(12R)-30-ethyl-33-[(1R,2R,4E)-1-hydroxy-2-methylhex-4-en-1-yl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-bis(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecone

• ChemBase ID: 179890
• Molecular Formular: C62H111N11O12
• Molecular Mass: 1202.61124
• Monoisotopic Mass: 1201.84136805
• SMILES: N1(C(=O)C(N(C(=O)C(N(C(=O)C(N(C(=O)[C@H](NC(=O)C(NC(=O)C(N(C(=O)C(NC(=O)C(N(C(=O)CN(C(=O)C(NC(=O)C1[C@@H]([C@@H](C/C=C/C)C)O)CC)C)C)CC(C)C)C(C)C)C)CC(C)C)C)C)C)CC(C)C)C)CC(C)C)C)C(C)C)C
• Canonical SMILES: C/C=C/C[C@H]([C@H](C1C(=O)NC(CC)C(=O)N(C)CC(=O)N(C)C(CC(C)C)C(=O)NC(C(C)C)C(=O)N(C)C(CC(C)C)C(=O)NC(C(=O)N[C@@H](C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N1C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)O)C
• InChI: InChI=1S/C62H111N11O12/c1-25-27-28-40(15)52(75)51-56(79)65-43(26-2)58(81)67(18)33-48(74)68(19)44(29-34(3)4)55(78)66-49(38(11)12)61(84)69(20)45(30-35(5)6)54(77)63-41(16)53(76)64-42(17)57(80)70(21)46(31-36(7)8)59(82)71(22)47(32-37(9)10)60(83)72(23)50(39(13)14)62(85)73(51)24/h25,27,34-47,49-52,75H,26,28-33H2,1-24H3,(H,63,77)(H,64,76)(H,65,79)(H,66,78)/b27-25+/t40-,41?,42-,43?,44?,45?,46?,47?,49?,50?,51?,52-/m1/s1
• InChIKey: PMATZTZNYRCHOR-NFOUMSERSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (12R)-30-ethyl-33-[(1R,2R,4E)-1-hydroxy-2-methylhex-4-en-1-yl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-bis(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecone
• IUPAC Traditional name: (12R)-30-ethyl-33-[(1R,2R,4E)-1-hydroxy-2-methylhex-4-en-1-yl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-bis(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecone
• Synonyms: Cyclosporine; Cyclorin; Neoral; Ramihyphin A; Sandimmun; Sandimmune; Cyclosporin A

Database IDs

• CAS Number: 59865-13-3
• PubChem SID: 164235800
• PubChem CID: 16404350

CALCULATED PROPERTIES

• Acid pKa: 11.825702
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): 3.6381571
• LogD (pH = 7.4): 3.6381428
• Log P: 3.6381574
• Molar Refractivity: 327.1417 cm^3
• Polarizability: 127.97144 Å^3
• Polar Surface Area: 278.8 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Calcineurin inhibitor

Product Information

• Description: Conformers
• Biological Source: Metab. of Trichoderma inflatum (previously Trichoderma polysporum). Also isol. from Fusarium solani and Tolypocladium sinense
• Application(s): Possesses antifungal activity and immunosuppressive props. with a specific action on T-lymphocytes; Used clinically as an immunosuppressant after transplant surgery

REFERENCES

• Merck Index 12 2821. Fruman et al (1992) Calcineurin phosphatase activity in T lymphocytes is inhibited by FK 506 and cyclosporin A. Proc.Natl.Acad.Sci.USA 89 3686.