CHEBI:4031 - cyclosporin A

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ChEBI Name cyclosporin A
ChEBI ID CHEBI:4031
Definition A cyclic nonribosomal peptide of eleven amino acids; 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. Also causes reversible inhibition of immunocompetent lymphocytes in the G0- and G1-phase of the cell cycle.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Secondary ChEBI IDs CHEBI:63586
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Formula C62H111N11O12
Net Charge 0
Average Mass 1202.61120
Monoisotopic Mass 1201.841
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-CGLBZJNRSA-N
SMILES CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O)C(C)C
Roles Classification
Biological Role(s): antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
carcinogenic agent
A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor
Any EC 3.1.3.* (phosphoric monoester hydrolase) inhibitor that interferes with the action of phosphoprotein phosphatase (EC 3.1.3.16).
Application(s): antirheumatic drug
A drug used to treat rheumatoid arthritis.
dermatologic drug
A drug used to treat or prevent skin disorders or for the routine care of skin.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
anti-asthmatic drug
A drug used to treat asthma.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cyclosporin A (CHEBI:4031) has role anti-asthmatic drug (CHEBI:49167)
cyclosporin A (CHEBI:4031) has role antifungal agent (CHEBI:35718)
cyclosporin A (CHEBI:4031) has role antirheumatic drug (CHEBI:35842)
cyclosporin A (CHEBI:4031) has role carcinogenic agent (CHEBI:50903)
cyclosporin A (CHEBI:4031) has role dermatologic drug (CHEBI:50177)
cyclosporin A (CHEBI:4031) has role EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor (CHEBI:37153)
cyclosporin A (CHEBI:4031) has role immunosuppressive agent (CHEBI:35705)
cyclosporin A (CHEBI:4031) has role metabolite (CHEBI:25212)
cyclosporin A (CHEBI:4031) is a homodetic cyclic peptide (CHEBI:24613)
IUPAC Name
30-ethyl-33-[(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-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
INNs Sources
ciclosporin KEGG DRUG
ciclosporina ChemIDplus
ciclosporine ChemIDplus
ciclosporinum ChemIDplus
Synonyms Sources
(R-[R*,R*-(E)])-Cyclic(L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-3-hydroxy-N,4-dimethyl-L-2-amino-6-octenoyl-L-α-aminobutyryl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl) ChEBI
1,11-cyclo[L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-(E)-(2S,3R,4R)-2-amino-3-hydroxy-N,4-dimethyloct-6-enoyl-L-2-aminobutanoyl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucine] JCBN
30-ethyl-33-[(4E)-1-hydroxy-2-methylhex-4-en-1-yl]-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone ChEBI
Antibiotic S 7481F1 ChemIDplus
Ciclosporin KEGG COMPOUND
Cyclo(L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-((3R,4R,6E)-6,7-didehydro-3-hydroxy-N,4-dimethyl-L-2-aminooctanoyl)-L-2-aminobutanoyl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methylleucyl) ChemIDplus
Cyclosporin A KEGG COMPOUND
Cyclosporine KEGG COMPOUND
Cyclosporine ChemIDplus
Brand Names Sources
Gengraf DrugBank
Neoral DrugBank
Sandimmune DrugBank
Database Links Databases
760 DrugCentral
C00001517 KNApSAcK
C05086 KEGG COMPOUND
Ciclosporin Wikipedia
D00184 KEGG DRUG
DB00091 DrugBank
US4117118 Patent
View more database links
Registry Numbers Types Sources
3647785 Beilstein Registry Number Beilstein
3647785 Reaxys Registry Number Reaxys
59865-13-3 CAS Registry Number ChemIDplus
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Last Modified
22 February 2017