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

• ChemBase ID: 165304
• Molecular Formular: C36H72N4O5
• Molecular Mass: 640.98068
• Monoisotopic Mass: 640.55027142
• SMILES: N(C(C(=O)C(=O)[C@H](C(C)C)NC)[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.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@H](C(C(=O)C(=O)[C@H](C(C)C)NC)N(C)C)O)C.CCCC
• InChI: InChI=1S/C17H32N2O3.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/h8-9,11-15,18,20H,10H2,1-7H3;10-12,14,16H,7-9H2,1-6H3,(H,17,19);3-4H2,1-2H3/b9-8+;;/t12-,13+,14?,15-;12-,14-;/m10./s1
• InChIKey: FDUWKYSKEFIMQZ-RFFSZQBWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-4-methyl-N-[(3S)-2-methyl-4-oxoheptan-3-yl]-2-(methylamino)pentanamide; (3S,7R,8R,10E)-6-(dimethylamino)-7-hydroxy-2,8-dimethyl-3-(methylamino)dodec-10-ene-4,5-dione; butane
• IUPAC Traditional name: (2S)-4-methyl-N-[(3S)-2-methyl-4-oxoheptan-3-yl]-2-(methylamino)pentanamide; (3S,7R,8R,10E)-6-(dimethylamino)-7-hydroxy-2,8-dimethyl-3-(methylamino)dodec-10-ene-4,5-dione; butane
• Synonyms: Val2-cyclosporine; Cyclosporin D

Database IDs

• CAS Number: 63775-96-2
• PubChem SID: 162259437
• PubChem CID: 71315129

CALCULATED PROPERTIES

• Acid pKa: 12.375206
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.5283954
• LogD (pH = 7.4): 2.112805
• Log P: 3.0494168
• Molar Refractivity: 90.9652 cm^3
• Polarizability: 35.61558 Å^3
• Polar Surface Area: 69.64 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Colorless Crystalline Solid
• Melting Point: 148-151°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C988910

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)