TRYPTOPHOL

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 Search

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

Title	Date	PubMed
5-Hydroxytryptophol in human cerebrospinal fluid: quantitative determination by gas chromatography-mass spectrometry using a deuterated internal standard.	1978 Mar 1	639316
Induction of estradiol metabolism by dietary indole-3-carbinol in humans.	1990 Jun 6	2342128
A new cytotoxic calyculinamide derivative, geometricin A, from the Australian sponge Luffariella geometrica.	2002 Jul	12141875
HPLC of tryptophan and its metabolites: as OPA derivatives and on the basis of their UV and fluorescence spectra, simultaneously.	2003	15206792
The relative contribution of monoamine oxidase and cytochrome p450 isozymes to the metabolic deamination of the trace amine tryptamine.	2003 Feb	12538805
Study of low molecular weight phenolic compounds during the aging of sparkling wines manufactured with red and white grape varieties.	2003 Mar 26	12643678
The catabolism of amino acids to long chain and complex alcohols in Saccharomyces cerevisiae.	2003 Mar 7	12499363
Indole derivatives produced by the fungus Colletotrichum acutatum causing lime anthracnose and postbloom fruit drop of citrus.	2003 Sep 12	13129603
Automation of gene assignments to metabolic pathways using high-throughput expression data.	2005 Aug 31	16135255
Hymeniacidon perleve associated bioactive bacterium pseudomonas sp. NJ6-3-1.	2005 Jan-Feb	15810730
Enhanced detergent extraction for analysis of membrane proteomes by two-dimensional gel electrophoresis.	2005 Jun 7	15941475
One electron oxidation induced dimerization of 5-hydroxytryptophol: role of 5-hydroxy substitution.	2005 Mar 17	16838976
Silicon-directed oxa-Pictet-Spengler cyclization and an unusual dimerization of 2-trimethylsilanyl tryptophols.	2005 May 12	15876050
Horseradish peroxidase-mediated aerobic and anaerobic oxidations of 3-alkylindoles.	2005 May 16	15848767
Rotationally resolved electronic spectroscopy of tryptophol in the gas phase.	2005 Nov 7	16358014
Spectrophotometric method for exploring 3-methyl-2-butene-1-thiol (MBT) formation in lager.	2006 Aug 23	16910696
Toward the control of Leptosphaeria maculans: design, syntheses, biological activity, and metabolism of potential detoxification inhibitors of the crucifer phytoalexin brassinin.	2006 Jul 15	16616505
Production of indolic compounds by rumen bacteria isolated from grazing ruminants.	2006 Jun	16696673
Quorum sensing: alcohols in a social situation.	2006 Jun 20	16782000
Eukaryotes learn how to count: quorum sensing by yeast.	2006 May 1	16651650
Feedback control of morphogenesis in fungi by aromatic alcohols.	2006 May 1	16618799
Targeted Gene Disruption of the Cyclo (L-Phe, L-Pro) Biosynthetic Pathway in Streptomyces sp. US24 Strain.	2007	17710112
Effect of neurotransmitters on NADPH-cytochrome P450 reductase in vitro activity.	2007 Aug	19356039
Tryptophol induces death receptor (DR) 5-mediated apoptosis in U937 cells.	2007 Aug	17690453
Inhibition of amyloid fibrillation of lysozyme by indole derivatives--possible mechanism of action.	2007 Dec	18028426
Isolation of tryptophol as an apoptosis-inducing component of vinegar produced from boiled extract of black soybean in human monoblastic leukemia U937 cells.	2007 Feb	17284845
Tryptophol cation conformations studied with ZEKE spectroscopy.	2007 Mar 15	17305323
Hybrid molecular imprinted membranes having selectivity and separation behavior to targeted indole derivatives.	2007 May 15	17456422
High-added-value antioxidants obtained from the degradation of wine phenolics by Lactobacillus plantarum.	2007 Nov	18044455
Benhamycin, novel alkaloid from terrestrial Streptomyces sp.	2007 Nov	17987502
Filament formation in Saccharomyces cerevisiae--a review.	2008	18481212
Electrospray ionization mass spectra of piperazimycins A and B and gamma-butyrolactones from a marine-derived Streptomyces sp.	2008 Dec	19194032
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 Feb 1	18023427
Genotoxicity of tryptophol in a battery of short-term assays on human white blood cells in vitro.	2008 May	18248512
An ipdC gene knock-out of Azospirillum brasilense strain SM and its implications on indole-3-acetic acid biosynthesis and plant growth promotion.	2008 May	17952626
Isolation and cytotoxicity of low-molecular-weight metabolites of Candida albicans.	2008 May 1	18508703
Integrative gene cloning and expression system for Streptomyces sp. US 24 and Streptomyces sp. TN 58 bioactive molecule producing strains.	2009	19547659
CgOpt1, a putative oligopeptide transporter from Colletotrichum gloeosporioides that is involved in responses to auxin and pathogenicity.	2009 Aug 21	19698103
Synthesis of tetrahydroisoquinocarbazoles via C-2 alkylation of indoles with 2-alkoxycyclopropanoate esters.	2009 Jul 2	19507849
Trichoderma virens, a plant beneficial fungus, enhances biomass production and promotes lateral root growth through an auxin-dependent mechanism in Arabidopsis.	2009 Mar	19176721
Indole derivatives from a marine sponge-derived yeast as DPPH radical scavengers.	2009 Nov	19943625
Auxin biosynthesis in pea: characterization of the tryptamine pathway.	2009 Nov	19710233
Inhibitory substrate binding site of human indoleamine 2,3-dioxygenase.	2009 Sep 16	19737010
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	21071871
Synthesis of the marine pyrroloiminoquinone alkaloids, discorhabdins.	2010 Apr 21	20479983
Transcriptional control of the quorum sensing response in yeast.	2010 Jan	20024075
Inhibitory activity of marine sponge-derived natural products against parasitic protozoa.	2010 Jan 15	20161970
Environmental and genetic determinants of colony morphology in yeast.	2010 Jan 22	20107600
Aniline-induced tryptophan production and identification of indole derivatives from three purple bacteria.	2010 Oct	20852980
Bioactive secondary metabolites from a new terrestrial Streptomyces sp. TN262.	2010 Sep	19842066

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:51:40 GMT 2023` Edited by `admin` on `Fri Dec 15 19:51:40 GMT 2023`
Record UNII	5809LZ7G1U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TRYPTOPHOL

Common 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

NSC-3884

Code

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