(7R,8R,10E)-6-(dimethylamino)-7-hydroxy-8-methyl(11,12,12,12-2H4)dodec-10-en-5-one; butane

• ChemBase ID: 165308
• Molecular Formular: C19H39NO2
• Molecular Mass: 313.51846
• Monoisotopic Mass: 313.29807949
• SMILES: CCCC.C(C(=O)CCCC)([C@@H]([C@@H](C/C=C/C)C)O)N(C)C
• Canonical SMILES: CCCCC(=O)C([C@@H]([C@@H](C/C=C/C)C)O)N(C)C.CCCC
• InChI: InChI=1S/C15H29NO2.C4H10/c1-6-8-10-12(3)15(18)14(16(4)5)13(17)11-9-7-2;1-3-4-2/h6,8,12,14-15,18H,7,9-11H2,1-5H3;3-4H2,1-2H3/b8-6+;/t12-,14?,15-;/m1./s1
• InChIKey: YWOHTTLEIZTTAR-QLERBJDDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (7R,8R,10E)-6-(dimethylamino)-7-hydroxy-8-methyl(11,12,12,12-^2H₄)dodec-10-en-5-one; butane
• IUPAC Traditional name: (7R,8R,10E)-6-(dimethylamino)-7-hydroxy-8-methyl(11,12,12,12-^2H₄)dodec-10-en-5-one; butane
• Synonyms: Cyclosporin H-d4

Database IDs

• PubChem SID: 162259441
• PubChem CID: 71315137

CALCULATED PROPERTIES

• Acid pKa: 14.1587
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.3255656
• LogD (pH = 7.4): 2.9900007
• Log P: 3.3851604
• Molar Refractivity: 77.8243 cm^3
• Polarizability: 30.340471 Å^3
• Polar Surface Area: 40.54 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C988922

Labelled analog of 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)