Showing Compound Glucobrassicin (FDB002066)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:13 UTC

Update date

2025-11-18 22:34:43 UTC

Primary ID

FDB002066

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Glucobrassicin

Description

Glucobrassicin belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. Glucobrassicin is an extremely weak basic (essentially neutral) compound (based on its pKa). Glucobrassicin is a bitter tasting compound. Outside of the human body, Glucobrassicin has been detected, but not quantified in, several different foods, such as cauliflowers, broccoli, horseradish, chinese mustards, and swedes. This could make glucobrassicin a potential biomarker for the consumption of these foods. A single glucosylation occurs attaching a glucose molecule to the indole hydroximate through a thioether linkage. Several derivatives of glucobrassicin are known. The biosynthesis of glucobrassicin begins with tryptophan produced through several steps from the Shikimic acid pathway compound, chorismic acid. The compound itself was first isolated from Brassica plants, hence the ending of the name. As for other glucosinolates, degradation by the enzyme myrosinase is expected to produce an isothiocyanate, indol-3-ylmethylisothiocyanate. However, a large number of other reaction products are known, and indole-3-carbinol is not the dominant degradation product when glucosinolate degradation takes place in crushed plant tissue or in intact plants. Currently, the following six derivatives are known from plants:1-Methoxyglucobrassicin (neoglucobrassicin)4-Hydroxyglucobrassicin4-Methoxyglucobrassicin1,4-Dimethoxyglucobrassicin1-Sulfoglucobrassicin6'-IsoferuloylglucobrassicinThe three first mentioned derivatives are as frequent in crucifers as glucobrassicin itself. Tryptophan is converted to indole-3-acetaldoxime (IAOx) by cytochrome p450 enzymes (the redundant CYP92B3 and CYP79B3 in Arabidopsis thaliana) using NADPH and molecular Oxygen.

CAS Number

4356-52-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
3-Indolylmethylglucosinolate	HMDB, MeSH
Glucobrassicine	HMDB
indol-3-Ylmethyl glucosinolate	MeSH
Glucobrassicin	db_source

Predicted Properties

Property	Value	Source
Water Solubility	1.81 g/L	ALOGPS
logP	-0.98	ALOGPS
logP	-2	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	-3.4	ChemAxon
pKa (Strongest Basic)	-0.29	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	181.9 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	101.23 m³·mol⁻¹	ChemAxon
Polarizability	42.44 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C16H20N2O9S2

IUPAC name

{[(E)-[2-(1H-indol-3-yl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}ethylidene]amino]oxy}sulfonic acid

InChI Identifier

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+

InChI Key

DNDNWOWHUWNBCK-LDADJPATSA-N

Isomeric SMILES

OCC1OC(S\C(CC2=CNC3=CC=CC=C23)=N\OS(O)(=O)=O)C(O)C(O)C1O

Average Molecular Weight

448.468

Monoisotopic Molecular Weight

448.061021628

Classification

Description

Belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Alkylglucosinolates

Alternative Parents

Substituents

Alkylglucosinolate
Glycosyl compound
S-glycosyl compound
3-alkylindole
Indole
Indole or derivatives
Oxane
Benzenoid
Substituted pyrrole
Monothioacetal
Heteroaromatic compound
Organic sulfuric acid or derivatives
Pyrrole
Secondary alcohol
Oxacycle
Azacycle
Polyol
Organoheterocyclic compound
Sulfenyl compound
Organosulfur compound
Organonitrogen compound
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Primary alcohol
Organopnictogen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 42.85%; H 4.49%; N 6.25%; O 32.11%; S 14.30%	DFC
Melting Point	Mp 149-150° (as Me4N salt)	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]22D -13.3 (Me4N salt)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Glucobrassicin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0089-9803400000-5780fef230bb0579eb03	Spectrum
Predicted GC-MS	Glucobrassicin, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0udj-3962038000-866ed4459356cdab81b4	Spectrum
Predicted GC-MS	Glucobrassicin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Glucobrassicin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-9000000000-b65c20894fd7bebf4975	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-9000000000-a638b0c9711619390857	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-9000000000-18a45c4a14ab1623b4c9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-9000000000-2c6defe07f0424391ff8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-9000000000-8f9b73131d7ad5e9ffc9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-9010100000-9e24bf87eacf9fab447d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-9000000000-42bec04e55256f3d644e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-9000000000-23f70d1ab75b41bb1737	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-0000900000-0729cb0d0eabee7ac62a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-0000900000-9ba5439d42050658ce10	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-8000900000-72813133542f3f30c006	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-2000900000-b077c107ece5047e8384	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-9010300000-417cc0a1a594a6ea4504	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000t-0940700000-667fecebc846ae563dca	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-029l-0937000000-fe84e444e901db4dae48	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-5900000000-ae8118bdec9079ffc50d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-3290000000-c1f3a1fda8a4d72ade78	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uk9-7970000000-a03ba08d3973bef3163f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0w9u-6940000000-e8f4aea93ac317ebf659	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dj-0900600000-53c0435a401f4bd28e4c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-007a-2759200000-f474bd3b1f699a2373bb	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-11or-0900000000-b59ed87ffb4b1a261fa7	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000900000-73c8252e6a81a741cc1b	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001j-0316900000-a94509905d65387c0210	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1901000000-ea928de13c5e8e5e7702	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

7875815

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

9601691

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB30243

CRC / DFC (Dictionary of Food Compounds) ID

CDQ62-K:CDQ62-K

EAFUS ID

Not Available

Dr. Duke ID

GLUCOBRASSICIN

BIGG ID

Not Available

KNApSAcK ID

C00000125

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Glucobrassicin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Quinone-reductase inducer		An agent that stimulates quinone reductase enzymatic activity, enhancing cellular antioxidant defenses and protecting against carcinogens, with therapeutic applications in cancer chemoprevention and potential uses in managing oxidative stress-related diseases.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
bitter	Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).