(2E,5R,6R)-5-methyl-7-(methylamino)-8-oxopentadec-2-en-6-yl (2S)-3-methyl-2-[(2S)-4-methyl-2-(methylamino)pentanamido]butanoate

• ChemBase ID: 171783
• Molecular Formular: C29H55N3O4
• Molecular Mass: 509.7647
• Monoisotopic Mass: 509.41925726
• SMILES: C(CCC)CCCC(=O)C([C@@H]([C@@H](C/C=C/C)C)OC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)NC
• Canonical SMILES: CCCCCCCC(=O)C([C@@H]([C@@H](C/C=C/C)C)OC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)NC
• InChI: InChI=1S/C29H55N3O4/c1-10-12-14-15-16-18-24(33)26(31-9)27(22(7)17-13-11-2)36-29(35)25(21(5)6)32-28(34)23(30-8)19-20(3)4/h11,13,20-23,25-27,30-31H,10,12,14-19H2,1-9H3,(H,32,34)/b13-11+/t22-,23+,25+,26?,27-/m1/s1
• InChIKey: WPQBWMHHEXUOHJ-HPJRLRKPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,5R,6R)-5-methyl-7-(methylamino)-8-oxopentadec-2-en-6-yl (2S)-3-methyl-2-[(2S)-4-methyl-2-(methylamino)pentanamido]butanoate
• IUPAC Traditional name: (2E,5R,6R)-5-methyl-7-(methylamino)-8-oxopentadec-2-en-6-yl (2S)-3-methyl-2-[(2S)-4-methyl-2-(methylamino)pentanamido]butanoate
• Synonyms: (2S,3R,4R,6E)-3-Hydroxy-4-methyl-2-(methylamino)-6-octenoyl-(2S)-2-aminobutanoyl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valine (111)-Lactone; Iso Cyclosporin A

Database IDs

• CAS Number: 59865-16-6
• PubChem SID: 164227693
• PubChem CID: 71749549

CALCULATED PROPERTIES

• Acid pKa: 12.695735
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.1160032
• LogD (pH = 7.4): 4.2888775
• Log P: 6.459245
• Molar Refractivity: 148.0789 cm^3
• Polarizability: 58.99966 Å^3
• Polar Surface Area: 96.53 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 148-152°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - I811500

Cyclosporin A (C988900) impurity.

REFERENCES

• Oliyai, R., et al.: Pharm. Res., 12, 323 (1995)
• Hermann, M., et al.: J. Pharm. Biomed. Anal., 30, 1263 (1995)
• Johnston, A., et al.: Ther. Drug Monit., 25, 167 (1995)