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
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4j-9000000000-388383b7e67bc9a78b31View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-052b-9000000000-c5244acf58fff3e4aa88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0002-9000000000-7b12a1fc25be25ecd884View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-9000000000-af65ce24e97d441c9c9eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-052b-9000000000-b48bd344861272ddd921View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-4c3d75c63fc1a2aad554View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-9000000000-e71258cb16f06217950bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9000000000-af65ce24e97d441c9c9eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052b-9000000000-b48bd344861272ddd921View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-4c3d75c63fc1a2aad554View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9000000000-e71258cb16f06217950bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-000i-9000000000-5fcd95fb9bb6f029867cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-7daa8fdc26ee8a9bae52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-9500000000-9e8414fb7b7ae1c01782View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-9100000000-ad21d817c30785ef1c81View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-fde57dbd7bb552649d7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-1c91e2936e306ff07e44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-9000000000-d54eabf82c98dd7ebee8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-b3098892d6bc4e516906View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-5289cc75fe7aae11de79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-9000000000-16cd54f70787a892bf2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-59b712b76240ebaa6888View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-0cc8aed45af20d83ec92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-821598b1a2e8057a3567View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9000000000-5e5e9fc82472025ff503View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0zg0-9100000000-52eb3e4847f5360388c3View in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, 5%_DMSO, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
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