(2E,4E,6E,8E)-9-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid

• ChemBase ID: 171274
• Molecular Formular: C20H28O3
• Molecular Mass: 316.43452
• Monoisotopic Mass: 316.20384476
• SMILES: C1(CCCC(=C1/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C)CO)(C)C
• Canonical SMILES: OCC1=C(/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C)C(CCC1)(C)C
• InChI: InChI=1S/C20H28O3/c1-15(7-5-8-16(2)13-19(22)23)10-11-18-17(14-21)9-6-12-20(18,3)4/h5,7-8,10-11,13,21H,6,9,12,14H2,1-4H3,(H,22,23)/b8-5+,11-10+,15-7+,16-13+
• InChIKey: XSJOIRFEYHJNAW-FCKHSPHMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,4E,6E,8E)-9-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid
• IUPAC Traditional name: (2E,4E,6E,8E)-9-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid
• Synonyms: 18-Hydroxy-all-trans-retinoic acid; 18-Hydroxyretinoic acid; Ro 12-4825; all-trans-18-Hydroxy Retinoic Acid

Database IDs

• CAS Number: 63531-93-1
• PubChem SID: 164227184
• PubChem CID: 6506224

CALCULATED PROPERTIES

• Acid pKa: 4.996648
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.112125
• LogD (pH = 7.4): 1.3598585
• Log P: 3.7335966
• Molar Refractivity: 99.5655 cm^3
• Polarizability: 36.76783 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H953340

all-trans-18-Hydroxy Retinoic Acid is hydroxylated metabolite of all-trans-Retinoic Acid (R250200) produce by cytochrome P450, CYP26C1.

REFERENCES

• Taimi, M. et al.: J. Biol. Chem., 279, 77 (2004)
• Idres, N. et al.: J. Biol. Chem., 277, 31491 (2004)
• Hanni, R. et al.: Helv. Chim. Acta, 60, 881 (2004)