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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 of 3-INDOLYLACRYLIC ACID

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

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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P0A881
Gene ID: 948917.0
Gene Symbol: trpR
Target Organism: Escherichia coli (strain K12)
Target ID: P0A879
Gene ID: 945768.0
Gene Symbol: trpB
Target Organism: Escherichia coli (strain K12)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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
Chemical genetics-based discovery of indole derivatives as HCV NS5B polymerase inhibitors.
2014 Mar 21
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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 Thu Jul 06 02:46:46 UTC 2023
Edited
by admin
on Thu Jul 06 02:46:46 UTC 2023
Record UNII
83X500J040
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Thu Jul 06 02:46:46 UTC 2023 , Edited by admin on Thu Jul 06 02:46:46 UTC 2023
PRIMARY
CHEBI
132244
Created by admin on Thu Jul 06 02:46:46 UTC 2023 , Edited by admin on Thu Jul 06 02:46:46 UTC 2023
PRIMARY
EPA CompTox
DTXSID90184060
Created by admin on Thu Jul 06 02:46:46 UTC 2023 , Edited by admin on Thu Jul 06 02:46:46 UTC 2023
PRIMARY
FDA UNII
83X500J040
Created by admin on Thu Jul 06 02:46:46 UTC 2023 , Edited by admin on Thu Jul 06 02:46:46 UTC 2023
PRIMARY
CAS
29953-71-7
Created by admin on Thu Jul 06 02:46:46 UTC 2023 , Edited by admin on Thu Jul 06 02:46:46 UTC 2023
PRIMARY
PUBCHEM
5375048
Created by admin on Thu Jul 06 02:46:46 UTC 2023 , Edited by admin on Thu Jul 06 02:46:46 UTC 2023
PRIMARY
CHEBI
90333
Created by admin on Thu Jul 06 02:46:46 UTC 2023 , Edited by admin on Thu Jul 06 02:46:46 UTC 2023
PRIMARY