Mevastatin (CHEM017578)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:28:26 UTC
Update Date2016-11-09 01:15:37 UTC
Accession NumberCHEM017578
Identification
Common NameMevastatin
ClassSmall Molecule
DescriptionA carboxylic ester that is pravastatin that is lacking the allylic hydroxy group. A hydroxymethylglutaryl-CoA reductase inhibitor (statin) isolated from Penicillium citrinum and from Penicillium brevicompactum, its clinical use as a lipid-regulating drug ceased following reports of toxicity in animals.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-2697563470-7ca60296a82091ed4d78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00du-2029000000-230330d5f35b89f697deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9382000000-710d05ac99dadf79d8fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-9320000000-15288041beb715274965Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-d82bc9efa8d3d29817b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-4129000000-1c5d65a8e9b64c606768Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9141000000-15497dc87d6790476388Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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