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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:55 UTC
Update Date2021-09-14 15:40:00 UTC
HMDB IDHMDB0014038
Secondary Accession Numbers
  • HMDB14038
Metabolite Identification
Common NameN-Deisopropyl-fluvastatin
DescriptionN-Deisopropyl-fluvastatin is only found in individuals that have used or taken Fluvastatin. N-Deisopropyl-fluvastatin is a metabolite of Fluvastatin. N-deisopropyl-fluvastatin belongs to the family of Indoles. These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
Structure
Data?1582753162
Synonyms
ValueSource
(3S,5R,6E)-7-[3-(4-Fluorophenyl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoateHMDB
Chemical FormulaC21H20FNO4
Average Molecular Weight369.3862
Monoisotopic Molecular Weight369.137636338
IUPAC Name(3S,5R,6E)-7-[3-(4-fluorophenyl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid
Traditional Name(3S,5R,6E)-7-[3-(4-fluorophenyl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid
CAS Registry NumberNot Available
SMILES
O[C@@H](C[C@@H](O)\C=C\C1=C(C2=CC=CC=C2N1)C1=CC=C(F)C=C1)CC(O)=O
InChI Identifier
InChI=1S/C21H20FNO4/c22-14-7-5-13(6-8-14)21-17-3-1-2-4-18(17)23-19(21)10-9-15(24)11-16(25)12-20(26)27/h1-10,15-16,23-25H,11-12H2,(H,26,27)/b10-9+/t15-,16-/m0/s1
InChI KeyPOFAWBXODXSMNI-IGXNXKSNSA-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
  • 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 DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP10(2.89) g/LALOGPS
logP10(2.83) g/LChemAxon
logS10(-4.4) g/LALOGPS
pKa (Strongest Acidic)4.72ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area93.55 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity100.79 m³·mol⁻¹ChemAxon
Polarizability38.68 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Deisopropyl-fluvastatinO[C@@H](C[C@@H](O)\C=C\C1=C(C2=CC=CC=C2N1)C1=CC=C(F)C=C1)CC(O)=O5582.2Standard polar33892256
N-Deisopropyl-fluvastatinO[C@@H](C[C@@H](O)\C=C\C1=C(C2=CC=CC=C2N1)C1=CC=C(F)C=C1)CC(O)=O2868.3Standard non polar33892256
N-Deisopropyl-fluvastatinO[C@@H](C[C@@H](O)\C=C\C1=C(C2=CC=CC=C2N1)C1=CC=C(F)C=C1)CC(O)=O3403.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Deisopropyl-fluvastatin,1TMS,isomer #1C[Si](C)(C)O[C@H](CC(=O)O)C[C@@H](O)/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2[NH]13244.1Semi standard non polar33892256
N-Deisopropyl-fluvastatin,1TMS,isomer #2C[Si](C)(C)O[C@@H](/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2[NH]1)C[C@H](O)CC(=O)O3300.2Semi standard non polar33892256
N-Deisopropyl-fluvastatin,1TMS,isomer #3C[Si](C)(C)OC(=O)C[C@@H](O)C[C@@H](O)/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2[NH]13279.6Semi standard non polar33892256
N-Deisopropyl-fluvastatin,1TMS,isomer #4C[Si](C)(C)N1C(/C=C/[C@H](O)C[C@H](O)CC(=O)O)=C(C2=CC=C(F)C=C2)C2=CC=CC=C213261.0Semi standard non polar33892256
N-Deisopropyl-fluvastatin,2TMS,isomer #1C[Si](C)(C)OC(=O)C[C@H](C[C@@H](O)/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2[NH]1)O[Si](C)(C)C3268.2Semi standard non polar33892256
N-Deisopropyl-fluvastatin,2TMS,isomer #2C[Si](C)(C)O[C@H](CC(=O)O)C[C@H](/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2[NH]1)O[Si](C)(C)C3275.6Semi standard non polar33892256
N-Deisopropyl-fluvastatin,2TMS,isomer #3C[Si](C)(C)O[C@H](CC(=O)O)C[C@@H](O)/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N1[Si](C)(C)C3224.4Semi standard non polar33892256
N-Deisopropyl-fluvastatin,2TMS,isomer #4C[Si](C)(C)OC(=O)C[C@@H](O)C[C@H](/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2[NH]1)O[Si](C)(C)C3292.6Semi standard non polar33892256
N-Deisopropyl-fluvastatin,2TMS,isomer #5C[Si](C)(C)O[C@@H](/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N1[Si](C)(C)C)C[C@H](O)CC(=O)O3272.6Semi standard non polar33892256
N-Deisopropyl-fluvastatin,2TMS,isomer #6C[Si](C)(C)OC(=O)C[C@@H](O)C[C@@H](O)/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N1[Si](C)(C)C3236.3Semi standard non polar33892256
N-Deisopropyl-fluvastatin,3TMS,isomer #1C[Si](C)(C)OC(=O)C[C@H](C[C@H](/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2[NH]1)O[Si](C)(C)C)O[Si](C)(C)C3307.2Semi standard non polar33892256
N-Deisopropyl-fluvastatin,3TMS,isomer #2C[Si](C)(C)OC(=O)C[C@H](C[C@@H](O)/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N1[Si](C)(C)C)O[Si](C)(C)C3218.2Semi standard non polar33892256
N-Deisopropyl-fluvastatin,3TMS,isomer #3C[Si](C)(C)O[C@H](CC(=O)O)C[C@H](/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N1[Si](C)(C)C)O[Si](C)(C)C3256.9Semi standard non polar33892256
N-Deisopropyl-fluvastatin,3TMS,isomer #4C[Si](C)(C)OC(=O)C[C@@H](O)C[C@H](/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N1[Si](C)(C)C)O[Si](C)(C)C3255.2Semi standard non polar33892256
N-Deisopropyl-fluvastatin,4TMS,isomer #1C[Si](C)(C)OC(=O)C[C@H](C[C@H](/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N1[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3271.4Semi standard non polar33892256
N-Deisopropyl-fluvastatin,4TMS,isomer #1C[Si](C)(C)OC(=O)C[C@H](C[C@H](/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N1[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2885.8Standard non polar33892256
N-Deisopropyl-fluvastatin,4TMS,isomer #1C[Si](C)(C)OC(=O)C[C@H](C[C@H](/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N1[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3348.4Standard polar33892256
N-Deisopropyl-fluvastatin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H](CC(=O)O)C[C@@H](O)/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2[NH]13527.4Semi standard non polar33892256
N-Deisopropyl-fluvastatin,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H](/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2[NH]1)C[C@H](O)CC(=O)O3573.5Semi standard non polar33892256
N-Deisopropyl-fluvastatin,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C[C@@H](O)C[C@@H](O)/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2[NH]13553.6Semi standard non polar33892256
N-Deisopropyl-fluvastatin,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C(/C=C/[C@H](O)C[C@H](O)CC(=O)O)=C(C2=CC=C(F)C=C2)C2=CC=CC=C213428.1Semi standard non polar33892256
N-Deisopropyl-fluvastatin,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@H](C[C@@H](O)/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2[NH]1)O[Si](C)(C)C(C)(C)C3762.6Semi standard non polar33892256
N-Deisopropyl-fluvastatin,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H](CC(=O)O)C[C@H](/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2[NH]1)O[Si](C)(C)C(C)(C)C3785.9Semi standard non polar33892256
N-Deisopropyl-fluvastatin,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H](CC(=O)O)C[C@@H](O)/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C3605.8Semi standard non polar33892256
N-Deisopropyl-fluvastatin,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C[C@@H](O)C[C@H](/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2[NH]1)O[Si](C)(C)C(C)(C)C3781.1Semi standard non polar33892256
N-Deisopropyl-fluvastatin,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)O[C@@H](/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C)C[C@H](O)CC(=O)O3674.5Semi standard non polar33892256
N-Deisopropyl-fluvastatin,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC(=O)C[C@@H](O)C[C@@H](O)/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C3624.7Semi standard non polar33892256
N-Deisopropyl-fluvastatin,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@H](C[C@H](/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2[NH]1)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3953.5Semi standard non polar33892256
N-Deisopropyl-fluvastatin,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C[C@H](C[C@@H](O)/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3789.7Semi standard non polar33892256
N-Deisopropyl-fluvastatin,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H](CC(=O)O)C[C@H](/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3831.5Semi standard non polar33892256
N-Deisopropyl-fluvastatin,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)C[C@@H](O)C[C@H](/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3852.7Semi standard non polar33892256
N-Deisopropyl-fluvastatin,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@H](C[C@H](/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4000.7Semi standard non polar33892256
N-Deisopropyl-fluvastatin,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@H](C[C@H](/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3585.4Standard non polar33892256
N-Deisopropyl-fluvastatin,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@H](C[C@H](/C=C/C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N1[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3586.2Standard polar33892256
Spectra
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID30776732
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131750727
PDB IDNot Available
ChEBI ID174922
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 ReferencesNot Available