Showing Compound Card for Phenylacetic acid (CDB005770)

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Record Information
Version1.0
Created at2020-04-27 16:54:52 UTC
Updated at2021-01-04 18:49:15 UTC
CannabisDB IDCDB005770
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePhenylacetic acid
DescriptionPhenylacetic acid, also known as phenylathanoic acid, phenylacetate, alpha tolylic acid or alpha-toluic acid, belongs to the class of organic compounds known as benzenes and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Phenylacetic acid exists as a white solid that has a strong, honey-like odor. It is a catabolic product of phenylalanine. It is found in nearly all organisms from microbes to plants to animals. In plants it has been found to function as an auxin-like phyotohormone that is particularly enriched in fruits. However, it is not as strong as the basic auxin molecule, indole-3-acetic acid. Phenylacetate is used industrially in in some perfumes, as it possesses a honey-like odor even in low concentrations. Medically, phenylacetate is also employed to treat type II hyperammonemia to help reduce the amounts of ammonia in a patient's bloodstream by forming phenylacetyl-CoA, which then reacts with nitrogen-rich glutamine to form phenylacetylglutamine. This compound is then excreted from the patient's body. The sodium salt of phenylacetic acid, sodium phenylacetate, is used as a drug for the treatment of urea cycle disorders. Phenylacetic acid occurs naturally and has been detected, but not quantified in, several different foods, such as banana, fenugreeks, lemon thymes, pears, and peach (var.). This could make phenylacetic acid a potential biomarker for the consumption of these foods. Phenylacetic acid is also found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-PHENYLACETIC ACIDChEBI
2-Phenylethanoic acidChEBI
alpha-Toluic acidChEBI
Benzeneacetic acidChEBI
Benzylformic acidChEBI
Omega-phenylacetic acidChEBI
PAChEBI
PhenylacetateKegg
2-PHENYLACETateGenerator
a-ToluateGenerator
a-Toluic acidGenerator
alpha-ToluateGenerator
Α-toluateGenerator
Α-toluic acidGenerator
BenzeneacetateGenerator
BenzylformateGenerator
Omega-phenylacetateGenerator
PhenylethanoateHMDB
W-PhenylacetateHMDB
W-Phenylacetic acidHMDB
Phenylacetic acid, potassium saltHMDB
Sodium phenylacetateHMDB
Phenylacetic acid, lithium saltHMDB
Phenylacetic acid, sodium saltHMDB
Phenylacetic acid, ammonium saltHMDB
Phenylacetic acid, calcium saltHMDB
Phenylacetic acid, cesium saltHMDB
Phenylacetic acid, mercury saltHMDB
Phenylacetic acid, rubidium saltHMDB
Phenylacetic acid, sodium salt , carboxy-(11)C-labeled CPDHMDB
PAAPhytoBank
ω-Phenylacetic acidPhytoBank
Phenylacetic acidHMDB
Chemical FormulaC8H8O2
Average Molecular Weight136.15
Monoisotopic Molecular Weight136.0524
IUPAC Name2-phenylacetic acid
Traditional Nameω-phenylacetic acid
CAS Registry Number103-82-2
SMILES
OC(=O)CC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
InChI KeyWLJVXDMOQOGPHL-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 Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Role

Indirect biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point76.7 °CNot Available
Boiling Point265.5 °CWikipedia
Water Solubility16.6 mg/mLNot Available
logP1.41HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP1.72ALOGPS
logP1.61ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)4.55ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.37 m³·mol⁻¹ChemAxon
Polarizability13.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-1e23fd8e6ce900cd8e4c2014-09-20View Spectrum
GC-MSPhenylacetic acid, 1 TMS, GC-MS Spectrumsplash10-0006-9700000000-c07461cdad68959aa53fSpectrum
GC-MSPhenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9100000000-de65c7c0092343a4e599Spectrum
GC-MSPhenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9700000000-c07461cdad68959aa53fSpectrum
GC-MSPhenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9700000000-43e86e45beae2fa6704fSpectrum
Predicted GC-MSPhenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9200000000-dc43e5e062b0ed500c5fSpectrum
Predicted GC-MSPhenylacetic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9100000000-aaef76d181aebe492bbeSpectrum
Predicted GC-MSPhenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhenylacetic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9100000000-de65c7c0092343a4e5992012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0006-9000000000-6ca33b098558bf13801c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-0900000000-f898aafe4cecc87d26f12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-9400000000-aa5bff1d7a8df7c97bdb2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-6a017c8136a375269f3e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-2900000000-d79f9224f2390d6b17a22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-e712b088c9a3d3855ec72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-01ri-9000000000-f0ed89dae2c22d4c538c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-053i-2900000000-3e4bf20b985893f203e72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-5419b00a9c7c126093db2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-1900000000-9a2e089c5511fa2bf2102021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-2900000000-94a6f40f937bf9d7e4c72016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9500000000-8d3540e40bfc0e4c0e5f2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-417ad1f13a593ac780b92016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-5900000000-0ed04a623daaf32fffda2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-8900000000-709928d6b823240d35282016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9600000000-4a7739132344f3dec7102016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-5671d4c535a6553aaf0d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-5671d4c535a6553aaf0d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-5e37e9f4d7b24c7633022021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kf-9800000000-aacb25995ab02725e0f42021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9100000000-930a2cbe3e9fb19150752021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-199de8006c0d100aaabb2021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Aldehyde dehydrogenase, dimeric NADP-preferringALDH3A117p11.2P30838 details
Aldehyde dehydrogenase family 1 member A3ALDH1A315q26.3P47895 details
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
Aldehyde dehydrogenase family 3 member B2ALDH3B211q13P48448 details
Aldehyde dehydrogenase family 3 member B1ALDH3B111q13P43353 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000209
DrugBank IDDB09269
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031100
KNApSAcK IDC00000750
Chemspider ID10181341
KEGG Compound IDC07086
BioCyc IDPHENYLACETATE
BiGG ID1486426
Wikipedia LinkPhenylacetic_acid
METLIN ID129
PubChem Compound999
PDB IDNot Available
ChEBI ID30745
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. Aldehyde dehydrogenase, dimeric NADP-preferring
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Molecular weight:
50394.57
Enzyme Details
2. Aldehyde dehydrogenase family 1 member A3
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Enzyme Details
3. 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
Enzyme Details
4. Aldehyde dehydrogenase family 3 member B2
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Molecular weight:
42623.62
Enzyme Details
5. Aldehyde dehydrogenase family 3 member B1
General function:
Involved in oxidoreductase activity
Specific function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Molecular weight:
51839.245