Fluvastatin (CHEM016315)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:27:12 UTC
Update Date2016-11-09 01:15:22 UTC
Accession NumberCHEM016315
Identification
Common NameFluvastatin
ClassSmall Molecule
DescriptionA (6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid diastereoisomer in which the stereocentres beta- and delta- to the carboxy group have S and R configuration, respectively. The drug fluvastatin is an equimolar mixture of this compound and its enantiomer.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(-)-(3S,5R)-FluvastatinChEBI
(3S,5R)-(-)-FluvastatinChEBI
(3S,5R,6E)-7-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acidChEBI
FluvasKegg
(3S,5R,6E)-7-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoateGenerator
FluindostatinHMDB
Fluvastatin sodium saltHMDB
Fluvastatin sodiumHMDB
7-(3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl)-3,5-dihydroxy-6-heptenoateHMDB
LescolHMDB
Chemical FormulaC24H26FNO4
Average Molecular Mass411.466 g/mol
Monoisotopic Mass411.185 g/mol
CAS Registry Number93957-54-1
IUPAC Name(3S,5R,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid
Traditional Namefluvastatin
SMILESCC(C)N1C(\C=C\[C@H](O)C[C@H](O)CC(O)=O)=C(C2=CC=C(F)C=C2)C2=CC=CC=C12
InChI IdentifierInChI=1S/C24H26FNO4/c1-15(2)26-21-6-4-3-5-20(21)24(16-7-9-17(25)10-8-16)22(26)12-11-18(27)13-19(28)14-23(29)30/h3-12,15,18-19,27-28H,13-14H2,1-2H3,(H,29,30)/b12-11+/t18-,19-/m0/s1
InChI KeyFJLGEFLZQAZZCD-JUFISIKESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrroles
Sub ClassSubstituted pyrroles
Direct ParentPhenylpyrroles
Alternative Parents
Substituents
  • 3-phenylpyrrole
  • N-alkylindole
  • Indole
  • Indole or derivatives
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Fluorobenzene
  • Halobenzene
  • Halogenated fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Benzenoid
  • Unsaturated fatty acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxylic acid derivative
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organohalogen compound
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
  • statin (synthetic) (CHEBI:5136 )
  • (6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid (CHEBI:5136 )
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 Solubility0.0044 g/LALOGPS
logP3.69ALOGPS
logP3.83ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.56ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area82.69 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity114.86 m³·mol⁻¹ChemAxon
Polarizability44.31 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-6229000000-e7e9a4f18c77b8a3f328Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03g0-9113255000-bbcec21c7d8450380f53Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03xr-0082900000-af0bcdb98404aa7485cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-01b9-0090000000-fbe9d82e356a4c40ed62Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00di-0290000000-4e6800fc8ed4bacd61c7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00di-0190000000-8d3aabcab51b7427b00cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-01b9-0091000000-91a05c153cd55276cb1eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03xr-0064900000-6073674eb901911a6505Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0009100000-48400cafdfe7b1ae8e91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fbc-2029000000-d4584fe54d4a4dee073eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-8196000000-fb302f9ef42c788b0d34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2009600000-fceb838edec69ac58798Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pi1-6109100000-0037246c25ef1a9001acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9124000000-574e6db0baf9d8f4ad3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0007900000-94ec3a6470255ed0e510Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kmj-2009000000-f827f5fc9e84c0d8a8eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01u3-5094000000-5b650479bc088483a8c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0019500000-b32ac44df58c44fecd76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ou-0039000000-533fcd1fe96ff3c27509Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-0091000000-fb70ed9366fe79b510e5Spectrum
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 IDDB01095
HMDB IDHMDB0015227
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFluvastatin
Chemspider ID1265982
ChEBI ID5136
PubChem Compound ID1548972
Kegg Compound IDC07014
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11817313
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12489926
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12891229
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=16480934
5. FDA label