L-Malic acid (PAMDB000058)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000058
Identification
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)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (-)-(S)-Malate
  • (-)-(S)-Malic acid
  • (-)-Hydroxysuccinate
  • (-)-Hydroxysuccinic acid
  • (-)-L-Malate
  • (-)-L-Malic acid
  • (-)-Malate
  • (-)-Malic acid
  • (2S)-2-Hydroxybutanedioate
  • (2S)-2-Hydroxybutanedioic acid
  • (S)-malic acid
  • (S)-(-)-Hydroxysuccinate
  • (S)-(-)-Hydroxysuccinic acid
  • (S)-hydroxy-Butanedioate
  • (S)-hydroxy-Butanedioic acid
  • (S)-Hydroxybutanedioate
  • (S)-Hydroxybutanedioic acid
  • (S)-malate
  • (S)-Malic acid
  • Apple acid
  • Hydroxybutanedioate
  • Hydroxybutanedioic acid
  • Hydroxysuccinate
  • Hydroxysuccinic acid
  • L-(-)-Malate
  • L-(-)-Malic acid
  • L-Apple acid
  • L-Hydroxybutanedioate
  • L-Hydroxybutanedioic acid
  • L-Hydroxysuccinate
  • L-Hydroxysuccinic acid
  • L-mal
  • L-Malate
  • L-Malic acid
  • Mal
  • Malate
  • Malic acid
  • S-(-)-Malate
  • S-(-)-Malic acid
  • S-2-Hydroxybutanedioate
  • S-2-Hydroxybutanedioic acid
Chemical Formula: C4H6O5
Average Molecular Weight: 134.0874
Monoisotopic Molecular Weight: 134.021523302
InChI Key: BJEPYKJPYRNKOW-UHFFFAOYSA-N
InChI:InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)
CAS number: 97-67-6
IUPAC Name:2-hydroxybutanedioic acid
Traditional IUPAC Name: malic acid
SMILES:OC(CC(O)=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acids and conjugates
Direct Parent Hydroxy fatty acids
Alternative Parents
Substituents
  • Hydroxy fatty acid
  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-2
Melting point: 107 °C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility218.0 mg/mLALOGPS
logP-0.87ALOGPS
logP-1.1ChemAxon
logS0.21ALOGPS
pKa (Strongest Acidic)3.2ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity24.88 m3·mol-1ChemAxon
Polarizability10.91 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Fumaric acid + Water <> L-Malic acid
Acetyl-CoA + Glyoxylic acid + Water <> Coenzyme A + Hydrogen ion + L-Malic acid
L-Malic acid + NAD > Carbon dioxide + NADH + Pyruvic acid
L-Malic acid + Ubiquinone-8 > Oxalacetic acid + Ubiquinol-8
L-Malic acid + Menaquinone 8 > Menaquinol 8 + Oxalacetic acid
L-Malic acid + NADP > Carbon dioxide + NADPH + Pyruvic acid
L-Malic acid + NAD <> Hydrogen ion + NADH + Oxalacetic acid
L-Malic acid + NAD <> Pyruvic acid + Carbon dioxide + NADH + Hydrogen ion
L-Malic acid + NADP <> Pyruvic acid + Carbon dioxide + NADPH + Hydrogen ion
L-Malic acid + Coenzyme A <> Acetyl-CoA + Water + Glyoxylic acid
L-Malic acid + FAD <> FADH2 + Oxalacetic acid
L-Malic acid + a quinone > Oxalacetic acid + a quinol
L-Malic acid + Oxygen <> Oxalacetic acid + Hydrogen peroxide
L-Malic acid + NAD > Oxalacetic acid + NADH
L-Malic acid + a quinone > Oxalacetic acid + reduced quinone
L-Malic acid + NAD + Oxalacetic acid <> Pyruvic acid + Carbon dioxide + NADH
L-Malic acid + Quinone <> Oxalacetic acid + Hydroquinone
L-Malic acid + NADP + Oxalacetic acid <> Pyruvic acid + Carbon dioxide + NADPH
L-Malic acid + L-Malic acid <> Fumaric acid + Water
L-Malic acid + NAD + L-Malic acid <> Oxalacetic acid + NADH + Hydrogen ion
L-Malic acid + Quinone + L-Malic acid > Oxalacetic acid + Hydroquinone
L-Malic acid + NADP + L-Malic acid > Carbon dioxide + NADPH + Pyruvic acid + NADPH
L-Malic acid + NAD + L-Malic acid > Carbon dioxide + NADH + Pyruvic acid
Glyoxylic acid + Water + Acetyl-CoA > Coenzyme A + Hydrogen ion + L-Malic acid + L-Malic acid
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0002-0920000000-d3afa3ad5c227740eae3View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-001i-0951000000-1d993823fa816ba3cfb1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03e9-3900000000-6112a756a8c8c7c7cd50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-9100000000-b3efe8bce2f89afcff34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00ec-9300000000-c0aaa5301dcac30685dbView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0076-9000000000-ad60ea592282d09e4bd8View in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Denayrolles M, Aigle M, Lonvaud-Funel A: Cloning and sequence analysis of the gene encoding Lactococcus lactis malolactic enzyme: relationships with malic enzymes. FEMS Microbiol Lett. 1994 Feb 1;116(1):79-86. Pubmed: 8132158
  • Fang TJ, Dalmasso JP: Antimicrobial activity of sulfur dioxide to certain lactic acid bacteria isolated from wines. Zhonghua Min Guo Wei Sheng Wu Ji Mian Yi Xue Za Zhi. 1993 Aug;26(3):116-31. Pubmed: 7982367
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
  • Splittstoesser DF, McLellan MR, Churey JJ: Heat resistance of Escherichia coli O157:H7 in apple juice. J Food Prot. 1996 Mar;59(3):226-9. Pubmed: 10463437
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. Pubmed: 8579834
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.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID15589
HMDB IDHMDB00156
Pubchem Compound ID222656
Kegg IDC00149
ChemSpider ID193317
WikipediaApple acid
BioCyc IDMAL
EcoCyc IDMAL
Ligand ExpoLMR

Enzymes

Protein Details
• Fumarate hydratase class II
General function:
Involved in fumarate hydratase activity
Specific function:
(S)-malate = fumarate + H(2)O
Gene Name:
fumC
Locus Tag:
PA0854
Molecular weight:
49.1 kDa
Reactions
(S)-malate = fumarate + H(2)O.
Protein Details
• NAD-dependent malic enzyme
General function:
Involved in oxidoreductase activity
Specific function:
(S)-malate + NAD(+) = pyruvate + CO(2) + NADH
Gene Name:
sfcA
Locus Tag:
PA3471
Molecular weight:
62.4 kDa
Reactions
(S)-malate + NAD(+) = pyruvate + CO(2) + NADH.
Protein Details
• Malate:quinone oxidoreductase
General function:
Involved in malate dehydrogenase (quinone) activity
Specific function:
(S)-malate + a quinone = oxaloacetate + reduced quinone
Gene Name:
mqo
Locus Tag:
PA3452
Molecular weight:
57.2 kDa
Reactions
(S)-malate + a quinone = oxaloacetate + reduced quinone.
Protein Details
• Malate synthase G
General function:
Involved in catalytic activity
Specific function:
Accounts for almost the entire malate-synthesizing activity in cells metabolizing glyoxylate
Gene Name:
glcB
Locus Tag:
PA0482
Molecular weight:
78.7 kDa
Reactions
Acetyl-CoA + H(2)O + glyoxylate = (S)-malate + CoA.
Protein Details
• NADP-dependent malic enzyme
General function:
Involved in oxidoreductase activity
Specific function:
(S)-malate + NADP(+) = pyruvate + CO(2) + NADPH
Gene Name:
maeB
Locus Tag:
PA5046
Molecular weight:
45.4 kDa
Reactions
(S)-malate + NADP(+) = pyruvate + CO(2) + NADPH.

Transporters

Protein Details
• Aerobic C4-dicarboxylate transport protein
General function:
Involved in symporter activity
Specific function:
Responsible for the aerobic transport of the dicarboxylates fumarate, L- and D-malate and to a lesser extent succinate, from the periplasm across the inner membrane
Gene Name:
dctA
Locus Tag:
PA1183
Molecular weight:
46 kDa