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

• ChemBase ID: 131022
• Molecular Formular: C20H33NO3S
• Molecular Mass: 367.54592
• Monoisotopic Mass: 367.21811492
• SMILES: CC(=CCC/C(=C/CC/C(=C/CSCC(C(=O)O)NC(=O)C)/C)/C)C
• Canonical SMILES: C/C(=C\CSCC(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+
• InChIKey: XTURYZYJYQRJDO-JTCWOHKRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-acetamido-3-{[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]sulfanyl}propanoic acid
• IUPAC Traditional name: 2-acetamido-3-{[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]sulfanyl}propanoic acid
• Synonyms: AFC; N-Acetyl-S-farnesyl-L-cysteine

Database IDs

• CAS Number: 135304-07-3
• MDL Number: MFCD00871540
• PubChem SID: 162225300
• PubChem CID: 5353378

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: 109.091 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

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

DETAILS

Sigma Aldrich - A9201

Biochem/physiol Actions
Has high affinity for S-farnesylcysteine methyl transferase thereby inhibiting carboxyterminal methylation of proteins, such as p21ras and Rap1