Auranofin (CED0004224)

Record Information

Version

1.0

Creation Date

2016-05-22 03:23:54 UTC

Update Date

2026-05-14 16:55:16 UTC

Accession Number

CHEM016236

Identification

Common Name

Auranofin

Class

Small Molecule

Description

Auranofin is a chemical compound with the molecular formula C20H34AuO9PS. Auranofin belongs to the tetracarboxylic acids and derivatives, a subclass of carboxylic acids and derivatives within the organic compounds. With an average molecular weight of 678.48 g/mol, Auranofin is a heavy molecule. This compound is found in or released from one recorded source: healthcare, pharmaceuticals, and veterinary products, specifically antiinflammatory and antirheumatic products. The recorded route of exposure for this substance is oral. Auranofin acts on five recorded protein targets, serving as an inhibitor or modulator of the Inhibitor of nuclear factor kappa-B kinase subunit beta (IKBKB), Peroxiredoxin-5, mitochondrial (PRDX5), Steroid hormone receptor ERR1 (ESRRA), and Steroid hormone receptor ERR2 (ESRRB), as well as one other protein.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Gold(1+) ion [(2R,3S,4R,5S,6S)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]sulphanide triethylphosphane	Generator

Chemical Formula

C₂₀H₃₄AuO₉PS

Average Molecular Mass

678.480 g/mol

Monoisotopic Mass

678.133 g/mol

CAS Registry Number

34031-32-8

IUPAC Name

gold(1+) ion [(2R,3S,4R,5S,6S)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]sulfanide triethylphosphane

Traditional Name

gold(1+) ion [(2R,3S,4R,5S,6S)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]sulfanide triethylphosphine

SMILES

[Au+].CCP(CC)CC.[H][C@]1([S-])O[C@@]([H])(COC(C)=O)[C@]([H])(OC(C)=O)[C@@]([H])(OC(C)=O)[C@]1([H])OC(C)=O

InChI Identifier

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+;;/m0../s1

InChI Key

AUJRCFUBUPVWSZ-PTNXSCMHSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Monosaccharide
Oxane
Carboxylic acid ester
Sulfenyl compound
Organoheterocyclic compound
Organic transition metal salt
Organic metal salt
Oxacycle
Hydrocarbon derivative
Organic oxide
Organosulfur compound
Organophosphorus compound
Organic salt
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	5.85 g/L	ALOGPS
logP	0.65	ALOGPS
logP	-0.2	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	8.63	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	114.43 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	79.49 m³·mol⁻¹	ChemAxon
Polarizability	34.64 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
6598.0	Log mg/kg	[3700:12000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
363	Antiinflammatory and antirheumatic products	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Anthrax toxin receptor 2	P58335	Humans	Predicted (SEA)	0.934191
Click to view 3D structure	Leukotriene C4 synthase	A6XA80	Cavia porcellus	Predicted (SEA)	1.47914
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	716.446
Click to view 3D structure	Dipeptidyl peptidase 1	P53634	Humans	Predicted (SEA)	197.192
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	1544.84
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	1296.81
Click to view 3D structure	Killer cell lectin-like receptor subfamily B member 1A	P27471	Rattus norvegicus	Predicted (SEA)	9.18621
Click to view 3D structure	Carbonic anhydrase 14	Q9ULX7	Humans	Predicted (SEA)	1883.09
Click to view 3D structure	Carbonic anhydrase 4	P22748	Humans	Predicted (SEA)	2180.56
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	4775.27
Click to view 3D structure	Carbonic anhydrase 7	P43166	Humans	Predicted (SEA)	2854.19
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	3818.35
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Predicted (SEA)	4886.98
Click to view 3D structure	Carbonic anhydrase 5B, mitochondrial	Q9Y2D0	Humans	Predicted (SEA)	2247.97
Click to view 3D structure	Protein kinase C alpha type	P17252	Humans	Predicted (SEA)	4540.17
Click to view 3D structure	NS3	A3EZJ3	Hepatitis C virus	Predicted (SEA)	1399.96
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08173	Humans	Predicted (SEA)	5312.2
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	6060.87
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08912	Humans	Predicted (SEA)	5342.56
Click to view 3D structure	Squalene monooxygenase	P52020	Rattus norvegicus	Predicted (SEA)	55.1172
Click to view 3D structure	Tyrosine-protein phosphatase non-receptor type 1	P18031	Humans	Predicted (SEA)	3477.45
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P08482	Rattus norvegicus	Predicted (SEA)	3614.62
Click to view 3D structure	Carbonic anhydrase 5A, mitochondrial	P35218	Humans	Predicted (SEA)	3832.28
Click to view 3D structure	Carnitine palmitoyltransferase 1A	Q9MYX2	Sus scrofa	Predicted (SEA)	65.9383
Click to view 3D structure	Ectonucleoside triphosphate diphosphohydrolase 1	P55772	Mus musculus	Predicted (SEA)	12.3002