U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C10H11NO
Molecular Weight 161.2004
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRYPTOPHOL

SMILES

OCCC1=CNC2=C1C=CC=C2

InChI

InChIKey=MBBOMCVGYCRMEA-UHFFFAOYSA-N
InChI=1S/C10H11NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,7,11-12H,5-6H2

HIDE SMILES / InChI

Molecular Formula C10H11NO
Molecular Weight 161.2004
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Aniline-induced tryptophan production and identification of indole derivatives from three purple bacteria.
2010-10
Bioactive secondary metabolites from a new terrestrial Streptomyces sp. TN262.
2010-09
Synthesis of the marine pyrroloiminoquinone alkaloids, discorhabdins.
2010-04-21
Environmental and genetic determinants of colony morphology in yeast.
2010-01-22
Inhibitory activity of marine sponge-derived natural products against parasitic protozoa.
2010-01-15
Transcriptional control of the quorum sensing response in yeast.
2010-01
Salkowski's reagent test as a primary screening index for functionalities of rhizobacteria isolated from wild dipterocarp saplings growing naturally on medium-strongly acidic tropical peat soil.
2010
Indole derivatives from a marine sponge-derived yeast as DPPH radical scavengers.
2009-11
Auxin biosynthesis in pea: characterization of the tryptamine pathway.
2009-11
Inhibitory substrate binding site of human indoleamine 2,3-dioxygenase.
2009-09-16
CgOpt1, a putative oligopeptide transporter from Colletotrichum gloeosporioides that is involved in responses to auxin and pathogenicity.
2009-08-21
Synthesis of tetrahydroisoquinocarbazoles via C-2 alkylation of indoles with 2-alkoxycyclopropanoate esters.
2009-07-02
Trichoderma virens, a plant beneficial fungus, enhances biomass production and promotes lateral root growth through an auxin-dependent mechanism in Arabidopsis.
2009-03
Integrative gene cloning and expression system for Streptomyces sp. US 24 and Streptomyces sp. TN 58 bioactive molecule producing strains.
2009
Electrospray ionization mass spectra of piperazimycins A and B and gamma-butyrolactones from a marine-derived Streptomyces sp.
2008-12
Isolation and cytotoxicity of low-molecular-weight metabolites of Candida albicans.
2008-05-01
Genotoxicity of tryptophol in a battery of short-term assays on human white blood cells in vitro.
2008-05
An ipdC gene knock-out of Azospirillum brasilense strain SM and its implications on indole-3-acetic acid biosynthesis and plant growth promotion.
2008-05
N-Alkoxy derivatization of indole-3-carbinol increases the efficacy of the G1 cell cycle arrest and of I3C-specific regulation of cell cycle gene transcription and activity in human breast cancer cells.
2008-02-01
Filament formation in Saccharomyces cerevisiae--a review.
2008
Inhibition of amyloid fibrillation of lysozyme by indole derivatives--possible mechanism of action.
2007-12
High-added-value antioxidants obtained from the degradation of wine phenolics by Lactobacillus plantarum.
2007-11
Benhamycin, novel alkaloid from terrestrial Streptomyces sp.
2007-11
Effect of neurotransmitters on NADPH-cytochrome P450 reductase in vitro activity.
2007-08
Tryptophol induces death receptor (DR) 5-mediated apoptosis in U937 cells.
2007-08
Hybrid molecular imprinted membranes having selectivity and separation behavior to targeted indole derivatives.
2007-05-15
Tryptophol cation conformations studied with ZEKE spectroscopy.
2007-03-15
Isolation of tryptophol as an apoptosis-inducing component of vinegar produced from boiled extract of black soybean in human monoblastic leukemia U937 cells.
2007-02
Targeted Gene Disruption of the Cyclo (L-Phe, L-Pro) Biosynthetic Pathway in Streptomyces sp. US24 Strain.
2007
Spectrophotometric method for exploring 3-methyl-2-butene-1-thiol (MBT) formation in lager.
2006-08-23
Toward the control of Leptosphaeria maculans: design, syntheses, biological activity, and metabolism of potential detoxification inhibitors of the crucifer phytoalexin brassinin.
2006-07-15
Quorum sensing: alcohols in a social situation.
2006-06-20
Production of indolic compounds by rumen bacteria isolated from grazing ruminants.
2006-06
Eukaryotes learn how to count: quorum sensing by yeast.
2006-05-01
Feedback control of morphogenesis in fungi by aromatic alcohols.
2006-05-01
Rotationally resolved electronic spectroscopy of tryptophol in the gas phase.
2005-11-07
Automation of gene assignments to metabolic pathways using high-throughput expression data.
2005-08-31
Enhanced detergent extraction for analysis of membrane proteomes by two-dimensional gel electrophoresis.
2005-06-07
Horseradish peroxidase-mediated aerobic and anaerobic oxidations of 3-alkylindoles.
2005-05-16
Silicon-directed oxa-Pictet-Spengler cyclization and an unusual dimerization of 2-trimethylsilanyl tryptophols.
2005-05-12
Hymeniacidon perleve associated bioactive bacterium pseudomonas sp. NJ6-3-1.
2005-04-07
One electron oxidation induced dimerization of 5-hydroxytryptophol: role of 5-hydroxy substitution.
2005-03-17
Indole derivatives produced by the fungus Colletotrichum acutatum causing lime anthracnose and postbloom fruit drop of citrus.
2003-09-12
Study of low molecular weight phenolic compounds during the aging of sparkling wines manufactured with red and white grape varieties.
2003-03-26
The catabolism of amino acids to long chain and complex alcohols in Saccharomyces cerevisiae.
2003-03-07
The relative contribution of monoamine oxidase and cytochrome p450 isozymes to the metabolic deamination of the trace amine tryptamine.
2003-02
HPLC of tryptophan and its metabolites: as OPA derivatives and on the basis of their UV and fluorescence spectra, simultaneously.
2003
A new cytotoxic calyculinamide derivative, geometricin A, from the Australian sponge Luffariella geometrica.
2002-07
Induction of estradiol metabolism by dietary indole-3-carbinol in humans.
1990-06-06
5-Hydroxytryptophol in human cerebrospinal fluid: quantitative determination by gas chromatography-mass spectrometry using a deuterated internal standard.
1978-03-01
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:59:14 GMT 2025
Edited
by admin
on Mon Mar 31 19:59:14 GMT 2025
Record UNII
5809LZ7G1U
Record Status Validated (UNII)
Record Version
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Name Type Language
TRYPTOPHOL
MI  
Common Name English
NSC-3884
Preferred Name English
3-.BETA.-HYDROXYETHYLINDOLE
Systematic Name English
3-.OMEGA.-HYDROXYETHYLINDOLE
Common Name English
2-(3-INDOLYL)ETHYL ALCOHOL
Systematic Name English
3-INDOLEETHANOL
Systematic Name English
INDOLE-3-ETHANOL
Systematic Name English
TRYPTOPHOL [MI]
Common Name English
2-INDOLYL(3)-ETHANOL
Common Name English
.BETA.-INDOLYLETHYL ALCOHOL
Systematic Name English
Code System Code Type Description
ECHA (EC/EINECS)
208-393-2
Created by admin on Mon Mar 31 19:59:14 GMT 2025 , Edited by admin on Mon Mar 31 19:59:14 GMT 2025
PRIMARY
MERCK INDEX
m11248
Created by admin on Mon Mar 31 19:59:14 GMT 2025 , Edited by admin on Mon Mar 31 19:59:14 GMT 2025
PRIMARY Merck Index
CAS
526-55-6
Created by admin on Mon Mar 31 19:59:14 GMT 2025 , Edited by admin on Mon Mar 31 19:59:14 GMT 2025
PRIMARY
CHEBI
17890
Created by admin on Mon Mar 31 19:59:14 GMT 2025 , Edited by admin on Mon Mar 31 19:59:14 GMT 2025
PRIMARY
EPA CompTox
DTXSID2060173
Created by admin on Mon Mar 31 19:59:14 GMT 2025 , Edited by admin on Mon Mar 31 19:59:14 GMT 2025
PRIMARY
FDA UNII
5809LZ7G1U
Created by admin on Mon Mar 31 19:59:14 GMT 2025 , Edited by admin on Mon Mar 31 19:59:14 GMT 2025
PRIMARY
MESH
C005949
Created by admin on Mon Mar 31 19:59:14 GMT 2025 , Edited by admin on Mon Mar 31 19:59:14 GMT 2025
PRIMARY
WIKIPEDIA
TRYPTOPHOL
Created by admin on Mon Mar 31 19:59:14 GMT 2025 , Edited by admin on Mon Mar 31 19:59:14 GMT 2025
PRIMARY
PUBCHEM
10685
Created by admin on Mon Mar 31 19:59:14 GMT 2025 , Edited by admin on Mon Mar 31 19:59:14 GMT 2025
PRIMARY
NSC
3884
Created by admin on Mon Mar 31 19:59:14 GMT 2025 , Edited by admin on Mon Mar 31 19:59:14 GMT 2025
PRIMARY