Showing metabocard for Tiglic acid (BMDB0001470)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:46:23 UTC
Update Date2020-04-22 15:08:19 UTC
BMDB IDBMDB0001470
Secondary Accession Numbers
  • BMDB01470
Metabolite Identification
Common NameTiglic acid
DescriptionTiglic acid, also known as tiglate or tiglinsaeure, 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. Based on a literature review a significant number of articles have been published on Tiglic acid.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(e)-2,3-Dimethylacrylic acidChEBI
(e)-2-Methylbut-2-enoic acidChEBI
(e)-2-Methylcrotonic acidChEBI
Methyl methacrylic acidChEBI
TiglinsaeureChEBI
trans-2,3-Dimethylacrylic acidChEBI
trans-2-Methyl-2-butenoic acidChEBI
trans-2-Methylcrotonic acidChEBI
trans-alpha,beta-Dimethylacrylic acidChEBI
(e)-2,3-DimethylacrylateGenerator
(e)-2-Methylbut-2-enoateGenerator
(e)-2-MethylcrotonateGenerator
Methyl methacrylateGenerator
trans-2,3-DimethylacrylateGenerator
trans-2-Methyl-2-butenoateGenerator
trans-2-MethylcrotonateGenerator
trans-a,b-DimethylacrylateGenerator
trans-a,b-Dimethylacrylic acidGenerator
trans-alpha,beta-DimethylacrylateGenerator
trans-Α,β-dimethylacrylateGenerator
trans-Α,β-dimethylacrylic acidGenerator
TiglateGenerator
(2E)-2-Methyl-2-butenoateHMDB
(2E)-2-Methyl-2-butenoic acidHMDB
(e)-2-Methyl-2-butenoateHMDB
(e)-2-Methyl-2-butenoic acidHMDB
(e)-2-Methyl-crotonateHMDB
(e)-2-Methyl-crotonic acidHMDB
2,3-DimethylacrylateHMDB
2,3-Dimethylacrylic acidHMDB
2-Methyl-(e)-2-butenoateHMDB
2-Methyl-(e)-2-butenoic acidHMDB
2-Methyl-2-butenoateHMDB
2-Methyl-2-butenoic acidHMDB
2-Methyl-crotonateHMDB
2-Methyl-crotonic acidHMDB
2-Methylbut-2-enoateHMDB
2-Methylbut-2-enoic acidHMDB
CevadateHMDB
Cevadic acidHMDB
e-TiglateHMDB
e-Tiglic acidHMDB
epsilon-TiglateHMDB
epsilon-Tiglic acidHMDB
MethylbutenoicacidHMDB
TiglinateHMDB
Tiglinic acidHMDB
trans-2-Methylcrotonic acid = trans-2-methyl-2-butenoateHMDB
trans-2-Methylcrotonic acid = trans-2-methyl-2-butenoic acidHMDB
trans-2-Methylcrotonic acid = trans-2-methyl-2-butenoic acid = tiglinateHMDB
trans-2-Methylcrotonic acid = trans-2-methyl-2-butenoic acid = tiglinic acidHMDB
Tiglic acid, (Z)-isomerHMDB
Tiglic acid, (e)-isomerHMDB
Chemical FormulaC5H8O2
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
IUPAC Name(2E)-2-methylbut-2-enoic acid
Traditional Nametiglic acid
CAS Registry Number80-59-1
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-ONEGZZNKSA-N
Chemical Taxonomy
Description 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
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point61 - 65 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Polarizability10.39 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001470
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000774
KNApSAcK IDC00001207
Chemspider ID111629
KEGG Compound IDC08279
BioCyc IDCPD-7077
BiGG IDNot Available
Wikipedia LinkTiglic_acid
METLIN ID6261
PubChem Compound125468
PDB IDNot Available
ChEBI ID9592
References
Synthesis ReferenceJacob, Carl; Hafner, Walter; Wick, Manfred. Tiglic acid. Ger. Offen. (1976), 6 pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available