(2R,3R,4R,5S,6R)-6-{[12-chloro-9-(2-chlorophenyl)-3-methyl-2,4,5,8-tetraazatricyclo[8.4.0.02,6]tetradeca-1(10),3,5,8,11,13-hexaen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 171403
• Molecular Formular: C23H20Cl2N4O7
• Molecular Mass: 535.3335
• Monoisotopic Mass: 534.07090436
• SMILES: O1[C@@H]([C@@H]([C@@H]([C@H]([C@H]1C(=O)O)O)O)O)OC1N=C(c2c(cccc2)Cl)c2c(n3c1nnc3C)ccc(c2)Cl
• Canonical SMILES: Clc1ccc2c(c1)C(=NC(c1n2c(C)nn1)O[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O)c1ccccc1Cl
• InChI: InChI=1S/C23H20Cl2N4O7/c1-9-27-28-20-21(36-23-18(32)16(30)17(31)19(35-23)22(33)34)26-15(11-4-2-3-5-13(11)25)12-8-10(24)6-7-14(12)29(9)20/h2-8,16-19,21,23,30-32H,1H3,(H,33,34)/t16-,17-,18+,19-,21?,23-/m1/s1
• InChIKey: MOOCXBVDYDHHAJ-VZOVWQOWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-6-{[12-chloro-9-(2-chlorophenyl)-3-methyl-2,4,5,8-tetraazatricyclo[8.4.0.0^2,^6]tetradeca-1(10),3,5,8,11,13-hexaen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-6-{[12-chloro-9-(2-chlorophenyl)-3-methyl-2,4,5,8-tetraazatricyclo[8.4.0.0^2,^6]tetradeca-1(10),3,5,8,11,13-hexaen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 8-Chloro-6-(2-chlorophenyl)-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl-β-D-Glucopyranosiduronic Acid; 4-Hydroxy Triazolam β-D-Glucuronide

Database IDs

• CAS Number: 76960-93-5
• PubChem SID: 164227313
• PubChem CID: 71749392

CALCULATED PROPERTIES

• Acid pKa: 2.9015398
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -1.7150288
• LogD (pH = 7.4): -2.707247
• Log P: 0.5577491
• Molar Refractivity: 137.1629 cm^3
• Polarizability: 49.606304 Å^3
• Polar Surface Area: 159.52 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: N/A

DETAILS

Toronto Research Chemicals - H971335

A metabolite of Triazolam (T767380).

REFERENCES

• Boxenbaum, H., et al.: J. Pharm. Pharm. Sci., 2, 47 (1999)
• Perloff, M., et al.: J. Pharmacol. Exp. Ther., 292, 618 (1999)
• Patki, K., et al.: Drug Metab. Dispos., 31, 938 (1999)