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Phenylacetate

HCID 4409936
NotesReactions
Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

Standard SMILES
O=C([O-])Cc1ccccc1
InChIKey
WLJVXDMOQOGPHL-UHFFFAOYSA-M
Molecular formula
C8H7O2-
Average molar mass
135.14 g/mol
Monoisotopic mass
135.04460446

Names & identifiers

Preferred name
Phenylacetate
IUPAC
2-phenylacetate

Names & synonyms

phenylacetate2-phenylethanoateCHEBI:18401RefChem:9290432-phenylacetateBenzeneacetatephenylacetate anionphenylacetate(1-)phenylacetic acid anionBDBM36183WLJVXDMOQOGPHL-UHFFFAOYSA-Mc0211
Show more names
AKOS024258138NS00010314AB01275449-01Q27103051

Database identifiers

PubChem CID
4409936
ChEBI
CHEBI:18401
Nikkaji
J1.455.714H

Properties

Computed structural properties

XLogP
2.1
Topological polar surface area
40.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
10
Formal charge
-1
Complexity
109

Safety & regulation

Toxicology

TreatmentKidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.
Health EffectsChronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.
Exposure RoutesEndogenous, Ingestion, Dermal (contact)
Toxicity Summary · 1 item

Uremic toxins such as phenylacetic acid are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869)

Signs and Symptoms · 1 item

As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Chemistry & industry

Pharmacology

Metabolism/MetabolitesUremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.
MeSH Pharmacological ClassificationAntimetabolites that are useful in cancer chemotherapy.

Uses & manufacturing

UsesNaturally produced by the body (endogenous).

Related reactions

10 records
New reaction record
HRID 103876 reaction equation
HRID 103876As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 1234312 reaction equation
HRID 1234312As productTraining data from https://doi.org/10.1039/C8SC04228D (5/10)
HRID 1294313 reaction equation
HRID 1294313As reactantuspto-grants-2007_07
HRID 1761703 reaction equation
HRID 1761703As reactantuspto-grants-1989_05
HRID 1885800 reaction equation
HRID 1885800As reactantuspto-grants-1992_09
HRID 2289120 reaction equation
HRID 2289120As reactantuspto-grants-2000_07
HRID 2289129 reaction equation
HRID 2289129As reactantuspto-grants-2000_07
HRID 2289135 reaction equation
HRID 2289135As reactantuspto-grants-2000_07
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Compound notes

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