Record Information
Version2.0
Creation Date2012-05-31 10:22:05 -0600
Update Date2015-10-15 16:15:00 -0600
Secondary Accession Numbers
  • ECMDB00156
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
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
Weight:Average: 134.0874
Monoisotopic: 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
DescriptionThis compound belongs to the class of organic compounds known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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:
SMPDB Pathways:
Gluconeogenesis from L-malic acidPW000819 Pw000819Pw000819 greyscalePw000819 simple
Secondary Metabolites: Glyoxylate cyclePW000967 Pw000967Pw000967 greyscalePw000967 simple
TCA cyclePW000779 Pw000779Pw000779 greyscalePw000779 simple
TCA cycle (ubiquinol-0)PW002023 Pw002023Pw002023 greyscalePw002023 simple
TCA cycle (ubiquinol-10)PW001010 Pw001010Pw001010 greyscalePw001010 simple
TCA cycle (ubiquinol-2)PW001002 Pw001002Pw001002 greyscalePw001002 simple
TCA cycle (ubiquinol-3)PW001003 Pw001003Pw001003 greyscalePw001003 simple
TCA cycle (ubiquinol-4)PW001004 Pw001004Pw001004 greyscalePw001004 simple
TCA cycle (ubiquinol-5)PW001005 Pw001005Pw001005 greyscalePw001005 simple
TCA cycle (ubiquinol-6)PW001006 Pw001006Pw001006 greyscalePw001006 simple
TCA cycle (ubiquinol-7)PW001007 Pw001007Pw001007 greyscalePw001007 simple
TCA cycle (ubiquinol-8)PW001008 Pw001008Pw001008 greyscalePw001008 simple
TCA cycle (ubiquinol-9)PW001009 Pw001009Pw001009 greyscalePw001009 simple
glycolate and glyoxylate degradationPW000827 Pw000827Pw000827 greyscalePw000827 simple
glycolate and glyoxylate degradation IIPW002021 Pw002021Pw002021 greyscalePw002021 simple
inner membrane transportPW000786 Pw000786Pw000786 greyscalePw000786 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
1680± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
3450± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerolMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
3330± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetateMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
Find out more about how we convert literature concentrations.
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
GC-MSGC-MS Spectrum - GC-MSsplash10-0006-9100000000-aba7652c885a434930efView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0002-0930000000-6a116527910d172eb561View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0002-0920000000-d3afa3ad5c227740eae3View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-001i-0951000000-1d993823fa816ba3cfb1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-02j9-7191000000-b78c78194b39deee0ca4View 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-7900000000-2a07c36db6acea9015afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00rj-9200000000-316c7803efd1dfb76523View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9000000000-a442bcaaacb6f4eec14dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-9800000000-03bfaee5de56f72ed927View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-9200000000-26a075efe73adc63a189View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059f-9000000000-a3281a79477ac14e2eaeView 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

General function:
Involved in fumarate hydratase activity
Specific function:
(S)-malate = fumarate + H(2)O
Gene Name:
fumC
Uniprot ID:
P05042
Molecular weight:
50488
Reactions
(S)-malate = fumarate + H(2)O.
General function:
Involved in catalytic activity
Specific function:
Acetyl-CoA + H(2)O + glyoxylate = (S)-malate + CoA
Gene Name:
aceB
Uniprot ID:
P08997
Molecular weight:
60273
Reactions
Acetyl-CoA + H(2)O + glyoxylate = (S)-malate + CoA.
General function:
Involved in lyase activity
Specific function:
It functions as an aerobic enzyme in the citric acid cycle. It accounts for about 80% of the fumarase activity when the bacteria grows aerobically
Gene Name:
fumA
Uniprot ID:
P0AC33
Molecular weight:
60298
Reactions
(S)-malate = fumarate + H(2)O.
General function:
Involved in lyase activity
Specific function:
It functions in the generation of fumarate for use as an anaerobic electron acceptor
Gene Name:
fumB
Uniprot ID:
P14407
Molecular weight:
60105
Reactions
(S)-malate = fumarate + H(2)O.
General function:
Involved in oxidoreductase activity
Specific function:
(S)-malate + NAD(+) = pyruvate + CO(2) + NADH
Gene Name:
sfcA
Uniprot ID:
P26616
Molecular weight:
63197
Reactions
(S)-malate + NAD(+) = pyruvate + CO(2) + NADH.
General function:
Involved in malate dehydrogenase (quinone) activity
Specific function:
(S)-malate + a quinone = oxaloacetate + reduced quinone
Gene Name:
mqo
Uniprot ID:
P33940
Molecular weight:
60229
Reactions
(S)-malate + a quinone = oxaloacetate + reduced quinone.
General function:
Involved in catalytic activity
Specific function:
Accounts for almost the entire malate-synthesizing activity in cells metabolizing glyoxylate
Gene Name:
glcB
Uniprot ID:
P37330
Molecular weight:
80488
Reactions
Acetyl-CoA + H(2)O + glyoxylate = (S)-malate + CoA.
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Catalyzes the reversible oxidation of malate to oxaloacetate
Gene Name:
mdh
Uniprot ID:
P61889
Molecular weight:
32337
Reactions
(S)-malate + NAD(+) = oxaloacetate + NADH.
General function:
Involved in oxidoreductase activity
Specific function:
(S)-malate + NADP(+) = pyruvate + CO(2) + NADPH
Gene Name:
maeB
Uniprot ID:
P76558
Molecular weight:
82417
Reactions
(S)-malate + NADP(+) = pyruvate + CO(2) + NADPH.

Transporters

General function:
Involved in C4-dicarboxylate transmembrane transporter activity
Specific function:
Responsible for the transport of C4-dicarboxylates from the periplasm across the inner membrane
Gene Name:
dcuA
Uniprot ID:
P0ABN5
Molecular weight:
45750
General function:
Involved in C4-dicarboxylate transmembrane transporter activity
Specific function:
Responsible for the transport of C4-dicarboxylates from the periplasm across the inner membrane
Gene Name:
dcuB
Uniprot ID:
P0ABN9
Molecular weight:
47935
General function:
Involved in C4-dicarboxylate transmembrane transporter activity
Specific function:
Responsible for the transport of C4-dicarboxylates during anaerobic growth
Gene Name:
dcuC
Uniprot ID:
P0ABP3
Molecular weight:
48412
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
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
Uniprot ID:
P0A830
Molecular weight:
45436
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368