(2R,6R,7R,9E)-2-(butylamino)-5-(dimethylamino)-6-hydroxy-7-methylundec-9-ene-3,4-dione; (2S)-4-methyl-N-[(3S)-2-methyl-4-oxoheptan-3-yl]-2-(methylamino)pentanamide

• ChemBase ID: 165300
• Molecular Formular: C33H64N4O5
• Molecular Mass: 596.88506
• Monoisotopic Mass: 596.48767117
• SMILES: N(C(C(=O)C(=O)[C@@H](C)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
• InChI: InChI=1S/C18H34N2O3.C15H30N2O2/c1-7-9-11-13(3)16(21)15(20(5)6)18(23)17(22)14(4)19-12-10-8-2;1-7-8-13(18)14(11(4)5)17-15(19)12(16-6)9-10(2)3/h7,9,13-16,19,21H,8,10-12H2,1-6H3;10-12,14,16H,7-9H2,1-6H3,(H,17,19)/b9-7+;/t13-,14-,15?,16-;12-,14-/m10/s1
• InChIKey: NDYIQLXISHEEOA-ZIBRUGRTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,6R,7R,9E)-2-(butylamino)-5-(dimethylamino)-6-hydroxy-7-methylundec-9-ene-3,4-dione; (2S)-4-methyl-N-[(3S)-2-methyl-4-oxoheptan-3-yl]-2-(methylamino)pentanamide
• IUPAC Traditional name: (2R,6R,7R,9E)-2-(butylamino)-5-(dimethylamino)-6-hydroxy-7-methylundec-9-ene-3,4-dione; (2S)-4-methyl-N-[(3S)-2-methyl-4-oxoheptan-3-yl]-2-(methylamino)pentanamide
• Synonyms: Ala2-cyclosporine; Antibiotic S 7481F2; Cyclosporin B

Database IDs

• CAS Number: 63775-95-1
• PubChem SID: 162259433
• PubChem CID: 71315120

CALCULATED PROPERTIES

• Acid pKa: 12.227869
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.049865182
• LogD (pH = 7.4): 2.5962985
• Log P: 3.4858205
• Molar Refractivity: 95.8432 cm^3
• Polarizability: 37.45767 Å^3
• Polar Surface Area: 69.64 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Amorphous White Solid
• Melting Point: 140-143°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C988903

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)