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=CC=CC2=C1C=CN2

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 8297	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 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16605241	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Radical-scavenging activity of butylated hydroxytoluene (BHT) and its metabolites.	2004 Jul	15172835
Protein engineering of toluene ortho-monooxygenase of Burkholderia cepacia G4 for regiospecific hydroxylation of indole to form various indigoid compounds.	2005 Jan	15290130
Inhibition of amyloid fibril formation and cytotoxicity by hydroxyindole derivatives.	2006 Apr 18	16605241
Synthesis and biological evaluation of novel angular fused Pyrrolocoumarins.	2008 Feb	18341252
Halogenated indole alkaloids from marine invertebrates.	2010 Apr 28	20559487
Bicyclic compounds repress membrane vesicle production and Pseudomonas quinolone signal synthesis in Pseudomonas aeruginosa.	2010 Mar	20146747
Glucuronidation of psilocin and 4-hydroxyindole by the human UDP-glucuronosyltransferases.	2010 Mar	20007669

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

4-HYDROXYINDOLE [INCI]

Common Name

English

INDOL-4-OL

Systematic Name

English

4-HYDROXY-1H-INDOLE

Systematic Name

English

1H-INDOL-4-OL

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