tacrolimus   

GtoPdb Ligand ID: 6784

Synonyms: FK506 | fujimycin | Prograf® | Protopic®
tacrolimus is an approved drug (FDA (1994), EMA (2002))
Compound class: Synthetic organic
Comment: Tacrolimus acts as a calcineurin inhibitor and has immunosuppressive effects.
2D Structure
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Physico-chemical Properties
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
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
Compound class Synthetic organic
Approved drug? Yes (FDA (1994), EMA (2002))
International Nonproprietary Names
INN number INN
6878 tacrolimus
Synonyms
FK506 | fujimycin | Prograf® | Protopic®
Database Links
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
Search UniChem for chemicals with the same backbone QJJXYPPXXYFBGM
SynPHARM 78882 (in complex with FK506 binding protein 1A)
Wikipedia Tacrolimus

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Tocris
FK 506
Cat. No. 3631