methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[5-amino-6-(2,3-dichlorophenyl)-3-imino-2,3-dihydro-1,2,4-triazin-2-yl]oxane-2-carboxylate

• ChemBase ID: 172191
• Molecular Formular: C22H23Cl2N5O9
• Molecular Mass: 572.35212
• Monoisotopic Mass: 571.0872827
• SMILES: c1(cccc(c1Cl)c1c(nc(=N)n(n1)[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)C(=O)OC)OC(=O)C)OC(=O)C)OC(=O)C)N)Cl
• Canonical SMILES: COC(=O)[C@H]1O[C@H]([C@@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)n1nc(c(nc1=N)N)c1cccc(c1Cl)Cl
• InChI: InChI=1S/C22H23Cl2N5O9/c1-8(30)35-15-16(36-9(2)31)18(21(33)34-4)38-20(17(15)37-10(3)32)29-22(26)27-19(25)14(28-29)11-6-5-7-12(23)13(11)24/h5-7,15-18,20H,1-4H3,(H3,25,26,27)/t15-,16-,17+,18-,20+/m0/s1
• InChIKey: YTJNERTYMPITJW-HBWRTXEVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[5-amino-6-(2,3-dichlorophenyl)-3-imino-2,3-dihydro-1,2,4-triazin-2-yl]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[5-amino-6-(2,3-dichlorophenyl)-3-imino-1,2,4-triazin-2-yl]oxane-2-carboxylate
• Synonyms: Lamotrigine N2-(2,3,4-Tri-O-acetyl-β-D-glucuronide Methyl Ester)Discontinued

Database IDs

• PubChem SID: 164228101
• PubChem CID: 71749734

CALCULATED PROPERTIES

• H Acceptors: 10
• H Donor: 2
• LogD (pH = 5.5): 1.1724434
• LogD (pH = 7.4): 1.2943391
• Log P: 1.2961426
• Molar Refractivity: 137.6882 cm^3
• Polarizability: 50.780636 Å^3
• Polar Surface Area: 192.26 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Brown Solid

DETAILS

Toronto Research Chemicals - L173300

Intermediate in the production of Lamotrigine metabolites.