(2S,3S,4S,5R,6R)-6-{[3-amino-6-(2,3-dichlorophenyl)-1,2,4-triazin-5-yl]amino}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 172188
• Molecular Formular: C15H15Cl2N5O6
• Molecular Mass: 432.2155
• Monoisotopic Mass: 431.03993859
• SMILES: c1ccc(c(c1Cl)Cl)c1c(nc(nn1)N)N[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Nc2nc(N)nnc2c2cccc(c2Cl)Cl)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C15H15Cl2N5O6/c16-5-3-1-2-4(6(5)17)7-12(20-15(18)22-21-7)19-13-10(25)8(23)9(24)11(28-13)14(26)27/h1-3,8-11,13,23-25H,(H,26,27)(H3,18,19,20,22)/t8-,9-,10+,11-,13+/m0/s1
• InChIKey: RARLFTPVZSDFBL-XPORZQOISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[3-amino-6-(2,3-dichlorophenyl)-1,2,4-triazin-5-yl]amino}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{[3-amino-6-(2,3-dichlorophenyl)-1,2,4-triazin-5-yl]amino}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[[3-Αmino-6-(2,3-dichlorophenyl)-1,2,4-triazin-5-yl]amino]-1-deoxy-β-D-glucopyranuronic Acid; Lamotrigine 5-N-β-D-GlucuronideDISCONTINUED

Database IDs

• CAS Number: 136565-77-0
• PubChem SID: 164228098
• PubChem CID: 71236569

CALCULATED PROPERTIES

• Acid pKa: 3.1458957
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -2.1775203
• LogD (pH = 7.4): -3.25727
• Log P: -1.9394646
• Molar Refractivity: 99.6426 cm^3
• Polarizability: 38.371983 Å^3
• Polar Surface Area: 183.94 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: N/A

DETAILS

Toronto Research Chemicals - L173265

A metabolite of Lamotrigine (L173250), a novel antiepileptic drug.

REFERENCES

• Doig, M.V., et al.: J. Chromatogr., 554, 181 (1991)