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=C2C=CC=C3)=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
Variation of glucosinolates in wild radish (Raphanus raphanistrum) accessions.	2010-11-24	20964435
Unveiling the phytoalexin biosynthetic puzzle in salt cress: unprecedented incorporation of glucobrassicin into wasalexins A and B.	2010-11-21	20848032
Breakdown products of neoglucobrassicin inhibit activation of Nrf2 target genes mediated by myrosinase-derived glucoraphanin hydrolysis products.	2010-11	20868228
The seed composition of Arabidopsis mutants for the group 3 sulfate transporters indicates a role in sulfate translocation within developing seeds.	2010-10	20702726
Radicals and radical ions derived from indole, indole-3-carbinol and diindolylmethane.	2010-07-01	20524680
3,3'-Diindolylmethane attenuates experimental arthritis and osteoclastogenesis.	2010-03-01	19854159
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.	2010-02	19558496
Crossfit analysis: a novel method to characterize the dynamics of induced plant responses.	2009-12-16	20015363
The biosynthetic pathway of crucifer phytoalexins and phytoanticipins: de novo incorporation of deuterated tryptophans and quasi-natural compounds.	2009-06	19560792
Influence of fermentation conditions on glucosinolates, ascorbigen, and ascorbic acid content in white cabbage (Brassica oleracea var. capitata cv. Taler) cultivated in different seasons.	2009-02-10	19200088
Ascorbigen: chemistry, occurrence, and biologic properties.	2009-01-27	19168003
Anti-adult T-cell leukemia/lymphoma effects of indole-3-carbinol.	2009-01-16	19146708
Dietary intake of individual glucosinolates in participants of the EPIC-Heidelberg cohort study.	2009	19295191
Metabolic engineering of aliphatic glucosinolates in Chinese cabbage plants expressing Arabidopsis MAM1, CYP79F1, and CYP83A1.	2008-06-30	18593532
Protective effect of the cruciferous vegetable mustard leaf (Brassica campestris) against in vivo chromosomal damage and oxidative stress induced by gamma-radiation and genotoxic chemicals.	2008-06	18418865
The impact of the absence of aliphatic glucosinolates on insect herbivory in Arabidopsis.	2008-04-30	18446225
Metabolic engineering of indole glucosinolates in Chinese cabbage plants by expression of Arabidopsis CYP79B2, CYP79B3, and CYP83B1.	2008-04-30	18414013
Performance of generalist and specialist herbivores and their endoparasitoids differs on cultivated and wild Brassica populations.	2008-02	18231835
Barbarea vulgaris glucosinolate phenotypes differentially affect performance and preference of two different species of lepidopteran herbivores.	2008-02	18213497
ESP and ESM1 mediate indol-3-acetonitrile production from indol-3-ylmethyl glucosinolate in Arabidopsis.	2008-02	17920088
Remarkable incorporation of the first sulfur containing indole derivative: another piece in the biosynthetic puzzle of crucifer phytoalexins.	2008-01-07	18075646
Seasonal variation in glucosinolate content in Brassica oleracea crops grown in northwestern Spain.	2008-01	17889044
Influence of nitrogen and sulfur on biomass production and carotenoid and glucosinolate concentrations in watercress (Nasturtium officinale R. Br.).	2007-12-26	18052091
Flower vs. leaf feeding by Pieris brassicae: glucosinolate-rich flower tissues are preferred and sustain higher growth rate.	2007-10	17828429
Chemical Investigation of Some Capparis Species Growing in Egypt and their Antioxidant Activity.	2007-09	18227928
Impact of foliar herbivory on the development of a root-feeding insect and its parasitoid.	2007-05	17334787
Jasmonic acid-induced changes in Brassica oleracea affect oviposition preference of two specialist herbivores.	2007-04	17334923
Factors affecting the glucosinolate content of kale (Brassica oleracea acephala group).	2007-02-07	17263499
Interaction between atmospheric CO2 and glucosinolates in broccoli.	2007-01	17165144
The natural chemopreventive compound indole-3-carbinol: state of the science.	2006-04-26	16634522
Prior exposure to indole-3-carbinol decreases the incidence of specific cyclophosphamide-induced developmental defects in mice.	2005-06	15954085
Effects of Brussels sprout juice on the cell cycle and adhesion of human colorectal carcinoma cells (HT29) in vitro.	2005-05-18	15884814
Quantification of glucosinolates in leaves of leaf rape (Brassica napus ssp. pabularia) by near-infrared spectroscopy.	2005-01	15652574
Glucosinolate derivatives in stored fermented cabbage.	2004-12-29	15612779
Chemical changes induced by methyl jasmonate in oilseed rape grown in the laboratory and in the field.	2004-12-15	15675811
Desulfoglucosinolate sulfotransferases from Arabidopsis thaliana catalyze the final step in the biosynthesis of the glucosinolate core structure.	2004-12-03	15358770
Correlation of glucosinolate content to myrosinase activity in horseradish (Armoracia rusticana).	2004-11-17	15537302
Indole-3-carbinol and 3,3'-diindolylmethane induce apoptosis in human prostate cancer cells.	2003-06	12738179
Health-promoting compounds in broccoli as influenced by refrigerated transport and retail sale period.	2003-05-07	12720387
Is induction response negatively correlated with constitutive resistance in black mustard?	2002-11	12487350
Occurrence and formation of indole-3-acetamide in Arabidopsis thaliana.	2002-11	12430025
Isolation and structure elucidation of a new thermal breakdown product of glucobrassicin, the parent indole glucosinolate.	2002-08-28	12188627
Plant allelochemicals differentially regulate Helicoverpa zea cytochrome P450 genes.	2002-08	12144700
Glucosinolates of seven medicinal plants from Thailand.	2002-06	12048016
A role for nitrilase 3 in the regulation of root morphology in sulphur-starving Arabidopsis thaliana.	2002-04	11967096
Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip.	2002-03	11867093
Sequestration of host plant glucosinolates in the defensive hemolymph of the sawfly Athalia rosae.	2001-12	11789955
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.	2001-10	11586482
Assembling the biosynthetic puzzle of crucifer metabolites: indole-3-acetaldoxime is incorporated efficiently into phytoalexins but glucobrassicin is not.	2001-09-07	12240387
The myrosinase-glucosinolate system in the interaction between Leptosphaeria maculans and Brassica napus.	2001-09-01	20573016

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:07:09 GMT 2025` Edited by `admin` on `Mon Mar 31 22:07:09 GMT 2025`
Record UNII	EA6EH0IU89
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GLUCOBRASSICIN

Common Name

English

3-INDOLEGLUCOBRASSICIN

Preferred 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

GLUCOBRASSICINE

Common Name

English

3-INDOLYLMETHYL GLUCOSINOLATE

Common Name

English

Code System Code Type Description

CHEBI

64962