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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:21 UTC
HMDB IDHMDB0000576
Secondary Accession Numbers
  • HMDB00576
Metabolite Identification
Common NameMonoethyl malonic acid
DescriptionMonoethyl malonic acid, also known as (ethoxycarbonyl)acetate or 3-ethoxy-3-oxopropanoate, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Monoethyl malonic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make monoethyl malonic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Monoethyl malonic acid.
Structure
Data?1582752141
Synonyms
ValueSource
Monoethyl malonateGenerator
(Ethoxycarbonyl)acetateHMDB
(Ethoxycarbonyl)acetic acidHMDB
3-Ethoxy-3-oxopropanoateHMDB
3-Ethoxy-3-oxopropanoic acidHMDB
Ethyl hydrogen malonateHMDB
Ethyl malonateHMDB
Malonic acid ethyl esterHMDB
Malonic acid monoethyl esterHMDB
Monoethyl hydrogen malonateHMDB
Ethyl hydrogen malonic acidHMDB
Chemical FormulaC5H8O4
Average Molecular Weight132.1146
Monoisotopic Molecular Weight132.042258744
IUPAC Name3-ethoxy-3-oxopropanoic acid
Traditional Nameethyl hydrogen malonate
CAS Registry Number1071-46-1
SMILES
CCOC(=O)CC(O)=O
InChI Identifier
InChI=1S/C5H8O4/c1-2-9-5(8)3-4(6)7/h2-3H2,1H3,(H,6,7)
InChI KeyHGINADPHJQTSKN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • 1,3-dicarbonyl compound
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point47 - 50 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility125 g/LALOGPS
logP0.01ALOGPS
logP0.17ChemAxon
logS-0.02ALOGPS
pKa (Strongest Acidic)3.92ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity28.51 m³·mol⁻¹ChemAxon
Polarizability12.29 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.55331661259
DarkChem[M-H]-123.85131661259
AllCCS[M+H]+131.332859911
AllCCS[M-H]-127.4232859911
DeepCCS[M+H]+129.7730932474
DeepCCS[M-H]-126.89130932474
DeepCCS[M-2H]-163.26730932474
DeepCCS[M+Na]+138.27830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Monoethyl malonic acidCCOC(=O)CC(O)=O1985.8Standard polar33892256
Monoethyl malonic acidCCOC(=O)CC(O)=O1018.7Standard non polar33892256
Monoethyl malonic acidCCOC(=O)CC(O)=O1108.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Monoethyl malonic acid,1TMS,isomer #1CCOC(=O)CC(=O)O[Si](C)(C)C1131.8Semi standard non polar33892256
Monoethyl malonic acid,1TBDMS,isomer #1CCOC(=O)CC(=O)O[Si](C)(C)C(C)(C)C1334.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Monoethyl malonic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-002r-9000000000-c6c43e5078e23d3ba5742017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Monoethyl malonic acid GC-MS (1 TMS) - 70eV, Positivesplash10-05di-9400000000-2c6d882c575000718ccd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Monoethyl malonic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Monoethyl malonic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Monoethyl malonic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-000l-9000000000-ed08eca90f357944aee92012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl malonic acid 10V, Positive-QTOFsplash10-014i-4900000000-52c4754240f62facc38a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl malonic acid 20V, Positive-QTOFsplash10-00ks-9200000000-d9bbb7ad0ed33cdb1b3b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl malonic acid 40V, Positive-QTOFsplash10-052f-9000000000-dd3e62652f541a2785652017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl malonic acid 10V, Negative-QTOFsplash10-001i-9600000000-99465d7057a0e4384baa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl malonic acid 20V, Negative-QTOFsplash10-053l-9100000000-7022aca82c5e2ce527442017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl malonic acid 40V, Negative-QTOFsplash10-052f-9000000000-f681ff96b4be3a18c2ca2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl malonic acid 10V, Negative-QTOFsplash10-053j-9200000000-253b9a3c42e3fb8ef9c02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl malonic acid 20V, Negative-QTOFsplash10-052f-9000000000-998b7db9fd01adae97632021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl malonic acid 40V, Negative-QTOFsplash10-0006-9000000000-5094aee48d975adc19cc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl malonic acid 10V, Positive-QTOFsplash10-000l-9200000000-1e3cd7778e100a4cf3142021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl malonic acid 20V, Positive-QTOFsplash10-000f-9000000000-05d677512b91583ac9b32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Monoethyl malonic acid 40V, Positive-QTOFsplash10-0006-9000000000-c4bbedec8129ce2075192021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
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 IDFDB022124
KNApSAcK IDNot Available
Chemspider ID63783
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5558
PubChem Compound70615
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceOzaki, Eiji; Endo, Ryuichi. Manufacture of malonic acid monoesters from cyanoacetate esters with microbial nitrilase. Jpn. Kokai Tokkyo Koho (1998), 4 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. [PubMed:14708889 ]