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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-02-23 10:17:33 UTC
Update Date2022-03-07 02:49:11 UTC
HMDB IDHMDB0001862
Secondary Accession Numbers
  • HMDB01862
Metabolite Identification
Common Name2-Ethylacrylic acid
Description2-ethylacrylic acid is an alpha, beta-unsaturated monocarboxylic acid that is acrylic acid in which the hydrogen at position 2 is substituted by an ethyl group. It has a role as a mammalian metabolite. It derives from an acrylic acid. It is a conjugate acid of a 2-ethylacrylate. 2-Ethylacrylic acid is an intermediate metabolite in the conversion of R-2-methylbutyrate into 2-ethylhydracrylic acid, which is variably increased in defects of isoleucine oxidation at distal steps in the catabolic pathway (3-oxoacyl-CoA thiolase deficiency and methylmalonyl-CoA mutase deficiency) (PMID 1016232 ).
Structure
Data?1582752213
Synonyms
ValueSource
2-Ethyl-2-propenoic acidChEBI
2-Ethylpropenoic acidChEBI
alpha-Methylene-butanoic acidChEBI
2-Ethyl-2-propenoateGenerator
2-EthylpropenoateGenerator
a-Methylene-butanoateGenerator
a-Methylene-butanoic acidGenerator
alpha-Methylene-butanoateGenerator
Α-methylene-butanoateGenerator
Α-methylene-butanoic acidGenerator
2-EthylacrylateGenerator
2-Methylene-6ci,7ci,8ci)-butyrateHMDB
2-Methylene-6ci,7ci,8ci)-butyric acidHMDB
2-MethylenebutyrateHMDB
2-Methylenebutyric acidHMDB
EthacrylateHMDB
Ethacrylic acidHMDB
Poly(2-ethylacrylic acid)MeSH, HMDB
2-Ethyl acrylateGenerator, HMDB
Chemical FormulaC5H8O2
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
IUPAC Name2-methylidenebutanoic acid
Traditional Nameethacrylic acid
CAS Registry Number3586-58-1
SMILES
CCC(=C)C(O)=O
InChI Identifier
InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h2-3H2,1H3,(H,6,7)
InChI KeyWROUWQQRXUBECT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as branched fatty acids. These are fatty acids containing a branched chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentBranched fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Unsaturated fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility62.6 g/LALOGPS
logP1.23ALOGPS
logP1.37ChemAxon
logS-0.2ALOGPS
pKa (Strongest Acidic)4.97ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.25 m³·mol⁻¹ChemAxon
Polarizability10.26 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+121.53431661259
DarkChem[M-H]-114.41631661259
AllCCS[M+H]+126.03432859911
AllCCS[M-H]-124.17632859911
DeepCCS[M+H]+127.5230932474
DeepCCS[M-H]-124.72230932474
DeepCCS[M-2H]-161.15830932474
DeepCCS[M+Na]+135.73330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Ethylacrylic acidCCC(=C)C(O)=O1669.1Standard polar33892256
2-Ethylacrylic acidCCC(=C)C(O)=O873.3Standard non polar33892256
2-Ethylacrylic acidCCC(=C)C(O)=O844.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Ethylacrylic acid,1TMS,isomer #1C=C(CC)C(=O)O[Si](C)(C)C979.1Semi standard non polar33892256
2-Ethylacrylic acid,1TBDMS,isomer #1C=C(CC)C(=O)O[Si](C)(C)C(C)(C)C1203.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Ethylacrylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zi0-9000000000-6b4a6a9b2cdfefbc13b62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Ethylacrylic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-9200000000-2de270e55791bfa7fd7f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Ethylacrylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Ethylacrylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Ethylacrylic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0zfr-9200000000-70057d2e916fe5d099e32012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Ethylacrylic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0k96-9000000000-404d85eb01c55fd5afcc2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Ethylacrylic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0006-9000000000-e2c0d6b93c24ab9497f92012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 10V, Positive-QTOFsplash10-0ue9-9600000000-ece9444150a982f96fa92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 20V, Positive-QTOFsplash10-0a59-9100000000-98d86f481b2b53f907ce2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-783f10b701ddd96d62d62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 10V, Negative-QTOFsplash10-0002-9000000000-34b601fb3823c5cc58de2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 20V, Negative-QTOFsplash10-0a4j-9000000000-eb97529a41ea9247efcd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 40V, Negative-QTOFsplash10-0pb9-9000000000-6388eb5218c3ba821c342017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 10V, Negative-QTOFsplash10-0002-9000000000-5289cc75fe7aae11de792021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 20V, Negative-QTOFsplash10-0002-9000000000-56ee768a1b761e35d2f22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 40V, Negative-QTOFsplash10-0006-9000000000-1d7274ae3a0240fd08102021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 10V, Positive-QTOFsplash10-001i-9000000000-0cc8aed45af20d83ec922021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 20V, Positive-QTOFsplash10-0a4i-9000000000-2e3c92755ff0c48e1af82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Ethylacrylic acid 40V, Positive-QTOFsplash10-0a4r-9000000000-27e4bf52a3171b19db572021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • 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 IDFDB022716
KNApSAcK IDNot Available
Chemspider ID18085
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID4141
PubChem Compound19166
PDB IDNot Available
ChEBI ID84978
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceWang, Yan-jun; Wang, Yu-xia; Tang, Xiang-yang; Zhao, Wen-tao; Qi, Xin. Synthesis and characterization of 2-ethylacrylic acid. Shiyou Huagong (2003), 32(3), 251-253.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Mamer OA, Tjoa SS, Scriver CR, Klassen GA: Demonstration of a new mammalian isoleucine catabolic pathway yielding an Rseries of metabolites. Biochem J. 1976 Dec 15;160(3):417-26. [PubMed:1016232 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
2-Ethylacrylic acid → 3,4,5-trihydroxy-6-[(2-methylidenebutanoyl)oxy]oxane-2-carboxylic aciddetails