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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 18:18:57 UTC
HMDB IDHMDB0000744
Secondary Accession Numbers
  • HMDB00744
Metabolite Identification
Common NameMalic acid
DescriptionMalic acid is a tart-tasting organic dicarboxylic acid that plays a role in many sour or tart foods. In its ionised 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.
Structure
Thumb
Synonyms
ValueSource
2-Hydroxybutanedioic acidChEBI
2-Hydroxyethane-1,2-dicarboxylic acidChEBI
2-Hydroxysuccinic acidChEBI
alpha-Hydroxysuccinic acidChEBI
AepfelsaeureChEBI
Apple acidChEBI
DL-Malic acidChEBI
e296ChEBI
H2MalChEBI
Hydroxybutanedioic acidChEBI
Hydroxysuccinic acidChEBI
2-HydroxybutanedioateGenerator
MalateGenerator
2-Hydroxyethane-1,2-dicarboxylateGenerator
2-HydroxysuccinateGenerator
a-HydroxysuccinateGenerator
a-Hydroxysuccinic acidGenerator
alpha-HydroxysuccinateGenerator
α-hydroxysuccinateGenerator
α-hydroxysuccinic acidGenerator
DL-MalateGenerator
HydroxybutanedioateGenerator
HydroxysuccinateGenerator
DeoxytetrarateHMDB
Deoxytetraric acidHMDB
Musashi-NO-ringosanHMDB
Pomalus acidHMDB
R,S-MalateHMDB
R,S-Malic acidHMDB
R,SMalateHMDB
R,SMalic acidHMDB
Malic acid, disodium saltMeSH
Malic acid, disodium salt, (R)-isomerMeSH
Malic acid, disodium salt, (S)-isomerMeSH
Malic acid, monopotassium salt, (+-)-isomerMeSH
Malic acid, (R)-isomerMeSH
Malic acid, calcium salt, (1:1), (S)-isomerMeSH
Malic acid, magnesium salt (2:1)MeSH
Calcium (hydroxy-1-malate) hexahydrateMeSH
Malic acid, potassium salt, (R)-isomerMeSH
Malic acid, sodium salt, (+-)-isomerMeSH
Chemical FormulaC4H6O5
Average Molecular Weight134.0874
Monoisotopic Molecular Weight134.021523302
IUPAC Name2-hydroxybutanedioic acid
Traditional Namemalic acid
CAS Registry Number6915-15-7
SMILES
OC(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)
InChI KeyBJEPYKJPYRNKOW-UHFFFAOYSA-N
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
Ontology
Physiological effect

Health effect:

  Health condition:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point131 - 133 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogP-1.26HANSCH,C ET AL. (1995)
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
Polarizability10.91 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0920000000-d3afa3ad5c227740eae3View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-001i-0951000000-1d993823fa816ba3cfb1View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-0930000000-6a116527910d172eb561View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0920000000-d3afa3ad5c227740eae3View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-0951000000-1d993823fa816ba3cfb1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-aba7652c885a434930efView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-02j9-7191000000-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 AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Fructose-1,6-diphosphatase deficiencyPw000538Pw000538 greyscalePw000538 simpleNot Available
GluconeogenesisPw000152Pw000152 greyscalePw000152 simpleMap00010
Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke DiseasePw000205Pw000205 greyscalePw000205 simpleNot Available
Glycogenosis, Type IA. Von gierke diseasePw000557Pw000557 greyscalePw000557 simpleNot Available
Glycogenosis, Type IBPw000549Pw000549 greyscalePw000549 simpleNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)Both
Normal
details
Cerebrospinal Fluid (CSF)Detected and Quantified3 uMChildren (1-13 years old)BothNormal details
FecesDetected but not Quantified Adult (>18 years old)BothNormal details
FecesDetected but not Quantified Infant (0-1 year 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 and Quantified22.448 +/- 19.987 uMNot SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected and Quantified542.929 +/- 378.857 uMNot SpecifiedNot Specified
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 and Quantified1.87 +/- 1.06 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
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 Quantified4.53 +/- 2.22 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SweatDetected but not Quantified Adult BothNormal details
UrineDetected and Quantified0-1.1 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Great Plains Labo...
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 Quantified0.41-0.65 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)BothColorectal cancer details
BloodDetected but not Quantified Adult (>18 years old)Both
Schizophrenia
details
SalivaDetected and Quantified5.36 +/- 2.50 uMAdult (>18 years old)BothTemporomandibular joint disorder (TMD)
    • Sugimoto et al. (...
details
SweatDetected but not Quantified Infant (0-1 year old)Not Specifiedscreen-positive CF details
UrineDetected but not Quantified Adult (>18 years old)BothColorectal cancer details
Associated Disorders and Diseases
Disease References
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 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008114
KNApSAcK IDNot Available
Chemspider ID510
KEGG Compound IDC00711
BioCyc IDMAL
BiGG IDNot Available
Wikipedia LinkMalic acid
METLIN ID118
PubChem Compound525
PDB IDNot Available
ChEBI ID6650
References
Synthesis ReferenceWeiss, J. M.; Downs, C. R. Preliminary study on the formation of malic acid. Journal of the American Chemical Society (1922), 44 1118-25.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. Hem SL: Elimination of aluminum adjuvants. Vaccine. 2002 May 31;20 Suppl 3:S40-3. [PubMed:12184363 ]
  3. 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 ]
  4. 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 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ME1
Uniprot ID:
P48163
Molecular weight:
64149.075
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
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ME3
Uniprot ID:
Q16798
Molecular weight:
67067.875
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
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ME2
Uniprot ID:
P23368
Molecular weight:
53585.73
General function:
Involved in fumarate hydratase activity
Specific function:
Not Available
Gene Name:
FH
Uniprot ID:
B1ANK7
Molecular weight:
54636.6