(2E,5R,16S)-7-(dimethylamino)-5,17-dimethyl-16-[(2S)-4-methyl-2-(methylamino)pentanamido]-8,15-dioxo(1,1,1,2-2H4)octadec-2-en-6-yl acetate

• ChemBase ID: 165294
• Molecular Formular: C31H57N3O5
• Molecular Mass: 551.80138
• Monoisotopic Mass: 551.42982194
• SMILES: C(CCC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)CCCC(=O)C(N(C)C)C([C@@H](C/C=C/C)C)OC(=O)C
• Canonical SMILES: C/C=C/C[C@H](C(C(C(=O)CCCCCCC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)N(C)C)OC(=O)C)C
• InChI: InChI=1S/C31H57N3O5/c1-11-12-17-23(6)30(39-24(7)35)29(34(9)10)27(37)19-16-14-13-15-18-26(36)28(22(4)5)33-31(38)25(32-8)20-21(2)3/h11-12,21-23,25,28-30,32H,13-20H2,1-10H3,(H,33,38)/b12-11+/t23-,25+,28+,29?,30?/m1/s1
• InChIKey: MJAWNADQWQTPRP-IUUVSZEYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,5R,16S)-7-(dimethylamino)-5,17-dimethyl-16-[(2S)-4-methyl-2-(methylamino)pentanamido]-8,15-dioxo(1,1,1,2-^2H₄)octadec-2-en-6-yl acetate
• IUPAC Traditional name: (2E,5R,16S)-7-(dimethylamino)-5,17-dimethyl-16-[(2S)-4-methyl-2-(methylamino)pentanamido]-8,15-dioxo(1,1,1,2-^2H₄)octadec-2-en-6-yl acetate
• Synonyms: 6-[(2S,3R,4R,6E)-3-(Acetyloxy)-4-methyl-2-(methylamino)-6-octenoic-d4 acid] Cyclosporin A; B 3-243-d4; O-Acetyl-C91-cyclosporin A-d4; O-Acetylcyclosporin A-d4; SDZ 33-243-d4; Cyclosporin A-d4 Acetate (Major)

Database IDs

• PubChem SID: 162259427
• PubChem CID: 71315112

CALCULATED PROPERTIES

• Acid pKa: 13.127856
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.8924342
• LogD (pH = 7.4): 4.2211614
• Log P: 5.8516765
• Molar Refractivity: 158.5901 cm^3
• Polarizability: 62.75373 Å^3
• Polar Surface Area: 104.81 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Benzene; Methanol
• Apperance: White Solid
• Melting Point: 144-159°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C988892

A non-immunosuppressive analog of Cyclosporin A.

REFERENCES

• Twentyman, P. R., et al.: Brit. J. Cancer, 57, 254 (1988)
• Twentyman, P. R., et al.: Brit. J. Cancer, 65, 335 (1988)
• Schneider, H., et al.: Biochem., 33, 8218 (1994).