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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:05:20 UTC
Update Date2023-02-21 17:28:19 UTC
HMDB IDHMDB0040531
Secondary Accession Numbers
  • HMDB40531
Metabolite Identification
Common Name2-Hydroxy-4-oxopentanoic acid
Description2-Hydroxy-4-oxopentanoic acid is found in alcoholic beverages. 2-Hydroxy-4-oxopentanoic acid is formed in beer wort fermentation Alitretinoin (9-cis-retinoic acid) is a naturally-occurring endogenous retinoid indicated for topical treatment of cutaneous lesions in patients with AIDS-related Kaposi's sarcoma. Alitretinoin inhibits the growth of Kaposi's sarcoma (KS) cells in vitro. Retinoic acid is the oxidized form of Vitamin A. It functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately control anterior/posterior patterning in early developmental stages. Retinoic acid acts by binding to heterodimers of the retinoic acid receptor (RAR) and the retinoid X receptor (RXR), which then bind to retinoic acid response elements (RAREs) in the regulatory regions of direct targets (including Hox genes), thereby activating gene transcription. Retinoic acid receptors mediate transcription of different sets of genes of cell differentiation, thus it also depends on the target cells. 2-Hydroxy-4-oxopentanoic acid is one of the target genes is the gene of the retinoic acid receptor itself which occurs during positive regulation. Control of retinoic acid levels is maintained by a suite of proteins. Retinoic acid is the oxidized form of Vitamin A. It functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately controls anterior/posterior patterning in early developmental stages (PMID: 17495912 ). It is an important regulator of gene expression during growth and development, and in neoplasms. Tretinoin, also known as retinoic acid and derived from maternal vitamin A, is essential for normal growth and embryonic development. 2-Hydroxy-4-oxopentanoic acid is an excess of tretinoin can be teratogenic. It is used in the treatment of psoriasis; acne vulgaris; and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute).
Structure
Data?1677000499
Synonyms
ValueSource
2-Hydroxy-4-oxopentanoateGenerator
2-Hydroxy-4-oxovaleric acidHMDB
a-Hydroxy-b-acetylpropionic acidHMDB
a-Hydroxylevulinic acidHMDB
Acetolactic acidHMDB
Chemical FormulaC5H8O4
Average Molecular Weight132.1146
Monoisotopic Molecular Weight132.042258744
IUPAC Name2-hydroxy-4-oxopentanoic acid
Traditional Name2-hydroxy-4-oxopentanoic acid
CAS Registry Number54031-97-9
SMILES
CC(=O)CC(O)C(O)=O
InChI Identifier
InChI=1S/C5H8O4/c1-3(6)2-4(7)5(8)9/h4,7H,2H2,1H3,(H,8,9)
InChI KeyQTSNVMMGKAPSRT-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassGamma-keto acids and derivatives
Direct ParentGamma-keto acids and derivatives
Alternative Parents
Substituents
  • Gamma-keto acid
  • Short-chain keto acid
  • Alpha-hydroxy acid
  • Beta-hydroxy ketone
  • Hydroxy acid
  • Secondary alcohol
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point181 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP6.30Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility181 g/LALOGPS
logP-0.9ALOGPS
logP-0.78ChemAxon
logS0.14ALOGPS
pKa (Strongest Acidic)3.6ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.43 m³·mol⁻¹ChemAxon
Polarizability11.97 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.76231661259
DarkChem[M-H]-123.24631661259
DeepCCS[M+H]+126.10830932474
DeepCCS[M-H]-123.32530932474
DeepCCS[M-2H]-159.79830932474
DeepCCS[M+Na]+134.64630932474
AllCCS[M+H]+131.332859911
AllCCS[M+H-H2O]+127.132859911
AllCCS[M+NH4]+135.132859911
AllCCS[M+Na]+136.232859911
AllCCS[M-H]-124.632859911
AllCCS[M+Na-2H]-127.332859911
AllCCS[M+HCOO]-130.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Hydroxy-4-oxopentanoic acidCC(=O)CC(O)C(O)=O2461.8Standard polar33892256
2-Hydroxy-4-oxopentanoic acidCC(=O)CC(O)C(O)=O946.6Standard non polar33892256
2-Hydroxy-4-oxopentanoic acidCC(=O)CC(O)C(O)=O1201.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Hydroxy-4-oxopentanoic acid,1TMS,isomer #1CC(=O)CC(O[Si](C)(C)C)C(=O)O1246.7Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,1TMS,isomer #2CC(=O)CC(O)C(=O)O[Si](C)(C)C1212.3Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,1TMS,isomer #3CC(=CC(O)C(=O)O)O[Si](C)(C)C1328.6Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,1TMS,isomer #4C=C(CC(O)C(=O)O)O[Si](C)(C)C1315.9Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,2TMS,isomer #1CC(=O)CC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1341.2Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,2TMS,isomer #2CC(=CC(O[Si](C)(C)C)C(=O)O)O[Si](C)(C)C1462.0Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,2TMS,isomer #3C=C(CC(O[Si](C)(C)C)C(=O)O)O[Si](C)(C)C1402.6Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,2TMS,isomer #4CC(=CC(O)C(=O)O[Si](C)(C)C)O[Si](C)(C)C1392.9Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,2TMS,isomer #5C=C(CC(O)C(=O)O[Si](C)(C)C)O[Si](C)(C)C1360.1Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,3TMS,isomer #1CC(=CC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C1499.7Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,3TMS,isomer #1CC(=CC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C1435.3Standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,3TMS,isomer #2C=C(CC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C1444.5Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,3TMS,isomer #2C=C(CC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)O[Si](C)(C)C1453.9Standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,1TBDMS,isomer #1CC(=O)CC(O[Si](C)(C)C(C)(C)C)C(=O)O1484.1Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,1TBDMS,isomer #2CC(=O)CC(O)C(=O)O[Si](C)(C)C(C)(C)C1448.2Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,1TBDMS,isomer #3CC(=CC(O)C(=O)O)O[Si](C)(C)C(C)(C)C1585.5Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,1TBDMS,isomer #4C=C(CC(O)C(=O)O)O[Si](C)(C)C(C)(C)C1545.1Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,2TBDMS,isomer #1CC(=O)CC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1768.0Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,2TBDMS,isomer #2CC(=CC(O[Si](C)(C)C(C)(C)C)C(=O)O)O[Si](C)(C)C(C)(C)C1928.6Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,2TBDMS,isomer #3C=C(CC(O[Si](C)(C)C(C)(C)C)C(=O)O)O[Si](C)(C)C(C)(C)C1823.2Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,2TBDMS,isomer #4CC(=CC(O)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1838.7Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,2TBDMS,isomer #5C=C(CC(O)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1806.2Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,3TBDMS,isomer #1CC(=CC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2123.7Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,3TBDMS,isomer #1CC(=CC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2071.0Standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,3TBDMS,isomer #2C=C(CC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2067.9Semi standard non polar33892256
2-Hydroxy-4-oxopentanoic acid,3TBDMS,isomer #2C=C(CC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2059.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-4-oxopentanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-e66d04210bcdaaec0f1f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-4-oxopentanoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0076-9340000000-7e77e0de3e7fb51244212017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxy-4-oxopentanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 10V, Positive-QTOFsplash10-014i-7900000000-134b9829ef446615f81e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 20V, Positive-QTOFsplash10-014j-9300000000-8172fac34150117643bf2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 40V, Positive-QTOFsplash10-014l-9000000000-1ba9dbbb6e61f679b4c42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 10V, Negative-QTOFsplash10-001i-6900000000-18c236e3427ea498fa322015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 20V, Negative-QTOFsplash10-01w0-9300000000-431e5906f2009cacfd362015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 40V, Negative-QTOFsplash10-0avu-9000000000-12a74b10e2c2bfca1fb92015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 10V, Negative-QTOFsplash10-01q9-7900000000-c98cddec2196e78ceb4d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 20V, Negative-QTOFsplash10-0006-9000000000-7df4f2d0321e470c3da62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 40V, Negative-QTOFsplash10-052f-9000000000-3f203d80defce9fc94252021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 10V, Positive-QTOFsplash10-014r-9000000000-8ebf358e48c5c00cee6f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 20V, Positive-QTOFsplash10-0006-9000000000-d5b8515c60ed019f79b82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxy-4-oxopentanoic acid 40V, Positive-QTOFsplash10-0006-9000000000-3a78789c386089a42b492021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB020299
KNApSAcK IDNot Available
Chemspider ID8278736
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10103208
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Holland LZ: Developmental biology: a chordate with a difference. Nature. 2007 May 10;447(7141):153-5. [PubMed:17495912 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .