MiMeDB: Showing metabocard for 2-oxopent-4-enoic acid (MMDBc0054185)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:57:54 UTC

Update Date

2025-10-07 16:08:24 UTC

Metabolite ID

MMDBc0054185

Metabolite Identification

Common Name

2-oxopent-4-enoic acid

Description

2-oxopent-4-enoic acid is a keto acid that belongs to the class of organic compounds known as carboxylic acids. It features a double bond between the fourth and fifth carbon atoms and a keto group at the second carbon, which contributes to its reactivity and involvement in various metabolic pathways. This compound has been implicated in the degradation of aromatic compounds, as evidenced by its identification as an intermediate in the metabolism of 2-hydroxymuconic 6-semialdehyde, where it is produced alongside 4-oxalocrotonic acid and 4-hydroxy-2-oxovaleric acid, ultimately leading to the formation of pyruvic acid (PMID:17090920 ). Additionally, 2-oxopent-4-enoic acid has been observed as a product in the metabolic pathways of catechol and 3-methylcatechol, demonstrating its role as a key intermediate in the catabolism of these aromatic compounds (PMID:5767053 ). Its structural features and involvement in these pathways highlight its significance in biochemical processes related to the breakdown of complex organic molecules.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Oxopent-4-enoate	ChEBI
Oxopent-4-enoic acid	Generator
2-Oxopent-4-enoic acid	Generator
2-Hydroxy-2,4-pentadienoic acid	Generator

Molecular Formula

C₅H₅O₃

Average Mass

113.093

Monoisotopic Mass

113.024417601

IUPAC Name

2-oxopent-4-enoate

Traditional Name

oxopent-4-enoate

CAS Registry Number

Not Available

SMILES

[O-]C(=O)C(=O)CC=C

InChI Identifier

InChI=1S/C5H6O3/c1-2-3-4(6)5(7)8/h2H,1,3H2,(H,7,8)/p-1

InChI Key

NOXRYJAWRSNUJD-UHFFFAOYSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-chain keto acids and derivatives

Alternative Parents

Substituents

Short-chain keto acid
Fatty acyl
Unsaturated fatty acid
Alpha-keto acid
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-oxo monocarboxylic acid anion (CHEBI:11641 )
a tautomer (OXOPENTENOATE )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	22.1 g/L	ALOGPS
logP	-0.21	ALOGPS
logP	0.91	ChemAxon
logS	-0.77	ALOGPS
pKa (Strongest Acidic)	3.26	ChemAxon
pKa (Strongest Basic)	-9.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.2 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	38.1 m³·mol⁻¹	ChemAxon
Polarizability	9.98 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-6900000000-a66b8824dd2fc937a92a	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-9200000000-82e5d9ac6d1152499ff7	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9000000000-3c4fc3ad8127ca6d94e4	2019-02-23	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	302.1
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	72.2
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-24	339.3
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	507.7
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	356.6
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	416.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	1482.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	222.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	691.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	361.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	337.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-24	295.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	153.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	129.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	626.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	132.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	345.5
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1059.8
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	901.6

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	2-oxopent-4-enoic acid_TMS_1	C=CC=C(O[Si](C)(C)C)C(=O)[O-]	standard non polar	2025-10-24	1786.99
Gas Chromatography	2-oxopent-4-enoic acid_TMS_1	C=CC=C(O[Si](C)(C)C)C(=O)[O-]	standard polar	2025-10-24	1871.63

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018846	2-oxopent-4-enoic acid	4-Hydroxy-2-oxopentanoate	2-keto-4-pentenoate hydratase	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0018874	2-oxopent-4-enoic acid	4-Hydroxy-2-oxopentanoate	Unknown Protein		PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites
Bacteria	Proteobacteria	4	Human ; Human subgingival plaque; Human supragingival plaque; Human feces
Bacteria/Eubacteria	Proteobacteria	6	Human ; Human subgingival plaque; Human supragingival plaque; Human feces
Bacteria/Eubacteria	Actinobacteria	2	Human

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Oxopent-4-enoic acid

METLIN ID

Not Available

PubChem Compound

9543147

PDB ID

Not Available

ChEBI ID

11641

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 2-oxopent-4-enoic acid (MMDBc0054185)

MOL for #<Metabolite:0x00007f9ad0f3c7b8>

3D MOL for #<Metabolite:0x00007f9ad0f3c7b8>

3D SDF for #<Metabolite:0x00007f9ad0f3c7b8>

3D-SDF for #<Metabolite:0x00007f9ad0f3c7b8>

PDB for #<Metabolite:0x00007f9ad0f3c7b8>

3D PDB for #<Metabolite:0x00007f9ad0f3c7b8>

SMILES for #<Metabolite:0x00007f9ad0f3c7b8>

INCHI for #<Metabolite:0x00007f9ad0f3c7b8>

Structure for #<Metabolite:0x00007f9ad0f3c7b8>

3D Structure for #<Metabolite:0x00007f9ad0f3c7b8>