Record Information
Version1.0
Creation Date2009-06-19 21:58:40 UTC
Update Date2016-11-09 01:08:28 UTC
Accession NumberCHEM001175
Identification
Common NameMercaptomerin
ClassSmall Molecule
DescriptionMercaptomerin is an organomercuric compound. Mercury is a heavy, silvery d-block metal and one of six elements that are liquid at or near room temperature and pressure. It is a naturally occuring substance, and combines with other elements such as chlorine, sulfur, or oxygen to form inorganic mercury compounds (salts). Mercury also combines with carbon to make organic mercury compounds. (6)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Ether
  • Industrial/Workplace Toxin
  • Mercury Compound
  • Organic Compound
  • Organometallic
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
Mercaptomerin sodiumMeSH
ThiomerinMeSH
Mercaptomerin, disodium saltMeSH
Chemical FormulaC16H27HgNO6S
Average Molecular Mass562.040 g/mol
Monoisotopic Mass563.127 g/mol
CAS Registry Number20223-84-1
IUPAC Name3-[(3-{[(carboxymethyl)sulfanyl]mercurio}-2-methoxypropyl)carbamoyl]-1,2,2-trimethylcyclopentane-1-carboxylic acid
Traditional Namemercaptomerin
SMILESCOC(CNC(=O)C1CCC(C)(C(O)=O)C1(C)C)C[Hg]SCC(O)=O
InChI IdentifierInChI=1S/C14H24NO4.C2H4O2S.Hg/c1-9(19-5)8-15-11(16)10-6-7-14(4,12(17)18)13(10,2)3;3-2(4)1-5;/h9-10H,1,6-8H2,2-5H3,(H,15,16)(H,17,18);5H,1H2,(H,3,4);/q;;+1/p-1
InChI KeyJGMQLDDGSMLGDU-UHFFFAOYSA-M
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha-mercaptocarboxylic acids. These are carboxylic acids that bear a thiol group at the C-2 position. Alpha-mercaptocarboxylic acids have the general formula RC(S)C(=O)O, where R = H, organyl group.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct Parentalpha-Mercaptocarboxylic acids
Alternative Parents
Substituents
  • 2-mercaptocarboxylic acid
  • Carboxamide group
  • Carboxylic acid salt
  • Secondary carboxylic acid amide
  • Alkylthiol
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic transition metal salt
  • Organic nitrogen compound
  • Organic zwitterion
  • Organic salt
  • Alkyl mercury compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organometallic compound
  • Organomercurial-compound
  • Organic transition metal moeity
  • Hydrocarbon derivative
  • Organic oxide
  • Transition metal alkyl
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.2 g/LALOGPS
logP1.32ALOGPS
logP1.09ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)3.33ChemAxon
pKa (Strongest Basic)0.69ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area112.93 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity89.91 m³·mol⁻¹ChemAxon
Polarizability39.81 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1110290000-115f27b798efc0ea10d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-8311190000-c3ba059a0e1977ab4c1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9800000000-c89b2ee3a019efbb5d36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dl-4330290000-34d587f9bd6b537615a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uka-1770590000-f1aa78de9c2fdb08ae94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ktf-3930000000-30300f98d7153e71ca1fSpectrum
Toxicity Profile
Route of ExposureOral (8) ; inhalation (8) ; dermal (8)
Mechanism of ToxicityHigh-affinity binding of the divalent mercuric ion to thiol or sulfhydryl groups of proteins is believed to be the major mechanism for the activity of mercury. Through alterations in intracellular thiol status, mercury can promote oxidative stress, lipid peroxidation, mitochondrial dysfunction, and changes in heme metabolism. Mercury is known to bind to microsomal and mitochondrial enzymes, resulting in cell injury and death. For example, mercury is known to inhibit aquaporins, halting water flow across the cell membrane. It also inhibits the protein LCK, which causes decreased T-cell signalling and immune system depression. Mercury is also believed to inhibit neuronal excitability by acting on the postsynaptic neuronal membrane. It also affects the nervous system by inhibiting protein kinase C and alkaline phosphatase, which impairs brain microvascular formation and function, as well as alters the blood-brain barrier. Organic mercury exerts developmental effects by binding to tubulin, preventing microtubule assembly and causing mitotic inhibition. Mercury also produces an autoimmune response, likely by modification of major histocompatibility complex (MHC) class II molecules, self peptides, T-cell receptors, or cell-surface adhesion molecules. (8, 3, 4, 5)
MetabolismOrganic mercury is absorbed mainly by the gastrointestinal tract, then distributed throughout the body via the bloodstream. Organic mercury complexes with free cysteine and the cysteine and sulfhydryl groups on proteins such as haemoglobin. These complexes are able to mimic methionine and thus be transported throughout the body, including through the blood-brain barrier and placenta. Organic mercury is metabolized into inorganic mercury, which is eventually excreted in the urine and faeces. (12)
Toxicity ValuesNot Available
Lethal Dose100 mg for an adult human (average for organic mercurials). (13)
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (11)
Uses/SourcesNot Available
Minimum Risk LevelChronic Inhalation: 0.0002 mg/m3 (10)
Health EffectsMercury mainly affects the nervous system. Exposure to high levels of metallic, inorganic, or organic mercury can permanently damage the brain, kidneys, and developing fetus. Effects on brain functioning may result in irritability, shyness, tremors, changes in vision or hearing, and memory problems. Acrodynia, a type of mercury poisoning in children, is characterized by pain and pink discoloration of the hands and feet. Mercury poisoning can also cause Hunter-Russell syndrome and Minamata disease. (8)
SymptomsCommon symptoms include peripheral neuropathy (presenting as paresthesia or itching, burning or pain), skin discoloration (pink cheeks, fingertips and toes), edema (swelling), and desquamation (dead skin peels off in layers). (1)
TreatmentMercury poisoning is treated by immediate decontamination and chelation therapy using DMSA, DMPS, DPCN, or dimercaprol. (2)
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID30005
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available