2-HYDROXYGLUTARIC ACID, (±)-

Details

Stereochemistry	RACEMIC
Molecular Formula	C5H8O5
Molecular Weight	148.114
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 2-HYDROXYGLUTARIC ACID, (±)-

Structure Search

SMILES

OC(CCC(O)=O)C(O)=O

InChI

InChIKey=HWXBTNAVRSUOJR-UHFFFAOYSA-N

InChI=1S/C5H8O5/c6-3(5(9)10)1-2-4(7)8/h3,6H,1-2H2,(H,7,8)(H,9,10)

HIDE SMILES / InChI

Molecular Formula	C5H8O5
Molecular Weight	148.114
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Approval Year

Targets

Primary Target	Pharmacology	Potency
Lysine-specific demethylase 4A 2 Target ID: O75164 Gene ID: 9682.0 Gene Symbol: KDM4A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21460794	Inhibitor 8504	79.0 µM [IC50]
Lysine-specific demethylase 2A 3 Target ID: CHEMBL1938210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21460794	Inhibitor 8504	48.0 µM [IC50]
DNA oxidative demethylase ALKBH2 1 Target ID: Q6NS38 Gene ID: 121642.0 Gene Symbol: ALKBH2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21460794	Inhibitor 8504	150.0 µM [IC50]

PubMed

Title	Date	PubMed
Vitamin C in combination with inhibition of mutant IDH1 synergistically activates TET enzymes and epigenetically modulates gene silencing in colon cancer cells.	2020-03	31505989
Magnetic Resonance Spectroscopic Assessment of Isocitrate Dehydrogenase Status in Gliomas: The New Frontiers of Spectrobiopsy in Neurodiagnostics.	2020-01	31526886
To be Wild or Mutant: Role of Isocitrate Dehydrogenase 1 (IDH1) and 2-Hydroxy Glutarate (2-HG) in Gliomagenesis and Treatment Outcome in Glioma.	2020-01	31485826
Discovery of new small molecule inhibitors targeting isocitrate dehydrogenase 1 (IDH1) with blood-brain barrier penetration.	2019-12-01	31561044
I-8, a novel inhibitor of mutant IDH1, inhibits cancer progression in vitro and in vivo.	2019-12-01	31518680
Friend or foe-IDH1 mutations in glioma 10 years on.	2019-11-25	31504231
Metabolic profiling of human gliomas assessed with NMR.	2019-10	31409545
Selective inhibition of mutant IDH1 by DS-1001b ameliorates aberrant histone modifications and impairs tumor activity in chondrosarcoma.	2019-10	31406254
Pharmacometabolomics of Bronchodilator Response in Asthma and the Role of Age-Metabolite Interactions.	2019-09-07	31500319
Quantitative Profiling of Oncometabolites in Frozen and Formalin-Fixed Paraffin-Embedded Tissue Specimens by Liquid Chromatography Coupled with Tandem Mass Spectrometry.	2019-08-02	31375752
IDH1 as a Cooperating Mutation in AML Arising in the Context of Shwachman-Diamond Syndrome.	2019	31475115
Untangling the Metabolic Reprogramming in Brain Cancer: Discovering Key Molecular Players Using Mass Spectrometry.	2019	31362676
The oncometabolite 2-hydroxyglutarate inhibits histone lysine demethylases.	2011-05	21460794

Substance Class	Chemical Created by `admin` on `Wed Apr 02 10:05:33 GMT 2025` Edited by `admin` on `Wed Apr 02 10:05:33 GMT 2025`
Record UNII	RS4M3UYS95
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALPHA-HYDROXYGLUTARIC ACID

Preferred Name

English

2-HYDROXYGLUTARIC ACID, (±)-

Systematic Name

English

PENTANEDIOIC ACID, 2-HYDROXY-

Systematic Name

English

2,3-DIDEOXYPENTARIC ACID

Systematic Name

English

GLUTARIC ACID, 2-HYDROXY-

Systematic Name

English

2-HYDROXYPENTANEDIOIC ACID

Systematic Name

English

(±)-2-HYDROXYGLUTARIC ACID

Systematic Name

English

DL-2-HYDROXYGLUTARIC ACID

Systematic Name

English

Code System Code Type Description

WIKIPEDIA

alpha-Hydroxyglutaric acid