4-HYDROXYINDOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H7NO
Molecular Weight	133.1473
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=C2C=CNC2=CC=C1

InChI

InChIKey=NLMQHXUGJIAKTH-UHFFFAOYSA-N

InChI=1S/C8H7NO/c10-8-3-1-2-7-6(8)4-5-9-7/h1-5,9-10H

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18341252 | https://www.ncbi.nlm.nih.gov/pubmed/25122565 | https://www.ncbi.nlm.nih.gov/pubmed/16605241

4-Hydroxyindole is a simple indole derivative. It effectively inhibits Abeta peptide-induced amyloid fibril formation and prevent cell death induced by the peptide in culture. 4-Hydroxyindole was glucuronidated mainly by UGT1A6, with minor activity by UGT1A9. 4-hydroxyindole is used for the synthesis of anti-inflammatory angular pyrrolocoumarins.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Beta amyloid A4 protein 9 Target ID: CHEMBL2487 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16605241	Inhibitor 8504	3.0 µM [Kd]
UDP-glucuronosyltransferase 1-6 5 Target ID: CHEMBL1743316 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28778465 \| https://www.ncbi.nlm.nih.gov/pubmed/25122565	Substrate 661
UDP-glucuronosyltransferase 1-9 11 Target ID: CHEMBL1743319 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25122565	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Alzheimer’s disease 278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16605241	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Halogenated indole alkaloids from marine invertebrates.	2010-04-28	20559487
Bicyclic compounds repress membrane vesicle production and Pseudomonas quinolone signal synthesis in Pseudomonas aeruginosa.	2010-03	20146747
Glucuronidation of psilocin and 4-hydroxyindole by the human UDP-glucuronosyltransferases.	2010-03	20007669
Synthesis and biological evaluation of novel angular fused Pyrrolocoumarins.	2008-02	18341252
Indoloxypropanolamine analogues as 5-HT(1A) receptor antagonists.	2007-10-15	17804228
Inhibition of amyloid fibril formation and cytotoxicity by hydroxyindole derivatives.	2006-04-18	16605241
Protein engineering of toluene ortho-monooxygenase of Burkholderia cepacia G4 for regiospecific hydroxylation of indole to form various indigoid compounds.	2005-01	15290130
Radical-scavenging activity of butylated hydroxytoluene (BHT) and its metabolites.	2004-07	15172835

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

4-hydroxyindole (4HI) had the most significant inhibitory effect on Abeta1-40 cytotoxicity. When 25 or 50 uM 4HI was added to a solution containing Abeta1-40, the viability rate of PC12 cells was elevated by ∼25% when compared with that under control conditions.

Name

Type

Language

4-HYDROXYINDOLE

Official Name

English

1H-INDOL-4-OL

Preferred Name

English

INDOL-4-OL

Systematic Name

English

4-HYDROXY-1H-INDOLE

Systematic Name

English

4-HYDROXYINDOLE [USP-RS]

Common Name

English

PINDOLOL IMPURITY E [EP IMPURITY]

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID3057696