3,5-diamino-2-[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]-6-(2,3-dichlorophenyl)-1,2λ5,4-triazin-2-ylium

• ChemBase ID: 172186
• Molecular Formular: C15H16Cl2N5O6+
• Molecular Mass: 433.22344
• Monoisotopic Mass: 432.04776362
• SMILES: c1(cccc(c1Cl)c1c(nc([n+](n1)[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C(=O)O)O)O)O)N)N)Cl
• Canonical SMILES: OC(=O)[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)[n+]1nc(c(nc1N)N)c1cccc(c1Cl)Cl
• InChI: InChI=1S/C15H15Cl2N5O6/c16-5-3-1-2-4(6(5)17)7-12(18)20-15(19)22(21-7)13-10(25)8(23)9(24)11(28-13)14(26)27/h1-3,8-11,13,23-25H,(H4,18,19,20,26,27)/p+1/t8-,9-,10+,11-,13+/m0/s1
• InChIKey: IEVMENHZPOWVGO-XPORZQOISA-O

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5-diamino-2-[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]-6-(2,3-dichlorophenyl)-1,2λ^5,4-triazin-2-ylium
• IUPAC Traditional name: 3,5-diamino-2-[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]-6-(2,3-dichlorophenyl)-1,2λ^5,4-triazin-2-ylium
• Synonyms: 3,5-Diamino-6-(2,3-dichlorophenyl)-2-D-glucopyranuronosyl-1,2,4-triazinium; Lamotrigine N2-Glucuronide 85%

Database IDs

• CAS Number: 133310-19-7
• PubChem SID: 164228096
• PubChem CID: 164342

CALCULATED PROPERTIES

• Acid pKa: 3.0288978
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -3.240227
• LogD (pH = 7.4): -3.2412636
• Log P: -3.0117762
• Molar Refractivity: 108.5913 cm^3
• Polarizability: 38.629498 Å^3
• Polar Surface Area: 188.92 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: >180°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - L173260

It is the major metabolite of Lamotrigine (L173250).This compound contains an unidentified positional isomer.

REFERENCES

• Sinz, M.W., et al.: Drug Metab. Dispos., 19, 149 ( (1991)
• Ohman I., et al.: Epilepsia, 49, 1075 (1991)