(3R,14S)-5-(dimethylamino)-3,15-dimethyl-14-[(2S)-4-methyl-2-(methylamino)pentanamido]-1,6,13-trioxohexadecan-4-yl acetate

• ChemBase ID: 159156
• Molecular Formular: C29H53N3O6
• Molecular Mass: 539.74762
• Monoisotopic Mass: 539.39343643
• SMILES: C(CCC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)CCCC(=O)C(N(C)C)C([C@@H](CC=O)C)OC(=O)C
• Canonical SMILES: O=CC[C@H](C(C(C(=O)CCCCCCC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)N(C)C)OC(=O)C)C
• InChI: InChI=1S/C29H53N3O6/c1-19(2)18-23(30-7)29(37)31-26(20(3)4)24(35)14-12-10-11-13-15-25(36)27(32(8)9)28(38-22(6)34)21(5)16-17-33/h17,19-21,23,26-28,30H,10-16,18H2,1-9H3,(H,31,37)/t21-,23+,26+,27?,28?/m1/s1
• InChIKey: DIZXHMGPGJSRNA-CBRXDTHZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,14S)-5-(dimethylamino)-3,15-dimethyl-14-[(2S)-4-methyl-2-(methylamino)pentanamido]-1,6,13-trioxohexadecan-4-yl acetate
• IUPAC Traditional name: (3R,14S)-5-(dimethylamino)-3,15-dimethyl-14-[(2S)-4-methyl-2-(methylamino)pentanamido]-1,6,13-trioxohexadecan-4-yl acetate
• Synonyms: 6-[(3R,4R)-3-(Acetyloxy)-N,4-dimethyl-6-oxo-L-norleucine] Cyclosporin A

Database IDs

• CAS Number: 121584-52-9
• PubChem SID: 162253291
• PubChem CID: 71312829

CALCULATED PROPERTIES

• Acid pKa: 13.069128
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 0.41205087
• LogD (pH = 7.4): 2.2448406
• Log P: 3.845603
• Molar Refractivity: 149.0115 cm^3
• Polarizability: 59.397633 Å^3
• Polar Surface Area: 121.88 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - A168650

Intermediate for the preparation of Cyclosporin derivatives for the treatment of immune disorders.

REFERENCES

• Billich, et al.: J. Biol. Chem., 262, 1725 (1987)
• Faulds, et al.: Drugs, 46, 953 (1987)
• Hogg, J., et al.: Lancet, 364, 709 (1987)