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

• ChemBase ID: 154260
• Molecular Formular: C23H28F3N3O5S2
• Molecular Mass: 547.6107296
• Monoisotopic Mass: 547.14224767
• SMILES: CSCC[C@@H](C(=O)O)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)O)NC(=O)c1ccc(cc1c1ccccc1)NC[C@H](CS)N
• InChI: InChI=1S/C21H27N3O3S2.C2HF3O2/c1-29-10-9-19(21(26)27)24-20(25)17-8-7-16(23-12-15(22)13-28)11-18(17)14-5-3-2-4-6-14;3-2(4,5)1(6)7/h2-8,11,15,19,23,28H,9-10,12-13,22H2,1H3,(H,24,25)(H,26,27);(H,6,7)/t15-,19+;/m1./s1
• InChIKey: IAVHISGQCODLHL-WSCVZUBPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(4-{[(2R)-2-amino-3-sulfanylpropyl]amino}-2-phenylphenyl)formamido]-4-(methylsulfanyl)butanoic acid; trifluoroacetic acid
• IUPAC Traditional name: (2S)-2-[(4-{[(2R)-2-amino-3-sulfanylpropyl]amino}-2-phenylphenyl)formamido]-4-(methylsulfanyl)butanoic acid; trifluoroacetic acid
• Synonyms: N-[4-[2-(R)-Amino-3-mercaptopropyl]amino-2-phenylbenzoyl]methionine trifluoroacetate salt; FTI-276 trifluoroacetate salt

Database IDs

• CAS Number: 170006-72-1(freebase)
• MDL Number: MFCD06409253
• PubChem SID: 162248399
• PubChem CID: 395753

CALCULATED PROPERTIES

• Acid pKa: 3.6656146
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): 0.2661691
• LogD (pH = 7.4): 0.26580292
• Log P: 0.269605
• Molar Refractivity: 123.1252 cm^3
• Polarizability: 48.131573 Å^3
• Polar Surface Area: 104.45 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: >5 mg/mL
• Apperance: off-white film

Safety Information

• Storage Condition: desiccated; under inert gas
• 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): C21H27N3O3S2 ·C2HF3O2

DETAILS

Sigma Aldrich - F9553

Biochem/physiol Actions
FTI-276 is a highly potent RasCAAX peptidomimetic. FTI-276 antagonizes both H and K-Ras oncogenic signaling. It is an inhibitor of farnesyltransferase (Ftase) in vitro with an IC50 of 500 pM and is an anti-cancer agent.