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Record Information
Version	2.0
Creation Date	2012-05-31 14:24:21 -0600
Update Date	2015-10-15 16:14:56 -0600
Secondary Accession Numbers	ECMDB20041
Identification
Name:	2-Hydroxy-2,4-pentadienoate
Description	2-hydroxy-2,4-pentadienoate is a member of the chemical class known as Unsaturated Fatty Acids. These are fatty acids whose chain contains at least one CC double bond.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xae6e0830> Close
Synonyms:	(2E)-2-hydroxypenta-2,4-dienoate (2E)-2-hydroxypenta-2,4-dienoic acid 2-Hydroxy-2,4-pentadienoate 2-Hydroxy-2,4-pentadienoic acid 2-Hydroxypent-2,4-dienoate 2-Hydroxypent-2,4-dienoic acid 2-Hydroxypenta-2,4-dienoate 2-Hydroxypenta-2,4-dienoic acid 2-Oxopent-4-enoate 2-Oxopent-4-enoic acid cis-2-hydroxypenta-2,4-dienoate Cis-2-Hydroxypenta-2,4-dienoate Cis-2-Hydroxypenta-2,4-dienoic acid HPD Oxopent-4-enoate Oxopent-4-enoic acid
Chemical Formula:	C5H6O3
Weight:	Average: 114.0993 Monoisotopic: 114.031694058
InChI Key:	NOXRYJAWRSNUJD-UHFFFAOYSA-N
InChI:	InChI=1S/C5H6O3/c1-2-3-4(6)5(7)8/h2H,1,3H2,(H,7,8)
CAS number:	159694-16-3
IUPAC Name:	2-oxopent-4-enoate
Traditional IUPAC Name:	oxopent-4-enoate
SMILES:	OC(=O)C(=O)CC=C
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	Unsaturated fatty acids Alpha-keto acids and derivatives Ketones Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Organic anions
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 )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
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 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 38.1 m³·mol⁻¹ ChemAxon Polarizability 9.98 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Water + 2-Hydroxy-6-ketononadienedicarboxylate > Hydrogen ion + 2-Hydroxy-2,4-pentadienoate + Succinic acid Water + 2-Hydroxy-6-ketononatrienedioate > Fumaric acid + Hydrogen ion + 2-Hydroxy-2,4-pentadienoate Water + 2-Hydroxy-2,4-pentadienoate <> 4-Hydroxy-2-oxopentanoate 2-Hydroxy-2,4-pentadienoate + Succinic acid <> 2-Hydroxy-6-ketononadienedicarboxylate + Water 2-Hydroxy-6-ketononatrienedioate + Water <> 2-Hydroxy-2,4-pentadienoate + Fumaric acid 2-Hydroxy-2,4-pentadienoate > 2-oxopent-4-enoate 4-Hydroxy-2-oxopentanoate > 2-Hydroxy-2,4-pentadienoate + Water 2-Hydroxy-6-ketononatrienedioate + Water > Hydrogen ion + Fumaric acid + 2-Hydroxy-2,4-pentadienoate + 2-Hydroxy-2,4-pentadienoate 2-oxopent-4-enoate + 2-Hydroxy-2,4-pentadienoate > Water + 4-hydroxy-2-oxopentanoate + 4-Hydroxy-2-oxopentanoate
SMPDB Pathways:	2-Oxopent-4-enoate metabolism PW001890 2-Oxopent-4-enoate metabolism 2 PW002035 Phenylalanine metabolism PW000921
KEGG Pathways:	1,4-Dichlorobenzene degradation ec00627 Benzoate degradation via hydroxylation ec00362 Biphenyl degradation ec00621 Carbazole degradation ec00629 Ethylbenzene degradation ec00642 Fluorene degradation ec00628 Metabolic pathways eco01100 Microbial metabolism in diverse environments ec01120 Phenylalanine metabolism ec00360 Styrene degradation ec00643 Toluene and xylene degradation ec00622
EcoCyc Pathways:	3-phenylpropionate and 3-(3-hydroxyphenyl)propionate degradation to 2-oxopent-4-enoate HCAMHPDEG-PWY cinnamate and 3-hydroxycinnamate degradation to 2-oxopent-4-enoate PWY-6690
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03di-6900000000-a66b8824dd2fc937a92a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-014i-9200000000-82e5d9ac6d1152499ff7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-014l-9000000000-3c4fc3ad8127ca6d94e4 View in MoNA
References
References:	Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 1113 HMDB ID Not Available Pubchem Compound ID 5280361 Kegg ID C00596 ChemSpider ID 951 Wikipedia ID 2-Oxopent-4-enoic acid BioCyc ID CPD-6761 EcoCyc ID CPD-6761

Enzymes