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Indole-3-acetate

HCID 801
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
1596-90-3
Standard SMILES
O=C([O-])Cc1c[nH]c2ccccc12
InChIKey
SEOVTRFCIGRIMH-UHFFFAOYSA-M
Molecular formula
C10H8NO2-
Average molar mass
174.18 g/mol
Monoisotopic mass
174.0555035

Overview

Indole-3-acetate is an indol-3-yl carboxylic acid anion that is the conjugate base of indole-3-acetic acid. It has a role as a Saccharomyces cerevisiae metabolite, a plant metabolite and a human metabolite. It is a conjugate base of an indole-3-acetic acid.

Names & identifiers

Preferred name
Indole-3-acetate
IUPAC
2-(1H-indol-3-yl)acetate

Names & synonyms

indole-3-acetate1H-indol-3-ylacetate(1H-indol-3-yl)acetate(indol-3-yl)acetateCHEBI:30854RefChem:10873482-(1H-indol-3-yl)acetate3-indoleacetate93672-51-62-(indol-3-yl)ethanoateIndole-3-acetic acid, 16BDBM92694
Show more names
DTXSID60274285STK372805AKOS005447098NCGC00340564-01AB01333784-02Q271041601596-90-3

Database identifiers

CAS
1596-90-3、93672-51-6
PubChem CID
801
DTXSID
DTXSID60274285
ChEBI
CHEBI:30854
Nikkaji
J754.931H

Properties

Computed structural properties

XLogP
2.1
Topological polar surface area
55.9 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
13
Formal charge
-1
Complexity
200

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Toxicology

Treatment · 1 item

Chronic Exposure: Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored. Acute Exposure: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice.

Health Effects · 1 item

Indoleacetic acid is listed in its MSDS as potentially mutagenic to mammalian somatic cells. It is also identified as a potential skin, eye, and respiratory irritant, and users are warned not to ingest it. Acute exposure to Indoleacetic acid can lead to some mild skin and eye irritation. Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Chronically high levels of Indoleacetic acid are associated with the inborn error of metabolism known as Hartnup disease.

Exposure RoutesEndogenous, Ingestion, Dermal (contact)
Toxicity Summary · 1 item

Uremic toxins such as indole-3-acetic 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.

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Indoleacetic acid (IAA) is a breakdown product of tryptophan metabolism and is often produced by the action of bacteria in the mammalian gut. Some endogenous production of IAA in mammalian tissues also occurs. It may be produced by the decarboxylation of tryptamine or the oxidative deamination of tryptophan.

Uses & manufacturing

UsesNaturally produced by the body (endogenous). Also a plant growth hormone (auxin).

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).