loading...| Preferred Name |
sirolimus |
|
| Synonyms |
(3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,27-dihydroxy-3-{(2R)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl}-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro-3H-23,27-epoxypyrido[2,1-c][1,4]oxazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone Sirolimus (-)-Rapamycin Antibiotic AY 22989 (1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-{(2S)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl}-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.0(4,9)]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone sirolimusum Rapamune rapamycin sirolimus |
|
| Definitions |
A macrolide lactam isolated from Streptomyces hygroscopicus consisting of a 29-membered ring containing 4 trans double bonds, three of which are conjugated. It is an antibiotic, immunosupressive and antineoplastic agent. |
|
| ID |
http://purl.obolibrary.org/obo/CHEBI_9168 |
|
| charge |
0 |
|
| chemical has protein target | ||
| chemical inhibits in vitro replication of virus | ||
| chemical inhibits protein |
http://purl.obolibrary.org/obo/PR_000007535 http://purl.obolibrary.org/obo/PR_000007532 http://purl.obolibrary.org/obo/PR_000009668 |
|
| database_cross_reference |
CAS:53123-88-9 HMDB:HMDB0015015 LIPID_MAPS_instance:LMPK06000003 KNApSAcK:C00018055 PMID:24409289 DrugBank:DB00877 Drug_Central:2446 Wikipedia:Rapamycin PMID:22960739 PMID:22984623 Reaxys:5848501 PMID:22981852 KEGG:D00753 PMID:24341993 KEGG:C07909 PMID:19587680 PDBeChem:RAP |
|
| definition source |
Reference: PMID: 15896331 https://www.drugbank.ca/drugs/DB00877 PMID: 25487801; PMID: 26868298 |
|
| formula |
C51H79NO13 |
|
| has exact synonym |
(3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,27-dihydroxy-3-{(2R)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl}-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro-3H-23,27-epoxypyrido[2,1-c][1,4]oxazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone Sirolimus |
|
| has role |
http://purl.obolibrary.org/obo/CHEBI_35705 http://purl.obolibrary.org/obo/CHEBI_35610 http://purl.obolibrary.org/obo/CHEBI_68481 http://purl.obolibrary.org/obo/CHEBI_149553 http://purl.obolibrary.org/obo/CHEBI_176497 |
|
| has_alternative_id |
CHEBI:45276 CHEBI:67812 |
|
| has_obo_namespace |
chebi_ontology |
|
| has_related_synonym |
(-)-Rapamycin Antibiotic AY 22989 (1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-{(2S)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl}-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.0(4,9)]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone sirolimusum Rapamune rapamycin sirolimus |
|
| has_role | ||
| id |
CHEBI:9168 |
|
| imported from | ||
| in subset | ||
| inchi |
InChI=1S/C51H79NO13/c1-30-16-12-11-13-17-31(2)42(61-8)28-38-21-19-36(7)51(60,65-38)48(57)49(58)52-23-15-14-18-39(52)50(59)64-43(33(4)26-37-20-22-40(53)44(27-37)62-9)29-41(54)32(3)25-35(6)46(56)47(63-10)45(55)34(5)24-30/h11-13,16-17,25,30,32-34,36-40,42-44,46-47,53,56,60H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12+,31-17+,35-25+/t30-,32-,33-,34-,36-,37+,38+,39+,40-,42+,43+,44-,46-,47+,51-/m1/s1 |
|
| inchikey |
QFJCIRLUMZQUOT-HPLJOQBZSA-N |
|
| label |
sirolimus |
|
| mass |
914.17190 |
|
| monoisotopicmass |
913.55514 |
|
| notation |
CHEBI:9168 |
|
| prefLabel |
sirolimus |
|
| smiles |
[H][C@]1(CC[C@@H](O)[C@@H](C1)OC)C[C@@H](C)[C@]1([H])CC(=O)[C@H](C)\C=C(C)\[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)\C=C\C=C\C=C(C)\[C@H](C[C@]2([H])CC[C@@H](C)[C@@](O)(O2)C(=O)C(=O)N2CCCC[C@@]2([H])C(=O)O1)OC |
|
| textual definition |
A macrolide lactam isolated from Streptomyces hygroscopicus consisting of a 29-membered ring containing 4 trans double bonds, three of which are conjugated. It is an antibiotic, immunosupressive and antineoplastic agent. |
|
| subClassOf |
http://purl.obolibrary.org/obo/CHEBI_59770 http://purl.obolibrary.org/obo/CHEBI_26979 http://purl.obolibrary.org/obo/CHEBI_25698 http://purl.obolibrary.org/obo/CHEBI_35681 http://purl.obolibrary.org/obo/CHEBI_145565 |
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