NAV

Mevalonic acid

Identification

Generic Name
Mevalonic acid
DrugBank Accession Number
DB03518
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 148.1571
Monoisotopic: 148.073558872
Chemical Formula
C6H12O4
Synonyms
  • (R)-3,5-dihydroxy-3-methylvaleric acid
  • (R)-mevalonate
  • (R)-mevalonic acid
  • 3,5-Dihydroxy-3-methylvaleric acid

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U3-hydroxy-3-methylglutaryl-coenzyme A reductaseNot AvailablePseudomonas mevalonii
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acids and conjugates
Direct Parent
Hydroxy fatty acids
Alternative Parents
Short-chain hydroxy acids and derivatives / Methyl-branched fatty acids / Tertiary alcohols / Monocarboxylic acids and derivatives / Carboxylic acids / Primary alcohols / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Alcohol / Aliphatic acyclic compound / Branched fatty acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Hydroxy fatty acid / Methyl-branched fatty acid / Monocarboxylic acid or derivatives
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
mevalonic acid (CHEBI:17710) / Hydroxy fatty acids (LMFA01050352)
Affected organisms
Not Available

Chemical Identifiers

UNII
S5UOB36OCZ
CAS number
150-97-0
InChI Key
KJTLQQUUPVSXIM-ZCFIWIBFSA-N
InChI
InChI=1S/C6H12O4/c1-6(10,2-3-7)4-5(8)9/h7,10H,2-4H2,1H3,(H,8,9)/t6-/m1/s1
IUPAC Name
(3R)-3,5-dihydroxy-3-methylpentanoic acid
SMILES
C[C@@](O)(CCO)CC(O)=O

References

General References
Not Available
Human Metabolome Database
HMDB0059629
KEGG Compound
C00418
PubChem Compound
439230
PubChem Substance
46508035
ChemSpider
388367
ChEBI
17710
ChEMBL
CHEMBL1794734
ZINC
ZINC000000895221
PDBe Ligand
MEV
Wikipedia
Mevalonic_acid

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility414.0 mg/mLALOGPS
logP-0.9ALOGPS
logP-1.1Chemaxon
logS0.45ALOGPS
pKa (Strongest Acidic)4.38Chemaxon
pKa (Strongest Basic)-2.4Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area77.76 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity34.51 m3·mol-1Chemaxon
Polarizability14.57 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6094
Blood Brain Barrier+0.9005
Caco-2 permeable-0.5577
P-glycoprotein substrateSubstrate0.5453
P-glycoprotein inhibitor INon-inhibitor0.9838
P-glycoprotein inhibitor IINon-inhibitor0.9349
Renal organic cation transporterNon-inhibitor0.9163
CYP450 2C9 substrateNon-substrate0.7833
CYP450 2D6 substrateNon-substrate0.8676
CYP450 3A4 substrateNon-substrate0.6005
CYP450 1A2 substrateNon-inhibitor0.6904
CYP450 2C9 inhibitorNon-inhibitor0.8174
CYP450 2D6 inhibitorNon-inhibitor0.9133
CYP450 2C19 inhibitorNon-inhibitor0.887
CYP450 3A4 inhibitorNon-inhibitor0.9382
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9486
Ames testNon AMES toxic0.9237
CarcinogenicityNon-carcinogens0.8237
BiodegradationReady biodegradable0.9565
Rat acute toxicity1.1053 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9789
hERG inhibition (predictor II)Non-inhibitor0.9067
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Details1. 3-hydroxy-3-methylglutaryl-coenzyme A reductase
Kind
Protein
Organism
Pseudomonas mevalonii
Pharmacological action
Unknown
General Function
Hydroxymethylglutaryl-coa reductase activity
Specific Function
P.mevalonii can use mevalonate as sole carbon source. With this enzyme mevalonate is deacetylated to HMG-CoA.
Gene Name
mvaA
Uniprot ID
P13702
Uniprot Name
3-hydroxy-3-methylglutaryl-coenzyme A reductase
Molecular Weight
45589.915 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52