3-[(1E,3E,5E,7E)-9-hydroxy-3,7-dimethylnona-1,3,5,7-tetraen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one

• ChemBase ID: 2423
• Molecular Formular: C20H28O2
• Molecular Mass: 300.43512
• Monoisotopic Mass: 300.20893014
• SMILES: C/C(=C\CO)/C=C/C=C(\C)/C=C/C1=C(C)C(=O)CCC1(C)C
• Canonical SMILES: OC/C=C(/C=C/C=C(/C=C/C1=C(C)C(=O)CCC1(C)C)\C)\C
• InChI: InChI=1S/C20H28O2/c1-15(7-6-8-16(2)12-14-21)9-10-18-17(3)19(22)11-13-20(18,4)5/h6-10,12,21H,11,13-14H2,1-5H3/b8-6+,10-9+,15-7+,16-12+
• InChIKey: PLIUCYCUYQIBDZ-RMWYGNQTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(1E,3E,5E,7E)-9-hydroxy-3,7-dimethylnona-1,3,5,7-tetraen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one
• IUPAC Traditional name: 4-oxoretinol
• Synonyms: 4-Oxoretinol; 15-Hydroxyretin-4-one; 3-(9-Hydroxy-3,7-dimethyl-1,3,5,7-nonatetraenyl)-2,4,4-trimethyl-2-cyclohexen-1-one; 4-Oxoretinol; all-trans-4-Oxoretinol; 4-Keto Retinol

Database IDs

• CAS Number: 62702-55-0
• PubChem SID: 160965874; 46506951
• PubChem CID: 5289090

CALCULATED PROPERTIES

JChem

• Acid pKa: 16.435617
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.0268097
• LogD (pH = 7.4): 4.0268097
• Log P: 4.0268097
• Molar Refractivity: 98.6166 cm^3
• Polarizability: 36.363087 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 5.31
• LOG S: -4.39
• Solubility (Water): 1.21e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: Yellow Solid
• Melting Point: 102-106°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Unstable! Light, Temperature and Moisture Sensitive

DETAILS

DrugBank - DB02699

Drug information: experimental

Toronto Research Chemicals - K205000

A metabolite of Retinol.

REFERENCES

• McCormick, A., et al.: J. Biol. Chem., 257, 1730 (1982)
• Levin, A., et al.: Nature, 355, 359 (1982)
• Meyer, E., et al.: Clin. Chem., 40, 48 (1982)