(2S)-N-[(1S)-1-{[(5R,6R,8E)-5-hydroxy-6-methyl-3-oxo(9,10-13C2,9,10,10,10-2H4)dec-8-en-4-yl](methyl)carbamoyl}-2-methylpropyl]-4-methyl-2-(methylamino)pentanamide; bis(butane)

• ChemBase ID: 165298
• Molecular Formular: C32H65N3O4
• Molecular Mass: 557.86150968
• Monoisotopic Mass: 557.50421725
• SMILES: C(CC)C.N(C(C(=O)CC)[C@@H]([C@@H](C/C=[13CH]/[13CH3])C)O)(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC.CCCC
• Canonical SMILES: [13CH3]/[13CH]=C/C[C@H]([C@H](C(N(C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)C)C(=O)CC)O)C.CCCC.CCCC
• InChI: InChI=1S/C24H45N3O4.2C4H10/c1-10-12-13-17(7)22(29)21(19(28)11-2)27(9)24(31)20(16(5)6)26-23(30)18(25-8)14-15(3)4;2*1-3-4-2/h10,12,15-18,20-22,25,29H,11,13-14H2,1-9H3,(H,26,30);2*3-4H2,1-2H3/b12-10+;;/t17-,18+,20+,21?,22-;;/m1../s1/i1+1,10+1
• InChIKey: NYYKRIRHZWQADC-YXIMXLRLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(1S)-1-{[(5R,6R,8E)-5-hydroxy-6-methyl-3-oxo(9,10-^1^3C₂,9,10,10,10-^2H₄)dec-8-en-4-yl](methyl)carbamoyl}-2-methylpropyl]-4-methyl-2-(methylamino)pentanamide; bis(butane)
• IUPAC Traditional name: (2S)-N-[(1S)-1-{[(5R,6R,8E)-5-hydroxy-6-methyl-3-oxo(9,10-^1^3C₂,9,10,10,10-^2H₄)dec-8-en-4-yl](methyl)carbamoyl}-2-methylpropyl]-4-methyl-2-(methylamino)pentanamide; bis(butane)
• Synonyms: Cyclosporine-13C2,d4; Ciclosporin-13C2,d4; Atopica-13C2,d4; Sandimmun(e)-13C2,d4; Neoral-13C2,d4; Optimmune-13C2,d4; Restasis-13C2,d4; Cyclosporin A-13C2,d4 (Major)

Database IDs

• PubChem SID: 162259431
• PubChem CID: 71315117

CALCULATED PROPERTIES

• Acid pKa: 12.799408
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.48988524
• LogD (pH = 7.4): 2.096803
• Log P: 3.4052186
• Molar Refractivity: 125.4883 cm^3
• Polarizability: 49.32773 Å^3
• Polar Surface Area: 98.74 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Benzene; Chloroform; Ethanol; Methanol
• Apperance: White Solid
• Melting Point: 140-145°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C988901

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)