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

• ChemBase ID: 160309
• Molecular Formular: C23H39ClN2O6S
• Molecular Mass: 507.08356
• Monoisotopic Mass: 506.22173566
• SMILES: N[C@H](COC(C(=O)N[C@H](C(=O)OC(C)C)CCS(=O)(=O)C)Cc1ccccc1)[C@@H](C)CC.Cl
• Canonical SMILES: CC[C@@H]([C@@H](COC(C(=O)N[C@H](C(=O)OC(C)C)CCS(=O)(=O)C)Cc1ccccc1)N)C.Cl
• InChI: InChI=1S/C23H38N2O6S.ClH/c1-6-17(4)19(24)15-30-21(14-18-10-8-7-9-11-18)22(26)25-20(12-13-32(5,28)29)23(27)31-16(2)3;/h7-11,16-17,19-21H,6,12-15,24H2,1-5H3,(H,25,26);1H/t17-,19+,20-,21?;/m0./s1
• InChIKey: BDEITASACKHYLY-GFRIYUNYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: propan-2-yl (2S)-2-(2-{[(2S,3S)-2-amino-3-methylpentyl]oxy}-3-phenylpropanamido)-4-methanesulfonylbutanoate hydrochloride
• IUPAC Traditional name: isopropyl (2S)-2-(2-{[(2S,3S)-2-amino-3-methylpentyl]oxy}-3-phenylpropanamido)-4-methanesulfonylbutanoate hydrochloride
• Synonyms: (2S)-2-[[2-[[(2S,3S)-2-Amino-3-methylpentyl]oxy]-1-oxo-3-phenylpropyl]amino]-4-(methylsulfonyl)butanoic Acid 1-Methylethyl Ester Hydrochloride; (2S)-[(2'S)-Amino-(3'S)-methyl-1-pentyloxy]-3-phenylpropionyl-methionine Sulfone, Isopropyl Ester, Hydrochloride

Database IDs

• CAS Number: 1356019-46-9
• PubChem SID: 162254444
• PubChem CID: 71313315

CALCULATED PROPERTIES

• Acid pKa: 12.170946
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.4420172
• LogD (pH = 7.4): -0.4949189
• Log P: 1.5448809
• Molar Refractivity: 124.0069 cm^3
• Polarizability: 50.0286 Å^3
• Polar Surface Area: 124.79 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Cyrstalline Solid
• Melting Point: 163-165°C

DETAILS

Toronto Research Chemicals - A616985

An intermediate in the Ras farnesyltransferase inhibitor L-744832.

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)