Methylcyclopentadienyl manganese tricarbonyl (CED0011938)

Record Information
Version1.0
Creation Date2009-06-19 21:58:21 UTC
Update Date2026-04-03 06:50:28 UTC
Accession NumberCHEM000970
Identification
Common NameMethylcyclopentadienyl manganese tricarbonyl
ClassSmall Molecule
Description
Methylcyclopentadienyl manganese tricarbonyl (C9H7MnO3) is an exogenous liquid with an average molecular weight of 218.09 g/mol. Methylcyclopentadienyl manganese tricarbonyl belongs to the olefins, a subclass of unsaturated hydrocarbons within the organic compounds. Industrially, the compound is used as a fuel additive (PMC4545267). The compound has been released from 22 recorded sources, including aquatic systems and sediments such as groundwater, surface water, seawater, and freshwater; drinking water and water supply including tap, bottled, and desalinated water; and wastewater, sanitation and biosolids including industrial wastewater, mine wastewater, and wastewater treatment effluent. It is also found in marine, shipping and aquaculture sources like bilge and ballast water, as well as electrical and electronic equipment such as television systems and amplifiers, and appliances including water heaters and water coolers. Recorded exposure routes include oral, inhalation, and touch. Methylcyclopentadienyl manganese tricarbonyl interacts with three recorded protein targets. It binds to the major prion protein (PRNP), displacing copper and altering the protein's conformation and the redox chemistry of the metal-protein complex in ways similar to those associated with prion disease. It also targets cytoplasmic aconitate hydratase (ACO1) and mitochondrial aconitate hydratase (ACO2), where manganese inhibits aconitase and disrupts the catalytic [4Fe-4S] cluster. This inhibition increases citrate levels and produces iron regulatory protein 1, altering cellular iron homeostasis. Additionally, manganese targets an unnamed protein, stabilizing iron regulatory protein 2 by competing for an iron-binding site, which disrupts the mechanisms responsible for its iron-dependent degradation.
Contaminant Type
  • Amine
  • Food Toxin
  • Household Toxin
  • Human Neurotoxin
  • Manganese Compound
  • Organic Compound
  • Organometallic
  • PMT
  • Pollutant
  • Synthetic Compound
Chemical Structure
SynonymsNot Available
Chemical FormulaC9H7MnO3
Average Molecular Mass218.088 g/mol
Monoisotopic Mass217.978 g/mol
CAS Registry Number12108-13-3
IUPAC Name2-methylcyclopenta-2,4-dien-1-yl tris(methanidylidyneoxidanium) manganese
Traditional Name2-methylcyclopenta-2,4-dien-1-yl tris(carbon monoxide) manganese
SMILES[Mn].[C-]#[O+].[C-]#[O+].[C-]#[O+].CC1=CC=C[CH]1
InChI IdentifierInChI=1S/C6H7.3CO.Mn/c1-6-4-2-3-5-6;3*1-2;/h2-5H,1H3;;;;
InChI KeyLYHJNAIHGFWRKM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cycloalkenes. These are unsaturated monocyclic hydrocarbons having one endocyclic double bond.
KingdomOrganic compounds
Super ClassHydrocarbons
ClassUnsaturated hydrocarbons
Sub ClassOlefins
Direct ParentCycloalkenes
Alternative Parents
Substituents
  • Organic transition metal salt
  • Cycloalkene
  • Organic oxygen compound
  • Unsaturated aliphatic hydrocarbon
  • Hydrocarbon derivative
  • Organic salt
  • 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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateLiquid
AppearanceYellow to dark orange liquid.
Experimental Properties
PropertyValue
Melting Point1.5°C
Boiling PointNot Available
Solubility0.029 mg/mL at 25°C [GARRISON,AW et al. (1995)]
Predicted Properties
PropertyValueSource
Water Solubility8.04 g/LALOGPS
logP2.21ALOGPS
logP1.55ChemAxon
logS-1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.31 m³·mol⁻¹ChemAxon
Polarizability9.47 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0090000000-618af413accb30414c94Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0090000000-618af413accb30414c94Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0090000000-618af413accb30414c94Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0090000000-f9b84666ff8e388846d9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0090000000-f9b84666ff8e388846d9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0090000000-f9b84666ff8e388846d9Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityManganese is a cellular toxicant that can impair transport systems, enzyme activities, and receptor functions. It primarily targets the central nervous system, particularily the globus pallidus of the basal ganglia. It is believed that the manganese ion, Mn(II), enhances the autoxidation or turnover of various intracellular catecholamines, leading to increased production of free radicals, reactive oxygen species, and other cytotoxic metabolites, along with a depletion of cellular antioxidant defense mechanisms, leading to oxidative damage and selective destruction of dopaminergic neurons. In addition to dopamine, manganese is thought to perturbations other neurotransmitters, such as GABA and glutamate. In order to produce oxidative damage, manganese must first overwhelm the antioxidant enzyme manganese superoxide dismutase. The neurotoxicity of Mn(II) has also been linked to its ability to substitute for Ca(II) under physiological conditions. It can enter mitochondria via the calcium uniporter and inhibit mitochondrial oxidative phosphorylation. It may also inhibit the efflux of Ca(II), which can result in a loss of mitochondrial membrane integrity. Mn(II) has been shown to inhibit mitochondrial aconitase activity to a significant level, altering amino acid metabolism and cellular iron homeostasis. (3)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelChronic Inhalation: 0.0003 mg/m3 (2)
SymptomsManganese mainly affects the nervous system and may cause behavioral changes and other nervous system effects, which include movements that may become slow and clumsy. This combination of symptoms when sufficiently severe is referred to as “manganism”. (3)
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
140.0mg/kg[140:795]RabbitLD50DermalexperimentalT32
58.0mg/kgNot AvailableRatLD50OralexperimentalA178
247.0mg/m3Not AvailableRatLC50Inhalation (1 hour)experimentalT32
862.0Log mg/kg[480:1500]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
3Irrigation waterAgriculture & land managementNot Available
27Water CoolersAppliances, HVAC & refrigerantsNot Available
43Water heatersAppliances, HVAC & refrigerantsNot Available
50GroundwaterAquatic systems & sedimentsNot Available
51Surface waterAquatic systems & sedimentsNot Available
52SeawaterAquatic systems & sedimentsNot Available
53FreshwaterAquatic systems & sedimentsNot Available
70Stormwater runoffAutomotive & urban infrastructureNot Available
88Waterproofing spraysBuilding & ConstructionNot Available
115Drinking waterDrinking water & water supplyNot Available
116Tap waterDrinking water & water supplyNot Available
117Bottled waterDrinking water & water supplyNot Available
118Desalinated waterDrinking water & water supplyNot Available
181Ballast waterMarine, shipping & aquacultureNot Available
182Bilge waterMarine, shipping & aquacultureNot Available
468Industrial wastewaterWastewater, sanitation & biosolidsNot Available
470Wastewater treatment effluentWastewater, sanitation & biosolidsNot Available
475Mine wastewaterWastewater, sanitation & biosolidsNot Available
477Wastewater, unspecifiedWastewater, sanitation & biosolidsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Porphobilinogen deaminase structureClick to view 3D structurePorphobilinogen deaminaseP08397HumansPredicted (SEA)1.94623
Click to view 3D structureGlucose-6-phosphate dehydrogenase-6-phosphogluconolactonaseQ9BHT9Plasmodium bergheiPredicted (SEA)7507.08
Replicase polyprotein 1ab structureClick to view 3D structureReplicase polyprotein 1abP0DTD1SARS-CoV-2Predicted (SEA)7773.56
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)7777.76
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)7773.4
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)7759.85
Cytochrome P450 2A6 structureClick to view 3D structureCytochrome P450 2A6P11509HumansPredicted (SEA)7582.44
Click to view 3D structureCytochrome P450 2A5P20852Mus musculusPredicted (SEA)2993.22
Click to view 3D structureProtein TatP04608Human immunodeficiency virus type 1 group M subtype B (isolate HXB2)(HIV-1)Predicted (SEA)7702.01
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)7770.99
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)7782.59
Tyrosine-protein phosphatase non-receptor type 7 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 7P35236HumansPredicted (SEA)7737.43
Alkaline phosphatase, tissue-nonspecific isozyme structureClick to view 3D structureAlkaline phosphatase, tissue-nonspecific isozymeP05186HumansPredicted (SEA)7568.35
Serine/threonine-protein kinase pim-1 structureClick to view 3D structureSerine/threonine-protein kinase pim-1P11309HumansPredicted (SEA)7776.75
Nuclear receptor subfamily 4immunitygroup A member 1 structureClick to view 3D structureNuclear receptor subfamily 4immunitygroup A member 1P22736HumansPredicted (SEA)7645.96
C-C chemokine receptor type 1 structureClick to view 3D structureC-C chemokine receptor type 1P32246HumansPredicted (SEA)7720.46
Click to view 3D structureL-lactate dehydrogenase B chainP16125Mus musculusPredicted (SEA)849.024
Gastrotropin structureClick to view 3D structureGastrotropinP51161HumansPredicted (SEA)1124.61
Click to view 3D structureStimulator of interferon genes proteinF1M391Rattus norvegicusPredicted (SEA)3406.06
Click to view 3D structureMannose-6-phosphate isomeraseP34949HumansPredicted (SEA)7418.49
C-C chemokine receptor type 8 structureClick to view 3D structureC-C chemokine receptor type 8P51685HumansPredicted (SEA)7524.44
Click to view 3D structureProtoporphyrinogen oxidase, chloroplasticO24163Nicotiana tabacumPredicted (SEA)3409.17
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)7780.25
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansPredicted (SEA)7780.17
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)7759.62
Click to view 3D structureAconitate hydratase, mitochondrialQ99798HumansKnownManganese interferes with amino acid metabolism by inhibiting aconitase, resulting in an increase in citrate levels. It is also believed that this direct disruption of the catalytic [4Fe-4S] cluster of aconitase by manganese produces iron regulary protein 1, resulting in alterations in cellular iron homeostasis. (A159)
Cytoplasmic aconitate hydratase structureClick to view 3D structureCytoplasmic aconitate hydrataseP21399HumansKnownManganese interferes with amino acid metabolism by inhibiting aconitase, resulting in an increase in citrate levels. It is also believed that this direct disruption of the catalytic [4Fe-4S] cluster of aconitase by manganese produces iron regulary protein 1, resulting in alterations in cellular iron homeostasis. (A159)
Major prion protein structureClick to view 3D structureMajor prion proteinP04156HumansKnownManganese binds to the prion protein, altering its conformation, displacing copper, and altering the redox chemistry of the metal-protein complex. These changes are similar to those associated with prion disease. (A158)
Concentrations
Not Available
External Links
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 LinkMethylcyclopentadienyl manganese tricarbonyl
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID10921955
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References