Page last updated: 2024-12-08

d-2-hydroxyglutarate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

(R)-2-hydroxyglutaric acid : The (R)-enantiomer of 2-hydroxyglutaric acid. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID439391
CHEMBL ID1614745
CHEBI ID32796
SCHEMBL ID8032
MeSH IDM000613471

Synonyms (54)

Synonym
CHEBI:32796 ,
(2r)-2-hydroxypentanedioic acid
636-67-9
13095-47-1
(r)-2-hydroxypentanedioic acid
C01087
(r)-2-hydroxyglutarate
(r)-2-hydroxyglutaric acid
(r)-hydroxyglutarate
93397C3E-3CE9-4FEA-A2ED-8F6FA59A1FEA
2hg ,
bdbm50361471
CHEMBL1614745 ,
d-hydroxyglutarate
SCHEMBL8032
pentanedioic acid, 2-hydroxy-, (2r)-
FD21404
d-2-hydroxyglutaric acid
AKOS027325193
d-alpha-hydroxyglutaric acid
CS-0059411
d-|a-hydroxyglutaric acid
HY-113038
2-hydroxy-delta-glutarate
d-a-hydroxyglutaric acid
(r)-a-hydroxyglutaric acid
delta-alpha-hydroxyglutarate
(r)-a-hydroxyglutarate
(r)-2-hydroxy-pentanedioic acid
2-hydroxy-delta-glutaric acid
delta-2-hydroxyglutaric acid
2-hydroxy-d-glutarate
2-hydroxy-d-glutaric acid
(r)-alpha-hydroxyglutaric acid
delta-alpha-hydroxyglutaric acid
(r)-alpha-hydroxyglutarate
(r)-2-hydroxy-pentanedioate
d-a-hydroxyglutarate
delta-2-hydroxyglutarate
Q27104222
BS-50252
DTXSID80897218
EN300-209542
pentanedioic acid, 2-hydroxy-, (r)-
unii-r9uk2g8y79
(r)-alpha-hydroxyglutaric acid-
glutaric acid, 2-hydroxy-, d-
(r)-(-)-2-hydroxyglutaric acid
r9uk2g8y79 ,
2-hydroxyglutaric acid, (r)-
d-?-hydroxyglutaric acid
(r)-.alpha.-hydroxyglutaric acid-
(r)-2-hydroxypentanedioicacid
Z1205493868
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
algal metaboliteAny eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
2-hydroxyglutaric acidA 2-hydroxydicarboxylic acid that is glutaric acid in which one hydrogen alpha- to a carboxylic acid group is substituted by a hydroxy group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (9)

PathwayProteinsCompounds
Metabolism14961108
The citric acid (TCA) cycle and respiratory electron transport14756
Pyruvate metabolism and Citric Acid (TCA) cycle4146
Interconversion of 2-oxoglutarate and 2-hydroxyglutarate310
The Oncogenic Action of D-2-Hydroxyglutarate in Hydroxyglutaric aciduria2936
Disease1278231
Diseases of metabolism69121
Abnormal conversion of 2-oxoglutarate to 2-hydroxyglutarate15
Biochemical pathways: part I0466

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Lysine-specific demethylase 4AHomo sapiens (human)IC50 (µMol)24.00000.20002.83194.7600AID639772
Prolyl 4-hydroxylaseParamecium bursaria Chlorella virus 1IC50 (µMol)500.00005.00006.26678.5000AID1543452
Alpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)IC50 (µMol)1,000.00003.00006.10009.8000AID734755
Lysine-specific demethylase 4CHomo sapiens (human)IC50 (µMol)79.00000.16002.11489.4000AID639774
Hypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)IC50 (µMol)189.00008.60008.60008.6000AID1916160
Lysine-specific demethylase 2AHomo sapiens (human)IC50 (µMol)106.00000.16002.45966.9000AID639773
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (38)

Processvia Protein(s)Taxonomy
negative regulation of autophagyLysine-specific demethylase 4AHomo sapiens (human)
positive regulation of gene expressionLysine-specific demethylase 4AHomo sapiens (human)
negative regulation of gene expressionLysine-specific demethylase 4AHomo sapiens (human)
cardiac muscle hypertrophy in response to stressLysine-specific demethylase 4AHomo sapiens (human)
apoptotic chromosome condensationLysine-specific demethylase 4AHomo sapiens (human)
response to nutrient levelsLysine-specific demethylase 4AHomo sapiens (human)
positive regulation of neuron differentiationLysine-specific demethylase 4AHomo sapiens (human)
negative regulation of DNA-templated transcriptionLysine-specific demethylase 4AHomo sapiens (human)
negative regulation of astrocyte differentiationLysine-specific demethylase 4AHomo sapiens (human)
chromatin remodelingLysine-specific demethylase 4AHomo sapiens (human)
regulation of gene expressionLysine-specific demethylase 4AHomo sapiens (human)
temperature homeostasisAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
DNA alkylation repairAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
regulation of lipid storageAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
snRNA processingAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
regulation of multicellular organism growthAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
RNA repairAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
regulation of respiratory system processAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
adipose tissue developmentAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
mRNA destabilizationAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
regulation of white fat cell proliferationAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
regulation of brown fat cell differentiationAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
blastocyst formationLysine-specific demethylase 4CHomo sapiens (human)
positive regulation of cell population proliferationLysine-specific demethylase 4CHomo sapiens (human)
stem cell population maintenanceLysine-specific demethylase 4CHomo sapiens (human)
androgen receptor signaling pathwayLysine-specific demethylase 4CHomo sapiens (human)
positive regulation of transcription by RNA polymerase IILysine-specific demethylase 4CHomo sapiens (human)
regulation of androgen receptor signaling pathwayLysine-specific demethylase 4CHomo sapiens (human)
regulation of stem cell differentiationLysine-specific demethylase 4CHomo sapiens (human)
regulation of gene expressionLysine-specific demethylase 4CHomo sapiens (human)
chromatin remodelingLysine-specific demethylase 4CHomo sapiens (human)
positive regulation of myoblast differentiationHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
negative regulation of Notch signaling pathwayHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
negative regulation of DNA-templated transcriptionHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
positive regulation of vasculogenesisHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
double-strand break repair via nonhomologous end joiningLysine-specific demethylase 2AHomo sapiens (human)
chromatin remodelingLysine-specific demethylase 2AHomo sapiens (human)
negative regulation of transcription by competitive promoter bindingLysine-specific demethylase 2AHomo sapiens (human)
circadian regulation of gene expressionLysine-specific demethylase 2AHomo sapiens (human)
regulation of circadian rhythmLysine-specific demethylase 2AHomo sapiens (human)
protein demethylationLysine-specific demethylase 2AHomo sapiens (human)
regulation of transcription by RNA polymerase IILysine-specific demethylase 2AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (32)

Processvia Protein(s)Taxonomy
protein bindingLysine-specific demethylase 4AHomo sapiens (human)
zinc ion bindingLysine-specific demethylase 4AHomo sapiens (human)
ubiquitin protein ligase bindingLysine-specific demethylase 4AHomo sapiens (human)
histone demethylase activityLysine-specific demethylase 4AHomo sapiens (human)
methylated histone bindingLysine-specific demethylase 4AHomo sapiens (human)
histone H3K36 demethylase activityLysine-specific demethylase 4AHomo sapiens (human)
histone H3K36me2/H3K36me3 demethylase activityLysine-specific demethylase 4AHomo sapiens (human)
histone H3K9me2/H3K9me3 demethylase activityLysine-specific demethylase 4AHomo sapiens (human)
histone H3K9 demethylase activityLysine-specific demethylase 4AHomo sapiens (human)
ferrous iron bindingAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
transferase activityAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
oxidative RNA demethylase activityAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
broad specificity oxidative DNA demethylase activityAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
mRNA N6-methyladenosine dioxygenase activityAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
tRNA demethylase activityAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
histone H3K9me2/H3K9me3 demethylase activityLysine-specific demethylase 4CHomo sapiens (human)
zinc ion bindingLysine-specific demethylase 4CHomo sapiens (human)
enzyme bindingLysine-specific demethylase 4CHomo sapiens (human)
nuclear receptor coactivator activityLysine-specific demethylase 4CHomo sapiens (human)
histone demethylase activityLysine-specific demethylase 4CHomo sapiens (human)
histone H3K9 demethylase activityLysine-specific demethylase 4CHomo sapiens (human)
nuclear androgen receptor bindingLysine-specific demethylase 4CHomo sapiens (human)
histone H3K36 demethylase activityLysine-specific demethylase 4CHomo sapiens (human)
H3K9me3 modified histone bindingLysine-specific demethylase 4CHomo sapiens (human)
histone H3K9me2/H3K9me3 demethylase activityLysine-specific demethylase 4CHomo sapiens (human)
transcription corepressor activityHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
Notch bindingHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
protein bindingHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
ferrous iron bindingHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
zinc ion bindingHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
oxygen sensor activityHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
carboxylic acid bindingHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
peptidyl-histidine dioxygenase activityHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
[protein]-asparagine 3-dioxygenase activityHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
protein homodimerization activityHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
NF-kappaB bindingHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
peptidyl-aspartic acid 3-dioxygenase activityHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
ankyrin repeat bindingHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
protein bindingLysine-specific demethylase 2AHomo sapiens (human)
zinc ion bindingLysine-specific demethylase 2AHomo sapiens (human)
histone demethylase activityLysine-specific demethylase 2AHomo sapiens (human)
unmethylated CpG bindingLysine-specific demethylase 2AHomo sapiens (human)
histone H3K36 demethylase activityLysine-specific demethylase 2AHomo sapiens (human)
histone H3K36me/H3K36me2 demethylase activityLysine-specific demethylase 2AHomo sapiens (human)
transcription coregulator activityLysine-specific demethylase 2AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
fibrillar centerLysine-specific demethylase 4AHomo sapiens (human)
nucleusLysine-specific demethylase 4AHomo sapiens (human)
nucleoplasmLysine-specific demethylase 4AHomo sapiens (human)
cytosolLysine-specific demethylase 4AHomo sapiens (human)
pericentric heterochromatinLysine-specific demethylase 4AHomo sapiens (human)
nucleusLysine-specific demethylase 4AHomo sapiens (human)
chromatinLysine-specific demethylase 4AHomo sapiens (human)
nucleusAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
nucleoplasmAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
cytoplasmAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
cytosolAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
plasma membraneAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
nuclear speckAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
intracellular membrane-bounded organelleAlpha-ketoglutarate-dependent dioxygenase FTOHomo sapiens (human)
nucleoplasmLysine-specific demethylase 4CHomo sapiens (human)
chromatinLysine-specific demethylase 4CHomo sapiens (human)
pericentric heterochromatinLysine-specific demethylase 4CHomo sapiens (human)
nucleusLysine-specific demethylase 4CHomo sapiens (human)
nucleusHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
nucleoplasmHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
cytoplasmHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
cytosolHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
perinuclear region of cytoplasmHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
cytoplasmHypoxia-inducible factor 1-alpha inhibitorHomo sapiens (human)
nucleoplasmLysine-specific demethylase 2AHomo sapiens (human)
chromosomeLysine-specific demethylase 2AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID1763196Inhibition of TET2 (unknown origin) at 50 mM in presence of alpha-KG relative to control2021Bioorganic & medicinal chemistry, 06-01, Volume: 39SAR insights into TET2 catalytic domain inhibition: Synthesis of 2-Hydroxy-4-Methylene-pentanedicarboxylates.
AID639772Inhibition of KDM4A2011Journal of medicinal chemistry, Dec-22, Volume: 54, Issue:24
Lysine demethylases inhibitors.
AID1763191Inhibition of TET (unknown origin)2021Bioorganic & medicinal chemistry, 06-01, Volume: 39SAR insights into TET2 catalytic domain inhibition: Synthesis of 2-Hydroxy-4-Methylene-pentanedicarboxylates.
AID1714493Displacement of sodium 5-(3-(8-(3-carboxy-N-hydroxyacrylamido)octyl)thioureido)-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoate from Naegleria Tet-1 incubated for 20 mins followed by sodium 5-(3-(8-(3-carboxy-N-hydroxyacrylamido)octyl)thioureido)-2-(6-hydroxy2016ACS medicinal chemistry letters, Feb-11, Volume: 7, Issue:2
A Fluorescence Polarization Biophysical Assay for the Naegleria DNA Hydroxylase Tet1.
AID1916160Inhibition of FIH (unknown origin) assessed as hydroxylation of HIF1alphaCAD by MALDI-TOF-MS analysis2021Journal of medicinal chemistry, 06-10, Volume: 64, Issue:11
Inhibition of the Oxygen-Sensing Asparaginyl Hydroxylase Factor Inhibiting Hypoxia-Inducible Factor: A Potential Hypoxia Response Modulating Strategy.
AID1543452Inhibition of N-terminal His6-tagged recombinant Paramecium bursaria chlorella virus 1 CPH expressed in Escherichia coli Rosetta 2 (DE3) cells pre-incubated for 5 mins before 2OG as substrate and Fe2 as co-factor addition in presence of L-ascorbate and me2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Inhibition of a viral prolyl hydroxylase.
AID1763198Inhibition of TET1 (unknown origin) at 50 mM in presence of alpha-KG relative to control2021Bioorganic & medicinal chemistry, 06-01, Volume: 39SAR insights into TET2 catalytic domain inhibition: Synthesis of 2-Hydroxy-4-Methylene-pentanedicarboxylates.
AID1763197Inhibition of TET1 (unknown origin) at 10 mM in presence of alpha-KG relative to control2021Bioorganic & medicinal chemistry, 06-01, Volume: 39SAR insights into TET2 catalytic domain inhibition: Synthesis of 2-Hydroxy-4-Methylene-pentanedicarboxylates.
AID639774Inhibition of KDM4C2011Journal of medicinal chemistry, Dec-22, Volume: 54, Issue:24
Lysine demethylases inhibitors.
AID639773Inhibition of KDM2A2011Journal of medicinal chemistry, Dec-22, Volume: 54, Issue:24
Lysine demethylases inhibitors.
AID1763195Inhibition of TET2 (unknown origin) at 10 mM in presence of alpha-KG relative to control2021Bioorganic & medicinal chemistry, 06-01, Volume: 39SAR insights into TET2 catalytic domain inhibition: Synthesis of 2-Hydroxy-4-Methylene-pentanedicarboxylates.
AID734755Inhibition of human hexahistidine-tagged full-length FTO expressed in Escherichia coli BL21 (DE3) using 3-methylthymidine as substrate assessed as inhibition of 3-methylthymidine conversion to thymidine after 1 hr by liquid chromatographic analysis2013Journal of medicinal chemistry, May-09, Volume: 56, Issue:9
Structural basis for inhibition of the fat mass and obesity associated protein (FTO).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's4 (66.67)24.3611
2020's2 (33.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.51

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index28.51 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.66 (4.65)
Search Engine Demand Index31.58 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.51)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (33.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other4 (66.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]