Identification
Name3-Hydroxy-3-Methyl-Glutaric Acid
Accession NumberDB04377  (EXPT02109)
TypeSmall Molecule
GroupsExperimental
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. [PubChem]

Structure
Thumb
SynonymsNot Available
External IDs CB 337 / CB-337
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNIICLA99KCD53
CAS numberNot Available
WeightAverage: 162.1406
Monoisotopic: 162.05282343
Chemical FormulaC6H10O5
InChI KeyNPOAOTPXWNWTSH-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
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
3-hydroxy-3-methylglutaryl-coenzyme A reductaseProteinunknownNot AvailableHumanP04035 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot 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 ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0002-0930000000-67cdb23f1a51498bb80dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-05nb-2950000000-10da019551eceff729ecView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0002-0960000000-75a1f0bc3ffb60117676View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0002-0920000000-77008c8c7fb6eb798e79View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0002-0920000000-77008c8c7fb6eb798e79View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-05fr-2900000000-d5b3d7ccc3617f392a63View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9800000000-1a510972071bf02a23f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0kdi-9300000000-6afee652d0eb18e589c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-ae679b03ae8cdbc1cc40View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-9300000000-8d7565d3b9cbed5d13acView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-d06ad8ce44567793a49dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-f3c4c2c0cb3ff49db482View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-98c0337e0bebe4fefe6cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-01qa-2900000000-182405b2867309ab7df8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03dj-5900000000-d9ffa79e6b62296f2626View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-2847ca367167b7cf107bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9300000000-f9ab44912911fd1e9ec7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-589bf77ae5f575911b64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-a3631689983e6d6a3be7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-2900000000-54e16eaede819dea2bdcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9600000000-31a4e319505eebd3d1d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-2900000000-405383db70ec0564b916View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07bg-5900000000-dfc057320722ae1d926cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-9300000000-e5a720c14cbc5de82d4dView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentHydroxy fatty acids
Alternative ParentsShort-chain hydroxy acids and derivatives / Methyl-branched fatty acids / Dicarboxylic acids and derivatives / Tertiary alcohols / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
SubstituentsMethyl-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 FrameworkAliphatic acyclic compounds
External Descriptorstertiary 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 ubiquinone and geranylgeranyl proteins.
Gene Name:
HMGCR
Uniprot ID:
P04035
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 June 24, 2017 13:22