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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-10-15 12:12:16 UTC
Update Date2017-10-23 19:05:45 UTC
HMDB IDHMDB0010720
Secondary Accession Numbers
  • HMDB10720
Metabolite Identification
Common NameBut-2-enoic acid
DescriptionBut-2-enoic acid is fatty acid formed by the action of fatty acid synthases from acetyl-CoA and malonyl-CoA precursors. It is involved in the fatty acid biosynthesis. Specifically, it is the product of reaction between (R)-3-Hydroxybutyric acid and fatty acid synthase.
Structure
Thumb
Synonyms
ValueSource
(2E)-2-Butenoic acidChEBI
(e)-2-Butenoic acidChEBI
(e)-But-2-enoic acidChEBI
(e)-Crotonic acidChEBI
2-Butenoic acidChEBI
3-Methylacrylic acidChEBI
alpha-Butenoic acidChEBI
alpha-Crotonic acidChEBI
BEOChEBI
beta-Methacrylic acidChEBI
beta-Methylacrylic acidChEBI
trans-2-Butenoic acidChEBI
trans-Crotonic acidChEBI
(2E)-2-ButenoateGenerator
But-2-enoateGenerator
(e)-2-ButenoateGenerator
(e)-But-2-enoateGenerator
(e)-CrotonateGenerator
2-ButenoateGenerator
3-MethylacrylateGenerator
a-ButenoateGenerator
a-Butenoic acidGenerator
alpha-ButenoateGenerator
α-butenoateGenerator
α-butenoic acidGenerator
a-CrotonateGenerator
a-Crotonic acidGenerator
alpha-CrotonateGenerator
α-crotonateGenerator
α-crotonic acidGenerator
b-MethacrylateGenerator
b-Methacrylic acidGenerator
beta-MethacrylateGenerator
β-methacrylateGenerator
β-methacrylic acidGenerator
b-MethylacrylateGenerator
b-Methylacrylic acidGenerator
beta-MethylacrylateGenerator
β-methylacrylateGenerator
β-methylacrylic acidGenerator
trans-2-ButenoateGenerator
trans-CrotonateGenerator
(2E)-But-2-enoateHMDB
(2E)-But-2-enoic acidHMDB
3-Methyl-acrylic acidHMDB
ButenoateHMDB
Butenoic acidHMDB
Crotonic acidHMDB
Kyselina krotonovaHMDB
Solid crotonic acidHMDB
Chemical FormulaC4H6O2
Average Molecular Weight86.0892
Monoisotopic Molecular Weight86.036779436
IUPAC Name(2E)-but-2-enoic acid
Traditional Namebutenoic acid
CAS Registry Number3724-65-0
SMILES
C\C=C\C(O)=O
InChI Identifier
InChI=1S/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/b3-2+
InChI KeyLDHQCZJRKDOVOX-NSCUHMNNSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentStraight chain fatty acids
Alternative Parents
Substituents
  • Unsaturated fatty acid
  • Straight chain 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:

  Subcellular:

  Biofluid and excreta:

Source:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

Role

Industrial application:

  Pharmaceutical industry:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point72 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.72HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility101 g/LALOGPS
logP0.94ALOGPS
logP0.92ChemAxon
logS0.07ALOGPS
pKa (Strongest Acidic)4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.96 m³·mol⁻¹ChemAxon
Polarizability8.44 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000l-9000000000-c066ee0b8aa28cc564f5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9000000000-dcef1149fbd6447033adView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0103-9100000000-bb87072a7225402c6d0eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-139e86f163451c657b84View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-b1e1c9a0bcfd328b1cd9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-e0d8bcef7823a57ace6bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-f496e2b96544aa9df21dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-9000000000-1dc3bc86132e73942861View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ko-9000000000-d17c17c2c66a97ee9c27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-4cd5b916c7ee6039effcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-dde621f263ff3ac72841View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-9000000000-dce352f985fb5e143263View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-acd6176b8c6ebe251635View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Fatty Acid BiosynthesisPw000167Pw000167 greyscalePw000167 simpleNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003282
KNApSAcK IDNot Available
Chemspider ID552744
KEGG Compound IDC01771
BioCyc ID1OXO2YLIDENE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound637090
PDB IDBEO
ChEBI ID41131
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.