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: 72716
• Molecular Formular: C62H111N11O12
• Molecular Mass: 1202.61124
• Monoisotopic Mass: 1201.84136805
• SMILES: C1(N(C)C(=O)C(NC(=O)C(NC(=O)C(CC(C)C)N(C(=O)C(NC(=O)C(CC(C)C)N(C)C(=O)CN(C)C(=O)C(CC)NC(=O)C(N(C(=O)C(N(C(=O)C(N(C)C1=O)CC(C)C)C)C(C)C)C)[C@@H]([C@@H](C/C=C/C)C)O)C(C)C)C)C)C)CC(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)NC(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-KMSBSJHKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 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: cyclosporine
• Synonyms: Sandimmune; Neoral; Gengraf; Restasis; Cyclosporine

Database IDs

• CAS Number: 79217-60-0
• PubChem SID: 162037637
• PubChem CID: 6435893

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

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1514

Research Area: Immunology
Biological Activity:
Cyclosporine (Neoral) is an immunosuppressant drug widely used in post-allogeneic organ transplant to reduce the activity of the patient’s immune system, and therefore the risk of organ rejection. Cyclosporine is thought to bind to the cytosolic protein cyclophilin (immunophilin) of immunocompetent lymphocytes, especially T-lymphocytes. This complex of cyclosporine and cyclophilin inhibits calcineurin, which, under normal circumstances, is responsible for activating the transcription of interleukin 2.