Record Information
Version1.0
Creation date2011-09-21 00:22:41 UTC
Update date2015-10-09 22:32:02 UTC
Primary IDFDB022977
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhenylpropiolic acid
DescriptionPhenylpropiolic acid is one of a number of phenylpropanoid, natural products occurring in plants pathways involved in plant resistance providing building units of physical barriers against pathogen invasion, synthesizing an array of antibiotic compounds, and producing signals implicated in the mounting of plant resistance. (PMID 15199968) Phenylpropiolic acid is a cis-pyrrolidinone that has been tested as an inhibitors of type II 17beta-hydroxysteroid dehydrogenase for the treatment of osteoporosis. (PMID 16806919) [HMDB]
CAS Number637-44-5
Structure
Thumb
Synonyms
SynonymSource
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
3-phenyl-propiolatehmdb
3-phenyl-propiolic acidhmdb
b-phenylpropargylatehmdb
b-phenylpropargylic acidhmdb
beta-phenylpropargylatehmdb
beta-phenylpropargylic acidhmdb
phenyl-(8CI)propiolatehmdb
phenyl-(8CI)propiolic acidhmdb
phenyl-propiolatehmdb
phenyl-propiolic acidhmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H6O2
IUPAC name3-phenylprop-2-ynoic acid
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
Isomeric SMILESOC(=O)C#CC1=CC=CC=C1
Average Molecular Weight146.1427
Monoisotopic Molecular Weight146.036779436
Classification
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
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPhenylpropiolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-1900000000-f3dcdea0585a8167ee36Spectrum
Predicted GC-MSPhenylpropiolic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0uk9-9830000000-feb73790a25f137386f9Spectrum
Predicted GC-MSPhenylpropiolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00mk-3900000000-03289f4e383657772129Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9800000000-ebfac1366623441b4fabSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9100000000-b111b793437863f24a8cSpectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-9100000000-480dfc61257dac300724Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00os-3900000000-c7f3388a9ad322e37bbaSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-9800000000-03950939b02a4a226b5dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-9ccdda8aa55c7fd5f179Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fb9-0900000000-39ffafabcb71dd5e4fb9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-2900000000-a61c9be6ba2e3e672a4bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-53fd8625b272fb8c0874Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-c01f026883e9d8371e78Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0900000000-d89d4873b06625bc98b2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-6044d949db2e286e5440Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-1f23da2395d60c767582Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-6900000000-eef250719433f4e47416Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udj-0900000000-e164e953b1394208fd0dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-b63c162ca0b38a8b1bb0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-4900000000-87bc643c2fbf1a8525c5Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID62682
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID69475
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02359
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPhenylpropiolic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference