<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-10-03 18:12:30 UTC</creation_date>
  <update_date>2020-05-21 16:27:14 UTC</update_date>
  <accession>BMDB0010720</accession>
  <secondary_accessions>
    <accession>BMDB10720</accession>
  </secondary_accessions>
  <name>But-2-enoic acid</name>
  <description>But-2-enoic acid, also known as but-2-enoic acid or (2E)-But-2-enoic acid, belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. But-2-enoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. But-2-enoic acid exists in all living species, ranging from bacteria to humans. But-2-enoic acid participates in a number of enzymatic reactions, within cattle. In particular, But-2-enoic acid can be biosynthesized from 3-hydroxybutyric acid; which is catalyzed by the enzyme fatty acid synthase. dyhydrase domain. In addition, But-2-enoic acid can be converted into butyric acid through its interaction with the enzyme fatty acid synthase. enoyl reductase domain. In cattle, but-2-enoic acid is involved in the metabolic pathway called fatty acid biosynthesis pathway.</description>
  <synonyms>
    <synonym>(2E)-2-Butenoic acid</synonym>
    <synonym>(e)-2-Butenoic acid</synonym>
    <synonym>(e)-But-2-enoic acid</synonym>
    <synonym>(e)-Crotonic acid</synonym>
    <synonym>2-Butenoic acid</synonym>
    <synonym>3-Methylacrylic acid</synonym>
    <synonym>alpha-Butenoic acid</synonym>
    <synonym>alpha-Crotonic acid</synonym>
    <synonym>BEO</synonym>
    <synonym>beta-Methacrylic acid</synonym>
    <synonym>beta-Methylacrylic acid</synonym>
    <synonym>trans-2-Butenoic acid</synonym>
    <synonym>trans-Crotonic acid</synonym>
    <synonym>Crotonic acid</synonym>
    <synonym>(2E)-2-Butenoate</synonym>
    <synonym>(e)-2-Butenoate</synonym>
    <synonym>(e)-But-2-enoate</synonym>
    <synonym>(e)-Crotonate</synonym>
    <synonym>2-Butenoate</synonym>
    <synonym>3-Methylacrylate</synonym>
    <synonym>a-Butenoate</synonym>
    <synonym>a-Butenoic acid</synonym>
    <synonym>alpha-Butenoate</synonym>
    <synonym>Α-butenoate</synonym>
    <synonym>Α-butenoic acid</synonym>
    <synonym>a-Crotonate</synonym>
    <synonym>a-Crotonic acid</synonym>
    <synonym>alpha-Crotonate</synonym>
    <synonym>Α-crotonate</synonym>
    <synonym>Α-crotonic acid</synonym>
    <synonym>b-Methacrylate</synonym>
    <synonym>b-Methacrylic acid</synonym>
    <synonym>beta-Methacrylate</synonym>
    <synonym>Β-methacrylate</synonym>
    <synonym>Β-methacrylic acid</synonym>
    <synonym>b-Methylacrylate</synonym>
    <synonym>b-Methylacrylic acid</synonym>
    <synonym>beta-Methylacrylate</synonym>
    <synonym>Β-methylacrylate</synonym>
    <synonym>Β-methylacrylic acid</synonym>
    <synonym>trans-2-Butenoate</synonym>
    <synonym>trans-Crotonate</synonym>
    <synonym>Crotonate</synonym>
    <synonym>But-2-enoate</synonym>
    <synonym>(2E)-But-2-enoate</synonym>
    <synonym>(2E)-But-2-enoic acid</synonym>
    <synonym>3-Methyl-acrylic acid</synonym>
    <synonym>Butenoate</synonym>
    <synonym>Butenoic acid</synonym>
    <synonym>Kyselina krotonova</synonym>
    <synonym>Solid crotonic acid</synonym>
  </synonyms>
  <chemical_formula>C4H6O2</chemical_formula>
  <average_molecular_weight>86.0892</average_molecular_weight>
  <monisotopic_moleculate_weight>86.036779436</monisotopic_moleculate_weight>
  <iupac_name>(2E)-but-2-enoic acid</iupac_name>
  <traditional_iupac>butenoic acid</traditional_iupac>
  <cas_registry_number>3724-65-0</cas_registry_number>
  <smiles>C\C=C\C(O)=O</smiles>
  <inchi>InChI=1S/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/b3-2+</inchi>
  <inchikey>LDHQCZJRKDOVOX-NSCUHMNNSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acids and conjugates</sub_class>
    <direct_parent>Straight chain fatty acids</direct_parent>
    <alternative_parents>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Unsaturated fatty acids</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Straight chain fatty acid</substituent>
      <substituent>Unsaturated fatty acid</substituent>
    </substituents>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>2-butenoic acid</external_descriptor>
      <external_descriptor>Unsaturated fatty acids</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
    <property>
      <kind>melting_point</kind>
      <value>72 °C</value>
      <source/>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.72</value>
      <source>HANSCH,C ET AL. (1995)</source>
    </property>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>0.94</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.07</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>0.92</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>4.9</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(2E)-but-2-enoic acid</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>86.0892</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>86.036779436</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>C\C=C\C(O)=O</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C4H6O2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C4H6O2/c1-2-3-4(5)6/h2-3H,1H3,(H,5,6)/b3-2+</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>LDHQCZJRKDOVOX-NSCUHMNNSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>37.3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>22.96</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>8.44</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>-1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
    <pathway>
      <name>Fatty Acid Biosynthesis</name>
      <smpdb_id>SMP0087257</smpdb_id>
      <kegg_map_id/>
    </pathway>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>2879</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>29452</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>39528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>99950</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>158315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>2474</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>2475</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsIr</type>
      <spectrum_id>2476</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>88608</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>88609</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>88610</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>151368</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>151369</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>151370</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437461</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437462</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437463</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>437464</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2252371</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2254446</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2256110</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2453008</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2453009</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2453010</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2482714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2482715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2482716</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>4601</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>266168</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>266169</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>266170</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>266171</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>266172</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>266173</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>266174</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>266175</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>266176</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>266177</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>266178</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>266179</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>266180</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>266181</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>266182</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>266183</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>266184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>266185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>266186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>266187</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB003283</foodb_id>
  <chemspider_id>552744</chemspider_id>
  <drugbank_id>DB02074</drugbank_id>
  <kegg_id>C01771</kegg_id>
  <pubchem_compound_id>637090</pubchem_compound_id>
  <chebi_id>41131</chebi_id>
  <pdbe_id>BEO</pdbe_id>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <meta_cyc_id>CROTONATE</meta_cyc_id>
  <bigg_id/>
  <wikipedia_id>Crotonic_acid</wikipedia_id>
  <metlin_id/>
  <synthesis_reference/>
  <general_references>
  </general_references>
  <protein_associations>
    <protein>
      <protein_accession>BMDBP00368</protein_accession>
      <name>Fatty acid synthase</name>
      <uniprot_id>Q71SP7</uniprot_id>
      <gene_name>FASN</gene_name>
      <protein_type>Enzyme</protein_type>
    </protein>
  </protein_associations>
</metabolite>
