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601-75-2 | 2-Ethylmalonic acid
CAS No: 601-75-2 Catalog No: AG0033AU MDL No:MFCD00002668
Product Description
Catalog Number:
AG0033AU
Chemical Name:
2-Ethylmalonic acid
CAS Number:
601-75-2
Molecular Formula:
C5H8O4
Molecular Weight:
132.1146
MDL Number:
MFCD00002668
IUPAC Name:
2-ethylpropanedioic acid
InChI:
InChI=1S/C5H8O4/c1-2-3(4(6)7)5(8)9/h3H,2H2,1H3,(H,6,7)(H,8,9)
InChI Key:
UKFXDFUAPNAMPJ-UHFFFAOYSA-N
SMILES:
CCC(C(=O)O)C(=O)O
EC Number:
210-007-2
UNII:
432NF49DFG
NSC Number:
96615
Properties
Complexity:
115
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
132.042g/mol
Formal Charge:
0
Heavy Atom Count:
9
Hydrogen Bond Acceptor Count:
4
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
132.115g/mol
Monoisotopic Mass:
132.042g/mol
Rotatable Bond Count:
3
Topological Polar Surface Area:
74.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.4
Literature
| Title | Journal |
|---|---|
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| Toxic response caused by a misfolding variant of the mitochondrial protein short-chain acyl-CoA dehydrogenase. | Journal of inherited metabolic disease 20110401 |
| Brown-Vialetto-Van Laere and Fazio Londe syndrome is associated with a riboflavin transporter defect mimicking mild MADD: a new inborn error of metabolism with potential treatment. | Journal of inherited metabolic disease 20110201 |
| Mutations of ACADS gene associated with short-chain acyl-coenzyme A dehydrogenase deficiency. | Annals of clinical and laboratory science 20110101 |
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| Vulnerability to oxidative stress in vitro in pathophysiology of mitochondrial short-chain acyl-CoA dehydrogenase deficiency: response to antioxidants. | PloS one 20110101 |
| Efficacy and outcome of expanded newborn screening for metabolic diseases--report of 10 years from South-West Germany. | Orphanet journal of rare diseases 20110101 |
| Ethylene glycol monomethyl ether-induced toxicity is mediated through the inhibition of flavoprotein dehydrogenase enzyme family. | Toxicological sciences : an official journal of the Society of Toxicology 20101201 |
| Risk factors of ocular involvement in children with mitochondrial respiratory chain complex defect. | Korean journal of pediatrics 20101201 |
| 6-[Bis(ethoxycarbonyl)methyl]-6-deoxy-1,2;3,4-di-O-isopropyl-idene-d-galacto-pyran-ose. | Acta crystallographica. Section E, Structure reports online 20101201 |
| Clinical aspects of short-chain acyl-CoA dehydrogenase deficiency. | Journal of inherited metabolic disease 20101001 |
| Pathogenesis and treatment of mitochondrial myopathies: recent advances. | Acta myologica : myopathies and cardiomyopathies : official journal of the Mediterranean Society of Myology 20101001 |
| Combined treatment with oral metronidazole and N-acetylcysteine is effective in ethylmalonic encephalopathy. | Nature medicine 20100801 |
| Antioxidant dysfunction: potential risk for neurotoxicity in ethylmalonic aciduria. | Journal of inherited metabolic disease 20100601 |
| Silent increase of urinary ethylmalonic acid is an indicator of nonspecific brain dysfunction. | NMR in biomedicine 20100501 |
| Flavin adenine dinucleotide status and the effects of high-dose riboflavin treatment in short-chain acyl-CoA dehydrogenase deficiency. | Pediatric research 20100301 |
| Promotion of lipid and protein oxidative damage in rat brain by ethylmalonic acid. | Neurochemical research 20100201 |
| Fasting and fat-loading tests provide pathophysiological insight into short-chain acyl-coenzyme a dehydrogenase deficiency. | The Journal of pediatrics 20100101 |
| Inborn errors of energy metabolism associated with myopathies. | Journal of biomedicine & biotechnology 20100101 |
| A systems biology approach uncovers cellular strategies used by Methylobacterium extorquens AM1 during the switch from multi- to single-carbon growth. | PloS one 20100101 |
| Chronic early postnatal administration of ethylmalonic acid to rats causes behavioral deficit. | Behavioural brain research 20090211 |
| Loss of ETHE1, a mitochondrial dioxygenase, causes fatal sulfide toxicity in ethylmalonic encephalopathy. | Nature medicine 20090201 |
| Short-chain acyl-coenzyme A dehydrogenase deficiency. | Molecular genetics and metabolism 20081201 |
| The ACADS gene variation spectrum in 114 patients with short-chain acyl-CoA dehydrogenase (SCAD) deficiency is dominated by missense variations leading to protein misfolding at the cellular level. | Human genetics 20080801 |
| 2-(4-Ethoxy-benzyl-idene)butanoic acid. | Acta crystallographica. Section E, Structure reports online 20080801 |
| [Short-chain acyl-CoA dehydrogenase deficiency (SCADD): relatively high prevalence in the Netherlands and strongly variable fenotype; neonatal screening not indicated]. | Nederlands tijdschrift voor geneeskunde 20080726 |
| Severe infantile hypotonia with ethylmalonic aciduria: case report. | Journal of child neurology 20080601 |
| Acquired multiple Acyl-CoA dehydrogenase deficiency in 10 horses with atypical myopathy. | Neuromuscular disorders : NMD 20080501 |
| (E)-2-(2-Fluoro-benzyl-idene)butanoic acid. | Acta crystallographica. Section E, Structure reports online 20080401 |
| A new case of short-chain acyl-CoA dehydrogenase deficiency: clinical, biochemical, genetic and (1)H-NMR spectroscopic studies. | Neurological sciences : official journal of the Italian Neurological Society and of the Italian Society of Clinical Neurophysiology 20071201 |
| Equine biochemical multiple acyl-CoA dehydrogenase deficiency (MADD) as a cause of rhabdomyolysis. | Molecular genetics and metabolism 20070801 |
| Lessons to learn from rare inborn errors of metabolism. | Neuropediatrics 20070401 |
| Ethylmalonic encephalopathy: clinical and biochemical observations. | Neuropediatrics 20070401 |
| Development of a newborn screening follow-up algorithm for the diagnosis of isobutyryl-CoA dehydrogenase deficiency. | Genetics in medicine : official journal of the American College of Medical Genetics 20070201 |
| Single-nucleotide variations in the genes encoding the mitochondrial Hsp60/Hsp10 chaperone system and their disease-causing potential. | Journal of human genetics 20070101 |
| Taxonomic revision of Aspergillus section Clavati based on molecular, morphological and physiological data. | Studies in mycology 20070101 |
| A case of ethylmalonic encephalopathy with atypical clinical and biochemical presentation. | Molecular genetics and metabolism 20061201 |
| Persistent increase of plasma butyryl/isobutyrylcarnitine concentrations as marker of SCAD defect and ethylmalonic encephalopathy. | Journal of inherited metabolic disease 20061001 |
| Clinical, biochemical, and genetic heterogeneity in short-chain acyl-coenzyme A dehydrogenase deficiency. | JAMA 20060823 |
| Ethylmalonic encephalopathy-report of two cases. | Brain & development 20060601 |
| ETHE1 mutations are specific to ethylmalonic encephalopathy. | Journal of medical genetics 20060401 |
| Metabolomic and bioinformatic analyses in asphyxiated neonates. | Clinical biochemistry 20060301 |
| Inhibition of the electron transport chain and creatine kinase activity by ethylmalonic acid in human skeletal muscle. | Metabolic brain disease 20060301 |
| Effect of in vivo administration of ethylmalonic acid on energy metabolism in rat tissues. | Metabolic brain disease 20060301 |
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| Acyl-CoA dehydrogenase deficiency: varieties with neurological involvement. | Developmental medicine and child neurology 20050301 |
| Clinical, biochemical, magnetic resonance imaging (MRI) and proton magnetic resonance spectroscopy (1H MRS) findings in a fourth case of combined D- and L-2 hydroxyglutaric aciduria. | Journal of inherited metabolic disease 20050101 |
| The putative elaiophylin biosynthetic gene cluster in Streptomyces sp. DSM4137 is adjacent to genes encoding adenosylcobalamin-dependent methylmalonyl CoA mutase and to genes for synthesis of cobalamin. | Journal of biotechnology 20040930 |
| Recent developments and new applications of tandem mass spectrometry in newborn screening. | Current opinion in pediatrics 20040801 |
| The role of methionine in ethylmalonic encephalopathy with petechiae. | Archives of neurology 20040401 |
| Ethylmalonic encephalopathy is caused by mutations in ETHE1, a gene encoding a mitochondrial matrix protein. | American journal of human genetics 20040201 |
| [Late-onset riboflavin-responsive multiple acyl-CoA dehydrogenase deficiency (glutaric aciduria type II)]. | Zhonghua er ke za zhi = Chinese journal of pediatrics 20031201 |
| A comparison of in vitro acylcarnitine profiling methods for the diagnosis of classical and variant short chain acyl-CoA dehydrogenase deficiency. | Clinica chimica acta; international journal of clinical chemistry 20031101 |
| Short-chain Acyl-CoA dehydrogenase deficiency: studies in a large family adding to the complexity of the disorder. | Pediatrics 20031101 |
| Ethylmalonic acid inhibits mitochondrial creatine kinase activity from cerebral cortex of young rats in vitro. | Neurochemical research 20030501 |
| Structure-based design of inhibitors of human L-xylulose reductase modelled into the active site of the enzyme. | Bioorganic & medicinal chemistry letters 20030417 |
| Recurrent vomiting and ethylmalonic aciduria associated with rare mutations of the short-chain acyl-CoA dehydrogenase gene. | Journal of inherited metabolic disease 20030101 |
| Mutation analysis of copper transporter genes in patients with ethylmalonic encephalopathy, mitochondriopathies and copper deficiency phenotypes. | Journal of inherited metabolic disease 20030101 |
| Inhibition of creatine kinase activity in vitro by ethylmalonic acid in cerebral cortex of young rats. | Neurochemical research 20021201 |
| Ethylmalonic encephalopathy: further clinical and neuroradiological characterization. | Journal of neurology 20021001 |
| Purification and characterization of two polymorphic variants of short chain acyl-CoA dehydrogenase reveal reduction of catalytic activity and stability of the Gly185Ser enzyme. | Biochemistry 20020917 |
| Hypoglycaemia and elevated urine ethylmalonic acid in a child homozygous for the short-chain acyl-CoA dehydrogenase 625G > A gene variation. | Acta paediatrica (Oslo, Norway : 1992) 20020101 |
| Therapeutic trial in the first three Asian cases of ethylmalonic encephalopathy: response to riboflavin. | Journal of inherited metabolic disease 20011201 |
| Artefactual pyruvate and 2-oxobutyrate produced by trimethylsilylation of methylmalonic and ethylmalonic acids in the presence of oxygen. | Journal of inherited metabolic disease 19991001 |
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