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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-03 18:18:24 UTC
HMDB IDHMDB0000156
Secondary Accession Numbers
  • HMDB0000744
  • HMDB00156
  • HMDB00744
Metabolite Identification
Common NameMalic acid
DescriptionMalic acid (CAS: 6915-15-7) is a tart-tasting organic dicarboxylic acid that plays a role in many sour or tart foods. 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). In its ionized form, malic acid is called malate. Malate is an intermediate of the TCA cycle along with fumarate. It can also be formed from pyruvate as one of the anaplerotic reactions. In humans, malic acid is both derived from food sources and synthesized in the body through the citric acid cycle or Krebs cycle which takes place in the mitochondria. Malate's importance to the production of energy in the body during both aerobic and anaerobic conditions is well established. Under aerobic conditions, the oxidation of malate to oxaloacetate provides reducing equivalents to the mitochondria through the malate-aspartate redox shuttle. During anaerobic conditions, where a buildup of excess reducing equivalents inhibits glycolysis, malic acid's simultaneous reduction to succinate and oxidation to oxaloacetate is capable of removing the accumulating reducing equivalents. This allows malic acid to reverse hypoxia's inhibition of glycolysis and energy production. In studies on rats, it has been found that only tissue malate is depleted following exhaustive physical activity. Other key metabolites from the citric acid cycle needed for energy production were found to be unchanged. Because of this, a deficiency of malic acid has been hypothesized to be a major cause of physical exhaustion. Notably, the administration of malic acid to rats has been shown to elevate mitochondrial malate and increase mitochondrial respiration and energy production. Malic acid has been found to be a metabolite in Aspergillus (Hugo Vanden Bossche, D.W.R. Mackenzie and G. Cauwenbergh. Aspergillus and Aspergillosis, 1987).
Structure
Data?1580753904
Synonyms
ValueSource
(-)-L-Malic acidChEBI
(S)-(-)-Hydroxysuccinic acidChEBI
L-2-Hydroxybutanedioic acidChEBI
L-Apple acidChEBI
MalateChEBI
Malic acidChEBI
S-2-Hydroxybutanedioic acidChEBI
L-MalateKegg
(-)-L-MalateGenerator
(S)-(-)-HydroxysuccinateGenerator
L-2-HydroxybutanedioateGenerator
S-2-HydroxybutanedioateGenerator
(-)-(S)-MalateHMDB
(-)-(S)-Malic acidHMDB
(-)-HydroxysuccinateHMDB
(-)-Hydroxysuccinic acidHMDB
(-)-Malic acidHMDB
(2S)-2-HydroxybutanedioateHMDB
(2S)-2-Hydroxybutanedioic acidHMDB
(S)-Hydroxy-butanedioateHMDB
(S)-Hydroxy-butanedioic acidHMDB
(S)-HydroxybutanedioateHMDB
(S)-Hydroxybutanedioic acidHMDB
(S)-Malic acidHMDB
Apple acidHMDB
L-(-)-Malic acidHMDB
L-HydroxybutanedioateHMDB
L-Hydroxybutanedioic acidHMDB
L-HydroxysuccinateHMDB
L-Hydroxysuccinic acidHMDB
S-(-)-MalateHMDB
S-(-)-Malic acidHMDB
(S)-MalateHMDB
L-Malic acidChEBI
(2S)-2-Hydroxysuccinic acidHMDB
(2S)-Malic acidHMDB
(S)-2-Hydroxysuccinic acidHMDB
2-Hydroxybutanedioic acidHMDB
2-Hydroxyethane-1,2-dicarboxylic acidHMDB
2-Hydroxysuccinic acidHMDB
Deoxytetraric acidHMDB
Hydroxybutanedioic acidHMDB
Hydroxysuccinic acidHMDB
Monohydroxybutanedioic acidHMDB
alpha-Hydroxysuccinic acidHMDB
α-Hydroxysuccinic acidHMDB
Chemical FormulaC4H6O5
Average Molecular Weight134.0874
Monoisotopic Molecular Weight134.021523302
IUPAC Name(2S)-2-hydroxybutanedioic acid
Traditional Name(-)-malic acid
CAS Registry Number97-67-6
SMILES
O[C@@H](CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1
InChI KeyBJEPYKJPYRNKOW-REOHCLBHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives 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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point107 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility218 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity24.88 m³·mol⁻¹ChemAxon
Polarizability10.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-000t-0940000000-142d6f5fc2efbf0d5109Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0002-0920000000-505483ce10ee3c4c9d20Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-9710000000-8f263d045d715ae9fe2bSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000t-0940000000-142d6f5fc2efbf0d5109Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0920000000-505483ce10ee3c4c9d20Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9710000000-8f263d045d715ae9fe2bSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0910000000-fadd80af55894555ea72Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-aba7652c885a434930efSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-02j9-7191000000-b78c78194b39deee0ca4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9300000000-acd7d0159b8bb70b80fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0096-9000000000-7359292556d9d393d8f4Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0097-9000000000-a111335688b3219c1fc1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00lr-0942120000-9504700a82dcf5dc3adbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0900000000-45e58d8a75d957cc5c41Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-4ec56105367de7bf0027Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-1decf12f117200e0f28dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-4900000000-86fd329658581c81c0ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-9100000000-82ffef2aa053f77cdbc5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00di-9000000000-424bd54bc81a9db65a55Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-a916941735427ee3c48dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-1decf12f117200e0f28dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-4900000000-86fd329658581c81c0ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9100000000-82ffef2aa053f77cdbc5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-424bd54bc81a9db65a55Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-a916941735427ee3c48dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03di-0900000000-afdfdad3edeeb90cb3e4Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-01b9-4900000000-01b3a756de8f5a3ae6deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-7900000000-2a07c36db6acea9015afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00rj-9200000000-316c7803efd1dfb76523Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9000000000-a442bcaaacb6f4eec14dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-9800000000-03bfaee5de56f72ed927Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-9200000000-26a075efe73adc63a189Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059f-9000000000-a3281a79477ac14e2eaeSpectrum
MSMass Spectrum (Electron Ionization)splash10-0076-9000000000-ad60ea592282d09e4bd8Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cellular Cytoplasm
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified12.0 (0.0-21.0) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified3.2 +/- 0.9 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
Cellular CytoplasmDetected and Quantified3200 (2800-3600) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified3 uMChildren (1-13 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified3.0 +/- 3.0 uMAdult (>18 years old)BothNormal details
FecesDetected but not Quantified Infant (0-1 year old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified22.448 +/- 19.987 nmol/g wet fecesNot SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected and Quantified542.929 +/- 378.857 nmol/g wet fecesNot SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
SalivaDetected and Quantified5.22 +/- 3.49 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified6.35 +/- 3.56 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected and Quantified1.87 +/- 1.06 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected and Quantified6.45 +/- 2.84 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
SalivaDetected and Quantified3.79 +/- 1.80 uMAdult (>18 years old)BothNormal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified6.45 +/- 2.09 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
SalivaDetected and Quantified4.15 +/- 6.21 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified4.15 +/- 6.21 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified20.45 +/- 10.87 uMAdult (>18 years old)FemaleNormal details
SalivaDetected and Quantified4.53 +/- 2.22 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SweatDetected but not Quantified Adult BothNormal details
UrineDetected and Quantified18.669 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified0-1.1 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Great Plains Labo...
details
UrineDetected and Quantified<8 umol/mmol creatinineNot SpecifiedNot Specified
Normal
details
UrineDetected and Quantified0.57-0.81 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified2.63 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified2.0 (0.7-5.3) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.41-0.65 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.46 +/- 0.79 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified0.5 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified116.959 +/- 45.313 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified36.1(12.4-121.6) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified38.9 (25.5-93.0) umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified9.0 (2.2-19.0) umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified8.3 (2.8-30.1) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)BothColorectal cancer details
BloodDetected but not Quantified Adult (>18 years old)Both
Schizophrenia
details
Cellular CytoplasmDetected and Quantified480 (470-490) uMAdult (>18 years old)BothAnoxia details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
SalivaDetected and Quantified5.36 +/- 2.50 uMAdult (>18 years old)BothTemporomandibular joint disorder (TMD)
    • Sugimoto et al. (...
details
SalivaDetected but not Quantified Adult (>18 years old)MaleAttachment loss  details
SalivaDetected but not Quantified Adult (>18 years old)MaleMissing teeth details
SalivaDetected but not Quantified Adult (>18 years old)MalePeriodontal Probing Depth details
SalivaDetected and Quantified22.27 +/- 14.67 uMAdult (>18 years old)MaleAlzheimer's disease details
SalivaDetected and Quantified18.70 +/- 15.26 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
SalivaDetected and Quantified24.13 +/- 19.54 uMAdult (>18 years old)BothLewy body disease details
SweatDetected but not Quantified Infant (0-1 year old)Not Specifiedscreen-positive CF details
UrineDetected and Quantified110 umol/mmol creatinineNewborn (0-30 days old)FemaleDeafness, Onychodystrophy, Osteodystrophy, Mental Retardation, and Seizures Syndrome details
UrineDetected and Quantified33.616 +/- 24.099 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified7-194 umol/mmol creatinineInfant (0-1 year old)Male
2-Ketoglutarate dehydrogenase complex deficiency
details
UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
UrineDetected but not Quantified Adult (>18 years old)BothColorectal cancer details
UrineDetected and Quantified65.119 +/- 40.319 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified187.187 +/- 183.405 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ]
  2. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  3. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  4. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Schizophrenia
  1. Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [PubMed:22024767 ]
Anoxia
  1. 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 ]
Alzheimer's disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Frontotemporal dementia
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lewy body disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Temporomandibular joint disorder
  1. (). Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles. . .
Attachment loss
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Missing teeth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Cystic fibrosis
  1. Adriana Nori de Macedo. Robust capillary electrophoresis methods for biomarker discovery and routine measurements in clinical and epidemiological applications. March 2017 [Link]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
2-Ketoglutarate dehydrogenase complex deficiency
  1. Bonnefont JP, Chretien D, Rustin P, Robinson B, Vassault A, Aupetit J, Charpentier C, Rabier D, Saudubray JM, Munnich A: Alpha-ketoglutarate dehydrogenase deficiency presenting as congenital lactic acidosis. J Pediatr. 1992 Aug;121(2):255-8. [PubMed:1640293 ]
Deafness, Onychodystrophy, Osteodystrophy, Mental Retardation, and Seizures Syndrome
  1. James AW, Miranda SG, Culver K, Hall BD, Golabi M: DOOR syndrome: clinical report, literature review and discussion of natural history. Am J Med Genet A. 2007 Dec 1;143A(23):2821-31. doi: 10.1002/ajmg.a.32054. [PubMed:17994565 ]
Associated OMIM IDs
  • 114500 (Colorectal cancer)
  • 181500 (Schizophrenia)
  • 104300 (Alzheimer's disease)
  • 600274 (Frontotemporal dementia)
  • 219700 (Cystic fibrosis)
  • 610247 (Eosinophilic esophagitis)
  • 203740 (2-Ketoglutarate dehydrogenase complex deficiency)
  • 220500 (Deafness, Onychodystrophy, Osteodystrophy, Mental Retardation, and Seizures Syndrome)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012047
KNApSAcK IDC00001192
Chemspider ID193317
KEGG Compound IDC00149
BioCyc IDMAL
BiGG ID34045
Wikipedia LinkMalic acid
METLIN IDNot Available
PubChem Compound222656
PDB IDNot Available
ChEBI ID30797
Food Biomarker OntologyNot Available
VMH IDMAL_L
References
Synthesis ReferenceMcKenzie, 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)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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. doi: 10.1038/nature07762. [PubMed:19212411 ]
  7. Hem SL: Elimination of aluminum adjuvants. Vaccine. 2002 May 31;20 Suppl 3:S40-3. [PubMed:12184363 ]
  8. Spiteller M, Spiteller G: [Occurrence of alpha-alkyl-substituted malic acids, and beta-hydroxy-beta-alkyl-substituted dicarboxylic and tricarboxylic acid derivatives in normal urine (author's transl)]. J Chromatogr. 1979 Nov 11;164(3):319-29. [PubMed:544608 ]
  9. Anneroth G, Nordenram G, Bengtsson S: Effect of saliva stimulants (Hybrin and malic acid) on cervical root surfaces in vitro. Scand J Dent Res. 1980 Jun;88(3):214-8. [PubMed:6932087 ]
  10. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ME1
Uniprot ID:
P48163
Molecular weight:
64149.075
Reactions
Malic acid + NADP → Pyruvic acid + CO(2) + NADPHdetails
Malic acid + NADP → Pyruvic acid + Carbon dioxide + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Not Available
Gene Name:
MDH2
Uniprot ID:
P40926
Molecular weight:
35502.935
Reactions
Malic acid + NAD → Oxalacetic acid + NADHdetails
Malic acid + NAD → Oxalacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ME3
Uniprot ID:
Q16798
Molecular weight:
67067.875
Reactions
Malic acid + NADP → Pyruvic acid + CO(2) + NADPHdetails
Malic acid + NADP → Pyruvic acid + Carbon dioxide + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
Not Available
Gene Name:
MDH1
Uniprot ID:
P40925
Molecular weight:
38627.255
Reactions
Malic acid + NAD → Oxalacetic acid + NADHdetails
Malic acid + NAD → Oxalacetic acid + NADH + Hydrogen Iondetails
General function:
Involved in fumarate hydratase activity
Specific function:
Also acts as a tumor suppressor.
Gene Name:
FH
Uniprot ID:
P07954
Molecular weight:
54636.585
Reactions
Malic acid → Fumaric acid + Waterdetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ME2
Uniprot ID:
P23368
Molecular weight:
53585.73
Reactions
Malic acid + NAD → Pyruvic acid + CO(2) + NADHdetails
Malic acid + NAD → Pyruvic acid + Carbon dioxide + NADH + Hydrogen Iondetails
General function:
Involved in fumarate hydratase activity
Specific function:
Not Available
Gene Name:
FH
Uniprot ID:
B1ANK7
Molecular weight:
54636.6