Showing Compound Card for Malic acid (CDB006173)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:22:30 UTC
Updated at2022-12-13 23:36:27 UTC
CannabisDB IDCDB006173
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameMalic acid
DescriptionMalic acid is odorless and 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. Indeed, malic acid was first isolated from apple juice by Carl Wilhelm Scheele in 1785. Malic acid can make a wine taste tart, although the amount decreases with increasing fruit ripeness. 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. Malic acid is an extremely weak acidic compound (based on its pKa). Malic acid exists in all living organisms, ranging from bacteria to humans. 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 is abundant in many fruits and is the main acid found in apricots, blackberries, blueberries, cherries, mirabelles, peaches, pears, plums, and quince. Malic acid is also present in grapes and in most wines with concentrations as high as 5 g/l. The taste of malic acid is very clear and pure in rhubarb, a plant for which it is the primary flavor. It is also a component of some artificial vinegar flavors, such as "salt and vinegar" flavored potato chips. Therefore malic acid is a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-D-Malic acidChEBI
(R)-2-Hydroxybutanedioic acidChEBI
2-HYDROXY-succinIC ACIDChEBI
D-MalateKegg
(+)-D-MalateGenerator
(R)-2-HydroxybutanedioateGenerator
2-HYDROXY-succinateGenerator
(R)-MalateHMDB
(R)-Hydroxybutanedioic acidHMDB
D-(+)-Malic acidHMDB
D-Hydroxybutanedioic acidHMDB
Hydroxy-(R)-butanedioic acidHMDB
R-Malic acidHMDB
D-Malic acidChEBI
Chemical FormulaC4H6O5
Average Molecular Weight134.09
Monoisotopic Molecular Weight134.0215
IUPAC Name(2R)-2-hydroxybutanedioic acid
Traditional Name.+-.-malic acid
CAS Registry Number636-61-3
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-/m1/s1
InChI KeyBJEPYKJPYRNKOW-UWTATZPHSA-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
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point101 °CNot Available
Boiling Point306.4 °CWikipedia
Water Solubility364 mg/mL at 20 °CNot Available
logP-1.26Not Available
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
Polarizability10.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSMalic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0930000000-53a536e3bc82b8e91612Spectrum
GC-MSMalic acid, non-derivatized, GC-MS Spectrumsplash10-00di-9610000000-883e07f52319a029b9f9Spectrum
GC-MSMalic acid, non-derivatized, GC-MS Spectrumsplash10-0002-0930000000-53a536e3bc82b8e91612Spectrum
GC-MSMalic acid, non-derivatized, GC-MS Spectrumsplash10-00di-9610000000-883e07f52319a029b9f9Spectrum
Predicted GC-MSMalic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9100000000-add08efe51cfe6d9243cSpectrum
Predicted GC-MSMalic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-02j9-7191000000-b78c78194b39deee0ca4Spectrum
Predicted GC-MSMalic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0159-3900000000-b601107a03ca7060bc562017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-01b9-7900000000-7e16d13cd13953520b722021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-ed4a8a4776b51e62327c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-22c9ebc50090b4cd66712021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-6900000000-3b7d14a7ed7bb42627e42015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01bj-9300000000-20f68e610aeba32d19472015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9000000000-044292489a383c81ae1d2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00m0-8900000000-9da4062d3c439ed2f7eb2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ri-9200000000-c4d019ab4961e5b1a1ae2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9000000000-bc073c2d0e1a2f8a82e32015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00y0-9400000000-b346287170f4b47937d92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00du-9000000000-94fcc5032bed94eae77e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-43c40f8a7715a996c55b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ri-9400000000-a20ca040dba0bb25ae2b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0095-9000000000-90064952bc6def150ecc2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-4dd1a07ea5d3aab2c6ea2021-09-23View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Polycystic kidney disease 2-like 1 proteinPKD2L110q24Q9P0L9 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Polycystic kidney disease 2-like 1 proteinPKD2L110q24Q9P0L9 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.716 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.288 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.583 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.216 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.921 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.475 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0031518
DrugBank IDDB03499
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008115
KNApSAcK IDNot Available
Chemspider ID83793
KEGG Compound IDC00497
BioCyc IDCPD-660
BiGG IDNot Available
Wikipedia LinkMalic_acid
METLIN IDNot Available
PubChem Compound92824
PDB IDDMR
ChEBI ID30796
References
General References
  1. Li D, Li W, Wang Q, Yang Z, Hou Z: Concise synthesis of Cannabisin G. Bioorg Med Chem Lett. 2010 Sep 1;20(17):5095-8. doi: 10.1016/j.bmcl.2010.07.028. Epub 2010 Jul 11. [PubMed:20667725 ]

Enzymes

Enzyme Details
1. Polycystic kidney disease 2-like 1 protein
General function:
Involved in calcium ion binding
Specific function:
May function as a subunit of an ion channel and act as a transducer of calcium-mediated signaling
Gene Name:
PKD2L1
Uniprot ID:
Q9P0L9
Molecular weight:
91981.2