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Record Information
Version	2.0
Creation Date	2012-05-31 13:00:27 -0600
Update Date	2015-09-13 12:56:08 -0600
Secondary Accession Numbers	ECMDB00694
Identification
Name:	L-2-Hydroxyglutaric acid
Description	L-2-hydroxyglutaric acid is a member of the chemical class known as Short-chain Hydroxy Acids and Derivatives. These are hydroxy acids with an alkyl chain the contains less than 6 carbon atoms. L-2-Hydroxyglutaric acid (2-hydroxyglutaric acid) is an alpha hydroxy acid. In bacteria it is formed by a 2-hydroxyglutarate synthase (EC 2.3.3.11) and oxidized by 2-hydroxyglutarate oxidase. (Wikipedia, PMID 14491016)
Structure	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xa0bd90fc> Close
Synonyms:	(2S)-2-hydroxypentanedioate (2S)-2-hydroxypentanedioic acid (S)-2-hydroxyglutaric acid (S)-2-Hydroxyglutarate (S)-2-Hydroxyglutaric acid (S)-a-Hydroxyglutarate (S)-a-Hydroxyglutaric acid (S)-alpha-Hydroxyglutarate (S)-alpha-Hydroxyglutaric acid (S)-α-Hydroxyglutarate (S)-α-Hydroxyglutaric acid 2-Hydroxy-(S)-Pentanedioate 2-Hydroxy-(S)-Pentanedioic acid 2-Hydroxy-L-Glutarate 2-Hydroxy-L-Glutaric acid L-2-Hydroxyglutarate L-2-hydroxyglutaric acid L-a-Hydroxyglutarate L-a-Hydroxyglutaric acid L-alpha-Hydroxyglutarate L-alpha-Hydroxyglutaric acid L-α-Hydroxyglutarate L-α-Hydroxyglutaric acid
Chemical Formula:	C5H8O5
Weight:	Average: 148.114 Monoisotopic: 148.037173366
InChI Key:	HWXBTNAVRSUOJR-VKHMYHEASA-N
InChI:	InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)/t3-/m0/s1
CAS number:	13095-48-2
IUPAC Name:	(2S)-2-hydroxypentanedioic acid
Traditional IUPAC Name:	L-2-hydroxyglutaric acid
SMILES:	[H][C@](O)(CCC(O)=O)C(O)=O
Chemical Taxonomy
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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Hydroxy acids and derivatives
Sub Class	Short-chain hydroxy acids and derivatives
Direct Parent	Short-chain hydroxy acids and derivatives
Alternative Parents	Monosaccharides Fatty acids and conjugates Dicarboxylic acids and derivatives Alpha hydroxy acids and derivatives Secondary alcohols Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
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 Framework	Aliphatic acyclic compounds
External Descriptors	2-hydroxyglutaric acid (CHEBI:32797 )
Physical Properties
State:	Not Available
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source Water Solubility: Soluble in water PhysProp LogP: -0.979 PhysProp
Predicted Properties	Property Value Source Water Solubility 157 g/L ALOGPS logP -1 ALOGPS logP -0.82 ChemAxon logS 0.03 ALOGPS pKa (Strongest Acidic) 3.28 ChemAxon pKa (Strongest Basic) -3.8 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 94.83 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 29.63 m³·mol⁻¹ ChemAxon Polarizability 12.97 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	L-2-Hydroxyglutaric acid + Oxygen > Oxoglutaric acid + Hydrogen peroxide
SMPDB Pathways:	Not Available
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) splash10-05mk-1900000000-c8b7818c2a1224f0b694 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) splash10-000i-9000000000-fc923f875e23e766078c View in MoNA LC-MS/MS LC-MS/MS Spectrum - 40V, Negative splash10-0a4i-9000000000-9fb296154571d7ea7d13 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 20V, Negative splash10-0a4i-9400000000-821ae25c1b9ac04003b7 View in MoNA LC-MS/MS LC-MS/MS Spectrum - 10V, Negative splash10-004i-3900000000-dc8454bb187902d1a08b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-001i-1900000000-68ac8b23cf0ed0cf09f5 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0m5r-9600000000-fb8fb6611cf2b1bca9f7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4i-9000000000-4912ecf3489ec68e9641 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-002b-0900000000-116ef9fca434a654a8f9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0zi9-5900000000-76cefbf1a7e32ce74bef View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4i-9000000000-c4562468d1b81effdb63 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0w39-4900000000-1385b471f7cdf14ca14d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-052r-9500000000-17ece6956644d4cf2069 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4r-9000000000-dbb4195080bddb5f6210 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0fbi-3900000000-f88fcf3ac0dd06636b16 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0k9i-9400000000-31bf8d3bb7203e7bf200 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a4u-9000000000-c0ac45c4d66178ac20cf View in MoNA 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 2D NMR [1H,13C] 2D NMR Spectrum Not Available View in JSpectraViewer
References
References:	Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 REEVES, H. C., AJL, S. J. (1962). "Alpha-hydroxyglutaric acid synthetase." J Bacteriol 84:186-187. Pubmed: 14491016
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Download (PDF)
Links
External Links:	Resource Link CHEBI ID 16782 HMDB ID HMDB00694 Pubchem Compound ID 439939 Kegg ID C03196 ChemSpider ID 388969 Wikipedia ID Alpha-Hydroxyglutaric acid BioCyc ID CPD-381 EcoCyc ID CPD-381 Ligand Expo S2G