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Record Information
Version	2.0
Creation Date	2012-05-31 14:26:54 -0600
Update Date	2015-09-17 15:41:53 -0600
Secondary Accession Numbers	ECMDB20090
Identification
Name:	4-Hydroxy-2-oxopentanoate
Description	4-hydroxy-2-oxopentanoate is a member of the chemical class known as Straight Chain Fatty Acids. These are fatty acids with a straight aliphatic chain. 4-hydroxy-2-oxopentanoate is invovled in Phenylpropionic acid degradation. r 15;80(8):2939-48.)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xac8ab8ec> Close
Synonyms:	2-Oxo-4-hydroxyvalerate 2-Oxo-4-hydroxyvaleric acid 2-oxo-4S-hydroxypentanoate 2-Oxo-4S-hydroxypentanoate 2-Oxo-4S-hydroxypentanoic acid 20-Hydroxyleukotriene E4 20-OH-Leukotriene E4 4-Hydroxy-2-keto-pentanoate 4-Hydroxy-2-keto-pentanoic acid 4-Hydroxy-2-ketovalerate 4-Hydroxy-2-ketovaleric acid 4-Hydroxy-2-oxo-pentanoate 4-Hydroxy-2-oxo-pentanoic acid 4-Hydroxy-2-oxo-valerate 4-Hydroxy-2-oxo-valeric acid 4-Hydroxy-2-oxopentanoate 4-Hydroxy-2-oxopentanoic acid 4-Hydroxy-2-oxovalerate 4-Hydroxy-2-oxovaleric acid HKP
Chemical Formula:	C5H7O4
Weight:	Average: 131.108 Monoisotopic: 131.034982285
InChI Key:	HFKQINMYQUXOCH-UHFFFAOYSA-M
InChI:	InChI=1S/C5H8O4/c1-3(6)2-4(7)5(8)9/h3,6H,2H2,1H3,(H,8,9)/p-1
CAS number:	3318-73-8
IUPAC Name:	4-hydroxy-2-oxopentanoic acid
Traditional IUPAC Name:	4-hydroxy-2-oxopentanoic acid
SMILES:	CC(O)CC(=O)C([O-])=O
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	Methyl-branched fatty acids Hydroxy fatty acids Beta-hydroxy ketones Alpha-keto acids and derivatives Alpha-hydroxy ketones Secondary alcohols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives
Substituents	Branched fatty acid Hydroxy fatty acid Short-chain keto acid Methyl-branched fatty acid Alpha-keto acid Beta-hydroxy ketone Fatty acyl Alpha-hydroxy ketone Secondary alcohol Ketone Monocarboxylic acid or derivatives Carboxylic acid Carboxylic acid derivative Organooxygen compound Carbonyl group Alcohol Hydrocarbon derivative Organic oxide Organic oxygen compound Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	2-oxo monocarboxylic acid (CHEBI:17655 ) 4-hydroxy monocarboxylic acid (CHEBI:17655 )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 116 g/L ALOGPS logP -0.67 ALOGPS logP -0.098 ChemAxon logS -0.06 ALOGPS pKa (Strongest Acidic) 3.11 ChemAxon pKa (Strongest Basic) -2.6 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 74.6 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 28.81 m³·mol⁻¹ ChemAxon Polarizability 11.94 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-2,4-pentadienoate <> 4-Hydroxy-2-oxopentanoate 4-Hydroxy-2-oxopentanoate > Acetaldehyde + Pyruvic acid Acetaldehyde + Pyruvic acid <> 4-Hydroxy-2-oxopentanoate 2-oxopent-4-enoate + Water > 4-Hydroxy-2-oxopentanoate 4-Hydroxy-2-oxopentanoate <> Acetaldehyde + Pyruvic acid 4-Hydroxy-2-oxopentanoate > 2-Hydroxy-2,4-pentadienoate + Water 2-oxopent-4-enoate + 2-Hydroxy-2,4-pentadienoate > Water + 4-hydroxy-2-oxopentanoate + 4-Hydroxy-2-oxopentanoate 4-hydroxy-2-oxopentanoate + 4-Hydroxy-2-oxopentanoate > Pyruvic acid + Acetaldehyde
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:	2-oxopentenoate degradation PWY-5162
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-014i-6900000000-77bd80438bf057c3f58e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-014j-9300000000-a558ba74d348e4ce38ed View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-00kf-9000000000-ad259a6c26684bb147ba View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-001r-8900000000-69a9d304a48dae20f25f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-000i-9300000000-b1c81e0d0119b884c932 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-00kf-9000000000-31da0362cef94ddab3c8 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 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 17655 HMDB ID HMDB12639 Pubchem Compound ID 124 Kegg ID C03589 ChemSpider ID 121 Wikipedia ID Not Available BioCyc ID 4-HYDROXY-2-KETOVALERATE EcoCyc ID 4-HYDROXY-2-KETOVALERATE

Enzymes