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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:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
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.
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