(2S)-N-[(1S)-1-{[(7R,8R,10E)-7,12-dihydroxy-8-methyl-5-oxododec-10-en-6-yl](methyl)carbamoyl}-2-methylpropyl]-4-methyl-2-(methylamino)pentanamide; butane

• ChemBase ID: 165306
• Molecular Formular: C30H59N3O5
• Molecular Mass: 541.80656
• Monoisotopic Mass: 541.445472
• SMILES: CCCCC(=O)C(N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)[C@@H]([C@@H](C/C=C/CO)C)O.CCCC
• Canonical SMILES: CCCCC(=O)C(N(C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)C)[C@@H]([C@@H](C/C=C/CO)C)O.CCCC
• InChI: InChI=1S/C26H49N3O5.C4H10/c1-9-10-14-21(31)23(24(32)19(6)13-11-12-15-30)29(8)26(34)22(18(4)5)28-25(33)20(27-7)16-17(2)3;1-3-4-2/h11-12,17-20,22-24,27,30,32H,9-10,13-16H2,1-8H3,(H,28,33);3-4H2,1-2H3/b12-11+;/t19-,20+,22+,23?,24-;/m1./s1
• InChIKey: UABJGHASCAVVRD-RFPPSOHNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(1S)-1-{[(7R,8R,10E)-7,12-dihydroxy-8-methyl-5-oxododec-10-en-6-yl](methyl)carbamoyl}-2-methylpropyl]-4-methyl-2-(methylamino)pentanamide; butane
• IUPAC Traditional name: (2S)-N-[(1S)-1-{[(7R,8R,10E)-7,12-dihydroxy-8-methyl-5-oxododec-10-en-6-yl](methyl)carbamoyl}-2-methylpropyl]-4-methyl-2-(methylamino)pentanamide; butane
• Synonyms: 6-[(2S,3R,4R,6E)-3,8-Dihydroxy-4-methyl-2-(methylamino)-6-octenoic acid]cyclosporin A; Cyclosporin A Metabolite 17; Cyclosporin Metabolite 17; M 17; OL 17; Cyclosporin AM 1

Database IDs

• CAS Number: 89270-28-0
• PubChem SID: 162259439
• PubChem CID: 71315133

CALCULATED PROPERTIES

• Acid pKa: 12.843668
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.09825075
• LogD (pH = 7.4): 1.7051687
• Log P: 3.0135846
• Molar Refractivity: 136.465 cm^3
• Polarizability: 53.636642 Å^3
• Polar Surface Area: 118.97 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 146-148°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C988915

A cyclosporine metabolite specifically inhibits growth of renal cells in culture.

REFERENCES

• Johnson, B., et al.: Drug Metab. Dispos., 34, 556 (1991)
• Westley, I.S., Drug Metab. Dispos., 36, 46 (2008).
• Schultz, J.C.; et al.: Biochem. Pharma., 42, 1403 (1991)