(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoyl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 159521
• Molecular Formular: C27H34O9
• Molecular Mass: 502.55346
• Monoisotopic Mass: 502.22028267
• SMILES: c1(c(c(cc(c1/C=C/C(=C/C=C/C(=C/C(=O)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)/C)/C)C)OC)C)C
• Canonical SMILES: COc1cc(C)c(c(c1C)C)/C=C/C(=C/C=C/C(=C/C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)/C)/C
• InChI: InChI=1S/C27H34O9/c1-14(10-11-19-16(3)13-20(34-6)18(5)17(19)4)8-7-9-15(2)12-21(28)35-27-24(31)22(29)23(30)25(36-27)26(32)33/h7-13,22-25,27,29-31H,1-6H3,(H,32,33)/b9-7+,11-10+,14-8+,15-12+/t22-,23-,24+,25-,27+/m0/s1
• InChIKey: JBZDSEGJHOGTFE-QOKVZKDXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoyl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoyl]oxy}oxane-2-carboxylic acid
• Synonyms: 1-9-(4-Methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate β-D-Glucopyranuronic Acid; Acitretin O-β-D-Glucuronide

Database IDs

• CAS Number: 99792-36-6
• PubChem SID: 162253656
• PubChem CID: 71313017

CALCULATED PROPERTIES

• Acid pKa: 3.38921
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 1.7746999
• LogD (pH = 7.4): 0.46696407
• Log P: 3.8725884
• Molar Refractivity: 136.4651 cm^3
• Polarizability: 51.71323 Å^3
• Polar Surface Area: 142.75 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A189905

A metabolite of the synthetic retinoid Acritretin (A189900).

REFERENCES

• Sato, T., et al.: J. Med. Chem., 51, 7705 (2008)
• Liu, X., et al.: Cancer Chemother. Pharmacol., 63, 167 (2008)