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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:17:04 UTC
Update Date2019-07-23 06:16:04 UTC
HMDB IDHMDB0034439
Secondary Accession Numbers
  • HMDB34439
Metabolite Identification
Common NameIsocrotonic acid
DescriptionIsocrotonic acid, also known as perisocrotonate or (Z)-2-butenoic acid, belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. Isocrotonic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563862564
Synonyms
ValueSource
(Z)-2-Butenoic acidChEBI
(Z)-But-2-enoic acidChEBI
(Z)-Crotonic acidChEBI
cis-2-Butenoic acidChEBI
cis-Crotonic acidChEBI
Perisocrotonic acidChEBI
(Z)-2-ButenoateGenerator
(Z)-But-2-enoateGenerator
(Z)-CrotonateGenerator
cis-2-ButenoateGenerator
cis-CrotonateGenerator
PerisocrotonateGenerator
IsocrotonateGenerator
(2Z)-2-Butenoic acidHMDB
(2Z)-But-2-enoic acidHMDB
b-Crotonic acidHMDB
Chemical FormulaC4H6O2
Average Molecular Weight86.0892
Monoisotopic Molecular Weight86.036779436
IUPAC Name(2Z)-but-2-enoic acid
Traditional Nameisocrotonic acid
CAS Registry Number503-64-0
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-IHWYPQMZSA-N
Chemical Taxonomy
Description 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

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point14.6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
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
Polarizability8.38 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9000000000-824e2d62774bcbbebff0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0103-9100000000-bb87072a7225402c6d0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-9000000000-1dc3bc86132e73942861Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ko-9000000000-d17c17c2c66a97ee9c27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-4cd5b916c7ee6039effcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-dde621f263ff3ac72841Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-9000000000-dce352f985fb5e143263Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-acd6176b8c6ebe251635Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB012845
KNApSAcK IDNot Available
Chemspider ID558890
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsocrotonic acid
METLIN IDNot Available
PubChem Compound643792
PDB IDNot Available
ChEBI ID36253
Food Biomarker OntologyNot Available
VMH IDNot Available
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.