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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:26 UTC
Update Date2017-12-07 02:58:26 UTC
HMDB IDHMDB0029608
Secondary Accession Numbers
  • HMDB29608
Metabolite Identification
Common NameAngelic acid
DescriptionAngelic acid is found in fats and oils. Angelic acid is a constituent of Angelica archangelica (angelica) Angelic acid has a double bond between the second and third carbons of the chain. Together with tiglic acid form a pair of cis-trans isomers. Angelic acid is a volatile body, of biting acid taste and pungent sour odour. It crystallizes in colorless monoclinic prisms. Angelic acid was formerly used therapeutically as a sedative. Angelic acid is a monocarboxylic unsaturated organic acid. It is found in garden angelica (Angelica archangelica), Umbelliferae, and many other plants. It was also isolated from the defensive secretion of certain carabid beetles
Structure
Thumb
Synonyms
ValueSource
(Z)-2-Methylcrotonic acidChEBI
2-Methyl-2Z-butenoic acidChEBI
2-Methylisocrotonic acidChEBI
Acide angeliqueChEBI
acido AngelicoChEBI
alpha-Methylisocrotonic acidChEBI
AngelicasaeureChEBI
AngelikasaeureChEBI
cis-2,3-Dimethylacrylic acidChEBI
cis-2-Dimethylcrotonic acidChEBI
cis-2-Methyl-2-butenoic acidChEBI
Z-2-Methyl-2-butenoic acidChEBI
Z-2-Methylcrotonic acidChEBI
(Z)-2-MethylcrotonateGenerator
AngelateGenerator
2-Methyl-2Z-butenoateGenerator
2-MethylisocrotonateGenerator
a-MethylisocrotonateGenerator
a-Methylisocrotonic acidGenerator
alpha-MethylisocrotonateGenerator
α-methylisocrotonateGenerator
α-methylisocrotonic acidGenerator
cis-2,3-DimethylacrylateGenerator
cis-2-DimethylcrotonateGenerator
cis-2-Methyl-2-butenoateGenerator
Z-2-Methyl-2-butenoateGenerator
Z-2-MethylcrotonateGenerator
(2Z)-2-Methylbut-2-enoic acidHMDB
(Z)-2-Methyl-2-butenoic acidHMDB
2-Methyl-(2Z)-2-butenoic acidHMDB
2-Methyl-(Z)-2-butenoic acidHMDB
2-Methyl-(Z)-crotonic acidHMDB
2-Methyl-2-butenoic acid, cisHMDB
alpha-Methyl isocrotonic acidHMDB
Crotonic acid, 2-methyl-, (Z)- (8ci)HMDB
Chemical FormulaC5H8O2
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
IUPAC Name(2Z)-2-methylbut-2-enoic acid
Traditional Nameangelic acid
CAS Registry Number565-63-9
SMILES
C\C=C(\C)C(O)=O
InChI Identifier
InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3-
InChI KeyUIERETOOQGIECD-ARJAWSKDSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Unsaturated 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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point45 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility83 g/LALOGPS
logP1.13ALOGPS
logP1.32ChemAxon
logS-0.08ALOGPS
pKa (Strongest Acidic)4.97ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.32 m³·mol⁻¹ChemAxon
Polarizability10.35 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zi0-9000000000-4314e75ba9656b7fb97fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-9200000000-1e8cf22de89b50fd327dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-8900000000-68b09835981f85d65f90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100000000-7999b5228e0df947f949View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-179be6ce006eb4e9f084View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-357a7c774a32d7c0444fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-9000000000-78eae8b34531c3c1bc27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-eb61c33f642ca5d4e676View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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 IDFDB000775
KNApSAcK IDNot Available
Chemspider ID559009
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAngelic_acid
METLIN IDNot Available
PubChem Compound643915
PDB IDNot Available
ChEBI ID36431
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.