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CHEBI:61049 - tacrolimus (anhydrous)

Default Structure
ChEBI IDCHEBI:61049
ChEBI Nametacrolimus (anhydrous)
Stars
DefinitionA macrolide lactam containing a 23-membered lactone ring, originally isolated from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis.
Secondary ChEBI IDsCHEBI:4958, CHEBI:42555
Last Modified3 December 2019
Submitterhdrabkin
DownloadsMolfile
FormulaC44H69NO12
Net Charge0
Average Mass804.031
Monoisotopic Mass803.48198
SMILESC=CC[C@@H]1/C=C(\C)C[C@H](C)C[C@H](OC)[C@H]2O[C@@](O)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@H](/C(C)=C/[C@@H]3CC[C@@H](O)[C@H](OC)C3)[C@H](C)[C@@H](O)CC1=O)[C@H](C)C[C@@H]2OC
InChIInChI=1S/C44H69NO12/c1-10-13-31-19-25(2)18-26(3)20-37(54-8)40-38(55-9)22-28(5)44(52,57-40)41(49)42(50)45-17-12-11-14-32(45)43(51)56-39(29(6)34(47)24-35(31)48)27(4)21-30-15-16-33(46)36(23-30)53-7/h10,19,21,26,28-34,36-40,46-47,52H,1,11-18,20,22-24H2,2-9H3/b25-19+,27-21+/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+,44+/m0/s1
InChIKeyQJJXYPPXXYFBGM-LFZNUXCKSA-N
Roles Classification
Biological Roles:
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.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
Application:
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.
ChEBI Ontology
Outgoing Relation(s)
tacrolimus (anhydrous) (CHEBI:61049) has role bacterial metabolite (CHEBI:76969)
tacrolimus (anhydrous) (CHEBI:61049) has role immunosuppressive agent (CHEBI:35705)
tacrolimus (anhydrous) (CHEBI:61049) is a macrolide lactam (CHEBI:145565)
Incoming Relation(s)
tacrolimus hydrate (CHEBI:61057) has part tacrolimus (anhydrous) (CHEBI:61049)
IUPAC Name 
(3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-5,19-dihydroxy-3-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl}-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(prop-2-en-1-yl)-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3H-15,19-epoxypyrido[2,1-c][1,4]oxazacyclotricosine-1,7,20,21(4H,23H)-tetrone
INN  Source
tacrolimusKEGG DRUG
Synonyms  Source
8-DEETHYL-8-[BUT-3-ENYL]-ASCOMYCINPDBeChem
(−)-FK 506ChemIDplus
FK 506KEGG COMPOUND
FK506KEGG COMPOUND
FK506KEGG COMPOUND
tacrolimusChemIDplus
Brand Name  Source
PrografChEBI
Manual XrefsDatabases
C01375KEGG COMPOUND
D08556KEGG DRUG
DB00864DrugBank
EP184162Patent
FK5PDBeChem
LMPK04000003LIPID MAPS
US5665727Patent
Registry NumbersSources
Reaxys:3647477Reaxys
Reaxys:8821611Reaxys
CAS:104987-11-3KEGG COMPOUND
CAS:104987-11-3ChemIDplus
CAS:104987-11-3KEGG DRUG