(2S)-4-methyl-N-[(3S)-2-methyl-4-oxoheptan-3-yl]-2-(methylamino)pentanamide; (3S,8R,10E)-6-(dimethylamino)-2,8-dimethyl-3-(methylamino)dodec-10-ene-4,5,7-trione; butane

• ChemBase ID: 179436
• Molecular Formular: C36H70N4O5
• Molecular Mass: 638.9648
• Monoisotopic Mass: 638.53462136
• SMILES: N(C(C(=O)C(=O)[C@H](C(C)C)NC)C(=O)[C@@H](C/C=C/C)C)(C)C.C(CC)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC.CCCC
• Canonical SMILES: CCCC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC.C/C=C/C[C@H](C(=O)C(C(=O)C(=O)[C@H](C(C)C)NC)N(C)C)C.CCCC
• InChI: InChI=1S/C17H30N2O3.C15H30N2O2.C4H10/c1-8-9-10-12(4)15(20)14(19(6)7)17(22)16(21)13(18-5)11(2)3;1-7-8-13(18)14(11(4)5)17-15(19)12(16-6)9-10(2)3;1-3-4-2/h8-9,11-14,18H,10H2,1-7H3;10-12,14,16H,7-9H2,1-6H3,(H,17,19);3-4H2,1-2H3/b9-8+;;/t12-,13+,14?;12-,14-;/m10./s1
• InChIKey: VAZOZNABZWSCPJ-UJUDLTFRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-4-methyl-N-[(3S)-2-methyl-4-oxoheptan-3-yl]-2-(methylamino)pentanamide; (3S,8R,10E)-6-(dimethylamino)-2,8-dimethyl-3-(methylamino)dodec-10-ene-4,5,7-trione; butane
• IUPAC Traditional name: (2S)-4-methyl-N-[(3S)-2-methyl-4-oxoheptan-3-yl]-2-(methylamino)pentanamide; (3S,8R,10E)-6-(dimethylamino)-2,8-dimethyl-3-(methylamino)dodec-10-ene-4,5,7-trione; butane
• Synonyms: 6-[(2S,4R,6E)-4-Methyl-2-(methylamino)-3-oxo-6-octenoic Acid]-7-L-valine-cyclosporin A; 6-[[R-(E)]-6,7-Didehydro-N,4-dimethyl-3-oxo-L-2-aminooctanoic acid]-7-L-valinecyclosporin A; 6-[(2S,4R,6E)-4-Methyl-2-(methylamino)-3-oxo-6-octenoic Acid]ccyclosporin D; Amdray; PSC 833; SDZ-PSC 833; Valpodar; Valspodar

Database IDs

• CAS Number: 121584-18-7
• PubChem SID: 164235346
• PubChem CID: 71752908

CALCULATED PROPERTIES

• Acid pKa: 9.467263
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.1873207
• LogD (pH = 7.4): 2.9692764
• Log P: 3.5748045
• Molar Refractivity: 90.2458 cm^3
• Polarizability: 35.068783 Å^3
• Polar Surface Area: 66.48 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 149-152°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - V096100

Antineoplastic adjunct (chemosensitizer).

REFERENCES

• Boesch, D., et al.: exp. Cell Res., 196, 26 (1991)
• Lush, R.M., et al.: J. Clin. Pharmacol., 37, 123 (1991)
• Scott, M.G., et al.: Clin. Chem., 43, 505 (1991)
• Advani, R., et al.: Blood, 93, 787 (1991)