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

• ChemBase ID: 38845
• Molecular Formular: C20H33NO3S
• Molecular Mass: 367.54592
• Monoisotopic Mass: 367.21811492
• SMILES: [C@@H](NC(=O)C)(C(=O)O)CSC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C
• Canonical SMILES: C/C(=C\CSC[C@@H](C(=O)O)NC(=O)C)/CC/C=C(/CCC=C(C)C)\C
• InChI: InChI=1S/C20H33NO3S/c1-15(2)8-6-9-16(3)10-7-11-17(4)12-13-25-14-19(20(23)24)21-18(5)22/h8,10,12,19H,6-7,9,11,13-14H2,1-5H3,(H,21,22)(H,23,24)/b16-10+,17-12+/t19-/m0/s1
• InChIKey: XTURYZYJYQRJDO-BNAHBJSTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-acetamido-3-{[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]sulfanyl}propanoic acid; (2R)-2-acetamido-3-[(3,7,11-trimethyldodeca-2,6,10-trien-1-yl)sulfanyl]propanoic acid
• IUPAC Traditional name: (2R)-2-acetamido-3-{[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]sulfanyl}propanoic acid; (2R)-2-acetamido-3-[(3,7,11-trimethyldodeca-2,6,10-trien-1-yl)sulfanyl]propanoic acid
• Synonyms: Ac-Cys(farnesyl)-OH; AFC; N-ACETYL-S-FARNESYL-L-CYSTEINE AFC

Database IDs

• CAS Number: 135304-07-3
• MDL Number: MFCD00871540
• PubChem SID: 161002152
• PubChem CID: 6438381

CALCULATED PROPERTIES

• Acid pKa: 4.1077337
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.8462276
• LogD (pH = 7.4): 1.1585307
• Log P: 4.252593
• Molar Refractivity: 109.090996 cm^3
• Polarizability: 41.622257 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C
• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 98%

DETAILS

MP Biomedicals - 02159030

Purity: 98%
Specific inhibitor of S-farnesyl-cysteinemethyl transferase. Also prevents carboxyl methylation of p21^ras platelet RAP 1 and the transduction γ subunit.

REFERENCES

• Volker, C., et al., J. Biol. Chem. , 266 : 21515, (1991).
• Huzoor-Akabar, et al., ibid. , 266 : 4387, (1991).
• Perez-Sala, D., et al., Proc. Natl. Acad. Sci. USA, 88 : 3043, (1991).