(2R,3S,7R,8R,10E)-3-(butylamino)-6-(dimethylamino)-2,7-dihydroxy-8-methyl(11,12,12,12-2H4)dodec-10-ene-4,5-dione; (2S)-4-methyl-N-[(3S)-2-methyl-4-oxoheptan-3-yl]-2-(methylamino)pentanamide

• ChemBase ID: 165303
• Molecular Formular: C34H66N4O6
• Molecular Mass: 626.91104
• Monoisotopic Mass: 626.49823585
• SMILES: N(C(C(=O)C(=O)[C@H]([C@@H](C)O)NCCCC)[C@@H]([C@@H](C/C=C/C)C)O)(C)C.C(CC)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC
• Canonical SMILES: CCCC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC.CCCCN[C@H](C(=O)C(=O)C([C@@H]([C@@H](C/C=C/C)C)O)N(C)C)[C@H](O)C
• InChI: InChI=1S/C19H36N2O4.C15H30N2O2/c1-7-9-11-13(3)17(23)16(21(5)6)19(25)18(24)15(14(4)22)20-12-10-8-2;1-7-8-13(18)14(11(4)5)17-15(19)12(16-6)9-10(2)3/h7,9,13-17,20,22-23H,8,10-12H2,1-6H3;10-12,14,16H,7-9H2,1-6H3,(H,17,19)/b9-7+;/t13-,14-,15+,16?,17-;12-,14-/m10/s1
• InChIKey: MFOWVEYETUNHKO-GNDJWJKYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,7R,8R,10E)-3-(butylamino)-6-(dimethylamino)-2,7-dihydroxy-8-methyl(11,12,12,12-^2H₄)dodec-10-ene-4,5-dione; (2S)-4-methyl-N-[(3S)-2-methyl-4-oxoheptan-3-yl]-2-(methylamino)pentanamide
• IUPAC Traditional name: (2R,3S,7R,8R,10E)-3-(butylamino)-6-(dimethylamino)-2,7-dihydroxy-8-methyl(11,12,12,12-^2H₄)dodec-10-ene-4,5-dione; (2S)-4-methyl-N-[(3S)-2-methyl-4-oxoheptan-3-yl]-2-(methylamino)pentanamide
• Synonyms: Thr2-cyclosporine-d4; Cyclosporin C-d4

Database IDs

• PubChem SID: 162259436
• PubChem CID: 71315127

CALCULATED PROPERTIES

• Acid pKa: 9.770271
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.35902664
• LogD (pH = 7.4): 2.2564726
• Log P: 2.7334445
• Molar Refractivity: 101.8057 cm^3
• Polarizability: 39.920734 Å^3
• Polar Surface Area: 89.87 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C988907

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)