Mevalonic acid

Identification

Name
Mevalonic acid
Accession Number
DB03518  (EXPT02156)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • (R)-3,5-dihydroxy-3-methylvaleric acid
  • (R)-mevalonate
  • (R)-mevalonic acid
  • 3,5-Dihydroxy-3-methylvaleric acid
Categories
Not Available
UNII
S5UOB36OCZ
CAS number
150-97-0
Weight
Average: 148.1571
Monoisotopic: 148.073558872
Chemical Formula
C6H12O4
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0059629
KEGG Compound
C00418
PubChem Compound
439230
PubChem Substance
46508035
ChemSpider
388367
ChEBI
17710
ChEMBL
CHEMBL1794734
HET
MEV
Wikipedia
Mevalonic_acid

Clinical Trials

Clinical Trials
Not Available

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

Taxonomy

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
Branched fatty acid / Hydroxy fatty acid / Short-chain hydroxy acid / Methyl-branched fatty acid / Tertiary alcohol / Carboxylic acid derivative / Carboxylic acid / Monocarboxylic acid or derivatives / Organic oxygen compound / Organic oxide
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
mevalonic acid (CHEBI:17710) / Hydroxy fatty acids (LMFA01050352)

Targets

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. [PubMed:17139284]
  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. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:36