(2S,3S,4S,5R,6S)-6-{[4-(4-chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 169836
• Molecular Formular: C27H31ClFNO8
• Molecular Mass: 551.9883432
• Monoisotopic Mass: 551.17222286
• SMILES: c1c(ccc(c1)C(=O)CCCN1CCC(CC1)(c1ccc(cc1)Cl)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)F
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](OC2(CCN(CC2)CCCC(=O)c2ccc(cc2)F)c2ccc(cc2)Cl)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C27H31ClFNO8/c28-18-7-5-17(6-8-18)27(38-26-23(34)21(32)22(33)24(37-26)25(35)36)11-14-30(15-12-27)13-1-2-20(31)16-3-9-19(29)10-4-16/h3-10,21-24,26,32-34H,1-2,11-15H2,(H,35,36)/t21-,22-,23+,24-,26-/m0/s1
• InChIKey: ZFNLYKVTHNLKNZ-AMWBNRJOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[4-(4-chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[4-(4-chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 4-(4-Chlorophenyl)-1-[4-(4-fluorophenyl)-4-oxobutyl]-4-piperidinyl β-D-Glucopyranosiduronic Acid; Haloperidol Glucuronide; Haloperidol β-D-Glucuronide

Database IDs

• CAS Number: 100442-88-4
• PubChem SID: 162263968
• PubChem CID: 71317190

CALCULATED PROPERTIES

• Acid pKa: 3.1706614
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -0.52066934
• LogD (pH = 7.4): -0.5672383
• Log P: -0.52095217
• Molar Refractivity: 134.8726 cm^3
• Polarizability: 53.12992 Å^3
• Polar Surface Area: 136.76 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H103705

A metabolite of Haloperidol (H103700).

REFERENCES

• Krishnaswamy, S., et al.: Xenobiotica, 33, 169 (2003)
• Krishnaswamy, S., et al.: Drug Metab. Dispos., 31, 133 (2003)