CHEBI:61057 - tacrolimus hydrate

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ChEBI Name tacrolimus hydrate
ChEBI ID CHEBI:61057
Definition A hydrate that is the monohydrate form of tacrolimus.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C44H71NO13
Net Charge 0
Average Mass 822.03340
Monoisotopic Mass 821.49254
InChI InChI=1S/C44H69NO12.H2O/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;1H2/b25-19+,27-21+;/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+,44+;/m0./s1
InChIKey NWJQLQGQZSIBAF-MLAUYUEBSA-N
SMILES O.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): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing tacrolimus hydrate (CHEBI:61057) has part tacrolimus (anhydrous) (CHEBI:61049)
tacrolimus hydrate (CHEBI:61057) has role immunosuppressive agent (CHEBI:35705)
tacrolimus hydrate (CHEBI:61057) is a hydrate (CHEBI:35505)
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—water (1/1)
Synonyms Sources
(−)-(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 monohydrate ChemIDplus
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 monohydrate ChEBI
tsukubaenolide hydrate ChemIDplus
Brand Names Sources
Prograf KEGG DRUG
Protopic KEGG DRUG
Manual Xrefs Databases
D00107 KEGG DRUG
DB00864 DrugBank
View more database links
Registry Numbers Types Sources
109581-93-3 CAS Registry Number KEGG DRUG
109581-93-3 CAS Registry Number ChemIDplus
6265275 Reaxys Registry Number Reaxys
Last Modified
19 January 2011
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.