CHEBI:61049 - tacrolimus (anhydrous)

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ChEBI Name tacrolimus (anhydrous)
ChEBI ID CHEBI:61049
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Harold Drabkin
Secondary ChEBI IDs CHEBI:42555, CHEBI:4958
Supplier Information
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Formula C44H69NO12
Net Charge 0
Average Mass 804.01820
Monoisotopic Mass 803.48198
InChI InChI=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
InChIKey QJJXYPPXXYFBGM-LFZNUXCKSA-N
SMILES CO[C@@H]1C[C@@H](CC[C@H]1O)\C=C(/C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@H]([C@H](C[C@@H](C)C\C(C)=C\[C@@H](CC=C)C(=O)C[C@H](O)[C@H]1C)OC)[C@H](C[C@H]2C)OC
Roles Classification
Biological Role(s): 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(s): 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.
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ChEBI Ontology
Outgoing 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 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
tacrolimus KEGG DRUG
Synonyms Sources
(−)-FK 506 ChemIDplus
8-DEETHYL-8-[BUT-3-ENYL]-ASCOMYCIN PDBeChem
FK 506 KEGG COMPOUND
FK506 KEGG COMPOUND
FK506 KEGG COMPOUND
Tacrolimus KEGG COMPOUND
tacrolimus
Note: (2011-01-19) Note that the name tacrolimus is used to refer both to the anhydrous form and to the monohydrate.
 ChemIDplus
tacrolimus anhydrous ChemIDplus
Brand Name Source
Prograf ChEBI
Manual Xrefs Databases
C01375 KEGG COMPOUND
D08556 KEGG DRUG
DB00864 DrugBank
EP184162 Patent
FK5 PDBeChem
LMPK04000003 LIPID MAPS
US5665727 Patent
View more database links
Registry Numbers Types Sources
104987-11-3 CAS Registry Number KEGG COMPOUND
104987-11-3 CAS Registry Number KEGG DRUG
104987-11-3 CAS Registry Number ChemIDplus
3647477 Reaxys Registry Number Reaxys
8821611 Reaxys Registry Number Reaxys
Last Modified
03 December 2019
General Comment
2011-01-19 A macrolide isolated from the culture broth of a strain of Streptomyces tsukubaensis, tacrolimus is an immunosuppressant. It is used, generally as the monohydrate, to prevent rejection following organ transplant. It is also applied topically for the management of severe atopic eczema.