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Record Information
Version3.6
Creation Date2006-10-17 09:06:20 UTC
Update Date2016-02-11 01:07:02 UTC
HMDB IDHMDB05022
Secondary Accession Numbers
  • HMDB14321
Metabolite Identification
Common NamePravastatin
DescriptionPravastatin is a member of the drug class of statins, used for lowering cholesterol and preventing cardiovascular disease. Pravastatin was identified originally in a mold called Nocardia autotrophica by researchers of the Sankyo Pharma Inc; An antilipemic fungal metabolite isolated from cultures of Nocardia autotrophica. It acts as a competitive inhibitor of HMG CoA reductase (hydroxymethylglutaryl CoA reductases); In medicine and pharmacology, pravastatin (Pravachol or Selektine) is a member of the drug class of statins, used for lowering cholesterol and preventing cardiovascular disease.
Structure
Thumb
Synonyms
ValueSource
(+)-(3R,5R)-3,5-Dihydroxy-7-[(1S,2S,6S,8S,8ar)-6-hydroxy-2-methyl-8-{[(S)-2-methylbutyryl]oxy}-1,2,6,7,8,8a-hexahydro-1-naphthyl]heptanoic acidChEBI
Pravastatin acidChEBI
PravastatinaChEBI
PravastatineChEBI
PravastatinumChEBI
(3R,5R)-7-[(1S,2S,6S,8S,8AR)-6-hydroxy-2-methyl-8-[(2S)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acidHMDB
3beta-HydroxycompactinHMDB
EptastatinHMDB
MevalothinHMDB
PravacholHMDB
Pravastatin sodiumHMDB
SelektineHMDB
Chemical FormulaC23H36O7
Average Molecular Weight424.5277
Monoisotopic Molecular Weight424.246103506
IUPAC Name(3R,5R)-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid
Traditional Namepravastatin
CAS Registry Number81093-37-0
SMILES
[H][C@]12[C@H](C[C@H](O)C=C1C=C[C@H](C)[C@@H]2CC[C@@H](O)C[C@@H](O)CC(O)=O)OC(=O)[C@@H](C)CC
InChI Identifier
InChI=1S/C23H36O7/c1-4-13(2)23(29)30-20-11-17(25)9-15-6-5-14(3)19(22(15)20)8-7-16(24)10-18(26)12-21(27)28/h5-6,9,13-14,16-20,22,24-26H,4,7-8,10-12H2,1-3H3,(H,27,28)/t13-,14-,16+,17+,18+,19-,20-,22-/m0/s1
InChI KeyInChIKey=TUZYXOIXSAXUGO-PZAWKZKUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as carbocyclic fatty acids. These are fatty acids containing a carbocylic ring .
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentCarbocyclic fatty acids
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Fatty alcohol
  • Carbocyclic fatty acid
  • Medium-chain fatty acid
  • Fatty acid ester
  • Branched fatty acid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anticholesteremic Agents
  • HMG-CoA Reductase Inhibitors
  • Hydroxymethylglutaryl-CoA Reductase Inhibitors
Application
  • Pharmaceutical
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point326 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.42e-01 g/LNot Available
LogP2.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.24 mg/mLALOGPS
logP2.23ALOGPS
logP1.65ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)4.21ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity113.6 m3·mol-1ChemAxon
Polarizability46.56 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Blood
  • Kidney
  • Platelet
  • Urine
Pathways
NameSMPDB LinkKEGG Link
Pravastatin PathwaySMP00089Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00175
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023593
KNApSAcK IDNot Available
Chemspider ID49398
KEGG Compound IDC01844
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPravastatin
NuGOwiki LinkHMDB05022
Metagene LinkHMDB05022
METLIN ID2053
PubChem Compound54687
PDB IDNot Available
ChEBI ID63618
References
Synthesis ReferencePeng, Yulin; Yashphe, Jacob; Demain, Arnold L. Biotransformation of compactin to pravastatin by Actinomadura sp. 2966. Journal of Antibiotics (1997), 50(12), 1032-1035.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Pokrovskaia EV, Vaulin NA, Gratsianskii NA, Averkov OV, Deev AD: [Markers of inflammation and platelet aggregation in patients with non ST elevation acute coronary syndrome treated with atorvastatin or pravastatin] Kardiologiia. 2003;43(1):7-18. [12891281 ]
  2. Tonelli M, Sacks F, Pfeffer M, Jhangri GS, Curhan G: Biomarkers of inflammation and progression of chronic kidney disease. Kidney Int. 2005 Jul;68(1):237-45. [15954913 ]
  3. Peverill RE, Smolich JJ, Malan E, Goldstat R, Davis SR: Comparison of effects of pravastatin and hormone therapy on soluble P-selectin and platelet P-selectin expression in postmenopausal hypercholesterolemic women. Maturitas. 2006 Jan 20;53(2):158-65. [16368469 ]
  4. Gaugler MH, Vereycken-Holler V, Squiban C, Vandamme M, Vozenin-Brotons MC, Benderitter M: Pravastatin limits endothelial activation after irradiation and decreases the resulting inflammatory and thrombotic responses. Radiat Res. 2005 May;163(5):479-87. [15850408 ]
  5. Bruni F, Puccetti L, Pasqui AL, Pastorelli M, Bova G, Cercignani M, Palazzuoli A, Leo A, Auteri A: Different effect induced by treatment with several statins on monocyte tissue factor expression in hypercholesterolemic subjects. Clin Exp Med. 2003 May;3(1):45-53. [12748879 ]
  6. Tonelli M, Isles C, Craven T, Tonkin A, Pfeffer MA, Shepherd J, Sacks FM, Furberg C, Cobbe SM, Simes J, West M, Packard C, Curhan GC: Effect of pravastatin on rate of kidney function loss in people with or at risk for coronary disease. Circulation. 2005 Jul 12;112(2):171-8. Epub 2005 Jul 5. [15998677 ]
  7. FDA label

Enzymes

General function:
Involved in hydroxymethylglutaryl-CoA reductase (NADPH) activity
Specific function:
Transmembrane glycoprotein that is the rate-limiting enzyme in cholesterol biosynthesis as well as in the biosynthesis of nonsterol isoprenoids that are essential for normal cell function including ubiquinone and geranylgeranyl proteins.
Gene Name:
HMGCR
Uniprot ID:
P04035
Molecular weight:
97475.155
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
General function:
Involved in GTP binding
Specific function:
Isoform B has an accelerated GEF-independent GDP/GTP exchange and an impaired GTP hydrolysis, which is restored partially by GTPase-activating proteins. It is able to bind to the GTPase-binding domain of PAK but not full-length PAK in a GTP- dependent manner, suggesting that the insertion does not completely abolish effector interaction
Gene Name:
RAC1
Uniprot ID:
P63000
Molecular weight:
21449.9
General function:
Involved in CAAX-protein geranylgeranyltransferase acti
Specific function:
Catalyzes the transfer of a geranyl-geranyl moiety from geranyl-geranyl pyrophosphate to a cysteine at the fourth position from the C-terminus of proteins having the C-terminal sequence Cys-aliphatic-aliphatic-X. Acts on the Rac1, Rac2, Rap1A and Rap1B proteins. The beta subunit is responsible for peptide-binding.
Gene Name:
PGGT1B
Uniprot ID:
P53609
Molecular weight:
42367.81
General function:
Not Available
Specific function:
Retroviral envelope proteins mediate receptor recognition and membrane fusion during early infection. Endogenous envelope proteins may have kept, lost or modified their original function during evolution
Gene Name:
Not Available
Uniprot ID:
P61568
Molecular weight:
21461.4

Transporters

General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular weight:
76448.0
General function:
Involved in ATP binding
Specific function:
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:
ABCC2
Uniprot ID:
Q92887
Molecular weight:
174205.6