2-{[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]sulfanyl}benzoic acid

• ChemBase ID: 168870
• Molecular Formular: C22H30O2S
• Molecular Mass: 358.5374
• Monoisotopic Mass: 358.1966512
• SMILES: c1cccc(c1SC/C=C(/CC/C=C(/CCC=C(C)C)\C)\C)C(=O)O
• Canonical SMILES: C/C(=C\CSc1ccccc1C(=O)O)/CC/C=C(/CCC=C(C)C)\C
• InChI: InChI=1S/C22H30O2S/c1-17(2)9-7-10-18(3)11-8-12-19(4)15-16-25-21-14-6-5-13-20(21)22(23)24/h5-6,9,11,13-15H,7-8,10,12,16H2,1-4H3,(H,23,24)/b18-11+,19-15+
• InChIKey: WUILNKCFCLNXOK-CFBAGHHKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]sulfanyl}benzoic acid
• IUPAC Traditional name: salirasib
• Synonyms: 2-[[(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl]thio]benzoic Acid; (E,E)-2-[(3,7,11-Trimethyl-2,6,10-dodecatrienyl)thio]benzoic Acid; FTS; Farnesylthiosalicylate; S-Farnesylthiosalicylic Acid; Salirasib; trans,trans Farnesyl Thiosalicylic Acid

Database IDs

• CAS Number: 162520-00-5
• PubChem SID: 162263002
• PubChem CID: 5469318

CALCULATED PROPERTIES

• Acid pKa: 3.405503
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.7536316
• LogD (pH = 7.4): 3.4344244
• Log P: 6.8359427
• Molar Refractivity: 112.8457 cm^3
• Polarizability: 42.6382 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Pale Yellow Solid
• Melting Point: 64-66°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - F102500

It is a new specific nontoxic drug with a mild hydrophobic nature, which acts as a Ras antagonist and can therefore be used for stent applications as well as for local cancer treatment.

REFERENCES

• Marciano, D., et al.: J. Med. Chem., 38, 1267 (1995)
• Li, Y., et al.: J. Cardiovasc. Pharmacol., 48, 184 (1995)
• Rao, S., et al.: Am. J. Cardiol., 97, 1478 (1995)