Record Information
Version1.0
Creation Date2009-06-19 21:58:40 UTC
Update Date2026-04-06 14:07:27 UTC
Accession NumberCHEM001178
Identification
Common NameMeralluride
ClassSmall Molecule
DescriptionMeralluride is an organomercuric compound. It is used as a diuretic. 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, 12)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Drug
  • Ether
  • Mercury Compound
  • Organic Compound
  • Organometallic
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
SynonymsNot Available
Chemical FormulaC9H16HgN2O6
Average Molecular Mass448.820 g/mol
Monoisotopic Mass450.071 g/mol
CAS Registry Number140-20-5
IUPAC Name4-({[3-(hydroxymercurio)-2-methoxypropyl]carbamoyl}amino)-4-oxobutanoic acid
Traditional Namemeralluride
SMILESCOC(CNC(=O)NC(=O)CCC(O)=O)C[Hg]O
InChI IdentifierInChI=1S/C9H15N2O5.Hg.H2O/c1-6(16-2)5-10-9(15)11-7(12)3-4-8(13)14;;/h6H,1,3-5H2,2H3,(H,13,14)(H2,10,11,12,15);;1H2/q;+1;/p-1
InChI KeyZRXNZKPGLBQLJV-UHFFFAOYSA-M
Chemical Taxonomy
Description belongs to the class of organic compounds known as fatty acids and conjugates. These are aliphatic monocarboxylic acids with a saturated or unsaturated aliphatic tail (with at least 4 Carbon atoms).
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentFatty acids and conjugates
Alternative Parents
Substituents
  • Fatty acid
  • Carbonic acid derivative
  • Organic transition metal salt
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organic zwitterion
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
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 Solubility17.4 g/LALOGPS
logP-1.1ALOGPS
logP-2.2ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.86ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.96 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity55.67 m³·mol⁻¹ChemAxon
Polarizability26.29 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zfr-1313900000-dd2f8a89c2202983d0ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ll3-4749200000-556c1ffcfd65e05b7210Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fr-9030000000-a5cc7f60b88ade53e203Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3794600000-0d364922847f125baadaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066r-4921000000-2e131ba92222b2e55ec4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9502000000-b56a75b35ae7dca4f2c0Spectrum
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. (13)
Toxicity ValuesNot Available
Lethal Dose100 mg for an adult human (average for organic mercurials). (14)
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (11)
Uses/SourcesMeralluride is used as a diuretic. (12)
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 LinkMeralluride
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID12358987
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available