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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:45:27 UTC
Update Date2019-07-23 06:31:48 UTC
HMDB IDHMDB0040220
Secondary Accession Numbers
  • HMDB40220
Metabolite Identification
Common NameDiethyl L-malate
DescriptionDiethyl L-malate is found in alcoholic beverages. Diethyl L-malate is a flavouring agent. Diethyl L-malate is present in guava fruit, papaya, kiwifruit, raspberry, chicory and various wines and spirits. Ethyl malate is a biomarker for the consumption of beer
Structure
Data?1563863508
Synonyms
ValueSource
Butanedioic acid, 2-hydroxy-, 1,4-diethyl esterHMDB
Butanedioic acid, hydroxy-, diethyl esterHMDB
Diethyl (1)-malateHMDB
Diethyl hydroxybutanedioateHMDB
Diethyl hydroxybutanoateHMDB
Diethyl malateHMDB
Ethyl DL-malateHMDB
Ethyl malateHMDB
Ethyl-DL-malateHMDB
Hydroxy-diethyl ester(.+/-.)-butanedioic acidHMDB
L-(-)-Malic acid diethyl esterHMDB
Malic acid, diethyl esterHMDB
Diethyl malate, (R)-isomerMeSH
Diethyl malate, (+-)-isomerMeSH
Diethyl malate, (S)-isomerMeSH
Chemical FormulaC8H14O5
Average Molecular Weight190.1938
Monoisotopic Molecular Weight190.084123558
IUPAC Name1,4-diethyl 2-hydroxybutanedioate
Traditional Name1,4-diethyl 2-hydroxybutanedioate
CAS Registry Number7554-28-1
SMILES
CCOC(=O)CC(O)C(=O)OCC
InChI Identifier
InChI=1S/C8H14O5/c1-3-12-7(10)5-6(9)8(11)13-4-2/h6,9H,3-5H2,1-2H3
InChI KeyVKNUORWMCINMRB-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
  • Fatty acid ester
  • Beta-hydroxy acid
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid ester
  • 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

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility96.5 g/LALOGPS
logP0.34ALOGPS
logP-0.11ChemAxon
logS-0.29ALOGPS
pKa (Strongest Acidic)12.44ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity43.91 m³·mol⁻¹ChemAxon
Polarizability18.75 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00vl-9200000000-0e2b63fa1358ecc4727dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00vl-9200000000-0e2b63fa1358ecc4727dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-9800000000-c3cb88ecf650c67efe5eJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-8920000000-732bc15836f011a383a3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0007-1900000000-815e69499173edb4db80JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000b-9800000000-b787dba980fd1db16e61JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9200000000-4e46a07b9fd73378c9caJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-3900000000-f255ae39fead1d6d56ddJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0075-9800000000-916e9fe90e1aecbe634dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dv-9100000000-c36e5fae8fc58b06cf20JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019933
KNApSAcK IDNot Available
Chemspider ID22619
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24197
PDB IDNot Available
ChEBI ID87368
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .