(2S)-N-[(3S,13R,14R,16E)-12-(dimethylamino)-13-hydroxy-2,14-dimethyl-4,11-dioxo(17,18,19,19-2H4)nonadeca-16,18-dien-3-yl]-4-methyl-2-(methylamino)pentanamide

• ChemBase ID: 179551
• Molecular Formular: C30H55N3O4
• Molecular Mass: 521.7754
• Monoisotopic Mass: 521.41925726
• SMILES: C(CCC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)CCCC(=O)C(N(C)C)[C@@H]([C@@H](C/C=C/C=C)C)O
• Canonical SMILES: C=C/C=C/C[C@H]([C@H](C(C(=O)CCCCCCC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC)N(C)C)O)C
• InChI: InChI=1S/C30H55N3O4/c1-10-11-14-17-23(6)29(36)28(33(8)9)26(35)19-16-13-12-15-18-25(34)27(22(4)5)32-30(37)24(31-7)20-21(2)3/h10-11,14,21-24,27-29,31,36H,1,12-13,15-20H2,2-9H3,(H,32,37)/b14-11+/t23-,24+,27+,28?,29-/m1/s1
• InChIKey: SNWQQRMYHUTHQX-QUBXXHBZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(3S,13R,14R,16E)-12-(dimethylamino)-13-hydroxy-2,14-dimethyl-4,11-dioxo(17,18,19,19-^2H₄)nonadeca-16,18-dien-3-yl]-4-methyl-2-(methylamino)pentanamide
• IUPAC Traditional name: (2S)-N-[(3S,13R,14R,16E)-12-(dimethylamino)-13-hydroxy-2,14-dimethyl-4,11-dioxo(17,18,19,19-^2H₄)nonadeca-16,18-dien-3-yl]-4-methyl-2-(methylamino)pentanamide
• Synonyms: 6-[(2S,3R,4R,6E)-3-Hydroxy-4-methyl-2-(methylamino)-6,8-nonadienoic acid]cyclosporin A-d4; ISATX 247-d4; R 1524-d4; trans-ISA 247-d4; Voclosporin-d4

Database IDs

• PubChem SID: 164235461
• PubChem CID: 71752983

CALCULATED PROPERTIES

• Acid pKa: 13.089188
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 1.1162388
• LogD (pH = 7.4): 3.8454351
• Log P: 5.5511317
• Molar Refractivity: 154.0837 cm^3
• Polarizability: 60.529335 Å^3
• Polar Surface Area: 98.74 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - V678502

Labelled Voclosporin (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 ration

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)