trifluoroacetic acid methyl (2S)-2-[(4-{[(2R)-2-amino-3-sulfanylpropyl]amino}-2-phenylphenyl)formamido]-4-(methylsulfanyl)butanoate

• ChemBase ID: 154249
• Molecular Formular: C24H30F3N3O5S2
• Molecular Mass: 561.6373096
• Monoisotopic Mass: 561.15789774
• SMILES: COC(=O)[C@H](CCSC)NC(=O)c1ccc(cc1c1ccccc1)NC[C@H](CS)N.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.CSCC[C@@H](C(=O)OC)NC(=O)c1ccc(cc1c1ccccc1)NC[C@H](CS)N
• InChI: InChI=1S/C22H29N3O3S2.C2HF3O2/c1-28-22(27)20(10-11-30-2)25-21(26)18-9-8-17(24-13-16(23)14-29)12-19(18)15-6-4-3-5-7-15;3-2(4,5)1(6)7/h3-9,12,16,20,24,29H,10-11,13-14,23H2,1-2H3,(H,25,26);(H,6,7)/t16-,20+;/m1./s1
• InChIKey: GJEFFRDWFVSCOJ-PXPMWPIZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: trifluoroacetic acid methyl (2S)-2-[(4-{[(2R)-2-amino-3-sulfanylpropyl]amino}-2-phenylphenyl)formamido]-4-(methylsulfanyl)butanoate
• IUPAC Traditional name: trifluoroacetic acid methyl (2S)-2-[(4-{[(2R)-2-amino-3-sulfanylpropyl]amino}-2-phenylphenyl)formamido]-4-(methylsulfanyl)butanoate
• Synonyms: N-[4-[2(R)-Amino-3-mercaptopropyl]amino-2-phenylbenzoyl]methionine methyl ester trifluoroacetate salt; FTI-277 trifluoroacetate salt

Database IDs

• CAS Number: 170006-73-2(freebase)
• MDL Number: MFCD06795840
• PubChem SID: 162248388
• PubChem CID: 71311821

CALCULATED PROPERTIES

• Acid pKa: 10.253076
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -0.27681676
• LogD (pH = 7.4): 0.85378045
• Log P: 2.4657767
• Molar Refractivity: 127.8943 cm^3
• Polarizability: 50.23145 Å^3
• Polar Surface Area: 93.45 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: ≥2 mg/mL
• Apperance: amorphous semi-solid

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C22H29N3O3S2 · xC2HF3O2

DETAILS

Sigma Aldrich - F9803

Biochem/physiol Actions
Highly potent (pM/nM) Ras CAAX peptidomimetic which antagonizes both H and K-Ras oncogenic signaling. Inhibitor of farnesyltransferase (Ftase) IC50 = 50 nM.
Packaging
Very hygroscopic material, package in a dry room with deoxygenated MeOH and pump down the solvent. Store with desiccant.