propan-2-yl (2S)-2-[(2S)-2-{[(2S,3R)-2-{[(2R)-2-amino-3-sulfanylpropyl]amino}-3-methylpentyl]oxy}-3-phenylpropanamido]-4-methanesulfonylbutanoate

• ChemBase ID: 172464
• Molecular Formular: C26H45N3O6S2
• Molecular Mass: 559.782
• Monoisotopic Mass: 559.27497818
• SMILES: N[C@H](CN[C@H](CO[C@H](C(=O)N[C@H](C(=O)OC(C)C)CCS(=O)(=O)C)Cc1ccccc1)[C@H](C)CC)CS
• Canonical SMILES: CC[C@H]([C@H](NC[C@H](CS)N)CO[C@H](C(=O)N[C@H](C(=O)OC(C)C)CCS(=O)(=O)C)Cc1ccccc1)C
• InChI: InChI=1S/C26H45N3O6S2/c1-6-19(4)23(28-15-21(27)17-36)16-34-24(14-20-10-8-7-9-11-20)25(30)29-22(12-13-37(5,32)33)26(31)35-18(2)3/h7-11,18-19,21-24,28,36H,6,12-17,27H2,1-5H3,(H,29,30)/t19-,21-,22+,23-,24+/m1/s1
• InChIKey: PGOKBMWPBDRDGN-ZXGKGEBGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: propan-2-yl (2S)-2-[(2S)-2-{[(2S,3R)-2-{[(2R)-2-amino-3-sulfanylpropyl]amino}-3-methylpentyl]oxy}-3-phenylpropanamido]-4-methanesulfonylbutanoate
• IUPAC Traditional name: isopropyl (2S)-2-[(2S)-2-{[(2S,3R)-2-{[(2R)-2-amino-3-sulfanylpropyl]amino}-3-methylpentyl]oxy}-3-phenylpropanamido]-4-methanesulfonylbutanoate
• Synonyms: (2S)-[(2S)-[(2R)-Amino-3-mercapto]-propylamino-(3S)-methyl]pentyloxy-3-phenylpropionyl-methionine Sulfone Isopropyl Ester Bis Hydrchloride; L-744832

Database IDs

• CAS Number: 1177806-11-9
• PubChem SID: 164228374
• PubChem CID: 16760043

CALCULATED PROPERTIES

• Acid pKa: 10.252534
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.9976766
• LogD (pH = 7.4): -0.5411499
• Log P: 1.378605
• Molar Refractivity: 148.8764 cm^3
• Polarizability: 60.129036 Å^3
• Polar Surface Area: 136.82 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetonitrile; Methanol
• Apperance: White Solid
• Melting Point: 165-168°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - L744832

Ras farnesyltransferase inhibitor. Induces tumor regression in transgenic mice with multiple oncogenic mutations by mediating alterations in both cell cycle control and apoptosis. Induces p21 expressoin and arrests cells at G1. Causes enhanced mitotic

REFERENCES

• Barrington, R.E., et al.: Mol. Cell. Biol., 18, 85 (1998, Sepp-Lorenzo, L. and Rosen, N.: J. Biol. Chem., 273, 20243 (1998)
• Moasser, M.M., et al.: Proc. Natl. Acad. Sci. USA, 95, 1369 (1998)
• Law, B.K., et al.: J. Biol. Chem., 275, 10796 (1998)