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Showing Compound D-2-Hydroxyglutaric acid (FDB022139)

Record Information
Version1.0
Creation date2011-09-21 00:09:03 UTC
Update date2020-09-17 15:38:37 UTC
Primary IDFDB022139
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameD-2-Hydroxyglutaric acid
DescriptionD-2-Hydroxyglutaric acid, also known as (R)-hydroxyglutarate or (R)-2-hydroxy-pentanedioate, belongs to the class of organic compounds known as short-chain hydroxy acids and derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms. D-2-Hydroxyglutaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). D-2-Hydroxyglutaric acid exists in all living organisms, ranging from bacteria to humans. D-2-hydroxyglutaric acid can be biosynthesized from oxoglutaric acid through the action of the enzyme D-2-hydroxyglutarate dehydrogenase, mitochondrial. In humans, D-2-hydroxyglutaric acid is involved in the metabolic disorder called the oncogenic action of d-2-hydroxyglutarate in hydroxyglutaric aciduria. Outside of the human body, D-2-Hydroxyglutaric acid has been detected, but not quantified in, milk (cow). This could make D-2-hydroxyglutaric acid a potential biomarker for the consumption of these foods. D-2-Hydroxyglutaric acid is a potentially toxic compound. D-2-Hydroxyglutaric acid, with regard to humans, has been found to be associated with several diseases such as d, l-2-hydroxyglutaric aciduria and spondyloenchondrodysplasia; D-2-hydroxyglutaric acid has also been linked to the inborn metabolic disorder d-2-hydroxyglutaric aciduria. The (R)-enantiomer of 2-hydroxyglutaric acid.
CAS Number13095-47-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(R)-2-HydroxyglutarateChEBI
(R)-HydroxyglutarateChEBI
(R)-2-Hydroxyglutaric acidGenerator
(R)-Hydroxyglutaric acidGenerator
D-2-HydroxyglutarateGenerator
(R)-2-Hydroxy-pentanedioateHMDB
(R)-2-Hydroxy-pentanedioic acidHMDB
(R)-a-HydroxyglutarateHMDB
(R)-a-Hydroxyglutaric acidHMDB
(R)-alpha-HydroxyglutarateHMDB
(R)-alpha-Hydroxyglutaric acidHMDB
2-Hydroxy-D-glutarateHMDB
2-Hydroxy-D-glutaric acidHMDB
2-Hydroxy-delta-glutarateHMDB
2-Hydroxy-delta-glutaric acidHMDB
D-a-HydroxyglutarateHMDB
D-a-Hydroxyglutaric acidHMDB
delta-2-HydroxyglutarateHMDB
delta-2-Hydroxyglutaric acidHMDB
delta-alpha-HydroxyglutarateHMDB
delta-alpha-Hydroxyglutaric acidHMDB
2-HydroxyglutarateHMDB
alpha-Hydroxyglutarate, (D)-isomerHMDB
alpha-Hydroxyglutarate, (DL)-isomerHMDB
2-Hydroxyglutaric acidHMDB
alpha-HydroxyglutarateHMDB
alpha-Hydroxyglutarate, (L)-isomerHMDB
alpha-Hydroxyglutarate, disodium saltHMDB
(R)-2-hydroxy-Pentanedioatehmdb
(R)-2-hydroxy-Pentanedioic acidhmdb
2-hydroxy-D-Glutaratehmdb
2-hydroxy-D-Glutaric acidhmdb
2-hydroxy-delta-Glutaratehmdb
2-hydroxy-delta-Glutaric acidhmdb
D-2-Hydroxyglutaric acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility157 g/LALOGPS
logP-1ALOGPS
logP-0.82ChemAxon
logS0.03ALOGPS
pKa (Strongest Acidic)3.28ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity29.63 m³·mol⁻¹ChemAxon
Polarizability12.97 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H8O5
IUPAC name(2R)-2-hydroxypentanedioic acid
InChI IdentifierInChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)/t3-/m1/s1
InChI KeyHWXBTNAVRSUOJR-GSVOUGTGSA-N
Isomeric SMILESO[C@H](CCC(O)=O)C(O)=O
Average Molecular Weight148.114
Monoisotopic Molecular Weight148.037173366
Classification
Description Belongs to the class of organic compounds known as short-chain hydroxy acids and derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassShort-chain hydroxy acids and derivatives
Direct ParentShort-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Short-chain hydroxy acid
  • Fatty acid
  • Monosaccharide
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Secondary 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
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Role

Indirect biological role:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
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
Predicted GC-MSD-2-Hydroxyglutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zgl-9300000000-805667744aba36281cecSpectrum
Predicted GC-MSD-2-Hydroxyglutaric acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00gv-8191000000-f6fdffd87ffe1acf65b4Spectrum
Predicted GC-MSD-2-Hydroxyglutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-2-Hydroxyglutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-2-Hydroxyglutaric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-2-Hydroxyglutaric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-2-Hydroxyglutaric acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-2-Hydroxyglutaric acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-2-Hydroxyglutaric acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-2-Hydroxyglutaric acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-2-Hydroxyglutaric acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-2-Hydroxyglutaric acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-2-Hydroxyglutaric acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-2-Hydroxyglutaric acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-2-Hydroxyglutaric acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-2-Hydroxyglutaric acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSD-2-Hydroxyglutaric acid, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-1900000000-dbf80fc2b86ec60d623e2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0m5r-9600000000-d1bc7ce2206164b5bc2c2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-df3e77cb42d6f7647a642016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-095c1140772d4cdd149b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-7900000000-ce158ac5b56eff8677352016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-e30760384709aa9789862016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fbi-3900000000-f88fcf3ac0dd06636b162021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0k9i-9400000000-31bf8d3bb7203e7bf2002021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4u-9000000000-c0ac45c4d66178ac20cf2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w39-4900000000-1385b471f7cdf14ca14d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-9500000000-17ece6956644d4cf20692021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9000000000-dbb4195080bddb5f62102021-09-22View Spectrum
NMRNot Available
ChemSpider ID388508
ChEMBL IDCHEMBL1614745
KEGG Compound IDC01087
Pubchem Compound ID439391
Pubchem Substance IDNot Available
ChEBI ID32796
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00606
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET ID2HG
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
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference