methyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate

• ChemBase ID: 171968
• Molecular Formular: C21H28O3
• Molecular Mass: 328.44522
• Monoisotopic Mass: 328.20384476
• SMILES: C1(=C(C(=O)CCC1(C)C)C)/C=C/C(=C\C=C\C(=C\C(=O)OC)\C)/C
• Canonical SMILES: COC(=O)/C=C(/C=C/C=C(\C=C\C1=C(C)C(=O)CCC1(C)C)/C)\C
• InChI: InChI=1S/C21H28O3/c1-15(8-7-9-16(2)14-20(23)24-6)10-11-18-17(3)19(22)12-13-21(18,4)5/h7-11,14H,12-13H2,1-6H3/b9-7+,11-10+,15-8-,16-14+
• InChIKey: VTSFDGSDUILKPM-WNACIYAKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate
• IUPAC Traditional name: methyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate
• Synonyms: 4-Oxo-9-cis-Retinoic Acid Methyl Ester; 4-Keto 9-cis Retinoic Acid Methyl Ester

Database IDs

• CAS Number: 163955-59-7
• PubChem SID: 164227878
• PubChem CID: 11724047

CALCULATED PROPERTIES

• Acid pKa: 19.89032
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.7263117
• LogD (pH = 7.4): 4.7263117
• Log P: 4.7263117
• Molar Refractivity: 103.2531 cm^3
• Polarizability: 38.32269 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - K204965

Retinoic acid derivative.

REFERENCES

• Tanaka, H., et al.: Chem. Pharm. Bull., 43, 356 (1995)