Back to Compounds

Showing Compound beta-Hydroxy-beta-methylglutaric acid (FDB004207)

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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
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-d5b3d7ccc3617f392a632012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9800000000-1a510972071bf02a23f72012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0kdi-9300000000-6afee652d0eb18e589c32012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-03di-0900000000-ae679b03ae8cdbc1cc402012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-9300000000-8d7565d3b9cbed5d13ac2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-d06ad8ce44567793a49d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-f3c4c2c0cb3ff49db4822012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-98c0337e0bebe4fefe6c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-01qa-2900000000-182405b2867309ab7df82012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-03dj-5900000000-d9ffa79e6b62296f26262012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0900000000-2847ca367167b7cf107b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9300000000-f9ab44912911fd1e9ec72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-589bf77ae5f575911b642017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-f3c4c2c0cb3ff49db4822017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-98c0337e0bebe4fefe6c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03dj-5900000000-d9ffa79e6b62296f26262017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01qa-2900000000-182405b2867309ab7df82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-f94de43a0b43873232bf2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4j-9300000000-9861bfd5df213d5b52e42021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-a3631689983e6d6a3be72015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-2900000000-54e16eaede819dea2bdc2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9600000000-31a4e319505eebd3d1d12015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-2900000000-405383db70ec0564b9162015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07bg-5900000000-dfc057320722ae1d926c2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-9300000000-e5a720c14cbc5de82d4d2015-04-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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).