Auranofin - Moligand™, 10mM in DMSO , Activator of TRPA1, CAS No.34031-32-8, Activator of TRPA1

CAS: 34031-32-8 Cat. No.: A423478 Molecular Weight: 678.48 EC Number: 251-801-9

GRADE & PURITY Moligand™, 10mM in DMSO

Synonyms

A937040 | 3,4,5-Triacetyloxy-6-(acetyloxymethyl) oxane-2-thiolate triethylphosphanium | D78135 | MFCD00080759 | 1-Thio- | (1-Thio-beta-D-glucopyranosato)(triethylphosphine)gold 2,3,4,6-tetraacetate | BCP08217 | AURANOFIN | MMV688978 | 1-Thio-beta-D-glucop

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Auranofin (Ridaura, SKF-39162) is an inhibitor of thioredoxin reductase (TrxR) with IC50 of 88 nM for purified H. pylori TrxR in cell-free assay. Auranofin has anti-cancer activity and can completely inhibit bacterial growth at 1.2 μM. Auranofin is an FDA-approved gold-containing compound used for the treatment of rheumatoid arthritis.

Auranofin inhibits both leukocyte activation pathways at multiple sites and the release of inflammatory mediators from human macrophages, basophils, and pulmonary mast cells. Auranofin also inhibits 5-lipoxygenase in human neutrophils, IKB kinase (IKK) by modifying Cys-179 of the IKKβ subunit 5 and selenoenzyme thioredoxin reductase (TrxR) which is involved in the defense against oxidative stress. Auranofin is a disease-modifying antirheumatic drug (DMARD) and has been used to study the anti-proliferative effects against OVCAR-3 human ovarian carcinoma cells.

Specifications

Synonyms

A937040 | 3, 4, 5-Triacetyloxy-6-(acetyloxymethyl) oxane-2-thiolate triethylphosphanium | D78135 | MFCD00080759 | 1-Thio- | (1-Thio-beta-D-glucopyranosato)(triethylphosphine)gold 2, 3, 4, 6-tetraacetate | BCP08217 | AURANOFIN | MMV688978 | 1-Thio-beta-D-glucop

Specifications & Purity

Moligand™, 10mM in DMSO

Biochemical and Physiological Mechanisms

Organic gold compound. Anti-inflammatory and antiproliferative agent. Glutathione S-transferase P1-1 inhibitor (IC 50 = 33 μM). Shows antiproliferative effects through STAT3 inhibition. Shows anti-inflammatory effects in vivo . Orally active.

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

ACTIVATOR

Mechanism of action

Activator of TRPA1

Names and Identifiers

• Canonical Smiles: CCP(CC)CC.CC(=O)OCC1C(C(C(C(O1)[S-])OC(=O)C)OC(=O)C)OC(=O)C.[Au+]
• IUPAC Name: gold(1+);3,4,5-triacetyloxy-6-(acetyloxymethyl)oxane-2-thiolate;triethylphosphane
• InChIKey: AUJRCFUBUPVWSZ-UHFFFAOYSA-M
• 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
• Isomeric SMILES: CCP(CC)CC.CC(=O)OCC1C(C(C(C(O1)[S-])OC(=O)C)OC(=O)C)OC(=O)C.[Au+]
• Molecular Weight: 678.48
• Reaxy-Rn: 16134185
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=16134185&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Tetracarboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Tetracarboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Tetracarboxylic acids and derivatives
• Alternative Parents: Hexoses Oxanes Organic phosphines and derivatives Carboxylic acid esters Oxacyclic compounds Organic transition metal salts Organosulfur compounds Organopnictogen compounds Organic zwitterions Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Not available
• Substituents: Tetracarboxylic acid or derivatives - Hexose monosaccharide - Monosaccharide - Oxane - Carboxylic acid ester - Phosphine - Organoheterocyclic compound - Organic transition metal salt - Oxacycle - Organic salt - Organic zwitterion - Hydrocarbon derivative - Organic oxide - Organosulfur compound - Organophosphorus compound - Organooxygen compound - Carbonyl group - Organopnictogen compound - Organic oxygen compound - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TRPA1 Tclin Transient receptor potential cation channel subfamily A member 1 (1 Activities)

Discover Target: TRPA1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Chemical and Physical Properties

• Sensitivity: Moisture sensitive;Light sensitive
• Melt Point(°C): 112-155℃
• Molecular Weight: 678.500 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 12
• Exact Mass: 678.133 Da
• Monoisotopic Mass: 678.133 Da
• Topological Polar Surface Area: 115.000 Ų
• Heavy Atom Count: 32
• Formal Charge: 0
• Complexity: 532.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 5
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 3

XLogP3

References

1. Li Jian-Guo, Zhang Chuan-Jian, Liang Liu-Yan, Lu Ting-Yin, Zhong Long-Gen, Zhong Wei-Cheng, Niu Chao-Yan, Sun Jian, Liao Xiao-Ping, Zhou Yu-Feng.  (2024)  Assessment of anti-MRSA activity of auranofin and florfenicol combination: a PK/PD analysis.  JOURNAL OF APPLIED MICROBIOLOGY,  135  (12):   [PMID:39694699] [10.1093/jambio/lxae299]

2. Hao Liu, Ke Huang, Hao Zhang, Xiaohui Liu, Hui Jiang, Xuemei Wang.  (2024)  Photo-Driven In Situ Solidification of Whole Cells through Inhibition of Trogocytosis for Immunotherapy.  Research,      [PMID:38384327] [10.34133/research.0318]

3. Xinrong Zou, Xinyao Fan, Ping Xu, Xiufeng Yu, Chan Luo, Zhuxi Kang, Xin Shen, Jiaoni Zheng, Jisheng Wang, Baicheng He, Zeng Tu, Xiaoming Fu, Yongbo Peng.  (2025)  Selenium-albumin corona rinse ameliorates diabetic periodontitis by inhibiting inflammation, anti-bacterial and improving osteogenesis via activating TrxR1/ROS/β-catenin anti-oxidation cascade.  BIOMATERIALS,      [PMID:41207151] [10.1016/j.biomaterials.2025.123835]

4. Jian-Guo Li, Wei-Cheng Zhong, Long-Gen Zhong, Chao-Yan Niu, Ting-Yin Lu, Chuan-Jian Zhang, Jian Sun, Xiao-Ping Liao, Yu-Feng Zhou.  (2025)  Auranofin potentiates linezolid activity against MRSA by disrupting redox homeostasis and inhibiting SarA-mediated virulence and biofilm.  Virulence,      [PMID:41400929] [10.1080/21505594.2025.2605759]