(3E,6R,17S)-8-(dimethylamino)-6,18-dimethyl-17-[(2S)-4-methyl-2-(methylamino)pentanamido]-9,16-dioxononadeca-1,3-dien-7-yl acetate

• ChemBase ID: 179550
• Molecular Formular: C32H57N3O5
• Molecular Mass: 563.81208
• Monoisotopic Mass: 563.42982194
• SMILES: C(CCC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)CCCC(=O)C(N(C)C)C([C@@H](C/C=C/C=C)C)OC(=O)C
• Canonical SMILES: C=C/C=C/C[C@H](C(C(C(=O)CCCCCCC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)N(C)C)OC(=O)C)C
• InChI: InChI=1S/C32H57N3O5/c1-11-12-15-18-24(6)31(40-25(7)36)30(35(9)10)28(38)20-17-14-13-16-19-27(37)29(23(4)5)34-32(39)26(33-8)21-22(2)3/h11-12,15,22-24,26,29-31,33H,1,13-14,16-21H2,2-10H3,(H,34,39)/b15-12+/t24-,26+,29+,30?,31?/m1/s1
• InChIKey: BDVOEHYJSAIGNA-DVWLGCSHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3E,6R,17S)-8-(dimethylamino)-6,18-dimethyl-17-[(2S)-4-methyl-2-(methylamino)pentanamido]-9,16-dioxononadeca-1,3-dien-7-yl acetate
• IUPAC Traditional name: (3E,6R,17S)-8-(dimethylamino)-6,18-dimethyl-17-[(2S)-4-methyl-2-(methylamino)pentanamido]-9,16-dioxononadeca-1,3-dien-7-yl acetate
• Synonyms: 6-[(2S,3R,4R,6E)-3-Hydroxy-4-methyl-2-(methylamino)-6,8-nonadienoic acid]cyclosporin A; ISATX 247; R 1524; trans-ISA 247; Voclosporin

Database IDs

• CAS Number: 515814-01-4
• PubChem SID: 164235460
• PubChem CID: 71752982

CALCULATED PROPERTIES

• Acid pKa: 13.127856
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.033015
• LogD (pH = 7.4): 4.361742
• Log P: 5.992257
• Molar Refractivity: 163.2352 cm^3
• Polarizability: 64.35441 Å^3
• Polar Surface Area: 104.81 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - V678500

A new agent for the treatment of noninfectious uveitis. Uveitis is an inflammatory, putative Th1-mediated autoimmune disease that affects various parts of the eye and is a leading cause of visual loss. Voclosporin, a rationally designed novel calcineurin

REFERENCES

• Aspeslet, L., et al.: Transplant Proc., 33, 1048 (2001)
• Cho, M., et al.: Arthritis Rheum., 46, 1202 (2001)
• Staatz, C., et al.: Clin. Pharmacokinet., 43, 623 (2001)