(2R,3R,4R,5S,6R)-6-[(7-chloro-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 178131
• Molecular Formular: C22H21ClN2O8
• Molecular Mass: 476.86374
• Monoisotopic Mass: 476.09864332
• SMILES: c1ccccc1C1=NC(C(=O)N(c2c1cc(cc2)Cl)C)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1O)O)O)C(=O)O
• Canonical SMILES: Clc1ccc2c(c1)C(=NC(C(=O)N2C)O[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O)c1ccccc1
• InChI: InChI=1S/C22H21ClN2O8/c1-25-13-8-7-11(23)9-12(13)14(10-5-3-2-4-6-10)24-19(20(25)29)33-22-17(28)15(26)16(27)18(32-22)21(30)31/h2-9,15-19,22,26-28H,1H3,(H,30,31)/t15-,16-,17+,18-,19?,22-/m1/s1
• InChIKey: KFYGTOURBGCWNQ-PVTOYSEVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-6-[(7-chloro-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-6-[(7-chloro-1-methyl-2-oxo-5-phenyl-3H-1,4-benzodiazepin-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 7-Chloro-2,3-dihydro-1-methyl-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-ylβ-D-Glucopyranosiduronic Acid; 3-Hydroxydiazepam Glucuronide; BA 2826; Temazepam Glucuronide; Temazepam β-D-Glucuronide, Mixture of Diastereomers

Database IDs

• CAS Number: 3703-53-5
• PubChem SID: 164234041
• PubChem CID: 10027983

CALCULATED PROPERTIES

• Acid pKa: 3.0008886
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -1.1249914
• LogD (pH = 7.4): -2.1377084
• Log P: 1.3367858
• Molar Refractivity: 113.291 cm^3
• Polarizability: 44.622498 Å^3
• Polar Surface Area: 149.12 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White to Off-White Solid
• Melting Point: >218°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - T017210

A glucuronide metabolite of Diazepam.Controlled substance (depressant). Sedative, hypnotic.

REFERENCES

• Sarteschi, P., et al.: Arzneim.-Forsch., 22, 93 (1972)
• Schwandt, H.J., et al.: Xenobiotica, 4, 733 (1972)
• Curry, S.H., et al.: Br. J. Pharmacol., 57, 427 (1972)
• Heel, R.C., et al.: Drugs, 21, 321 (1972)