Showing metabocard for Pravastatin (BMDB0005022)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:14:43 UTC
Update Date2020-05-11 20:45:55 UTC
BMDB IDBMDB0005022
Secondary Accession Numbers
  • BMDB05022
Metabolite Identification
Common NamePravastatin
DescriptionPravastatin, also known as pravastatin acid or pravator, belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain. Thus, pravastatin is considered to be a fatty alcohol lipid molecule. Pravastatin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
PravatorKegg
(+)-(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]heptanoateGenerator
(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
ElisorHMDB
Nu-pravastatinHMDB
PravasinHMDB
Apo pravastatinHMDB
Aventis brand OF pravastatin sodiumHMDB
Bristol-myers squibb brand OF pravastatin sodiumHMDB
Juste brand OF pravastatin sodiumHMDB
Lin pravastatinHMDB
MevalotinHMDB
Pravastatin monosodium salt, (6 beta)-isomerHMDB
Pravastatin sodium saltHMDB
Pravastatin, (6 beta)-isomerHMDB
RMS-431HMDB
Squibb brand OF pravastatin sodiumHMDB
VastenHMDB
Apo-pravastatinHMDB
Apotex brand OF pravastatin sodiumHMDB
Linson pharma brand OF pravastatin sodiumHMDB
LiplatHMDB
LipostatHMDB
Nu-pharma brand OF pravastatin sodiumHMDB
PrareductHMDB
Pravastatin tert-octylamine saltHMDB
RMS 431HMDB
Sankyo brand OF pravastatin sodiumHMDB
Sodium salt, pravastatinHMDB
BristacolHMDB
Esteve brand OF pravastatin sodiumHMDB
Lin-pravastatinHMDB
LipemolHMDB
Nu pravastatinHMDB
PravacolHMDB
Pravastatin tert octylamine saltHMDB
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 KeyTUZYXOIXSAXUGO-PZAWKZKUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Fatty alcohol
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid ester
  • Branched fatty acid
  • Beta-hydroxy acid
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity113.6 m³·mol⁻¹ChemAxon
Polarizability46.56 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
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, Positivesplash10-0a4i-6194400000-5f7280491acf9312a516View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-004i-8202269000-c5995d4b5b537e3a6f6eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0uk9-0009000000-967b377abafe64b73071View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0002900000-bd7fd66d793ae64426ffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-4809000000-0ed5a8797dfc49ecf5afView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-2900000000-91b125182ce5d90f16abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-1900000000-e8fc6384260de93c5aa8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-1900000000-11e99968bc0ba393b6f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-4900000000-0e4265e6dc1468c1471dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0002900000-8795ee00dded0ef8be48View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-3709000000-aa45be15af0471c0a46eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-2900000000-5617409991f5c58e5130View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-2900000000-2bf5c13979a639625d1cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-2900000000-9a233e521607e82ab7a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0900000000-2083dfbb67bf2b03ccf9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0uk9-0009000000-4b2c09a295ba7f3ce41bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-0607900000-e57e263ad3f74bfda195View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0uk9-0209000000-e1f3357e6db2a045c733View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-053r-0890100000-343e9a2af9d9e56f3078View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0fk9-3209000000-4e7af37985a2d2fdf90cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0pb9-9600000000-1e8b86b20daa312fd4c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-1009600000-9928021021dc6868847dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-4019100000-bea6aa9fed446c2cdd3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-9023000000-7b0213c49b76e864814eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-1007900000-cb1ad55355bd717f1c23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-5209300000-f017d063b98b59e6d5f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9244000000-d95d5ae750ad620ba728View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • Kidney
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0005022
DrugBank IDDB00175
Phenol Explorer Compound IDNot Available
FooDB IDFDB023593
KNApSAcK IDC00000565
Chemspider ID49398
KEGG Compound IDC01844
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPravastatin
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)Not Available
General ReferencesNot Available