(2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-[2-(4-{3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl}piperazin-1-yl)ethoxy]oxane-2-carboxylic acid

• ChemBase ID: 169285
• Molecular Formular: C28H34F3N3O7S
• Molecular Mass: 613.6456696
• Monoisotopic Mass: 613.2069561
• SMILES: O([C@H]1O[C@@H]([C@H](O)[C@@H](O)[C@H]1O)C(=O)O)CCN1CCN(CCCN2c3ccccc3Sc3c2cc(cc3)C(F)(F)F)CC1
• Canonical SMILES: OC(=O)[C@H]1O[C@H](OCCN2CCN(CC2)CCCN2c3ccccc3Sc3c2cc(cc3)C(F)(F)F)[C@@H]([C@@H]([C@H]1O)O)O
• InChI: InChI=1S/C28H34F3N3O7S/c29-28(30,31)17-6-7-21-19(16-17)34(18-4-1-2-5-20(18)42-21)9-3-8-32-10-12-33(13-11-32)14-15-40-27-24(37)22(35)23(36)25(41-27)26(38)39/h1-2,4-7,16,22-25,27,35-37H,3,8-15H2,(H,38,39)/t22-,23-,24+,25-,27+/m1/s1
• InChIKey: FPAXYGQWHAIDFV-NUPXYHBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-[2-(4-{3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl}piperazin-1-yl)ethoxy]oxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6S)-3,4,5-trihydroxy-6-[2-(4-{3-[2-(trifluoromethyl)phenothiazin-10-yl]propyl}piperazin-1-yl)ethoxy]oxane-2-carboxylic acid
• Synonyms: 2-[4-[3-[2-(Trifluoromethyl)-10H-phenothiazin-10-yl]propyl]-1-piperazinyl]ethyl β-D-Glucopyranosiduronic Acid; Fluphenazine β-D-Glucuronide

Database IDs

• CAS Number: 133310-09-5
• PubChem SID: 162263417
• PubChem CID: 71316895

CALCULATED PROPERTIES

• Acid pKa: 2.3690376
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -0.21563467
• LogD (pH = 7.4): -0.29765582
• Log P: -0.21707767
• Molar Refractivity: 149.5483 cm^3
• Polarizability: 57.54708 Å^3
• Polar Surface Area: 126.17 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F598410

A metabolite of Fluphenazine.

REFERENCES

• Jackson, C.J.C., et al.: Xenobiotica, 21, 383 (1991)
• Jackson, C.J.C., et al.: Drug Metab. Dispos., 19, 188 (1991)