Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C5H8O4 |
| Molecular Weight | 132.1146 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(CC(O)=O)C(O)=O
InChI
InChIKey=WXUAQHNMJWJLTG-UHFFFAOYSA-N
InChI=1S/C5H8O4/c1-3(5(8)9)2-4(6)7/h3H,2H2,1H3,(H,6,7)(H,8,9)
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Risk factors of ocular involvement in children with mitochondrial respiratory chain complex defect. | 2010-12 |
|
| A systems biology approach uncovers cellular strategies used by Methylobacterium extorquens AM1 during the switch from multi- to single-carbon growth. | 2010-11-24 |
|
| Genome sequence of the deltaproteobacterial strain NaphS2 and analysis of differential gene expression during anaerobic growth on naphthalene. | 2010-11-19 |
|
| Streamlined pentafluorophenylpropyl column liquid chromatography-tandem quadrupole mass spectrometry and global (13)C-labeled internal standards improve performance for quantitative metabolomics in bacteria. | 2010-11-19 |
|
| Mechanism of neurodegeneration of neurons with mitochondrial DNA mutations. | 2010-03 |
|
| Albumin uptake in OK cells exposed to rotenone: a model for studying the effects of mitochondrial dysfunction on endocytosis in the proximal tubule? | 2010 |
|
| Effect of asafoetida extract on growth and quality of Pleurotus ferulic. | 2009-12-29 |
|
| Glucagon-like peptide-1 induced signaling and insulin secretion do not drive fuel and energy metabolism in primary rodent pancreatic beta-cells. | 2009-07-13 |
|
| Absolute configuration of ceriporic acids, the iron redox-silencing metabolites produced by a selective lignin-degrading fungus, Ceriporiopsis subvermispora. | 2009-06 |
|
| Abnormal tricarboxylic acid cycle metabolites in isovaleric acidaemia. | 2009-06 |
|
| Global phenotypic characterization of bacteria. | 2009-01 |
|
| Start-up strategies of thermophilic anaerobic digestion of sewage sludge. | 2009 |
|
| Important discoveries from analysing bacterial phenotypes. | 2008-10 |
|
| Anaerobic metabolic models for phosphorus- and glycogen-accumulating organisms with mixed acetic and propionic acids as carbon sources. | 2008-08 |
|
| Metabolic modelling of polyhydroxyalkanoate copolymers production by mixed microbial cultures. | 2008-07-08 |
|
| Acquired multiple Acyl-CoA dehydrogenase deficiency in 10 horses with atypical myopathy. | 2008-05 |
|
| Identification of transport pathways for citric acid cycle intermediates in the human colon carcinoma cell line, Caco-2. | 2008-04 |
|
| Methane as fuel for anaerobic microorganisms. | 2008-03 |
|
| Fluorescence determination of N-acetylaspartic acid in the rat cerebrum homogenate using high-performance liquid chromatography with pre-column fluorescence derivatization. | 2008-01 |
|
| Organic acid concentrations in amniotic fluid found in normal and Down syndrome pregnancies. | 2008 |
|
| Stereocomplementary bioreduction of alpha,beta-unsaturated dicarboxylic acids and dimethyl esters using enoate reductases: enzyme- and substrate-based stereocontrol. | 2007-12-20 |
|
| Equine biochemical multiple acyl-CoA dehydrogenase deficiency (MADD) as a cause of rhabdomyolysis. | 2007-08 |
|
| Enhanced mitochondrial metabolism may account for the adaptation to insulin resistance in islets from C57BL/6J mice fed a high-fat diet. | 2007-01 |
|
| Classical polarization in hybrid QM/MM methods. | 2006-05-25 |
|
| Fumarate reductase: structural and mechanistic insights from the catalytic reduction of 2-methylfumarate. | 2006-03-06 |
|
| Phase changes during hygroscopic cycles of mixed organic/inorganic model systems of tropospheric aerosols. | 2006-02-09 |
|
| Development of an HPLC-fluorescence determination method for carboxylic acids related to the tricarboxylic acid cycle as a metabolome tool. | 2005-12 |
|
| Acyl-CoA dehydrogenase deficiency: varieties with neurological involvement. | 2005-03 |
|
| D-Serine-induced nephrotoxicity: a HPLC-TOF/MS-based metabonomics approach. | 2005-02-14 |
|
| Vitamin E analogues as inducers of apoptosis: structure-function relation. | 2003-06-16 |
|
| Organic anion transporter 3 (Slc22a8) is a dicarboxylate exchanger indirectly coupled to the Na+ gradient. | 2003-04 |
|
| Human renal organic anion transporter 1-dependent uptake and toxicity of mercuric-thiol conjugates in Madin-Darby canine kidney cells. | 2003-03 |
|
| Ethylmalonic encephalopathy: further clinical and neuroradiological characterization. | 2002-10 |
|
| Microsphaerones A and B, two novel gamma-pyrone derivatives from the sponge-derived fungus Microsphaeropsis sp. | 2002-05 |
|
| A constitutive nitric oxide synthase modulates insulin secretion in the INS-1 cell line. | 2001-10-25 |
|
| Antimalarial halorosellinic acid from the marine fungus Halorosellinia oceanica. | 2001-08-06 |
|
| Clinical and biochemical characterization of short-chain acyl-coenzyme A dehydrogenase deficiency. | 1995-06 |
|
| Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. | 1994-06 |
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10349
Created by
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207-857-1
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2-Methylsuccinic acid
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89843
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DTXSID9025663
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498-21-5
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H1547KG7UZ
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5276
Created by
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SUBSTANCE RECORD
