NAV

Mevinolinic acid

Identification

Generic Name
Mevinolinic acid
DrugBank Accession Number
DB03785
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 422.5549
Monoisotopic: 422.266838948
Chemical Formula
C24H38O6
Synonyms
  • Lovastatin acid
External IDs
  • L 154819
  • L-154819
  • MK 819
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Pharmacology

Indication

Not Available

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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 medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Hydroxy acids and derivatives
Sub Class
Medium-chain hydroxy acids and derivatives
Direct Parent
Medium-chain hydroxy acids and derivatives
Alternative Parents
Fatty alcohols / Medium-chain fatty acids / Hydroxy fatty acids / Fatty acid esters / Branched fatty acids / Beta hydroxy acids and derivatives / Dicarboxylic acids and derivatives / Secondary alcohols / Carboxylic acid esters / Carboxylic acids
show 3 more
Substituents
Alcohol / Aliphatic homopolycyclic compound / Beta-hydroxy acid / Branched fatty acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Carboxylic acid ester / Dicarboxylic acid or derivatives / Fatty acid ester
show 10 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
polyketide, fatty acid ester, dihydroxy monocarboxylic acid, carbobicyclic compound (CHEBI:82985)
Affected organisms
Not Available

Chemical Identifiers

UNII
5CLV35Y90C
CAS number
75225-51-3
InChI Key
QLJODMDSTUBWDW-BXMDZJJMSA-N
InChI
InChI=1S/C24H38O6/c1-5-15(3)24(29)30-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-18(25)12-19(26)13-22(27)28/h6-7,10,14-16,18-21,23,25-26H,5,8-9,11-13H2,1-4H3,(H,27,28)/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1
IUPAC Name
(3R,5R)-7-[(1S,2S,6R,8S,8aR)-2,6-dimethyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid
SMILES
[H][C@]12[C@H](C[C@@H](C)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

References

General References
Not Available
PubChem Compound
64727
PubChem Substance
46506686
ChemSpider
58269
BindingDB
50406681
ChEBI
82985
ChEMBL
CHEMBL1201373
ZINC
ZINC000004134473
PDBe Ligand
LVA
PDB Entries
1t02 / 3hlg / 6kjd

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 Solubility0.0641 mg/mLALOGPS
logP3.74ALOGPS
logP3.24Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.21Chemaxon
pKa (Strongest Basic)-2.7Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area104.06 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity116.67 m3·mol-1Chemaxon
Polarizability47.54 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9714
Blood Brain Barrier+0.639
Caco-2 permeable-0.6631
P-glycoprotein substrateSubstrate0.7964
P-glycoprotein inhibitor INon-inhibitor0.8324
P-glycoprotein inhibitor IIInhibitor0.6601
Renal organic cation transporterNon-inhibitor0.8617
CYP450 2C9 substrateNon-substrate0.8503
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.7206
CYP450 1A2 substrateNon-inhibitor0.8952
CYP450 2C9 inhibitorNon-inhibitor0.8909
CYP450 2D6 inhibitorNon-inhibitor0.8903
CYP450 2C19 inhibitorNon-inhibitor0.8513
CYP450 3A4 inhibitorInhibitor0.6571
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7992
Ames testNon AMES toxic0.8927
CarcinogenicityNon-carcinogens0.9523
BiodegradationNot ready biodegradable0.8854
Rat acute toxicity2.6058 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8359
hERG inhibition (predictor II)Non-inhibitor0.6699
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0649000000-0f0917a4218ef5e89dff
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0mb9-1097400000-22a72124aef6aebc2af1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00xr-1497200000-a7ddb7f1d06a082c0fa0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0m30-5195000000-c23628b497458dbfc227
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0600-5795100000-6a7ed8b31f99bccbb7af
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ki6-7179400000-6a54afd71057eb347ae0
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-216.6408757
predicted
DarkChem Lite v0.1.0
[M-H]-211.0701757
predicted
DarkChem Lite v0.1.0
[M-H]-211.19438
predicted
DeepCCS 1.0 (2019)
[M+H]+216.2228757
predicted
DarkChem Lite v0.1.0
[M+H]+212.3261757
predicted
DarkChem Lite v0.1.0
[M+H]+212.9181
predicted
DeepCCS 1.0 (2019)
[M+Na]+215.3348757
predicted
DarkChem Lite v0.1.0
[M+Na]+212.4040757
predicted
DarkChem Lite v0.1.0
[M+Na]+219.24706
predicted
DeepCCS 1.0 (2019)

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]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

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