3-INDOLYLACRYLIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H9NO2
Molecular Weight	187.1947
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C\C1=CNC2=CC=CC=C12

InChI

InChIKey=PLVPPLCLBIEYEA-AATRIKPKSA-N

InChI=1S/C11H9NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-7,12H,(H,13,14)/b6-5+

HIDE SMILES / InChI

Molecular Formula	C11H9NO2
Molecular Weight	187.1947
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.scbt.com/scbt/product/3-indoleacrylic-acid-1204-06-4 | https://www.ncbi.nlm.nih.gov/pubmed/8373197 | https://www.ncbi.nlm.nih.gov/pubmed/4259663

3-Indoleacrylic acid (IAA) is a natural auxin from lentil roots. 3-Indoleacrylic acid (IAA) induces transcription of genes under the control of the trpE promoter, including a family of proteins that contain nuclear localization signals. IAA also transcriptionally activates gene expression in plants. Trans-beta-Indoleacrylic acid (IAA) binds with moderately high affinity to the dimeric protein, trp aporepressor from Escherichia coli. 3-Indoleacrylic acid inhibits the growth of mycelia of Neurospora crassa and causes the cells to accumulate indoleglycerol phosphate.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Trp operon repressor 1 Target ID: P0A881 Gene ID: 948917.0 Gene Symbol: trpR Target Organism: Escherichia coli (strain K12) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8373197	Binding Agent 1064
Microcystis aeruginosa 1 Target ID: CHEMBL612942 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23412070 \| https://www.ncbi.nlm.nih.gov/pubmed/18609613	Inhibitor 8297
Tryptophan synthase beta chain 2 Target ID: P0A879 Gene ID: 945768.0 Gene Symbol: trpB Target Organism: Escherichia coli (strain K12) Sources: https://www.ncbi.nlm.nih.gov/pubmed/4259663 \| https://www.ncbi.nlm.nih.gov/pubmed/123527	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
A urinary metabonomics study on biochemical changes in yeast-induced pyrexia rats: a new approach to elucidating the biochemical basis of the febrile response.	2013 Jun 25	23583517
Chemical genetics-based discovery of indole derivatives as HCV NS5B polymerase inhibitors.	2014 Mar 21	24561671

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

The effective concentration of trans-3-indoleacrylic acid against M. aeruginosa was tested to be 0.5 mg/l

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:44:02 UTC 2023` Edited by `admin` on `Fri Dec 15 19:44:02 UTC 2023`
Record UNII	83X500J040
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

3-INDOLYLACRYLIC ACID

Systematic Name

English

2-PROPENOIC ACID, 3-(1H-INDOL-3-YL)-, (2E)-

Common Name

English

TRANS-.BETA.-INDOLEACRYLIC ACID

Common Name

English

2-PROPENOIC ACID, 3-(1H-INDOL-3-YL)-, (E)-

Common Name

English

INDOLEACRYLIC ACID

Systematic Name

English

INDOLE-3-ACRYLIC ACID

Systematic Name

English

INDOLE-3-ACRYLIC ACID, (E)-

Common Name

English

TRANS-3-INDOLEACRYLIC ACID

Systematic Name

English

Code System Code Type Description

MESH

C001446