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CHEBI:4031 - cyclosporin A

Default Structure
ChEBI IDCHEBI:4031
ChEBI Namecyclosporin A
Stars
DefinitionA 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.
Secondary ChEBI IDsCHEBI:63586, CHEBI:91802
Last Modified9 April 2024
DownloadsMolfile
FormulaC62H111N11O12
Net Charge0
Average Mass1202.635
Monoisotopic Mass1201.84137
SMILESC/C=C/C[C@@H](C)[C@@H](O)[C@H]1C(=O)N[C@@H](CC)C(=O)N(C)CC(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N(C)[C@@H](C(C)C)C(=O)N1C
InChIInChI=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
InChIKeyPMATZTZNYRCHOR-CGLBZJNRSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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).
antifungal agent  An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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.
anticoronaviral agent  Any antiviral agent which inhibits the activity of coronaviruses.
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.
Applications:
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
dermatologic drug  A drug used to treat or prevent skin disorders or for the routine care of skin.
anti-asthmatic drug  A drug used to treat asthma.
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.
antirheumatic drug  A drug used to treat rheumatoid arthritis.
ChEBI Ontology
Outgoing Relation(s)
cyclosporin A (CHEBI:4031) has role anti-asthmatic drug (CHEBI:49167)
cyclosporin A (CHEBI:4031) has role anticoronaviral agent (CHEBI:149553)
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 geroprotector (CHEBI:176497)
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)
Incoming Relation(s)
cyclosporin A derivative (CHEBI:140151) has functional parent cyclosporin A (CHEBI:4031)
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  Source
ciclosporinKEGG DRUG
ciclosporinaChemIDplus
ciclosporineChemIDplus
ciclosporinumChemIDplus
Synonyms  Source
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-undeconeChEBI
Antibiotic S 7481F1ChemIDplus
CiclosporinKEGG 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 AKEGG COMPOUND
Brand Names  Source
GengrafDrugBank
NeoralDrugBank
SandimmuneDrugBank
UniProt Name  Source
cyclosporin AUniProt
Manual XrefsDatabases
1765VSDB
4447449ChemSpider
760DrugCentral
C00001517KNApSAcK
C05086KEGG COMPOUND
CiclosporinWikipedia
CPD-20532MetaCyc
D00184KEGG DRUG
DB00091DrugBank
HMDB0250682HMDB
LMPK14000003LIPID MAPS
LSM-1703LINCS
US4117118Patent
Registry NumbersSources
Reaxys:3647785Reaxys
CAS:59865-13-3KEGG COMPOUND
CAS:59865-13-3ChemIDplus
Citations