(2S)-N-[(3S,13R,14R,16E)-12-(dimethylamino)-13-hydroxy-2,14-dimethyl-4,11-dioxo(17,18,18,18-2H4)octadec-16-en-3-yl]-4-methyl-2-(methylamino)pentanamide

• ChemBase ID: 165299
• Molecular Formular: C29H55N3O4
• Molecular Mass: 509.7647
• Monoisotopic Mass: 509.41925726
• 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](C/C=C/C)C)O
• Canonical SMILES: C/C=C/C[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/C29H55N3O4/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/h10-11,20-23,26-28,30,35H,12-19H2,1-9H3,(H,31,36)/b11-10+/t22-,23+,26+,27?,28-/m1/s1
• InChIKey: OVRSPEVBEPEKGL-BGAWTGSHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(3S,13R,14R,16E)-12-(dimethylamino)-13-hydroxy-2,14-dimethyl-4,11-dioxo(17,18,18,18-^2H₄)octadec-16-en-3-yl]-4-methyl-2-(methylamino)pentanamide
• IUPAC Traditional name: (2S)-N-[(3S,13R,14R,16E)-12-(dimethylamino)-13-hydroxy-2,14-dimethyl-4,11-dioxo(17,18,18,18-^2H₄)octadec-16-en-3-yl]-4-methyl-2-(methylamino)pentanamide
• Synonyms: Cyclosporine-d4; Ciclosporin-d4; Atopica-d4; Sandimmun(e)-d4; Neoral-d4; Optimmune-d4; Cyclosporin A-d4 (Major)

Database IDs

• PubChem SID: 162259432
• PubChem CID: 71315119

CALCULATED PROPERTIES

• Acid pKa: 13.089189
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.9756581
• LogD (pH = 7.4): 3.7048545
• Log P: 5.410551
• Molar Refractivity: 149.4386 cm^3
• Polarizability: 58.9265 Å^3
• Polar Surface Area: 98.74 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Benzene; Chloroform; Ethanol
• Apperance: White Solid
• Melting Point: 133-136°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C988902

An immunosuppressant that has revolutionized organ transplantation through its use in the prevention of graft rejection.A group of nonpolar cyclic oligopeptides with immunosupppressant activity.

REFERENCES

• van Wartburg, A., et al.: Prog. Med. Chem., 25, 1 (1988)
• Jorgensen, K.A., et al.: Scand. J. Imunol., 57, 93 (1988)
• Vollenbroeker, et al.: Transplant. Proc., 37, 1741 (1988)