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

• ChemBase ID: 162516
• Molecular Formular: C28H46N2O8S
• Molecular Mass: 570.73844
• Monoisotopic Mass: 570.29748744
• SMILES: N([C@H](CO[C@H](C(=O)N[C@H](C(=O)OC(C)C)CCS(=O)(=O)C)Cc1ccccc1)[C@H](CC)C)C(=O)OC(C)(C)C
• Canonical SMILES: CC[C@@H]([C@H](NC(=O)OC(C)(C)C)CO[C@H](C(=O)N[C@H](C(=O)OC(C)C)CCS(=O)(=O)C)Cc1ccccc1)C
• InChI: InChI=1S/C28H46N2O8S/c1-9-20(4)23(30-27(33)38-28(5,6)7)18-36-24(17-21-13-11-10-12-14-21)25(31)29-22(15-16-39(8,34)35)26(32)37-19(2)3/h10-14,19-20,22-24H,9,15-18H2,1-8H3,(H,29,31)(H,30,33)/t20-,22-,23+,24-/m0/s1
• InChIKey: XSTLYYSUOLGWPF-XGAJZPNHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: propan-2-yl (2S)-2-[(2S)-2-{[(2S,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-methylpentyl]oxy}-3-phenylpropanamido]-4-methanesulfonylbutanoate
• IUPAC Traditional name: isopropyl (2S)-2-[(2S)-2-{[(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-methylpentyl]oxy}-3-phenylpropanamido]-4-methanesulfonylbutanoate
• Synonyms: (2S)-[(2'S)-t-Boc-amino-(3'S)-methyl-1-pentyloxy]-3-phenylpropionyl-methionine Sulfone, Isopropyl Ester

Database IDs

• CAS Number: 1356016-69-7
• PubChem SID: 162256651
• PubChem CID: 57369105

CALCULATED PROPERTIES

• Acid pKa: 11.886021
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 3.036978
• LogD (pH = 7.4): 3.0369656
• Log P: 3.0369782
• Molar Refractivity: 148.8799 cm^3
• Polarizability: 59.646843 Å^3
• Polar Surface Area: 137.1 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Cyrstalline Powder
• Melting Point: 153-156°C

DETAILS

Toronto Research Chemicals - B619850

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)