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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:58 UTC

HMDB ID

HMDB0000576

Secondary Accession Numbers

HMDB00576

Metabolite Identification

Common Name

Monoethyl malonic acid

Description

Monoethyl 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Monoethyl malonate	Generator
(Ethoxycarbonyl)acetate	HMDB
(Ethoxycarbonyl)acetic acid	HMDB
3-Ethoxy-3-oxopropanoate	HMDB
3-Ethoxy-3-oxopropanoic acid	HMDB
Ethyl hydrogen malonate	HMDB
Ethyl malonate	HMDB
Malonic acid ethyl ester	HMDB
Malonic acid monoethyl ester	HMDB
Monoethyl hydrogen malonate	HMDB
Ethyl hydrogen malonic acid	HMDB

Chemical Formula

C₅H₈O₄

Average Molecular Weight

132.1146

Monoisotopic Molecular Weight

132.042258744

IUPAC Name

3-ethoxy-3-oxopropanoic acid

Traditional Name

ethyl hydrogen malonate

CAS Registry Number

1071-46-1

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 Key

HGINADPHJQTSKN-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic 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 Framework

Aliphatic acyclic compounds

External Descriptors

aromatic carboxylic acid (CHEBI:86907 )
pyridinemonocarboxylic acid (CHEBI:86907 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0000576)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0000576)

Source

Endogenous

Endogenous (HMDB: HMDB0000576)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	47 - 50 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	125 g/L	ALOGPS
logP	0.01	ALOGPS
logP	0.17	ChemAxon
logS	-0.02	ALOGPS
pKa (Strongest Acidic)	3.92	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	28.51 m³·mol⁻¹	ChemAxon
Polarizability	12.29 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	128.553	31661259
DarkChem	[M-H]-	123.851	31661259
AllCCS	[M+H]+	131.3	32859911
AllCCS	[M-H]-	127.42	32859911
DeepCCS	[M+H]+	129.77	30932474
DeepCCS	[M-H]-	126.891	30932474
DeepCCS	[M-2H]-	163.267	30932474
DeepCCS	[M+Na]+	138.278	30932474
AllCCS	[M+H]+	131.3	32859911
AllCCS	[M+H-H2O]+	127.2	32859911
AllCCS	[M+NH4]+	135.1	32859911
AllCCS	[M+Na]+	136.2	32859911
AllCCS	[M-H]-	127.4	32859911
AllCCS	[M+Na-2H]-	130.2	32859911
AllCCS	[M+HCOO]-	133.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Monoethyl malonic acid	CCOC(=O)CC(O)=O	1985.8	Standard polar	33892256
Monoethyl malonic acid	CCOC(=O)CC(O)=O	1018.7	Standard non polar	33892256
Monoethyl malonic acid	CCOC(=O)CC(O)=O	1108.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Monoethyl malonic acid,1TMS,isomer #1	CCOC(=O)CC(=O)O[Si](C)(C)C	1131.8	Semi standard non polar	33892256
Monoethyl malonic acid,1TBDMS,isomer #1	CCOC(=O)CC(=O)O[Si](C)(C)C(C)(C)C	1334.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Monoethyl malonic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-002r-9000000000-c6c43e5078e23d3ba574	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Monoethyl malonic acid GC-MS (1 TMS) - 70eV, Positive	splash10-05di-9400000000-2c6d882c575000718ccd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Monoethyl malonic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Monoethyl malonic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Monoethyl malonic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)	splash10-000l-9000000000-ed08eca90f357944aee9	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethyl malonic acid 10V, Positive-QTOF	splash10-014i-4900000000-52c4754240f62facc38a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethyl malonic acid 20V, Positive-QTOF	splash10-00ks-9200000000-d9bbb7ad0ed33cdb1b3b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethyl malonic acid 40V, Positive-QTOF	splash10-052f-9000000000-dd3e62652f541a278565	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethyl malonic acid 10V, Negative-QTOF	splash10-001i-9600000000-99465d7057a0e4384baa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethyl malonic acid 20V, Negative-QTOF	splash10-053l-9100000000-7022aca82c5e2ce52744	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethyl malonic acid 40V, Negative-QTOF	splash10-052f-9000000000-f681ff96b4be3a18c2ca	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethyl malonic acid 10V, Negative-QTOF	splash10-053j-9200000000-253b9a3c42e3fb8ef9c0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethyl malonic acid 20V, Negative-QTOF	splash10-052f-9000000000-998b7db9fd01adae9763	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethyl malonic acid 40V, Negative-QTOF	splash10-0006-9000000000-5094aee48d975adc19cc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethyl malonic acid 10V, Positive-QTOF	splash10-000l-9200000000-1e3cd7778e100a4cf314	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethyl malonic acid 20V, Positive-QTOF	splash10-000f-9000000000-05d677512b91583ac9b3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Monoethyl malonic acid 40V, Positive-QTOF	splash10-0006-9000000000-c4bbedec8129ce207519	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 400 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022124

KNApSAcK ID

Not Available

Chemspider ID

63783

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5558

PubChem Compound

70615

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Ozaki, 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)

Not Available

General References

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 ]

Showing metabocard for Monoethyl malonic acid (HMDB0000576)

MOL for HMDB0000576 (Monoethyl malonic acid)

3D MOL for HMDB0000576 (Monoethyl malonic acid)

3D SDF for HMDB0000576 (Monoethyl malonic acid)

3D-SDF for HMDB0000576 (Monoethyl malonic acid)

PDB for HMDB0000576 (Monoethyl malonic acid)

3D PDB for HMDB0000576 (Monoethyl malonic acid)

SMILES for HMDB0000576 (Monoethyl malonic acid)

INCHI for HMDB0000576 (Monoethyl malonic acid)

Structure for HMDB0000576 (Monoethyl malonic acid)

3D Structure for HMDB0000576 (Monoethyl malonic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra