Showing metabocard for Malic acid (BMDB0000744)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:35:52 UTC
Update Date2020-06-04 20:22:03 UTC
BMDB IDBMDB0000744
Secondary Accession Numbers
  • BMDB00744
Metabolite Identification
Common NameMalic acid
DescriptionMalic acid, also known as malate or aepfelsaeure, 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. Malic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Malic acid exists in all living organisms, ranging from bacteria to humans. In cattle, malic acid is involved in the metabolic pathway called the transfer OF acetyl groups into mitochondria pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
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
MalateKegg
2-HydroxybutanedioateGenerator
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 saltHMDB
Malic acid, disodium salt, (R)-isomerHMDB
Malic acid, disodium salt, (S)-isomerHMDB
Malic acid, monopotassium salt, (+-)-isomerHMDB
Malic acid, (R)-isomerHMDB
Malic acid, calcium salt, (1:1), (S)-isomerHMDB
Malic acid, magnesium salt (2:1)HMDB
Calcium (hydroxy-1-malate) hexahydrateHMDB
Malic acid, potassium salt, (R)-isomerHMDB
Malic acid, sodium salt, (+-)-isomerHMDB
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
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
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point131 - 133 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000.0 mg/mLNot Available
LogP-1.26HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
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 Spectrum (1D, 400 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 90 MHz, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 1H]-TOCSY 2D NMR Spectrum (experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Liver
  • Milk
  • Placenta
  • Prostate Tissue
  • Semen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified92.79 +/- 29.23 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified8 - 441 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
 details
MilkDetected and Quantified83.66 +/- 28.83 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified151 +/- 19 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified141 +/- 23 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified142 +/- 17 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified144 +/- 15 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified91.15 +/- 26.69 uMNot SpecifiedNot Specified
Normal		 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000744
DrugBank IDDB12751
Phenol Explorer Compound IDNot Available
FooDB IDFDB008114
KNApSAcK IDNot Available
Chemspider ID510
KEGG Compound IDC03668
BioCyc IDRS-Malate
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)Not Available
General References
  1. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
  2. Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. [PubMed:25108860 ]
  3. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  4. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  5. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.