1-[(2R,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-1-methyl-4-{3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl}piperazin-1-ium

• ChemBase ID: 178824
• Molecular Formular: C27H32F3N3O6S
• Molecular Mass: 583.6196896
• Monoisotopic Mass: 583.19639142
• SMILES: c1ccc2c(c1)N(c1c(S2)ccc(c1)C(F)(F)F)CCCN1CC[N+](CC1)([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+]1(C)CCN(CC1)CCCN1c2ccccc2Sc2c1cc(cc2)C(F)(F)F
• InChI: InChI=1S/C27H32F3N3O6S/c1-33(25-23(36)21(34)22(35)24(39-25)26(37)38)13-11-31(12-14-33)9-4-10-32-17-5-2-3-6-19(17)40-20-8-7-16(15-18(20)32)27(28,29)30/h2-3,5-8,15,21-25,34-36H,4,9-14H2,1H3/t21-,22-,23+,24-,25+/m0/s1
• InChIKey: AFYPHWNGUDUHIW-ARXROMJUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-1-methyl-4-{3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl}piperazin-1-ium
• IUPAC Traditional name: 1-[(2R,3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]-1-methyl-4-{3-[2-(trifluoromethyl)phenothiazin-10-yl]propyl}piperazin-1-ium
• Synonyms: 1-β-D-Glucopyranuronosyl-1-methyl-4-[3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl]piperazinium Inner Salt; Trifluoperazine N-Glucuronide; Trifluoperazine N-β-D-GlucuronideDISCONTINUED

Database IDs

• CAS Number: 165602-90-4
• PubChem SID: 164234734
• PubChem CID: 71752653

CALCULATED PROPERTIES

• Acid pKa: 3.089345
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -0.8445445
• LogD (pH = 7.4): -0.82980216
• Log P: -1.1750253
• Molar Refractivity: 165.2555 cm^3
• Polarizability: 54.8145 Å^3
• Polar Surface Area: 116.53 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T779210

A metabolite of Trifluoperazine (T779200); antidepressant antipsychotic quaternary amine.

REFERENCES

• Luo, H., et al.: Xenobiotica, 25, 291 (1995)
• Kurkela, M., et al.: J. Biol. Chem., 278, 3536 (1995)
• Ghosal, A., et al.: Drug Metab. Dispos. 32, 267 (1995)