Mevastatin (CED0006737)

Record Information
Version1.0
Creation Date2016-05-22 04:28:26 UTC
Update Date2026-08-22 02:01:40 UTC
Accession NumberCHEM017578
Identification
Common NameMevastatin
ClassSmall Molecule
Description
Mevastatin is an organoheterocyclic compound with the formula $\text{C}_{23}\text{H}_{34}\text{O}_5$ and an average molecular weight of 390.52 g/mol. Mevastatin belongs to the delta valerolactones, a subclass of lactones within the organic compounds. In terms of biological activity, it is recorded as an inhibitor of the protein target 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGCR). The compound is found in or released from 37 recorded sources across multiple sectors. Within Electrical & Electronic Equipment, it is associated with cell phones, capacitors, wires and cables, batteries, printed circuit boards, and 10 additional sources. In Building & Construction, it is linked to ceilings, fencing, ladders, stairs and ramps, sunshades awnings or outside screens, and 2 others. Its presence is noted in Food, food processing & cookware, specifically regarding food packaging, food preservation, fermentation processes for beer, processing meats, and the preparation of wine or sparkling wine. Additional sources include healthcare, pharmaceuticals & veterinary products, such as medical devices and antibiotics; textiles, leather & furnishings, including carpets and rugs and synthetic textiles; and household cleaning & consumer products, such as soap detergents and perfumes within detergents and soaps, among 4 more sectors. Recorded routes of exposure for mevastatin include touch, oral, and inhalation.
Contaminant Type
  • Mycotoxin
  • PFAS
Chemical Structure
Synonyms
ValueSource
Antibiotic ML 236bChEBI
CompactinChEBI
CS 500ChEBI
MevastatinaChEBI
MevastatineChEBI
MevastatinumChEBI
ML 236 bChEBI
ML-236bChEBI
[(1S,7S,8S,8Ar)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoic acidGenerator
6-DemethylmevinolinMeSH
ML 236bMeSH
MevastatinMeSH
Chemical FormulaC23H34O5
Average Molecular Mass390.520 g/mol
Monoisotopic Mass390.241 g/mol
CAS Registry Number73573-88-3
IUPAC Name(1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate
Traditional Namemevastatin
SMILES[H][C@]12[C@H](CCC=C1C=C[C@H](C)[C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1)OC(=O)[C@@H](C)CC
InChI IdentifierInChI=1S/C23H34O5/c1-4-14(2)23(26)28-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-18-12-17(24)13-21(25)27-18/h6,8-9,14-15,17-20,22,24H,4-5,7,10-13H2,1-3H3/t14-,15-,17+,18+,19-,20-,22-/m0/s1
InChI KeyAJLFOPYRIVGYMJ-INTXDZFKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassDelta valerolactones
Direct ParentDelta valerolactones
Alternative Parents
Substituents
  • Delta valerolactone
  • Fatty acid ester
  • Delta_valerolactone
  • Dicarboxylic acid or derivatives
  • Oxane
  • Fatty acyl
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.032 g/LALOGPS
logP4.13ALOGPS
logP3.62ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)14.91ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity108.63 m³·mol⁻¹ChemAxon
Polarizability43.57 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-2697563470-7ca60296a82091ed4d78Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00du-2029000000-230330d5f35b89f697deNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-9382000000-710d05ac99dadf79d8fcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-9320000000-15288041beb715274965Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0009000000-d82bc9efa8d3d29817b6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uxr-4129000000-1c5d65a8e9b64c606768Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9141000000-15497dc87d6790476388Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
697.0Log mg/kg[390:1200]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
7PesticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
120Wires and cablesElectrical & Electronic EquipmentNot Available
121Printed circuit boardsElectrical & Electronic EquipmentNot Available
125BatteriesElectrical & Electronic EquipmentNot Available
130SemiconductorsElectrical & Electronic EquipmentNot Available
138LubricantsEnergy, oil & gasNot Available
147Food packagingFood, food processing & cookwareNot Available
174LubricantsIndustrial manufacturing & chemical processingNot Available
234Medical devicesHealthcare, pharmaceuticals & veterinary productsNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
451Carpets and RugsTextiles, leather & furnishingsNot Available
454Synthetic textilesTextiles, leather & furnishingsNot Available
490Personal care & cosmeticsNot Available
492Cell phonesElectrical & Electronic EquipmentNot Available
493CapacitorsElectrical & Electronic EquipmentNot Available
495CeilingsBuilding & ConstructionNot Available
496FencingBuilding & ConstructionNot Available
498LaddersBuilding & ConstructionNot Available
500Stairs And RampsBuilding & ConstructionNot Available
501Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
502Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
504Adjustable ResistorsElectrical & Electronic EquipmentNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
533Sparking PlugsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
656Snap FastenersTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
3-hydroxy-3-methylglutaryl-coenzyme A reductase structureClick to view 3D structure3-hydroxy-3-methylglutaryl-coenzyme A reductaseP04035HumansPredicted (SEA)0.311397
Click to view 3D structure3-hydroxy-3-methylglutaryl-coenzyme A reductaseP51639Rattus norvegicusPredicted (SEA)0.544945
Click to view 3D structure3-hydroxy-3-methylglutaryl-coenzyme A reductaseQ01237Mus musculusPredicted (SEA)0.155698
Solute carrier organic anion transporter family member 1B1 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B1Q9Y6L6HumansPredicted (SEA)4.5931
Click to view 3D structureAcetylcholinesteraseO42275Electrophorus electricusPredicted (SEA)65.8604
ATP-dependent translocase ABCB1 structureClick to view 3D structureATP-dependent translocase ABCB1P08183HumansPredicted (SEA)30.5169
Click to view 3D structureCholinesteraseP81908Equus caballusPredicted (SEA)68.663
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)359.819
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)333.817
Substance-K receptor structureClick to view 3D structureSubstance-K receptorP21452HumansPredicted (SEA)345.806
Photoreceptor-specific nuclear receptor structureClick to view 3D structurePhotoreceptor-specific nuclear receptorQ9Y5X4HumansPredicted (SEA)161.537
Click to view 3D structureTegument protein VP16P06492Herpes simplex virus (type 1 / strain 17)Predicted (SEA)108.444
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)322.763
Cytochrome P450 2C8 structureClick to view 3D structureCytochrome P450 2C8P10632HumansPredicted (SEA)1545.0
Nuclear receptor subfamily 4 group A member 2 structureClick to view 3D structureNuclear receptor subfamily 4 group A member 2P43354HumansPredicted (SEA)114.828
Histone deacetylase 1 structureClick to view 3D structureHistone deacetylase 1Q13547HumansPredicted (SEA)3442.49
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansPredicted (SEA)3938.55
Click to view 3D structureActin, alpha skeletal muscleP68135Oryctolagus cuniculusPredicted (SEA)0.311397
Click to view 3D structureDiacylglycerol lipase-alphaQ9Y4D2HumansPredicted (SEA)665.299
Click to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1CQ01815Mus musculusPredicted (SEA)1.79053
Histone deacetylase 2 structureClick to view 3D structureHistone deacetylase 2Q92769HumansPredicted (SEA)4425.88
Cannabinoid receptor 1 structureClick to view 3D structureCannabinoid receptor 1P21554HumansPredicted (SEA)3911.53
Click to view 3D structureATP-dependent clpX-like chaperone, mitochondrialO76031HumansPredicted (SEA)16.1148
Click to view 3D structureSynaptic vesicle glycoprotein 2AQ02563Rattus norvegicusPredicted (SEA)11.9888
Interleukin-6 receptor subunit beta structureClick to view 3D structureInterleukin-6 receptor subunit betaP40189HumansPredicted (SEA)27.2472
Concentrations
Not Available
External Links
DrugBank IDDB06693
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00000564
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMevastatin
Chemspider IDNot Available
ChEBI ID34848
PubChem Compound ID64715
Kegg Compound IDC13963
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11283400
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12403272
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15274361
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15531285
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15786722
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=18672387
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=18936176
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=20629200
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23918904
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24462564
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=3170348
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=3719857