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Record Information
Version3.6
Creation Date2012-09-11 17:31:26 UTC
Update Date2016-02-11 01:41:49 UTC
HMDB IDHMDB29608
Secondary Accession NumbersNone
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. Angelic acid belongs to the family of Branched Fatty Acids. These are fatty acids containing a branched chain.
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 KeyInChIKey=UIERETOOQGIECD-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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrient
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
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 Solubility83.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.32 m3·mol-1ChemAxon
Polarizability10.35 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot 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 IDFDB000775
KNApSAcK IDNot Available
Chemspider ID559009
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAngelic_acid
NuGOwiki LinkHMDB29608
Metagene LinkHMDB29608
METLIN IDNot Available
PubChem Compound643915
PDB IDNot Available
ChEBI ID36431
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.