715
• Molar Refractivity: 105.8807 cm^3
• Polarizability: 41.141865 Å^3
• Polar Surface Area: 162.78 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H884110

3-Hydroxy Carbamazepine β-D-Glucuronide is a metabolite of 3-Hydroxy Carbamazepine (H884105).