(2E,4E,6Z,8E)-9-[3-hydroxy-2-(2H3)methyl-6,6-dimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid

• ChemBase ID: 171268
• Molecular Formular: C20H28O3
• Molecular Mass: 316.43452
• Monoisotopic Mass: 316.20384476
• SMILES: C1(=C(C(CCC1(C)C)O)C)/C=C/C(=C\C=C\C(=C\C(=O)O)\C)/C
• Canonical SMILES: C/C(=C/C=C/C(=C/C(=O)O)/C)/C=C/C1=C(C)C(O)CCC1(C)C
• InChI: InChI=1S/C20H28O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13,18,21H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7-,15-13+
• InChIKey: KGUMXGDKXYTTEY-NAXRMXIQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,4E,6Z,8E)-9-[3-hydroxy-2-(^2H₃)methyl-6,6-dimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid
• IUPAC Traditional name: (2E,4E,6Z,8E)-9-[3-hydroxy-2-(^2H₃)methyl-6,6-dimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid
• Synonyms: rac 4-Hydroxy-9-cis-retinoic Acid-d3

Database IDs

• PubChem SID: 164227178
• PubChem CID: 71749326

CALCULATED PROPERTIES

• Acid pKa: 4.996648
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.162085
• LogD (pH = 7.4): 1.4098185
• Log P: 3.7835567
• Molar Refractivity: 99.3063 cm^3
• Polarizability: 36.76783 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H953312

A labelled metabolite of 9-cis-Retinoic acid (R245000).

REFERENCES

• Omiecinski, C., et al.: Cancer Res., 50, 4315 (1990)
• Chapman, D., et al.: Biochem. Pharmacol., 48, 1807 (1990)
• White, J., et al.: J. Biol. Chem., 271, 29922 (1990)
• Chen, H., et al.: Drug Metab. Dispos., 28, 1051 (1990)