loading...| Preferred Name |
Cyclosporine |
|
| Synonyms |
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 cyclosporin A Cyclosporin A Antibiotic S 7481F1 Cyclosporine ciclosporin Ciclosporin 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] ciclosporinum 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 (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-alpha-aminobutyryl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl) ciclosporine InChIKey=PMATZTZNYRCHOR-VJRYSDSKSA-N 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 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) 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 ciclosporina C62H111N11O12 Gengraf Neoral Sandimmune |
|
| Definitions |
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. |
|
| ID |
http://purl.obolibrary.org/obo/CHEBI_4031 |
|
| charge |
0 |
|
| chemical binds protein |
http://purl.obolibrary.org/obo/PR_P49069 |
|
| chemical inhibits in vitro replication of virus | ||
| chemical inhibits protein | ||
| database_cross_reference |
PMID:11676831 CiteXplore:18259730 CiteXplore:11442023 PMID:16898534 CiteXplore:18299432 PMID:34561200 CiteXplore:18217899 PMID:17192032 Wikipedia:Ciclosporin PMID:11481617 PMID:18818682 PMID:17229932 CiteXplore:18359899 PMID:21752960 PMID:17265451 CiteXplore:11079273 Chemspider:4447449 PMID:34561814 CAS:59865-13-3 MetaCyc:CPD-20532 CiteXplore:11069928 CiteXplore:19589783 Beilstein:3647785 CiteXplore:1566062 PMID:18931077 PMID:11315347 PMID:12761440 PMID:11069928 CiteXplore:11406057 PMID:14638917 PMID:15175101 CiteXplore:15541012 PMID:11256490 LINCS:LSM-1703 CiteXplore:11481617 PMID:16372476 PMID:17220244 PMID:15383526 CiteXplore:18171316 CiteXplore:14743390 CiteXplore:17220244 CiteXplore:12950728 PMID:15541012 PMID:12021257 PMID:17083576 CiteXplore:15306697 PMID:11406057 HMDB:HMDB0250682 CiteXplore:11564166 LIPID_MAPS_instance:LMPK14000003 CiteXplore:15030555 CiteXplore:16724420 PMID:15210365 PMID:11058832 PMID:17446460 CiteXplore:15613074 CiteXplore:14621732 CiteXplore:11493684 CiteXplore:11238591 PMID:18191430 CiteXplore:11080188 CiteXplore:17117422 PMID:12603598 CiteXplore:15811524 PMID:18975184 CiteXplore:12050171 PMID:15030555 CiteXplore:11370709 PMID:18217899 Patent:US4117118 CiteXplore:15711594 PMID:16801218 PMID:14521916 PMID:15811524 PMID:31144214 CiteXplore:15210365 CiteXplore:18931077 KEGG COMPOUND:C05086 KEGG COMPOUND:59865-13-3 PMID:11564166 CiteXplore:16898534 PMID:18359899 CiteXplore:15383526 DrugBank:DB00091 CiteXplore:15657176 CiteXplore:16372476 PMID:18299432 CiteXplore:18597363 CiteXplore:17032751 PMID:11529914 KEGG DRUG:D00184 PMID:11278005 PMID:12950728 CiteXplore:19282398 CiteXplore:14672695 PMID:17032751 ChemIDplus:59865-13-3 PMID:18790203 KNApSAcK:C00001517 CiteXplore:11870366 PMID:14621732 PMID:15613074 PMID:16404634 CiteXplore:14521916 CiteXplore:15962181 PMID:18259730 CiteXplore:11426833 CiteXplore:11676831 CiteXplore:11278005 Reaxys:3647785 PMID:19282398 PMID:23620378 PMID:15711594 KEGG:D00184 CiteXplore:15175101 PMID:18171316 CiteXplore:11557554 CiteXplore:18790203 CiteXplore:18583716 CiteXplore:12929192 CiteXplore:11256490 PMID:11080188 CiteXplore:12761440 PMID:12929192 CiteXplore:11529914 PMID:11426833 PMID:24134630 PMID:11870366 PMID:11079273 PMID:16724420 CiteXplore:17265451 CiteXplore:17603747 PMID:14743390 PMID:11442023 CiteXplore:12603598 PMID:19589783 PMID:15962181 CiteXplore:16404634 PMID:18597363 CiteXplore:18191430 CiteXplore:15626898 PMID:12050171 PMID:11493684 PMID:15306697 PMID:11238591 PMID:1566062 PMID:18076075 PMID:17603747 CiteXplore:17446460 KEGG:C05086 CiteXplore:17229932 CiteXplore:18818682 PMID:18583716 Drug_Central:760 CiteXplore:14682659 CiteXplore:11058832 CiteXplore:17083576 PMID:15657176 PMID:14682659 PMID:11557554 CiteXplore:16801218 CiteXplore:11315347 CiteXplore:12021257 CiteXplore:17192032 PMID:17117422 PMID:11370709 CiteXplore:18975184 CiteXplore:14638917 PMID:15626898 PMID:14672695 CiteXplore:18076075 VSDB:1765 |
|
| definition source |
https://www.drugbank.ca/drugs/DB00091 PMID: 27478032; PMID: 27344959 |
|
| formula |
C62H111N11O12 |
|
| has exact synonym |
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 cyclosporin A Cyclosporin A |
|
| has role |
http://purl.obolibrary.org/obo/CHEBI_35705 http://purl.obolibrary.org/obo/CHEBI_37153 http://purl.obolibrary.org/obo/CHEBI_149553 http://purl.obolibrary.org/obo/CHEBI_176497 http://purl.obolibrary.org/obo/CHEBI_50903 http://purl.obolibrary.org/obo/CHEBI_25212 http://purl.obolibrary.org/obo/CHEBI_50177 http://purl.obolibrary.org/obo/CHEBI_35718 |
|
| has_alternative_id |
CHEBI:91802 CHEBI:63586 |
|
| has_obo_namespace |
chebi_ontology |
|
| has_related_synonym |
Antibiotic S 7481F1 Cyclosporine ciclosporin Ciclosporin 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] ciclosporinum 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 (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-alpha-aminobutyryl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl) ciclosporine InChIKey=PMATZTZNYRCHOR-VJRYSDSKSA-N 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 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) 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 ciclosporina C62H111N11O12 Gengraf Neoral Sandimmune |
|
| has_RxCUI |
3008 |
|
| id |
CHEBI:4031 |
|
| imported from | ||
| in subset | ||
| 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 |
|
| label |
Cyclosporine cyclosporin A |
|
| mass |
1202.61120 |
|
| monoisotopicmass |
1201.84137 |
|
| notation |
CHEBI:4031 |
|
| prefLabel |
Cyclosporine |
|
| 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 |
|
| textual 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. |
|
| subClassOf |
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