(2S)-N-[(3S,13R,14R)-12-(dimethylamino)-13-hydroxy-2,14-dimethyl-4,11-dioxooctadecan-3-yl]-4-methyl-2-(methylamino)pentanamide

• ChemBase ID: 167561
• Molecular Formular: C29H57N3O4
• Molecular Mass: 511.78058
• Monoisotopic Mass: 511.43490732
• SMILES: C(CCC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)CCCC(=O)C(N(C)C)[C@@H]([C@@H](CCCC)C)O
• Canonical SMILES: CCCC[C@H]([C@H](C(C(=O)CCCCCCC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)N(C)C)O)C
• InChI: InChI=1S/C29H57N3O4/c1-10-11-16-22(6)28(35)27(32(8)9)25(34)18-15-13-12-14-17-24(33)26(21(4)5)31-29(36)23(30-7)19-20(2)3/h20-23,26-28,30,35H,10-19H2,1-9H3,(H,31,36)/t22-,23+,26+,27?,28-/m1/s1
• InChIKey: TTYSITHIYSFMJA-AEGQMGLXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(3S,13R,14R)-12-(dimethylamino)-13-hydroxy-2,14-dimethyl-4,11-dioxooctadecan-3-yl]-4-methyl-2-(methylamino)pentanamide
• IUPAC Traditional name: (2S)-N-[(3S,13R,14R)-12-(dimethylamino)-13-hydroxy-2,14-dimethyl-4,11-dioxooctadecan-3-yl]-4-methyl-2-(methylamino)pentanamide
• Synonyms: 6-[(2S,3R,4R)-3-Hydroxy-4-methyl-2-(methylamino)octanoic acid]cyclosporin A; Dihydrocyclosporin A; Dihydro Cyclosporin A

Database IDs

• CAS Number: 59865-15-5
• PubChem SID: 162261694
• PubChem CID: 71316150

CALCULATED PROPERTIES

• Acid pKa: 13.09005
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 1.3371304
• LogD (pH = 7.4): 4.0666685
• Log P: 5.772473
• Molar Refractivity: 148.322 cm^3
• Polarizability: 59.166965 Å^3
• Polar Surface Area: 98.74 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 120-125°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D448865

A Cyclosporin A (C988900) analog, an immunosuppressant.

REFERENCES

• Emmer, G., et al.: J. Med. Chem., 37, 1918 (1994)
• High, K., et al.: J. Biol. Chem., 269, 9105 (1994)