Meglutol

Identification

Name
Meglutol
Accession Number
DB04377  (EXPT02109)
Type
Small Molecule
Groups
Experimental
Description

An antilipemic agent which lowers cholesterol, triglycerides, serum beta-lipoproteins and phospholipids. It acts by interfering with the enzymatic steps involved in the conversion of acetate to hydroxymethylglutaryl coenzyme A as well as inhibiting the activity of HYDROXYMETHYLGLUTARYL COA REDUCTASES which is the rate limiting enzyme in the biosynthesis of cholesterol.

Structure
Thumb
Synonyms
  • 3-hydroxy-3-methylglutaric acid
  • Dicrotalic acid
External IDs
CB 337 / CB-337
Categories
Not Available
UNII
CLA99KCD53
CAS number
503-49-1
Weight
Average: 162.1406
Monoisotopic: 162.05282343
Chemical Formula
C6H10O5
InChI Key
NPOAOTPXWNWTSH-UHFFFAOYSA-N
InChI
InChI=1S/C6H10O5/c1-6(11,2-4(7)8)3-5(9)10/h11H,2-3H2,1H3,(H,7,8)(H,9,10)
IUPAC Name
3-hydroxy-3-methylpentanedioic acid
SMILES
CC(O)(CC(O)=O)CC(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U3-hydroxy-3-methylglutaryl-coenzyme A reductaseNot AvailableHuman
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

Synthesis Reference

Luigi Turbanti, Giorgio Garzelli, "Process for preparation of 3-hydroxy-3-methyl-glutaric acid." U.S. Patent US4966993, issued October, 1985.

US4966993
General References
Not Available
External Links
Human Metabolome Database
HMDB0000355
KEGG Drug
D04897
KEGG Compound
C03761
PubChem Compound
1662
PubChem Substance
46508063
ChemSpider
1600
BindingDB
50160720
ChEBI
16831
ChEMBL
CHEMBL50444
HET
MAH
Wikipedia
Meglutol
PDB Entries
1dq8 / 1dqa / 2liw

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 Solubility275.0 mg/mLALOGPS
logP-0.88ALOGPS
logP-0.75ChemAxon
logS0.23ALOGPS
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.14 m3·mol-1ChemAxon
Polarizability14.55 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6339
Blood Brain Barrier+0.9359
Caco-2 permeable-0.657
P-glycoprotein substrateNon-substrate0.5874
P-glycoprotein inhibitor INon-inhibitor0.967
P-glycoprotein inhibitor IINon-inhibitor0.9396
Renal organic cation transporterNon-inhibitor0.9581
CYP450 2C9 substrateNon-substrate0.7836
CYP450 2D6 substrateNon-substrate0.8892
CYP450 3A4 substrateNon-substrate0.6472
CYP450 1A2 substrateNon-inhibitor0.9103
CYP450 2C9 inhibitorNon-inhibitor0.9173
CYP450 2D6 inhibitorNon-inhibitor0.9444
CYP450 2C19 inhibitorNon-inhibitor0.9203
CYP450 3A4 inhibitorNon-inhibitor0.8487
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9781
Ames testNon AMES toxic0.9445
CarcinogenicityNon-carcinogens0.6285
BiodegradationReady biodegradable0.551
Rat acute toxicity1.9397 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9877
hERG inhibition (predictor II)Non-inhibitor0.9734
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
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0002-0930000000-67cdb23f1a51498bb80d
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-05nb-2950000000-10da019551eceff729ec
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0002-0960000000-75a1f0bc3ffb60117676
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0930000000-67cdb23f1a51498bb80d
GC-MS Spectrum - GC-MSGC-MSsplash10-05nb-2950000000-10da019551eceff729ec
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0920000000-77008c8c7fb6eb798e79
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-05fr-2900000000-d5b3d7ccc3617f392a63
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-004i-9800000000-1a510972071bf02a23f7
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0kdi-9300000000-6afee652d0eb18e589c3
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-03di-0900000000-ae679b03ae8cdbc1cc40
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0002-9300000000-8d7565d3b9cbed5d13ac
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0a4i-9000000000-d06ad8ce44567793a49d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0a4i-9000000000-f3c4c2c0cb3ff49db482
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0a4i-9000000000-98c0337e0bebe4fefe6c
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-01qa-2900000000-182405b2867309ab7df8
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-03dj-5900000000-d9ffa79e6b62296f2626
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-a3631689983e6d6a3be7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-002b-2900000000-54e16eaede819dea2bdc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-9600000000-31a4e319505eebd3d1d1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03xr-2900000000-405383db70ec0564b916
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-07bg-5900000000-dfc057320722ae1d926c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4m-9300000000-e5a720c14cbc5de82d4d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-03di-0900000000-2847ca367167b7cf107b
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-9300000000-f9ab44912911fd1e9ec7
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-589bf77ae5f575911b64
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-f3c4c2c0cb3ff49db482
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9000000000-98c0337e0bebe4fefe6c
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-03dj-5900000000-d9ffa79e6b62296f2626
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01qa-2900000000-182405b2867309ab7df8
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

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 / Dicarboxylic acids and derivatives / Tertiary alcohols / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Methyl-branched fatty acid / Short-chain hydroxy acid / Hydroxy fatty acid / Branched fatty acid / Dicarboxylic acid or derivatives / Tertiary alcohol / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organic oxide
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
tertiary alcohol, dicarboxylic acid, 3-hydroxy carboxylic acid (CHEBI:16831)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Nadph binding
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...
Gene Name
HMGCR
Uniprot ID
P04035
Uniprot Name
3-hydroxy-3-methylglutaryl-coenzyme A reductase
Molecular Weight
97475.155 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 October 01, 2018 13:49