(2E,4E,6Z,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: 177445
• 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-ZVCIMWCZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,4E,6Z,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,4E,6Z,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: (2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoic Acid-d5; 9-cis-Tretinoin-d5; AGN 192013-d5; ALRT 1057-d5; Alitretinoin-d5; LG 100057-d5; LGD 100057-d5; LGD 1057-d5; NSC 659772-d5; Panretin-d5; Panretyn-d5; Panrexin-d5; 9-cis-Retinoic Acid-d5

Database IDs

• PubChem SID: 164233355
• PubChem CID: 71752027

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 - R245002

An endogenous retinoic acid isomer, which is capable of binding to both retinoic acid receptors (RAR) and retinoid X receptors (RXR). A biologically active ligand for members of the RAR and RXR subfamilies, implying that it may play a critical role in r

REFERENCES

• Heyman, R.A., et al.: Cell, 68, 397 (1992)
• Levin, A.A., et al.: Nature, 355, 359 (1992)
• Allenby, G., et al.: Proc. Natl. Acad. Sci. U.S.A., 90, 30 (1993)