bis(butane) (6R,8E)-4-[(2S)-N,3-dimethyl-2-[(2S)-4-methyl-2-(methylamino)pentanamido]butanamido]-6-methyl-3-oxo(9,10-13C2,9,10,10,10-2H4)dec-8-en-5-yl acetate

• ChemBase ID: 165295
• Molecular Formular: C34H67N3O5
• Molecular Mass: 599.89818968
• Monoisotopic Mass: 599.51478194
• SMILES: C(CC)C.N(C(C(=O)CC)C([C@@H](C/C=[13CH]/[13CH3])C)OC(=O)C)(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(C(N(C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)C)C(=O)CC)OC(=O)C)C.CCCC.CCCC
• InChI: InChI=1S/C26H47N3O5.2C4H10/c1-11-13-14-18(7)24(34-19(8)30)23(21(31)12-2)29(10)26(33)22(17(5)6)28-25(32)20(27-9)15-16(3)4;2*1-3-4-2/h11,13,16-18,20,22-24,27H,12,14-15H2,1-10H3,(H,28,32);2*3-4H2,1-2H3/b13-11+;;/t18-,20+,22+,23?,24?;;/m1../s1/i1+1,11+1
• InChIKey: YDZAHIVASHKKKB-DZCNNOCESA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• PubChem SID: 162259428
• PubChem CID: 71315113

CALCULATED PROPERTIES

• Acid pKa: 12.723776
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.9310117
• LogD (pH = 7.4): 2.5379293
• Log P: 3.846344
• Molar Refractivity: 134.6398 cm^3
• Polarizability: 53.163414 Å^3
• Polar Surface Area: 104.81 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Benzene; Chloroform
• Apperance: White Foam

Safety Information

• Storage Condition: Refrigerator, under inert atmosphere

DETAILS

Toronto Research Chemicals - C988893

Labelled Cyclosporin A (C988901) derivative. 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 (2005)