auranofin   Click here for help

GtoPdb Ligand ID: 6306

Synonyms: MMV688978 | Ridaura® | SK&F-39162 | SK-39162
Approved drug Immunopharmacology Ligand
auranofin is an approved drug (FDA (1985))
Compound class: Synthetic organic
Comment: Auranofin is a gold-containing complex, antirheumatic agent. It demonstrates potent antibacterial activity in vitro against Gram-positive bacteria and both replicating and nonreplicating Mycobacterium tuberculosis [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 0
Rotatable bonds 15
Topological polar surface area 139.73
Molecular weight 678.13
XLogP 2.93
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey
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Canonical SMILES CC[P+]([Au-]SC1OC(COC(=O)C)C(C(C1OC(=O)C)OC(=O)C)OC(=O)C)(CC)CC
Isomeric SMILES CC[P+]([Au-]S[C@@H]1O[C@H](COC(=O)C)[C@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C)(CC)CC
InChI InChI=1S/C14H20O9S.C6H15P.Au/c1-6(15)19-5-10-11(20-7(2)16)12(21-8(3)17)13(14(24)23-10)22-9(4)18;1-4-7(5-2)6-3;/h10-14,24H,5H2,1-4H3;4-6H2,1-3H3;/q;;+1/p-1/t10-,11-,12+,13-,14+;;/m1../s1
InChI Key AUJRCFUBUPVWSZ-XTZHGVARSA-M

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

References
1. Gromer S, Arscott LD, Williams Jr CH, Schirmer RH, Becker K. (1998)
Human placenta thioredoxin reductase. Isolation of the selenoenzyme, steady state kinetics, and inhibition by therapeutic gold compounds.
J Biol Chem, 273 (32): 20096-101. [PMID:9685351]
2. Harbut MB, Vilchèze C, Luo X, Hensler ME, Guo H, Yang B, Chatterjee AK, Nizet V, Jacobs Jr WR, Schultz PG et al.. (2015)
Auranofin exerts broad-spectrum bactericidal activities by targeting thiol-redox homeostasis.
Proc Natl Acad Sci U S A, 112 (14): 4453-8. [PMID:25831516]
3. Hatano N, Suzuki H, Muraki Y, Muraki K. (2013)
Stimulation of human TRPA1 channels by clinical concentrations of the antirheumatic drug auranofin.
Am J Physiol, Cell Physiol, 304 (4): C354-61. [PMID:23220116]