(2S,3S,4S,5R,6R)-6-{dimethyl[1-(10H-phenothiazin-10-yl)propan-2-yl]azaniumyl}-3,4,5-trihydroxyoxane-2-carboxylate

• ChemBase ID: 176977
• Molecular Formular: C23H28N2O6S
• Molecular Mass: 460.54322
• Monoisotopic Mass: 460.16680763
• SMILES: c1ccc2c(c1)N(c1c(S2)cccc1)CC([N+]([C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)[O-])(C)C)C
• Canonical SMILES: [O-]C(=O)[C@@H]1O[C@H]([C@H]([C@H]([C@@H]1O)O)O)[N+](C(CN1c2ccccc2Sc2c1cccc2)C)(C)C
• InChI: InChI=1S/C23H28N2O6S/c1-13(25(2,3)22-20(28)18(26)19(27)21(31-22)23(29)30)12-24-14-8-4-6-10-16(14)32-17-11-7-5-9-15(17)24/h4-11,13,18-22,26-28H,12H2,1-3H3/t13?,18-,19-,20+,21-,22+/m0/s1
• InChIKey: ABNKYMDJQOWLOF-JGSZSWCSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{dimethyl[1-(10H-phenothiazin-10-yl)propan-2-yl]azaniumyl}-3,4,5-trihydroxyoxane-2-carboxylate
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{dimethyl[1-(phenothiazin-10-yl)propan-2-yl]ammonio}-3,4,5-trihydroxyoxane-2-carboxylate
• Synonyms: N-β-D-Glucopyranuronosyl-N,N,α-trimethyl-10H-phenothiazine-10-ethanaminium Inner Salt; Promethazine N-Glucuronide; Promethazine N-β-D-Glucuronide

Database IDs

• CAS Number: 137908-81-7
• PubChem SID: 164232887
• PubChem CID: 71751807

CALCULATED PROPERTIES

• Acid pKa: 3.278191
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.2000779
• LogD (pH = 7.4): -1.197991
• Log P: -1.9684534
• Molar Refractivity: 142.7851 cm^3
• Polarizability: 47.355877 Å^3
• Polar Surface Area: 113.29 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P757005

Promethazine N-β-D-Glucuronide is a glucuronide metabolite of Promethazine (P757000).

REFERENCES

• Luo, H., et al.: Xenobiotica, 21, 1281 (1991)