Showing Compound Card for Phenylisopropionic acid (CDB006064)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Created at2020-04-27 17:25:45 UTC
Updated at2021-01-06 19:07:02 UTC
CannabisDB IDCDB006064
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePhenylisopropionic acid
Description2-Phenylpropionic acid, also known as (+/-)-hydratropic acid, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. A characteristic reaction of phenylpropanoic acid is its cyclization to 1-indanone. 2-Phenylpropionate is a weakly acidic compound (based on its pKa). Shelved foods are protected from microorganism by adding phenylpropanoic acid to prevent deterioration to the food by microorganisms as well as acting as an antioxidant to prolong shelf life. When the side chain is homologated by the Arndt-Eistert reaction, subsequent cyclization affords 2-tetralone derivatives. 2-Phenylpropionate is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ). Phenylpropanoic acid has a wide variety of uses including cosmetics, food additives, and pharmaceuticals. This compound is used frequently in cosmetic products such as perfumes, bath gels, detergent powders, liquid detergents, fabric softeners, and soaps as it gives off a floral scent. Phenylpropanoic acid is used in the food industry to preserve and maintain the original aroma quality of frozen foods. It is a white, crystalline solid with a sweet, floral scent at room temperature. 2-Phenylpropionate is an intermediate in alpha-Methylstyrene (2-phenylpropylene) metabolism. It was identified in human liver slices in small amounts. It is. likely that 2-Phenylpropionate derives from 2-phenylpropionaldehyde, formed from a 1,2-hydride shift during the transfer of active oxygen to the vinyl group, as has been proposed for the cytochrome P450-mediated oxidation of styrene to form phenylacetaldehyde (PMID: 11159807 ). 2-Phenylpropionate has been found to be a metabolite of Acinetobacter, Bacteroides, Bifidobacterium, Clostridium, Enterococcus, Escherichia, Eubacterium, Klebsiella, Lactobacillus, Pseudomonas and Staphylococcus (PMID: 19961416 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+-)-HydratropasaeureChEBI
(+-)-Hydratropic acidChEBI
2-Phenylpropionic acidChEBI
alpha-Methylbenzeneacetic acidChEBI
alpha-Methylphenylacetic acidChEBI
alpha-Phenylpropionic acidChEBI
HydratropasaeureChEBI
(+-)-HydratropateGenerator
a-MethylbenzeneacetateGenerator
a-Methylbenzeneacetic acidGenerator
alpha-MethylbenzeneacetateGenerator
Α-methylbenzeneacetateGenerator
Α-methylbenzeneacetic acidGenerator
a-MethylphenylacetateGenerator
a-Methylphenylacetic acidGenerator
alpha-MethylphenylacetateGenerator
Α-methylphenylacetateGenerator
Α-methylphenylacetic acidGenerator
a-PhenylpropionateGenerator
a-Phenylpropionic acidGenerator
alpha-PhenylpropionateGenerator
Α-phenylpropionateGenerator
Α-phenylpropionic acidGenerator
2-PhenylpropanoateHMDB
2-Phenylpropanoic acidHMDB
alpha-PhenylpropioateHMDB
alpha-Phenylpropioic acidHMDB
Hydratropic acidHMDB
PhenylpropionateHMDB
Hydratropic acid, (R)-isomerHMDB
Hydratropic acid, (+-)-isomerHMDB
Hydratropic acid, (S)-isomerHMDB
HydratropateHMDB
2-PhenylpropionateGenerator
Chemical FormulaC9H10O2
Average Molecular Weight150.17
Monoisotopic Molecular Weight150.0681
IUPAC Name2-phenylpropanoic acid
Traditional Name2-phenylpropionic acid
CAS Registry Number492-37-5
SMILES
CC(C(O)=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H10O2/c1-7(9(10)11)8-5-3-2-4-6-8/h2-7H,1H3,(H,10,11)
InChI KeyYPGCWEMNNLXISK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 2-phenylpropanoic-acid
  • Benzenoid
  • 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 Descriptors
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.17ALOGPS
logP2.15ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)4.59ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity41.94 m³·mol⁻¹ChemAxon
Polarizability15.77 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSPhenylisopropionic acid, non-derivatized, GC-MS Spectrumsplash10-0zfr-0941000000-2f10a7e26d01d9e7085dSpectrum
GC-MSPhenylisopropionic acid, non-derivatized, GC-MS Spectrumsplash10-0zfr-0941000000-2f10a7e26d01d9e7085dSpectrum
Predicted GC-MSPhenylisopropionic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0pb9-5900000000-05490efdd6c98b3ce82aSpectrum
Predicted GC-MSPhenylisopropionic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-9600000000-26dae48b72bfc2ca9759Spectrum
Predicted GC-MSPhenylisopropionic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0002-0900000000-e53ef142c9412380df552020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-0002-0900000000-29c3d5fe28bb9f6c40d12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-0002-0900000000-82af54e1d6af45e429c42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, negativesplash10-0a4i-0900000000-a7098d20de07020e22312020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0a4i-0900000000-075f367a42fbc68964482020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0a4i-1900000000-2ed09d6fc9f1aabaabf12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0a4i-3900000000-8527a4a6e8ee0bdee3792020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0a6r-5900000000-91464b7282caefce7c572020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0a6r-8900000000-6af8501efd3a965287572020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-056r-9700000000-da767035d624aa0474e22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-0zi0-9400000000-7f0b4bb235bff9727a2b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-004i-9000000000-dc545560bfc652d6c7592020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-664100ae6aaf810f18672016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-1900000000-be2ddda93cd5e199df442016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdi-9700000000-e4fa8c169fd74948e53c2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-07dca2cefa0ac465cc862016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-1900000000-e6c60c33501a07cbc77d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9400000000-378acac48334d166eee52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-6b3d4e1b557147f638272021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-930ae846bea291d5ca182021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9300000000-beef29c8d5993e4d6c702021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-3900000000-c17d7c6430ffec5df7052021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-a46351f80403da280fae2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-1ab829396e40b06657d72021-09-23View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0011743
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028418
KNApSAcK IDNot Available
Chemspider ID9874
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenylpropanoic acid
METLIN IDNot Available
PubChem Compound10296
PDB IDNot Available
ChEBI ID48526
References
General References
  1. De Costa KS, Black SR, Thomas BF, Burgess JP, Mathews JM: Metabolism and disposition of alpha-methylstyrene in rats. Drug Metab Dispos. 2001 Feb;29(2):166-71. [PubMed:11159807 ]
  2. Beloborodova NV, Khodakova AS, Bairamov IT, Olenin AY: Microbial origin of phenylcarboxylic acids in the human body. Biochemistry (Mosc). 2009 Dec;74(12):1350-5. doi: 10.1134/s0006297909120086. [PubMed:19961416 ]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91