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D-α-Hydroxyglutaric acid (disodium) (Standard)

CAT: 0804-HY-100542R-01Size: 5 mgDry Ice: NoHazardous: No
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Description
D-α-Hydroxyglutaric acid (disodium) (Standard) is the analytical standard of D-α-Hydroxyglutaric acid (disodium) . This product is intended for research and analytical applications. D-α-Hydroxyglutaric acid disodium (Disodium (R) -2-hydroxyglutarate) is the principal metabolite accumulating in neurometabolic disease D-2-hydroxyglutaric aciduria. D-α-Hydroxyglutaric acid disodium is a weak competitive antagonist of α-ketoglutarate (α-KG) and inhibits multiple α-KG-dependent dioxygenases with a Ki of 10.87 mM. D-α-Hydroxyglutaric acid disodium increases reactive oxygen species (ROS) production. D-α-Hydroxyglutaric acid disodium binds and inhibits ATP synthase and inhibits mTOR signaling[1][2][3][4][5].
CAS Number
103404-90-6
Product Name Alternative
Disodium (R) -2-hydroxyglutarate (Standard)
UNSPSC
12352211
Target
ATP Synthase; Endogenous Metabolite; mTOR; Reactive Oxygen Species (ROS) ; Reference Standards
Related Pathways
Immunology/Inflammation; Membrane Transporter/Ion Channel; Metabolic Enzyme/Protease; NF-κB; Others; PI3K/Akt/mTOR
Field of Research
Cancer; Inflammation/Immunology; Neurological Disease
Smiles
O=C(O[Na])[C@H](O)CCC(O[Na])=O
Molecular Formula
C5H6Na2O5
Molecular Weight
192.08
References & Citations
[1]Xu W, et al. Oncometabolite 2-hydroxyglutarate is a competitive inhibitor of α-ketoglutarate-dependent dioxygenases. Cancer Cell. 2011 Jan 18;19 (1) :17-30.|[2]Fu X, et al. 2-Hydroxyglutarate Inhibits ATP Synthase and mTOR Signaling. Cell Metab. 2015 Sep 1;22 (3) :508-15.|[3]Martijn Kranendijk, et al. Progress in understanding 2-hydroxyglutaric acidurias. J Inherit Metab Dis. 2012 Jul;35 (4) :571-87.|[4]Martin Böttcher, et al. D-2-hydroxyglutarate interferes with HIF-1α stability skewing T-cell metabolism towards oxidative phosphorylation and impairing Th17 polarization. Oncoimmunology. 2018 Mar 26;7 (7) :e1445454.|[5]Alexandra Latini , et al. D-2-hydroxyglutaric acid induces oxidative stress in cerebral cortex of young rats. Eur J Neurosci. 2003 May;17 (10) :2017-22.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

Sodium (R)-2-hydroxypentanedioate
CAS Number103404-90-6
PubChem CID51051608
IUPAC Namedisodium;(2R)-2-hydroxypentanedioate
Molecular FormulaC5H6Na2O5
Molecular Weight192.08
Topological Polar Surface Area100
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Heavy Atom Count12
Formal Charge0
Complexity130
SMILES
C(CC(=O)[O-])[C@H](C(=O)[O-])O.[Na+].[Na+]
InChI
InChI=1S/C5H8O5.2Na/c6-3(5(9)10)1-2-4(7)8;;/h3,6H,1-2H2,(H,7,8)(H,9,10);;/q;2*+1/p-2/t3-;;/m1../s1
InChIKey
DZHFTEDSQFPDPP-HWYNEVGZSA-L
Chemical Structure
2D Structure
2D structure of Sodium (R)-2-hydroxypentanedioate
CAS: 103404-90-6
CID: 51051608
Formula: C5H6Na2O5
MW: 192.08
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight192.08
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Exact Mass192.00106185
Monoisotopic Mass192.00106185
Topological Polar Surface Area100 Ų
Heavy Atom Count12
Formal Charge0
Complexity130
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count3
Compound Is CanonicalizedYes

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