tacrolimus   Click here for help

GtoPdb Ligand ID: 6784

Synonyms: FK506 | fujimycin | Prograf® | Protopic®
Approved drug PDB Ligand
tacrolimus is an approved drug (FDA (1994), EMA (2002))
Compound class: Synthetic organic
Comment: Tacrolimus acts as a calcineurin inhibitor and has immunosuppressive effects.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 13
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 178.36
Molecular weight 803.48
XLogP 3.31
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES C=CCC1C=C(C)CC(C)CC(OC)C2OC(O)(C(CC2OC)C)C(=O)C(=O)N2C(C(=O)OC(C(C(CC1=O)O)C)C(=CC1CCC(C(C1)OC)O)C)CCCC2
Isomeric SMILES C=CC[C@@H]1/C=C(\C)/C[C@H](C)C[C@H](OC)[C@H]2O[C@](O)([C@@H](C[C@@H]2OC)C)C(=O)C(=O)N2[C@H](C(=O)O[C@@H]([C@@H]([C@H](CC1=O)O)C)/C(=C/[C@@H]1CC[C@H]([C@@H](C1)OC)O)/C)CCCC2
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
InChI Key QJJXYPPXXYFBGM-LFZNUXCKSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1994), EMA (2002))
International Nonproprietary Names Click here for help
INN number INN
6878 tacrolimus
Synonyms Click here for help
FK506 | fujimycin | Prograf® | Protopic®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9678991
Reactome Reaction Reactome logo R-HSA-9690461
Other databases
CAS Registry No. 104987-11-3
ChEMBL Ligand CHEMBL269732
DrugBank Ligand DB00864
GtoPdb PubChem SID 178103390
Immunopaedia Search tacrolimus
PubChem CID 445643
RCSB PDB Ligand FK5
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Search UniChem for chemical match using the InChIKey QJJXYPPXXYFBGM-LFZNUXCKSA-N
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SynPHARM 78882 (in complex with FK506 binding protein 1A)
Wikipedia Tacrolimus

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Tocris
FK 506
Cat. No. 3631