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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:45:27 UTC
Update Date2023-02-21 17:27:57 UTC
HMDB IDHMDB0040220
Secondary Accession Numbers
  • HMDB40220
Metabolite Identification
Common NameDiethyl L-malate
DescriptionDiethyl L-malate 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. Diethyl L-malate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on Diethyl L-malate.
Structure
Data?1677000477
Synonyms
ValueSource
Diethyl L-malic acidGenerator
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, HMDB
Diethyl malate, (+-)-isomerMeSH, HMDB
Diethyl malate, (S)-isomerMeSH, HMDB
Diethyl malic acidGenerator
Diethyl D-malic acidGenerator
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
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
  • 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+143.5631661259
DarkChem[M-H]-141.66831661259
DeepCCS[M+H]+141.90130932474
DeepCCS[M-H]-139.18130932474
DeepCCS[M-2H]-175.54430932474
DeepCCS[M+Na]+150.84330932474
AllCCS[M+H]+144.832859911
AllCCS[M+H-H2O]+141.132859911
AllCCS[M+NH4]+148.232859911
AllCCS[M+Na]+149.232859911
AllCCS[M-H]-142.932859911
AllCCS[M+Na-2H]-144.432859911
AllCCS[M+HCOO]-146.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Diethyl L-malateCCOC(=O)CC(O)C(=O)OCC2317.9Standard polar33892256
Diethyl L-malateCCOC(=O)CC(O)C(=O)OCC1182.5Standard non polar33892256
Diethyl L-malateCCOC(=O)CC(O)C(=O)OCC1331.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Diethyl L-malate,1TMS,isomer #1CCOC(=O)CC(O[Si](C)(C)C)C(=O)OCC1386.6Semi standard non polar33892256
Diethyl L-malate,1TBDMS,isomer #1CCOC(=O)CC(O[Si](C)(C)C(C)(C)C)C(=O)OCC1594.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Diethyl L-malate EI-B (Non-derivatized)splash10-00vl-9200000000-0e2b63fa1358ecc4727d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diethyl L-malate EI-B (Non-derivatized)splash10-00vl-9200000000-0e2b63fa1358ecc4727d2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diethyl L-malate GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-9800000000-c3cb88ecf650c67efe5e2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diethyl L-malate GC-MS (1 TMS) - 70eV, Positivesplash10-0079-8920000000-732bc15836f011a383a32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diethyl L-malate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethyl L-malate 10V, Positive-QTOFsplash10-0007-1900000000-815e69499173edb4db802016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethyl L-malate 20V, Positive-QTOFsplash10-000b-9800000000-b787dba980fd1db16e612016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethyl L-malate 40V, Positive-QTOFsplash10-0002-9200000000-4e46a07b9fd73378c9ca2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethyl L-malate 10V, Negative-QTOFsplash10-000l-3900000000-f255ae39fead1d6d56dd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethyl L-malate 20V, Negative-QTOFsplash10-0075-9800000000-916e9fe90e1aecbe634d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethyl L-malate 40V, Negative-QTOFsplash10-00dv-9100000000-c36e5fae8fc58b06cf202016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethyl L-malate 10V, Negative-QTOFsplash10-0079-3900000000-349bf26b0d73cd973a8c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethyl L-malate 20V, Negative-QTOFsplash10-00fv-9400000000-2464ee9878c2e2c698a02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethyl L-malate 40V, Negative-QTOFsplash10-0076-9000000000-888ebde00273a66ebeb02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethyl L-malate 10V, Positive-QTOFsplash10-00kb-3900000000-8c2cbe244fa84072171c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethyl L-malate 20V, Positive-QTOFsplash10-0fxt-8900000000-7b232d5d7b06aaf439bb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethyl L-malate 40V, Positive-QTOFsplash10-006w-9100000000-a25e4bfa8d5a0b9203da2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .