(2S)-2-[(2S)-2-{[(2S)-2-{[(2R)-2-amino-3-sulfanylpropyl]amino}-3-methylbutyl]amino}-3-phenylpropanamido]-4-(methylsulfanyl)butanoic acid

• ChemBase ID: 153743
• Molecular Formular: C22H38N4O3S2
• Molecular Mass: 470.69212
• Monoisotopic Mass: 470.2385331
• SMILES: CC(C)[C@@H](CN[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCSC)C(=O)O)NC[C@H](CS)N
• Canonical SMILES: CSCC[C@@H](C(=O)O)NC(=O)[C@H](Cc1ccccc1)NC[C@H](C(C)C)NC[C@H](CS)N
• InChI: InChI=1S/C22H38N4O3S2/c1-15(2)20(24-12-17(23)14-30)13-25-19(11-16-7-5-4-6-8-16)21(27)26-18(22(28)29)9-10-31-3/h4-8,15,17-20,24-25,30H,9-14,23H2,1-3H3,(H,26,27)(H,28,29)/t17-,18+,19+,20-/m1/s1
• InChIKey: QISLMXIYRQCLIR-FUMNGEBKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-{[(2S)-2-{[(2R)-2-amino-3-sulfanylpropyl]amino}-3-methylbutyl]amino}-3-phenylpropanamido]-4-(methylsulfanyl)butanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-{[(2S)-2-{[(2R)-2-amino-3-sulfanylpropyl]amino}-3-methylbutyl]amino}-3-phenylpropanamido]-4-(methylsulfanyl)butanoic acid
• Synonyms: N-[2(S)-(2(R)-2-Amino-3-mercaptopropylamino)-3-methylbutyl]-L-phenylalanyl-L-methionine trifluoroacetate salt; B581

Database IDs

• CAS Number: 149759-96-6
• MDL Number: MFCD00236999
• PubChem SID: 24891659; 162247882
• PubChem CID: 132887

CALCULATED PROPERTIES

• Acid pKa: 3.462416
• H Acceptors: 6
• H Donor: 6
• LogD (pH = 5.5): -2.5530422
• LogD (pH = 7.4): -0.7975865
• Log P: -0.3099113
• Molar Refractivity: 130.5107 cm^3
• Polarizability: 52.208668 Å^3
• Polar Surface Area: 116.48 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble
• Apperance: white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: rat ... Fnta(25318)

Product Information

• Purity: >95% (HPLC)
• Compostion: Peptide content, ~60%
• Empirical Formula (Hill Notation): C22H38N4O3S2

DETAILS

Sigma Aldrich - B2559

Amino Acid Sequence
Cys-(R)-Val-(R)-Phe-Met
Biochem/physiol Actions
Stable and membrane permeable inhibitor of farnesyltransferase.
Packaging
Packaged under nitrogen and with desiccant.