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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2021-09-14 15:47:46 UTC
HMDB IDHMDB0015227
Secondary Accession Numbers
  • HMDB15227
Metabolite Identification
Common NameFluvastatin
DescriptionFluvastatin, also known as fluvas or fluindostatin, 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. In humans, fluvastatin is involved in the fluvastatin action pathway. Fluvastatin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Fluvastatin.
Structure
Data?1582753272
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 Weight411.4659
Monoisotopic Molecular Weight411.18458653
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
CAS Registry Number93957-54-1
SMILES
CC(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 Identifier
InChI=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 )
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point194 - 197 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0044 g/LNot Available
LogP4.5Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0044 g/LALOGPS
logP10(3.69) g/LALOGPS
logP10(3.83) g/LChemAxon
logS10(-5) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fluvastatin,1TMS,#1CC(C)N1C(/C=C/[C@@H](C[C@H](O)CC(=O)O)O[Si](C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C213355.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Fluvastatin,1TMS,#2CC(C)N1C(/C=C/[C@H](O)C[C@@H](CC(=O)O)O[Si](C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C213307.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Fluvastatin,1TMS,#3CC(C)N1C(/C=C/[C@H](O)C[C@H](O)CC(=O)O[Si](C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C213299.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Fluvastatin,2TMS,#1CC(C)N1C(/C=C/[C@@H](C[C@@H](CC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C213324.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Fluvastatin,2TMS,#2CC(C)N1C(/C=C/[C@@H](C[C@H](O)CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C213310.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Fluvastatin,2TMS,#3CC(C)N1C(/C=C/[C@H](O)C[C@@H](CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C213277.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Fluvastatin,3TMS,#1CC(C)N1C(/C=C/[C@@H](C[C@@H](CC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C213304.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Fluvastatin,1TBDMS,#1CC(C)N1C(/C=C/[C@@H](C[C@H](O)CC(=O)O)O[Si](C)(C)C(C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C213576.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Fluvastatin,1TBDMS,#2CC(C)N1C(/C=C/[C@H](O)C[C@@H](CC(=O)O)O[Si](C)(C)C(C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C213522.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Fluvastatin,1TBDMS,#3CC(C)N1C(/C=C/[C@H](O)C[C@H](O)CC(=O)O[Si](C)(C)C(C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C213530.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Fluvastatin,2TBDMS,#1CC(C)N1C(/C=C/[C@@H](C[C@@H](CC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C213714.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Fluvastatin,2TBDMS,#2CC(C)N1C(/C=C/[C@@H](C[C@H](O)CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C213719.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Fluvastatin,2TBDMS,#3CC(C)N1C(/C=C/[C@H](O)C[C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C213669.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Fluvastatin,3TBDMS,#1CC(C)N1C(/C=C/[C@@H](C[C@@H](CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C(C2=CC=C(F)C=C2)C2=CC=CC=C213862.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01095 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01095 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01095
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1265982
KEGG Compound IDC07014
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFluvastatin
METLIN IDNot Available
PubChem Compound1548972
PDB IDNot Available
ChEBI ID5136
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). FDA label . .