(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-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 170319
• Molecular Formular: C21H20N2O8
• Molecular Mass: 428.3921
• Monoisotopic Mass: 428.12196561
• SMILES: [C@@H]1([C@@H](O[C@@H]([C@H]([C@H]1O)O)C(=O)O)Oc1ccc2c(c1)C=Cc1c(N2C(=O)N)cccc1)O
• Canonical SMILES: OC(=O)[C@H]1O[C@@H](Oc2ccc3c(c2)C=Cc2c(N3C(=O)N)cccc2)[C@@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H20N2O8/c22-21(29)23-13-4-2-1-3-10(13)5-6-11-9-12(7-8-14(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: RCHUZFNSBQUWSY-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-6-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-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 2-Hydroxy-5H-dibenz[b,f]azepine-5-carboxamide β-D-Glucuronide; 2-Hydroxy Carbamazepine Glucuronide; 2-Hydroxy Carbamazepine β-D-Glucuronide

Database IDs

• PubChem SID: 164226229
• PubChem CID: 71748920

CALCULATED PROPERTIES

• Acid pKa: 3.1339962
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -1.8243693
• LogD (pH = 7.4): -2.9416847
• Log P: 0.5146715
• Molar Refractivity: 105.8807 cm^3
• Polarizability: 41.141922 Å^3
• Polar Surface Area: 162.78 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H884095

2-Hydroxy Carbamazepine β-D-Glucuronide is a metabolite of 2-Hydroxy Carbamazepine (H884100).