Phenylpropiolic acid (CHEM035423)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:45:19 UTC
Update Date2016-11-09 01:21:18 UTC
Accession NumberCHEM035423
Identification
Common NamePhenylpropiolic acid
ClassSmall Molecule
DescriptionAn acetylenic compound that is propynoic acid in which the acetylenic hydrogen is replaced by a phenyl group.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3-Phenylpropiolic acidChEBI
3-Phenylpropynoic acidChEBI
beta-Phenylpropargylic acidChEBI
Phenylacetylene monocarboxylic acidChEBI
Phenylacetylenecarboxylic acidChEBI
Phenylpropynoic acidChEBI
3-PhenylpropiolateGenerator
3-PhenylpropynoateGenerator
b-PhenylpropargylateGenerator
b-Phenylpropargylic acidGenerator
beta-PhenylpropargylateGenerator
Β-phenylpropargylateGenerator
Β-phenylpropargylic acidGenerator
Phenylacetylene monocarboxylateGenerator
PhenylacetylenecarboxylateGenerator
PhenylpropynoateGenerator
PhenylpropiolateGenerator
3-Phenyl-2-propynoateHMDB
3-Phenyl-2-propynoic acidHMDB
3-Phenyl-propiolateHMDB
3-Phenyl-propiolic acidHMDB
Phenyl-(8ci)propiolateHMDB
Phenyl-(8ci)propiolic acidHMDB
Phenyl-propiolateHMDB
Phenyl-propiolic acidHMDB
PhenylpropioplateHMDB
Phenylpropioplic acidHMDB
Chemical FormulaC9H6O2
Average Molecular Mass146.143 g/mol
Monoisotopic Mass146.037 g/mol
CAS Registry Number637-44-5
IUPAC Name3-phenylprop-2-ynoic acid
Traditional Namephenylpropiolic acid
SMILESOC(=O)C#CC1=CC=CC=C1
InChI IdentifierInChI=1S/C9H6O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,(H,10,11)
InChI KeyXNERWVPQCYSMLC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP1.7ALOGPS
logP2.15ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)2.77ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.45 m³·mol⁻¹ChemAxon
Polarizability14.96 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-1900000000-f3dcdea0585a8167ee36Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0uk9-9830000000-feb73790a25f137386f9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00mk-3900000000-03289f4e383657772129Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9800000000-ebfac1366623441b4fabSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9100000000-b111b793437863f24a8cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-9100000000-480dfc61257dac300724Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00os-3900000000-c7f3388a9ad322e37bbaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-9800000000-03950939b02a4a226b5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-9ccdda8aa55c7fd5f179Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fb9-0900000000-39ffafabcb71dd5e4fb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2900000000-a61c9be6ba2e3e672a4bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-53fd8625b272fb8c0874Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-c01f026883e9d8371e78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0900000000-d89d4873b06625bc98b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-6044d949db2e286e5440Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-1f23da2395d60c767582Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-6900000000-eef250719433f4e47416Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-0900000000-e164e953b1394208fd0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-b63c162ca0b38a8b1bb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-4900000000-87bc643c2fbf1a8525c5Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002359
FooDB IDFDB022977
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6644
PDB IDNot Available
Wikipedia LinkPhenylpropiolic_acid
Chemspider ID62682
ChEBI ID90355
PubChem Compound ID69475
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11924854
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16826299
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25652283
4. La Camera S, Gouzerh G, Dhondt S, Hoffmann L, Fritig B, Legrand M, Heitz T: Metabolic reprogramming in plant innate immunity: the contributions of phenylpropanoid and oxylipin pathways. Immunol Rev. 2004 Apr;198:267-84.
5. Wood J, Bagi CM, Akuche C, Bacchiocchi A, Baryza J, Blue ML, Brennan C, Campbell AM, Choi S, Cook JH, Conrad P, Dixon BR, Ehrlich PP, Gane T, Gunn D, Joe T, Johnson JS, Jordan J, Kramss R, Liu P, Levy J, Lowe DB, McAlexander I, Natero R, Redman AM, Scott WJ, Town C, Wang M, Wang Y, Zhang Z: 4,5-Disubstituted cis-pyrrolidinones as inhibitors of type II 17beta-hydroxysteroid dehydrogenase. Part 3. Identification of lead candidate. Bioorg Med Chem Lett. 2006 Sep 15;16(18):4965-8. Epub 2006 Jun 27.