Showing metabocard for Malic acid (BMDB0000744)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:35:52 UTC
Update Date2020-06-04 20:22:03 UTC
MCDB ID BMDB0000744
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
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
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0920000000-d3afa3ad5c227740eae32014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-001i-0951000000-1d993823fa816ba3cfb12014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-0930000000-6a116527910d172eb5612017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0920000000-d3afa3ad5c227740eae32017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-0951000000-1d993823fa816ba3cfb12017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-aba7652c885a434930ef2017-08-28View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-02j9-7191000000-b78c78194b39deee0ca42017-10-06View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03e9-3900000000-6112a756a8c8c7c7cd502012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00di-9100000000-b3efe8bce2f89afcff342012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-00ec-9300000000-c0aaa5301dcac30685db2012-07-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-7900000000-2a07c36db6acea9015af2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00rj-9200000000-316c7803efd1dfb765232017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9000000000-a442bcaaacb6f4eec14d2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-9800000000-03bfaee5de56f72ed9272017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-9200000000-26a075efe73adc63a1892017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059f-9000000000-a3281a79477ac14e2eae2017-07-26View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0076-9000000000-ad60ea592282d09e4bd82015-03-01View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, D2O, experimental)Not Available2015-03-01View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)Not Available2015-03-12View Spectrum
2D NMR[1H, 1H]-TOCSY 2D NMR Spectrum (experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified8 - 441 uM details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
Detected and Quantified151 +/- 19 uM details
Detected and Quantified141 +/- 23 uM details
Detected and Quantified142 +/- 17 uM details
Detected and Quantified144 +/- 15 uM details
Detected and Quantified84 +/- 29 uM details
Detected and Quantified91 +/- 27 uM details
Detected and Quantified93 +/- 29 uM details
HMDB IDHMDB0000744
DrugBank IDDB12751
Phenol Explorer Compound IDNot Available
FoodDB 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)Download (PDF)
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.