GLUCOBRASSICIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H20N2O9S2
Molecular Weight	448.468
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@H]1O[C@@H](S\C(CC2=CNC3=CC=CC=C23)=N/OS(O)(=O)=O)[C@H](O)[C@@H](O)[C@@H]1O

InChI

InChIKey=DNDNWOWHUWNBCK-PIAXYHQTSA-N

InChI=1S/C16H20N2O9S2/c19-7-11-13(20)14(21)15(22)16(26-11)28-12(18-27-29(23,24)25)5-8-6-17-10-4-2-1-3-9(8)10/h1-4,6,11,13-17,19-22H,5,7H2,(H,23,24,25)/b18-12-/t11-,13-,14+,15-,16+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C16H20N2O9S2
Molecular Weight	448.468
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	1
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Biochemical effects of dietary intake of different broccoli samples. II. Multivariate analysis of contributions of specific glucosinolates in modulating cytochrome P-450 and antioxidant defense enzyme activities.	2001 Oct	11586482
The myrosinase-glucosinolate system in the interaction between Leptosphaeria maculans and Brassica napus.	2001 Sep 1	20573016
Assembling the biosynthetic puzzle of crucifer metabolites: indole-3-acetaldoxime is incorporated efficiently into phytoalexins but glucobrassicin is not.	2001 Sep 7	12240387
Isolation and structure elucidation of a new thermal breakdown product of glucobrassicin, the parent indole glucosinolate.	2002 Aug 28	12188627
Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip.	2002 Mar	11867093
Is induction response negatively correlated with constitutive resistance in black mustard?	2002 Nov	12487350
Occurrence and formation of indole-3-acetamide in Arabidopsis thaliana.	2002 Nov	12430025
Health-promoting compounds in broccoli as influenced by refrigerated transport and retail sale period.	2003 May 7	12720387
Correlation of glucosinolate content to myrosinase activity in horseradish (Armoracia rusticana).	2004 Nov 17	15537302
Effects of Brussels sprout juice on the cell cycle and adhesion of human colorectal carcinoma cells (HT29) in vitro.	2005 May 18	15884814
Jasmonic acid-induced changes in Brassica oleracea affect oviposition preference of two specialist herbivores.	2007 Apr	17334923
Influence of nitrogen and sulfur on biomass production and carotenoid and glucosinolate concentrations in watercress (Nasturtium officinale R. Br.).	2007 Dec 26	18052091
Impact of foliar herbivory on the development of a root-feeding insect and its parasitoid.	2007 May	17334787
Flower vs. leaf feeding by Pieris brassicae: glucosinolate-rich flower tissues are preferred and sustain higher growth rate.	2007 Oct	17828429
Chemical Investigation of Some Capparis Species Growing in Egypt and their Antioxidant Activity.	2007 Sep	18227928
Barbarea vulgaris glucosinolate phenotypes differentially affect performance and preference of two different species of lepidopteran herbivores.	2008 Feb	18213497
Metabolic engineering of aliphatic glucosinolates in Chinese cabbage plants expressing Arabidopsis MAM1, CYP79F1, and CYP83A1.	2008 Jun 30	18593532
Dietary intake of individual glucosinolates in participants of the EPIC-Heidelberg cohort study.	2009	19295191
Crossfit analysis: a novel method to characterize the dynamics of induced plant responses.	2009 Dec 16	20015363
Anti-adult T-cell leukemia/lymphoma effects of indole-3-carbinol.	2009 Jan 16	19146708
Influence of fermentation conditions on glucosinolates, ascorbigen, and ascorbic acid content in white cabbage (Brassica oleracea var. capitata cv. Taler) cultivated in different seasons.	2009 Jan-Feb	19200088
The biosynthetic pathway of crucifer phytoalexins and phytoanticipins: de novo incorporation of deuterated tryptophans and quasi-natural compounds.	2009 Jun	19560792
Ascorbigen: chemistry, occurrence, and biologic properties.	2009 Mar-Apr	19168003
Sulforaphane but not ascorbigen, indole-3-carbinole and ascorbic acid activates the transcription factor Nrf2 and induces phase-2 and antioxidant enzymes in human keratinocytes in culture.	2010 Feb	19558496
Radicals and radical ions derived from indole, indole-3-carbinol and diindolylmethane.	2010 Jul 1	20524680
3,3'-Diindolylmethane attenuates experimental arthritis and osteoclastogenesis.	2010 Mar 1	19854159
Breakdown products of neoglucobrassicin inhibit activation of Nrf2 target genes mediated by myrosinase-derived glucoraphanin hydrolysis products.	2010 Nov	20868228
Unveiling the phytoalexin biosynthetic puzzle in salt cress: unprecedented incorporation of glucobrassicin into wasalexins A and B.	2010 Nov 21	20848032
Variation of glucosinolates in wild radish (Raphanus raphanistrum) accessions.	2010 Nov 24	20964435
The seed composition of Arabidopsis mutants for the group 3 sulfate transporters indicates a role in sulfate translocation within developing seeds.	2010 Oct	20702726

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:29:48 GMT 2023` Edited by `admin` on `Sat Dec 16 08:29:48 GMT 2023`
Record UNII	EA6EH0IU89
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GLUCOBRASSICIN

Common Name

English

GLUCOPYRANOSE, 1-THIO-, 1-INDOLE-3-ACETOHYDROXIMATE NO-(HYDROGEN SULFATE), .BETA.-D-

Systematic Name

English

.BETA.-D-GLUCOPYRANOSE, 1-THIO-, 1-(N-(SULFOOXY)-1H-INDOLE-3-ETHANIMIDATE), Z-

Systematic Name

English

3-INDOLEGLUCOBRASSICIN

Common Name

English

GLUCOBRASSICINE

Common Name

English

3-INDOLYLMETHYL GLUCOSINOLATE

Common Name

English

Code System Code Type Description

CHEBI

64962