4-[(2S,3S,4R,5R,6R)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-12-chloro-9-(2-fluorophenyl)-3-methyl-2,4λ5,8-triazatricyclo[8.4.0.02,6]tetradeca-1(10),3,5,8,11,13-hexaen-4-ylium

• ChemBase ID: 174621
• Molecular Formular: C24H21ClFN3O6
• Molecular Mass: 501.8914432
• Monoisotopic Mass: 501.11029131
• SMILES: c1(c(cccc1)F)C1=NCc2n(c3c1cc(cc3)Cl)c([n+](c2)[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)[O-])C
• Canonical SMILES: [O-]C(=O)[C@H]1O[C@@H]([C@@H]([C@@H]([C@H]1O)O)O)[n+]1cc2n(c1C)c1ccc(cc1C(=NC2)c1ccccc1F)Cl
• InChI: InChI=1S/C24H21ClFN3O6/c1-11-28(23-21(32)19(30)20(31)22(35-23)24(33)34)10-13-9-27-18(14-4-2-3-5-16(14)26)15-8-12(25)6-7-17(15)29(11)13/h2-8,10,19-23,30-32H,9H2,1H3/t19-,20-,21+,22-,23+/m1/s1
• InChIKey: ULVPQZCKSQYJQR-ZQGJOIPISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(2S,3S,4R,5R,6R)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-12-chloro-9-(2-fluorophenyl)-3-methyl-2,4λ^5,8-triazatricyclo[8.4.0.0^2,^6]tetradeca-1(10),3,5,8,11,13-hexaen-4-ylium
• IUPAC Traditional name: 4-[(2S,3S,4R,5R,6R)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-12-chloro-9-(2-fluorophenyl)-3-methyl-2,4λ^5,8-triazatricyclo[8.4.0.0^2,^6]tetradeca-1(10),3,5,8,11,13-hexaen-4-ylium
• Synonyms: 8-Chloro-6-(2-fluorophenyl)-2-β-D-glucopyranuronosyl-1-methyl-4H-ιmidazo[1,5-a][1,4]benzodiazepinium Inner Salt; Midazolam N-β-D-Glucuronide

Database IDs

• CAS Number: 1033824-50-8
• PubChem SID: 164230531
• PubChem CID: 71750734

CALCULATED PROPERTIES

• Acid pKa: 2.663917
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -3.173684
• LogD (pH = 7.4): -3.1736977
• Log P: -3.2916617
• Molar Refractivity: 153.5052 cm^3
• Polarizability: 47.625046 Å^3
• Polar Surface Area: 131.22 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Pale Orange Solid
• Melting Point: 177-1780°C

Safety Information

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

DETAILS

Toronto Research Chemicals - M343010

Α glucuronide metabolite of Midazolam (M343000).

REFERENCES

• Dundee, J., et al.: Drugs, 28, 519 (1984)
• Fabre, G., et al.: Biochem. Pharmacol., 37, 4389 (1984)
• Chung, E., et al.: Clin. Pharmacol. Ther., 79, 350 (1984)
• Zhu, B., et al.: Drug Metab. Dispos., 36, 331 (1984)