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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:01:05 UTC

Update Date

2023-02-21 17:26:02 UTC

HMDB ID

HMDB0037759

Secondary Accession Numbers

HMDB37759

Metabolite Identification

Common Name

2-Methylene-4-oxopentanedioic acid

Description

2-Methylene-4-oxopentanedioic acid, also known as 4-carboxy-2-oxo-4-pentenoate, belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. 2-Methylene-4-oxopentanedioic acid exists in all living organisms, ranging from bacteria to humans. 2-Methylene-4-oxopentanedioic acid has been detected, but not quantified in, nuts. This could make 2-methylene-4-oxopentanedioic acid a potential biomarker for the consumption of these foods. 2-Methylene-4-oxopentanedioic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 2-Methylene-4-oxopentanedioic 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
2-Methylidene-4-oxopentanedioic acid	Kegg
4-Carboxy-2-oxo-4-pentenoate	Kegg
2-Methylidene-4-oxopentanedioate	Generator
4-Carboxy-2-oxo-4-pentenoic acid	Generator
2-Methylene-4-oxopentanedioate	Generator
2-Methylene-4-oxoglutaric acid	HMDB
g-Methylene-a-ketoglutaric acid	HMDB
2-Methylene-4-oxo-pentanedioate	Generator
2-oxo-4-Methylenepentanedioate	Generator

Chemical Formula

C₆H₆O₅

Average Molecular Weight

158.1088

Monoisotopic Molecular Weight

158.021523302

IUPAC Name

2-methylidene-4-oxopentanedioic acid

Traditional Name

4-methylene-2-oxoglutarate

CAS Registry Number

Not Available

SMILES

OC(=O)C(=C)CC(=O)C(O)=O

InChI Identifier

InChI=1S/C6H6O5/c1-3(5(8)9)2-4(7)6(10)11/h1-2H2,(H,8,9)(H,10,11)

InChI Key

OARCEFMISOKEKI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Gamma-keto acids and derivatives

Direct Parent

Gamma-keto acids and derivatives

Alternative Parents

Substituents

Gamma-keto acid
Branched fatty acid
Short-chain keto acid
Alpha-keto acid
Dicarboxylic acid or derivatives
Unsaturated fatty acid
Fatty acyl
Alpha-hydroxy ketone
Ketone
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

oxo carboxylic acid (CHEBI:1898 )
Dicarboxylic acids (LMFA01170047 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037759)
Cytoplasm (HMDB: HMDB0037759)

Source

Exogenous

Exogenous (HMDB: HMDB0037759)

Food

Nut

Nuts (FooDB: FOOD00869)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	5.27 g/L	ALOGPS
logP	0.08	ALOGPS
logP	0.34	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	2.76	ChemAxon
pKa (Strongest Basic)	-9.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	33.26 m³·mol⁻¹	ChemAxon
Polarizability	13 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
DeepCCS	[M+H]+	130.092	30932474
DeepCCS	[M-H]-	126.264	30932474
DeepCCS	[M-2H]-	163.563	30932474
DeepCCS	[M+Na]+	139.102	30932474
AllCCS	[M+H]+	135.2	32859911
AllCCS	[M+H-H2O]+	131.2	32859911
AllCCS	[M+NH4]+	138.9	32859911
AllCCS	[M+Na]+	140.0	32859911
AllCCS	[M-H]-	127.7	32859911
AllCCS	[M+Na-2H]-	129.5	32859911
AllCCS	[M+HCOO]-	131.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methylene-4-oxopentanedioic acid	OC(=O)C(=C)CC(=O)C(O)=O	2305.6	Standard polar	33892256
2-Methylene-4-oxopentanedioic acid	OC(=O)C(=C)CC(=O)C(O)=O	1341.0	Standard non polar	33892256
2-Methylene-4-oxopentanedioic acid	OC(=O)C(=C)CC(=O)C(O)=O	1463.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Methylene-4-oxopentanedioic acid,1TMS,isomer #1	C=C(CC(=O)C(=O)O)C(=O)O[Si](C)(C)C	1460.2	Semi standard non polar	33892256
2-Methylene-4-oxopentanedioic acid,1TMS,isomer #2	C=C(CC(=O)C(=O)O[Si](C)(C)C)C(=O)O	1429.9	Semi standard non polar	33892256
2-Methylene-4-oxopentanedioic acid,1TMS,isomer #3	C=C(C=C(O[Si](C)(C)C)C(=O)O)C(=O)O	1565.9	Semi standard non polar	33892256
2-Methylene-4-oxopentanedioic acid,2TMS,isomer #1	C=C(CC(=O)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1549.5	Semi standard non polar	33892256
2-Methylene-4-oxopentanedioic acid,2TMS,isomer #2	C=C(C=C(O[Si](C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C	1620.1	Semi standard non polar	33892256
2-Methylene-4-oxopentanedioic acid,2TMS,isomer #3	C=C(C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O	1595.9	Semi standard non polar	33892256
2-Methylene-4-oxopentanedioic acid,3TMS,isomer #1	C=C(C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1611.5	Semi standard non polar	33892256
2-Methylene-4-oxopentanedioic acid,3TMS,isomer #1	C=C(C=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1564.7	Standard non polar	33892256
2-Methylene-4-oxopentanedioic acid,1TBDMS,isomer #1	C=C(CC(=O)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	1694.2	Semi standard non polar	33892256
2-Methylene-4-oxopentanedioic acid,1TBDMS,isomer #2	C=C(CC(=O)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	1673.0	Semi standard non polar	33892256
2-Methylene-4-oxopentanedioic acid,1TBDMS,isomer #3	C=C(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O	1782.9	Semi standard non polar	33892256
2-Methylene-4-oxopentanedioic acid,2TBDMS,isomer #1	C=C(CC(=O)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1997.0	Semi standard non polar	33892256
2-Methylene-4-oxopentanedioic acid,2TBDMS,isomer #2	C=C(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2073.7	Semi standard non polar	33892256
2-Methylene-4-oxopentanedioic acid,2TBDMS,isomer #3	C=C(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2045.0	Semi standard non polar	33892256
2-Methylene-4-oxopentanedioic acid,3TBDMS,isomer #1	C=C(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2263.7	Semi standard non polar	33892256
2-Methylene-4-oxopentanedioic acid,3TBDMS,isomer #1	C=C(C=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2110.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylene-4-oxopentanedioic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03du-9400000000-81a3083c94780ee6323b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylene-4-oxopentanedioic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00y0-9620000000-3344cc5d1e92eee5e1a9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylene-4-oxopentanedioic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylene-4-oxopentanedioic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 10V, Positive-QTOF	splash10-0bt9-1900000000-17aef9adbe7e535d1ffa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 20V, Positive-QTOF	splash10-03xs-8900000000-7b5f27985e9bb72f81f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 40V, Positive-QTOF	splash10-014i-9100000000-52fdc268b6e52b7c1f2e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 10V, Negative-QTOF	splash10-0a4i-0900000000-0b7020a966666da8b45d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 20V, Negative-QTOF	splash10-03xr-6900000000-e2547b7568b2bba09116	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 40V, Negative-QTOF	splash10-014l-9100000000-86549e52114ff94d73c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 10V, Negative-QTOF	splash10-0900-3900000000-7650ff0d40f36ed5f00c	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 20V, Negative-QTOF	splash10-014i-9100000000-0a89795103a146e12003	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 40V, Negative-QTOF	splash10-014l-9000000000-58868b223aba342f62c7	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 10V, Positive-QTOF	splash10-0295-9500000000-66ebaa22cffbf3a55f13	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 20V, Positive-QTOF	splash10-00ko-9000000000-1afef919158b681142d5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylene-4-oxopentanedioic acid 40V, Positive-QTOF	splash10-00ko-9000000000-21f482923176566f4842	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB019205

KNApSAcK ID

Not Available

Chemspider ID

389673

KEGG Compound ID

C06035

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440813

PDB ID

Not Available

ChEBI ID

1898

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2-Methylene-4-oxopentanedioic acid (HMDB0037759)

MOL for HMDB0037759 (2-Methylene-4-oxopentanedioic acid)

3D MOL for HMDB0037759 (2-Methylene-4-oxopentanedioic acid)

3D SDF for HMDB0037759 (2-Methylene-4-oxopentanedioic acid)

3D-SDF for HMDB0037759 (2-Methylene-4-oxopentanedioic acid)

PDB for HMDB0037759 (2-Methylene-4-oxopentanedioic acid)

3D PDB for HMDB0037759 (2-Methylene-4-oxopentanedioic acid)

SMILES for HMDB0037759 (2-Methylene-4-oxopentanedioic acid)

INCHI for HMDB0037759 (2-Methylene-4-oxopentanedioic acid)

Structure for HMDB0037759 (2-Methylene-4-oxopentanedioic acid)

3D Structure for HMDB0037759 (2-Methylene-4-oxopentanedioic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra