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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:12:35 UTC
Update Date2017-12-07 18:40:46 UTC
HMDB IDHMDB0061014
Secondary Accession Numbers
  • HMDB61014
Metabolite Identification
Common Namepara-hydroxyatorvastatin
Descriptionpara-hydroxyatorvastatin is a metabolite of atorvastatin. Atorvastatin, marketed by Pfizer as a calcium salt under the trade name Lipitor, is a member of the drug class known as statins, used for lowering blood cholesterol. It also stabilizes plaque and prevents strokes through anti-inflammatory and other mechanisms. Like all statins, atorvastatin works by inhibiting HMG-CoA reductase, an enzyme found in liver tissue that plays a key role in production of cholesterol in the body. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC33H35FN2O6
Average Molecular Weight574.6392
Monoisotopic Molecular Weight574.247915067
IUPAC Name7-[2-(4-fluorophenyl)-4-[(4-hydroxyphenyl)carbamoyl]-3-phenyl-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoic acid
Traditional Name7-[2-(4-fluorophenyl)-4-[(4-hydroxyphenyl)carbamoyl]-5-isopropyl-3-phenylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid
CAS Registry NumberNot Available
SMILES
CC(C)C1=C(C(=O)NC2=CC=C(O)C=C2)C(=C(N1CCC(O)CC(O)CC(O)=O)C1=CC=C(F)C=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C33H35FN2O6/c1-20(2)31-30(33(42)35-24-12-14-25(37)15-13-24)29(21-6-4-3-5-7-21)32(22-8-10-23(34)11-9-22)36(31)17-16-26(38)18-27(39)19-28(40)41/h3-15,20,26-27,37-39H,16-19H2,1-2H3,(H,35,42)(H,40,41)
InChI KeySOZOATLLFFVAPM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as diphenylpyrroles. These are aromatic heterocyclic compounds with a structure based on a pyrrole ring linked to exactly two phenyl groups.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPyrroles
Direct ParentDiphenylpyrroles
Alternative Parents
Substituents
  • 2,3-diphenylpyrrole
  • Aromatic anilide
  • Medium-chain hydroxy acid
  • Pyrrole-3-carboxamide
  • Pyrrole-3-carboxylic acid or derivatives
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fluorobenzene
  • Halobenzene
  • Halogenated fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Phenol
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Benzenoid
  • Vinylogous amide
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organofluoride
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Carbonyl group
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0017 g/LALOGPS
logP4.37ALOGPS
logP5.08ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.33ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area132.02 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity160.18 m³·mol⁻¹ChemAxon
Polarizability61.27 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05tu-5210890000-f93c29d83db2f4ae1307View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-003u-6101289000-b60baa3db9c377be5274View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0000190000-8238c11759c1b916067bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05pa-1200970000-346e5758f0badd06ae5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-024l-3359720000-274cb22c8a933f789220View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-0000190000-0fa5d409e614c5af85a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-4301890000-c651c32514e27ce6be50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-6889600000-bd190a94c23f2b1e349bView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00351
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available