(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-methyl-3-(2-methylphenyl)-4-oxo-3,4-dihydroquinazolin-6-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 172723
• Molecular Formular: C22H22N2O8
• Molecular Mass: 442.41868
• Monoisotopic Mass: 442.13761567
• SMILES: c1c(cc2c(c1)nc(n(c2=O)c1c(cccc1)C)C)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](Oc2ccc3c(c2)c(=O)n(c(n3)C)c2ccccc2C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C22H22N2O8/c1-10-5-3-4-6-15(10)24-11(2)23-14-8-7-12(9-13(14)20(24)28)31-22-18(27)16(25)17(26)19(32-22)21(29)30/h3-9,16-19,22,25-27H,1-2H3,(H,29,30)/t16-,17-,18+,19-,22+/m0/s1
• InChIKey: WKXWFAVXGQVYFU-KSSXRGRSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-methyl-3-(2-methylphenyl)-4-oxo-3,4-dihydroquinazolin-6-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-methyl-3-(2-methylphenyl)-4-oxoquinazolin-6-yl]oxy}oxane-2-carboxylic acid
• Synonyms: 3,4-Dihydro-2-methyl-3-(2-methylphenyl)-4-oxo-6-quinazolinyl β-D-Glucopyranosiduronic Acid; Methaqualone 6-O-β-D-Glucuronide

Database IDs

• CAS Number: 67982-37-0
• PubChem SID: 164228633
• PubChem CID: 71749991

CALCULATED PROPERTIES

• Acid pKa: 2.762668
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -1.7561164
• LogD (pH = 7.4): -2.5797336
• Log P: 0.9171375
• Molar Refractivity: 111.0981 cm^3
• Polarizability: 42.5725 Å^3
• Polar Surface Area: 149.12 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M225985

A glucuronide metabolite Methaqualone (M225900). Controlled substance.

REFERENCES

• Ericsson, O., et al.: Acta Pharmaceut. Suecica, 15, 81 (1978)
• Wilson, K., et al.: Eur. J. Drug Metab. Pharmacokinet., 9, 301 (1978)