Record Information
Version1.0
Creation date2011-09-21 00:31:53 UTC
Update date2015-07-21 06:57:46 UTC
Primary IDFDB023579
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAtorvastatin
DescriptionAtorvastatin (INN) is a member of the drug class known as statins, used for lowering cholesterol and thereby reducing cardiovascular disease. Atorvastatin inhibits a rate-determining enzyme located in hepatic tissue used in cholesterol synthesis, which lowers the amount of cholesterol produced. This also has the effect of lowering the total amount of LDL cholesterol; Atorvastatin is a member of the drug class known as statins, used for lowering cholesterol and thereby reducing cardiovascular disease. Atorvastatin inhibits a rate-determining enzyme located in hepatic tissue used in cholesterol synthesis, which lowers the amount of cholesterol produced. This also has the effect of lowering the total amount of LDL cholesterol; As with other statins, atorvastatin is a competitive inhibitor of HMG-CoA reductase. Unlike most others, however, it is a completely synthetic compound. HMG-CoA reductase catalyzes the reduction of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) to mevalonate, which is the rate-limiting step in hepatic cholesterol biosynthesis. Inhibition of the enzyme decreases de novo cholesterol synthesis, increasing expression of low-density lipoprotein receptors (LDL receptors) on hepatocytes. This increases the LDL uptake by the hepatocytes, decreasing the amount of LDL in the blood. [HMDB]
CAS Number134523-00-5
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.00063 g/LALOGPS
logP4.24ALOGPS
logP5.39ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.33ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area111.79 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity158.2 m³·mol⁻¹ChemAxon
Polarizability59.45 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC33H35FN2O5
IUPAC name(3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoic acid
InChI IdentifierInChI=1S/C33H35FN2O5/c1-21(2)31-30(33(41)35-25-11-7-4-8-12-25)29(22-9-5-3-6-10-22)32(23-13-15-24(34)16-14-23)36(31)18-17-26(37)19-27(38)20-28(39)40/h3-16,21,26-27,37-38H,17-20H2,1-2H3,(H,35,41)(H,39,40)/t26-,27-/m1/s1
InChI KeyXUKUURHRXDUEBC-KAYWLYCHSA-N
Isomeric SMILESCC(C)C1=C(C(=O)NC2=CC=CC=C2)C(=C(N1CC[C@@H](O)C[C@@H](O)CC(O)=O)C1=CC=C(F)C=C1)C1=CC=CC=C1
Average Molecular Weight558.6398
Monoisotopic Molecular Weight558.253000445
Classification
Description Belongs to the class of organic compounds known as diphenylpyrroles. These are aromatic heterocyclic compounds with a structure based on a pyrrole ring linked to exactly two phenyl groups.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrroles
Sub ClassSubstituted pyrroles
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
  • 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
  • Vinylogous amide
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Organohalogen compound
  • Organofluoride
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Role

Environmental role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAtorvastatin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000f-5100950000-b76d194b9679e4b35417Spectrum
Predicted GC-MSAtorvastatin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-082i-5320938000-c1984e6bf123460d28acSpectrum
Predicted GC-MSAtorvastatin, "Atorvastatin,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TMS_3_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAtorvastatin, TBDMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0000090000-ae5c999b091a2bc939332017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-0000190000-dd563e18b1f0f74aadd52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zfs-0007960000-cb66a18d2f0a687261ba2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-002b-0059000000-0942bc1e35434cd7d0d32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0093000000-f42ba46820a3cf3295c52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udj-0005910000-b09ba5f3b86948c7f3cb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0000090000-6f297ca79ae1761aac332017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-1009300000-9479520f395dcdd585e72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0092000000-9b561b8d35c3bdc5e46a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0090000000-3aad87273e7f9942a50f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-01t9-1090000000-3f0efff41ebdb5320ce42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03di-2090000000-0227638704b90c4249d02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0a4i-0000090000-65c729c6734f6533c4312017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-1009300000-9122e4479d8c0c32bb0d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0092000000-22d639a8882509e1bcdb2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0090000000-30a0198165bae85fa2582017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-01t9-1090000000-cb3feea45f5280f05c372017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03di-2090000000-8db2f70b373277f143c02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udj-0005910000-a63c845ca248d958068d2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-1000190000-5418613834968283e5a82017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006y-3101940000-2906ea9feb05e2fc0cfc2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-8438900000-f5abfdde8ad50c98b16e2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1000290000-949ba837ddf712ee85582017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4s-6203960000-9adcd151fdfe389c7d002017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054o-9158000000-7b64ce4c34d6e9fae2b82017-07-26View Spectrum
NMRNot Available
ChemSpider ID54810
ChEMBL IDCHEMBL1487
KEGG Compound IDC06834
Pubchem Compound ID60823
Pubchem Substance IDNot Available
ChEBI ID2910
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB05006
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET ID117
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAtorvastatin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference