Record Information
Version1.0
Creation date2010-04-08 22:06:08 UTC
Update date2019-11-26 02:59:52 UTC
Primary IDFDB004207
Secondary Accession Numbers
  • FDB005950
Chemical Information
FooDB Namebeta-Hydroxy-beta-methylglutaric acid
Description3-hydroxymethylglutaric acid, also known as meglutol or dicrotalic acid, is a member of the class of compounds known as hydroxy fatty acids. Hydroxy fatty acids are fatty acids in which the chain bears a hydroxyl group. 3-hydroxymethylglutaric acid is soluble (in water) and a weakly acidic compound (based on its pKa). 3-hydroxymethylglutaric acid can be synthesized from glutaric acid. 3-hydroxymethylglutaric acid is also a parent compound for other transformation products, including but not limited to, viscumneoside VII, viscumneoside IV, and yanuthone D. 3-hydroxymethylglutaric acid can be found in flaxseed, which makes 3-hydroxymethylglutaric acid a potential biomarker for the consumption of this food product. 3-hydroxymethylglutaric acid can be found primarily in saliva and urine. 3-hydroxymethylglutaric acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Chronically high levels of 3-hydroxymethylglutaric acid are associated with the inborn error of metabolism: 3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency (T3DB).
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
(S)-3-Hydroxy-3-methylglutaric acidChEBI
(S)-MeglutolChEBI
3-HYDROXY-3-methyl-glutarIC ACIDChEBI
3-Hydroxy-3-methylpentanedioic acidChEBI
beta-Hydroxy-beta-methylglutaric acidChEBI
Dicrotalic acidChEBI
MeglutolChEBI
MeglutolumChEBI
3-Hydorxy-3-methylglutaric acidKegg
(S)-3-Hydroxy-3-methylglutarateGenerator
3-HYDROXY-3-methyl-glutarateGenerator
3-Hydroxy-3-methylpentanedioateGenerator
b-Hydroxy-b-methylglutarateGenerator
b-Hydroxy-b-methylglutaric acidGenerator
beta-Hydroxy-beta-methylglutarateGenerator
Β-hydroxy-β-methylglutarateGenerator
Β-hydroxy-β-methylglutaric acidGenerator
DicrotalateGenerator
3-Hydorxy-3-methylglutarateGenerator
3-HydroxymethylglutarateGenerator
3-Hydroxy-3-methylglutarateHMDB
3-Hydroxy-3-methylglutaric acidHMDB
3-Methyl-3-hydroxyglutarateHMDB
3-Methyl-3-hydroxyglutaric acidHMDB
CB 337HMDB
3 Hydroxy 3 methylpentanedioic acidHMDB
Acid, 3-hydroxy-3-methylglutaricHMDB
Acid, 3-hydroxy-3-methylpentanedioicHMDB
beta Hydroxy beta methylglutarateHMDB
3 Hydroxy 3 methylglutaric acidHMDB
3-Methyl-3-hydroxypentanedioateHMDB
3-Methyl-3-hydroxypentanedioic acidHMDB
HMGHMDB
HMGAHMDB
LipoglutarenHMDB
MedroglutarateHMDB
Medroglutaric acidHMDB
Predicted Properties
PropertyValueSource
Water Solubility275 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.14 m³·mol⁻¹ChemAxon
Polarizability14.55 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H10O5
IUPAC name3-hydroxy-3-methylpentanedioic acid
InChI IdentifierInChI=1S/C6H10O5/c1-6(11,2-4(7)8)3-5(9)10/h11H,2-3H2,1H3,(H,7,8)(H,9,10)
InChI KeyNPOAOTPXWNWTSH-UHFFFAOYSA-N
Isomeric SMILESCC(O)(CC(O)=O)CC(O)=O
Average Molecular Weight162.1406
Monoisotopic Molecular Weight162.05282343
Classification
Description Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Indirect biological role:

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSbeta-Hydroxy-beta-methylglutaric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0930000000-67cdb23f1a51498bb80dSpectrum
GC-MSbeta-Hydroxy-beta-methylglutaric acid, 3 TMS, GC-MS Spectrumsplash10-05nb-2950000000-10da019551eceff729ecSpectrum
GC-MSbeta-Hydroxy-beta-methylglutaric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0960000000-75a1f0bc3ffb60117676Spectrum
GC-MSbeta-Hydroxy-beta-methylglutaric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0930000000-67cdb23f1a51498bb80dSpectrum
GC-MSbeta-Hydroxy-beta-methylglutaric acid, non-derivatized, GC-MS Spectrumsplash10-05nb-2950000000-10da019551eceff729ecSpectrum
GC-MSbeta-Hydroxy-beta-methylglutaric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0920000000-77008c8c7fb6eb798e79Spectrum
Predicted GC-MSbeta-Hydroxy-beta-methylglutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-4900000000-ae0329f185525bab6028Spectrum
Predicted GC-MSbeta-Hydroxy-beta-methylglutaric acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-9253000000-af0bf7551c9147193ed4Spectrum
Predicted GC-MSbeta-Hydroxy-beta-methylglutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-Hydroxy-beta-methylglutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-Hydroxy-beta-methylglutaric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-Hydroxy-beta-methylglutaric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-Hydroxy-beta-methylglutaric acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-Hydroxy-beta-methylglutaric acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-Hydroxy-beta-methylglutaric acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-Hydroxy-beta-methylglutaric acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-Hydroxy-beta-methylglutaric acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-Hydroxy-beta-methylglutaric acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-Hydroxy-beta-methylglutaric acid, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-05fr-2900000000-d5b3d7ccc3617f392a63Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9800000000-1a510972071bf02a23f7Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0kdi-9300000000-6afee652d0eb18e589c3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-ae679b03ae8cdbc1cc40Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-9300000000-8d7565d3b9cbed5d13acSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-d06ad8ce44567793a49dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-f3c4c2c0cb3ff49db482Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-98c0337e0bebe4fefe6cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-01qa-2900000000-182405b2867309ab7df8Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03dj-5900000000-d9ffa79e6b62296f2626Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-2847ca367167b7cf107bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9300000000-f9ab44912911fd1e9ec7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-589bf77ae5f575911b64Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-f3c4c2c0cb3ff49db482Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-98c0337e0bebe4fefe6cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03dj-5900000000-d9ffa79e6b62296f2626Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01qa-2900000000-182405b2867309ab7df8Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-f94de43a0b43873232bfSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-9300000000-9861bfd5df213d5b52e4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-a3631689983e6d6a3be7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-2900000000-54e16eaede819dea2bdcSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9600000000-31a4e319505eebd3d1d1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-2900000000-405383db70ec0564b916Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07bg-5900000000-dfc057320722ae1d926cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-9300000000-e5a720c14cbc5de82d4dSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDBETA-HYDROXY-BETA-METHYL-GLUTARIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).