(2E,4Z,6E,8E)-3,7-dimethyl-9-[2-(2H3)methyl-6,6-dimethyl(3,3-2H2)cyclohex-1-en-1-yl]nona-2,4,6,8-tetraenoic acid

• ChemBase ID: 177447
• Molecular Formular: C20H28O2
• Molecular Mass: 300.43512
• Monoisotopic Mass: 300.20893014
• SMILES: C1(=C(CCCC1(C)C)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)CCCC1(C)C
• InChI: InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6-,12-11+,15-8+,16-14+
• InChIKey: SHGAZHPCJJPHSC-JPXMXQIXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,4Z,6E,8E)-3,7-dimethyl-9-[2-(^2H₃)methyl-6,6-dimethyl(3,3-^2H₂)cyclohex-1-en-1-yl]nona-2,4,6,8-tetraenoic acid
• IUPAC Traditional name: (2E,4Z,6E,8E)-3,7-dimethyl-9-[2-(^2H₃)methyl-6,6-dimethyl(3,3-^2H₂)cyclohex-1-en-1-yl]nona-2,4,6,8-tetraenoic acid
• Synonyms: 11-cis-Retinoic Acid-d5; 11-cis-Retinoic Acid-d5

Database IDs

• PubChem SID: 164233357
• PubChem CID: 71752028

CALCULATED PROPERTIES

• Acid pKa: 4.996648
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.392896
• LogD (pH = 7.4): 2.6406298
• Log P: 5.0143676
• Molar Refractivity: 97.7908 cm^3
• Polarizability: 36.17498 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - R245022

A labelled retinoid compound with reduced toxicity than the starting or parent retinoid.

REFERENCES

• Carter, H.E., et al.: J. Biol. Chem., 175, 683 (1943)