You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2008-10-15 12:12:16 UTC
Update Date2016-02-11 01:20:04 UTC
HMDB IDHMDB10720
Secondary Accession NumbersNone
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
2-Butenoic acidKegg
Crotonic acidKegg
3-Methylacrylic acidKegg
2-ButenoateGenerator
But-2-enoateGenerator
CrotonateGenerator
3-MethylacrylateGenerator
(2E)-2-ButenoateHMDB
(2E)-2-Butenoic acidHMDB
(2E)-But-2-enoateHMDB
(2E)-But-2-enoic acidHMDB
(e)-2-ButenoateHMDB
(e)-2-Butenoic acidHMDB
(e)-But-2-enoateHMDB
(e)-But-2-enoic acidHMDB
(e)-Crotonic acidHMDB
3-Methyl-acrylic acidHMDB
a-ButenoateHMDB
a-Butenoic acidHMDB
a-Crotonic acidHMDB
alpha-ButenoateHMDB
alpha-Butenoic acidHMDB
alpha-Crotonic acidHMDB
b-Methylacrylic acidHMDB
BEOHMDB
beta-Methacrylic acidHMDB
beta-Methylacrylic acidHMDB
ButenoateHMDB
Butenoic acidHMDB
Kyselina krotonovaHMDB
Solid crotonic acidHMDB
trans-2-ButenoateHMDB
trans-2-Butenoic acidHMDB
trans-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 KeyInChIKey=LDHQCZJRKDOVOX-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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 Solubility101.0 mg/mLALOGPS
logP0.94ALOGPS
logP0.92ChemAxon
logS0.07ALOGPS
pKa (Strongest Acidic)4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.96 m3·mol-1ChemAxon
Polarizability8.44 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Fatty Acid BiosynthesisSMP00456Not 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
NuGOwiki LinkHMDB10720
Metagene LinkHMDB10720
METLIN IDNot Available
PubChem Compound637090
PDB IDBEO
ChEBI ID41131
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available