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Bovine Metabolome Database



Showing metabocard for L-Malic acid (BMDB00156)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:43
Accession Number BMDB00156
Common Name L-Malic acid
Description Malic acid is a tart-tasting organic dicarboxylic acid that plays a role in many sour or tart foods. In its ionized form it is malate, an intermediate of the TCA cycle along with fumarate. It can also be formed from pyruvate as one of the anaplerotic reactions. Apples contain malic acid, which contributes to the sourness of a green apple. Malic acid can make a wine taste tart, although the amount decreases with increasing fruit ripeness. (wikipedia)
Synonyms
  1. (-)-(S)-Malate
  2. (-)-(S)-Malic acid
  3. (-)-Hydroxysuccinate
  4. (-)-Hydroxysuccinic acid
  5. (-)-L-Malic acid
  6. (-)-Malic acid
  7. (2S)-2-Hydroxybutanedioate
  8. (2S)-2-Hydroxybutanedioic acid
  9. (S)-(-)-Hydroxysuccinate
  10. (S)-(-)-Hydroxysuccinic acid
  11. (S)-Hydroxybutanedioate
  12. (S)-Hydroxybutanedioic acid
  13. (S)-Malic acid
  14. (S)-hydroxy-Butanedioate
  15. (S)-hydroxy-Butanedioic acid
  16. Apple acid
  17. L-(-)-Malic acid
  18. L-Apple acid
  19. L-Hydroxybutanedioate
  20. L-Hydroxybutanedioic acid
  21. L-Hydroxysuccinate
  22. L-Hydroxysuccinic acid
  23. Malic acid
  24. S-(-)-Malate
  25. S-(-)-Malic acid
  26. S-2-Hydroxybutanedioate
  27. S-2-Hydroxybutanedioic acid
Chemical IUPAC Name (2S)-2-hydroxybutanedioic acid
Chemical Formula C4H6O5
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Dicarboxylic Acids
Sub Class
  • Short chain dicarboxylic acids
Family
  • Mammalian_Metabolite
Species
  • secondary alcohol; carboxylic acid; alpha-hydroxyacid
Biofunction
  • Component of Glyoxylate and dicarboxylate metabolism; Component of Pyruvate metabolism
Application
Source
  • Endogenous
Average Molecular Weight 134.087
Monoisotopic Molecular Weight 134.021530
Isomeric SMILES O[C@@H](CC(O)=O)C(O)=O
Canonical SMILES OC(CC(O)=O)C(O)=O
KEGG Compound ID C00149 Link Image
BioCyc ID Not Available
BiGG ID 34045 Link Image
Wikipedia Link Apple acid Link Image
METLIN ID 118 Link Image
PubChem Compound 222656 Link Image
PubChem Substance 827429 Link Image
ChEBI ID 15589 Link Image
CAS Registry Number 97-67-6
InChI Identifier InChI=1/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1
Synthesis Reference McKenzie, Alex.; Plenderleith, H. J.; Walker, Nellie. Optical activation of racemic acid by d-malic acid. Journal of the Chemical Society, Transactions (1923), 123 2875-80.
Melting Point (Experimental) 107 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 218.0 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -2
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -0.87 [Predicted by ALOGPS]; -1.5 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
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PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Download Spectrum
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Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Show Image
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BMRB Spectrum Show Image
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Cellular Location
  • Cytoplasm
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Citrate Cycle
  • Glyoxylate and Dicarboxylate Metabolism
  • Pyruvate Metabolism
HMDB Pathways
Name Citrate Cycle
Image Show Link Image
Name Glyoxylate and Dicarboxylate Metabolism
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Name Pyruvate Metabolism
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KEGG Pathways
Name Citrate Cycle
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Name Glyoxylate and Dicarboxylate Metabolism
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Name Pyruvate Metabolism
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SimCell Pathways
Name Citrate Cycle
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SBML Download (XML) Link Image
Name Glyoxylate and Dicarboxylate Metabolism
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Graph
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Name Pyruvate Metabolism
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General References
  1. Wikipedia Link Image