Structure Database (LMSD)

Common Name
Methylsuccinic acid
Systematic Name
2-methyl-butanedioic acid
Synonyms
LM ID
LMFA01170119
Formula
C5H8O4
Exact Mass
Calculate m/z
132.04226
Sum Composition
FA 5:1;O2
Status
Curated
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View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Dicarboxylic acids [FA0117]
Branched fatty acids [FA0102]

Biological Context

Methylsuccinic acid is a dicarboxylic acid and metabolite of the essential amino acid L-isoleucine and branched-chain amino acid L-alloisoleucine .1 It is formed from L-isoleucine and L-alloisoleucine via an R-2-oxo-3-methylvaleric acid intermediate. Urinary levels of methylsuccinic acid are increased in patients with ethylmalonic encephalopathy, an inborn error of metabolism characterized by developmental delay, hypotonia, vascular instability, petechiae, acrocyanosis, chronic diarrhea, and lactic acidemia. Urinary levels of methylsuccinic acid are also increased in patients with short-chain acyl-CoA dehydrogenase deficiency or type 2 diabetes.2,3 It has been found in urban and industrial aerosols of fine particulate matter less than 2.5 µm (PM2.5).4

This information has been provided by Cayman Chemical

References

1. Nowaczyk, M.J.M., Lehotay, D.C., Platt, B.-A., et al. Ethylmalonic and methylsuccinic aciduria in ethylmalonic encephalopathy arise from abnormal isoleucine metabolism. Metabolism 47(7), 836-839 (1998).
2. Gallant, N.M., Leydiker, K., Tang, H., et al. Biochemical, molecular, and clinical characteristics of children with short chain acyl-CoA dehydrogenase deficiency detected by newborn screening in California. Mol. Genet. Metab. 106(1), 55-61 (2012).
3. Urpi-Sarda, M., Almanza-Aguilera, E., Llorach, R., et al. Non-targeted metabolomic biomarkers and metabotypes of type 2 diabetes: A cross-sectional study of PREDIMED trial participants. Diabetes Metab. 45(2), 167-174 (2019).
4. Crenn, V., Fronval, I., Petitprez, D., et al. Fine particles sampled at an urban background site and an industrialized coastal site in Northern France - Part 1: Seasonal variations and chemical characterization. Sci. Total Environ. 578, 203-218 (2017).

String Representations

InChiKey (Click to copy)
WXUAQHNMJWJLTG-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C5H8O4/c1-3(5(8)9)2-4(6)7/h3H,2H2,1H3,(H,6,7)(H,8,9)
SMILES (Click to copy)
C(=O)(O)C(C)CC(O)=O

Other Databases

HMDB ID
HMDB0001844
CHEBI ID
91315
PubChem CID
10349
Cayman ID
36430

Calculated Physicochemical Properties

Heavy Atoms 9
Rings 0
Aromatic Rings 0
Rotatable Bonds 3
Van der Waals Molecular Volume 124.94
Topological Polar Surface Area 74.60
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 4
logP 0.18
Molar Refractivity 29.05

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Updated at
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