3,5-diamino-2-[(2S,3S,4R,5R,6R)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-6-(2,3-dichlorophenyl)(3,5,6-13C3)-1,2λ5,4-triazin-2-ylium

• ChemBase ID: 172187
• Molecular Formular: C15H15Cl2N5O6
• Molecular Mass: 435.19346451
• Monoisotopic Mass: 434.0500031
• SMILES: [C@H]1([C@H]([C@@H](O[C@@H]([C@H]1O)[n+]1[13c](n[13c]([13c](c2cccc(c2Cl)Cl)n1)N)N)C(=O)[O-])O)O
• Canonical SMILES: [O-]C(=O)[C@@H]1O[C@@H]([C@H]([C@@H]([C@H]1O)O)O)[n+]1n[13c]([13c](n[13c]1N)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)/t8-,9-,10+,11-,13+/m1/s1/i7+1,12+1,15+1
• InChIKey: IEVMENHZPOWVGO-ZRIYKEGNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5-diamino-2-[(2S,3S,4R,5R,6R)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-6-(2,3-dichlorophenyl)(3,5,6-^1^3C₃)-1,2λ^5,4-triazin-2-ylium
• IUPAC Traditional name: 3,5-diamino-2-[(2S,3S,4R,5R,6R)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-6-(2,3-dichlorophenyl)(3,5,6-^1^3C₃)-1,2λ^5,4-triazin-2-ylium
• Synonyms: 3,5-Diamino-6-(2,3-dichlorophenyl)-2-D-glucopyranuronosyl-1,2,4-triazinium-13C3; Lamotrigine-13C3 N2-Glucuronide 85% DISCONTINUED

Database IDs

• PubChem SID: 164228097
• PubChem CID: 71749732

CALCULATED PROPERTIES

• Acid pKa: 3.0288978
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -3.240227
• LogD (pH = 7.4): -3.2412636
• Log P: -3.0117762
• Molar Refractivity: 119.4284 cm^3
• Polarizability: 38.51307 Å^3
• Polar Surface Area: 191.75 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L173262

It is the major labelled metabolite of Lamotrigine (L173250).

REFERENCES

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