Cannabis Compound Database: Showing Compound Card for Phenylacetic acid (CDB005770)

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Record Information

Version

1.0

Created at

2020-04-27 16:54:52 UTC

Updated at

2021-01-04 18:49:15 UTC

CannabisDB ID

CDB005770

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Phenylacetic acid

Description

Phenylacetic 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-PHENYLACETIC ACID	ChEBI
2-Phenylethanoic acid	ChEBI
alpha-Toluic acid	ChEBI
Benzeneacetic acid	ChEBI
Benzylformic acid	ChEBI
Omega-phenylacetic acid	ChEBI
PA	ChEBI
Phenylacetate	Kegg
2-PHENYLACETate	Generator
a-Toluate	Generator
a-Toluic acid	Generator
alpha-Toluate	Generator
Α-toluate	Generator
Α-toluic acid	Generator
Benzeneacetate	Generator
Benzylformate	Generator
Omega-phenylacetate	Generator
Phenylethanoate	HMDB
W-Phenylacetate	HMDB
W-Phenylacetic acid	HMDB
Phenylacetic acid, potassium salt	HMDB
Sodium phenylacetate	HMDB
Phenylacetic acid, lithium salt	HMDB
Phenylacetic acid, sodium salt	HMDB
Phenylacetic acid, ammonium salt	HMDB
Phenylacetic acid, calcium salt	HMDB
Phenylacetic acid, cesium salt	HMDB
Phenylacetic acid, mercury salt	HMDB
Phenylacetic acid, rubidium salt	HMDB
Phenylacetic acid, sodium salt , carboxy-(11)C-labeled CPD	HMDB
PAA	PhytoBank
ω-Phenylacetic acid	PhytoBank
Phenylacetic acid	HMDB

Chemical Formula

C₈H₈O₂

Average Molecular Weight

136.15

Monoisotopic Molecular Weight

136.0524

IUPAC Name

2-phenylacetic acid

Traditional Name

ω-phenylacetic acid

CAS Registry Number

103-82-2

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 Key

WLJVXDMOQOGPHL-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:30745 )
benzenes (CHEBI:30745 )

Ontology

Dermal

Enteral:

Ingestion

Biological location:

Biofluid and excreta:

Indirect biological role:

Toxin

Industrial application:

Food and nutrition

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	76.7 °C	Not Available
Boiling Point	265.5 °C	Wikipedia
Water Solubility	16.6 mg/mL	Not Available
logP	1.41	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.72	ALOGPS
logP	1.61	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	4.55	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	37.37 m³·mol⁻¹	ChemAxon
Polarizability	13.85 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0006-9100000000-1e23fd8e6ce900cd8e4c	2014-09-20	View Spectrum
GC-MS	Phenylacetic acid, 1 TMS, GC-MS Spectrum	splash10-0006-9700000000-c07461cdad68959aa53f	Spectrum
GC-MS	Phenylacetic acid, non-derivatized, GC-MS Spectrum	splash10-0006-9100000000-de65c7c0092343a4e599	Spectrum
GC-MS	Phenylacetic acid, non-derivatized, GC-MS Spectrum	splash10-0006-9700000000-c07461cdad68959aa53f	Spectrum
GC-MS	Phenylacetic acid, non-derivatized, GC-MS Spectrum	splash10-0006-9700000000-43e86e45beae2fa6704f	Spectrum
Predicted GC-MS	Phenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9200000000-dc43e5e062b0ed500c5f	Spectrum
Predicted GC-MS	Phenylacetic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9100000000-aaef76d181aebe492bbe	Spectrum
Predicted GC-MS	Phenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phenylacetic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0006-9100000000-de65c7c0092343a4e599	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0006-9000000000-6ca33b098558bf13801c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-000i-0900000000-f898aafe4cecc87d26f1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9400000000-aa5bff1d7a8df7c97bdb	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-6a017c8136a375269f3e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-2900000000-d79f9224f2390d6b17a2	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-e712b088c9a3d3855ec7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-01ri-9000000000-f0ed89dae2c22d4c538c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-053i-2900000000-3e4bf20b985893f203e7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1900000000-5419b00a9c7c126093db	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-1900000000-9a2e089c5511fa2bf210	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-2900000000-94a6f40f937bf9d7e4c7	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9500000000-8d3540e40bfc0e4c0e5f	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-417ad1f13a593ac780b9	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000l-5900000000-0ed04a623daaf32fffda	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000l-8900000000-709928d6b823240d3528	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9600000000-4a7739132344f3dec710	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-9000000000-5671d4c535a6553aaf0d	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-5671d4c535a6553aaf0d	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-5e37e9f4d7b24c763302	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kf-9800000000-aacb25995ab02725e0f4	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9100000000-930a2cbe3e9fb1915075	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-199de8006c0d100aaabb	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phenylacetate Metabolism

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Aldehyde dehydrogenase, dimeric NADP-preferring	ALDH3A1	17p11.2	P30838	details
Aldehyde dehydrogenase family 1 member A3	ALDH1A3	15q26.3	P47895	details
UDP-glucuronosyltransferase 1-1	UGT1A1	2q37	P22309	details
Aldehyde dehydrogenase family 3 member B2	ALDH3B2	11q13	P48448	details
Aldehyde dehydrogenase family 3 member B1	ALDH3B1	11q13	P43353	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000209

DrugBank ID

DB09269

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

30745

References

General References

Not 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

Showing Compound Card for Phenylacetic acid (CDB005770)

Structure for CDB005770 (Phenylacetic acid)

Enzymes