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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-02-23 10:17:33 UTC
Update Date2019-07-23 05:45:08 UTC
HMDB IDHMDB0001862
Secondary Accession Numbers
  • HMDB01862
Metabolite Identification
Common Name2-Ethylacrylic acid
Description2-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?1563860708
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)HMDB
2-Ethyl acrylateGenerator
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

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zi0-9000000000-6b4a6a9b2cdfefbc13b6JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-9200000000-2de270e55791bfa7fd7fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0zfr-9200000000-70057d2e916fe5d099e3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0k96-9000000000-404d85eb01c55fd5afccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-e2c0d6b93c24ab9497f9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-9600000000-ece9444150a982f96fa9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-9100000000-98d86f481b2b53f907ceJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-783f10b701ddd96d62d6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-34b601fb3823c5cc58deJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-9000000000-eb97529a41ea9247efcdJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9000000000-6388eb5218c3ba821c34JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
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
FoodDB 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
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