AFCDB: Glucoraphanin (FDB017756)

Record Information

Version

1.0

Creation date

2010-04-08 22:13:17 UTC

Update date

2019-11-26 03:15:10 UTC

Primary ID

FDB017756

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Glucoraphanin

Description

Glucoraphanin belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. Glucoraphanin is an extremely weak basic (essentially neutral) compound (based on its pKa). Glucoraphanin has been detected, but not quantified in, several different foods, such as radish, cauliflowers, cabbages, broccoli, and brassicas. This could make glucoraphanin a potential biomarker for the consumption of these foods.

CAS Number

21414-41-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	24.7 g/L	ALOGPS
logP	-0.98	ALOGPS
logP	-4.7	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	-3.7	ChemAxon
pKa (Strongest Basic)	-0.44	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	186.01 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	92.5 m³·mol⁻¹	ChemAxon
Polarizability	40.16 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C12H22NO10S3

IUPAC name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(1E)-5-methanesulfinyl-1-[(sulfooxy)imino]pentyl]sulfanyl}oxane-3,4,5-triol

InChI Identifier

InChI=1S/C12H23NO10S3/c1-25(18)5-3-2-4-8(13-23-26(19,20)21)24-12-11(17)10(16)9(15)7(6-14)22-12/h7,9-12,14-17H,2-6H2,1H3,(H,19,20,21)/p-1/b13-8+/t7-,9-,10+,11-,12+,25?/m1/s1

InChI Key

GMMLNKINDDUDCF-RFOBZYEESA-M

Isomeric SMILES

CS(=O)CCCC\C(S[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=N/OS([O-])(=O)=O

Average Molecular Weight

436.499

Monoisotopic Molecular Weight

436.040582999

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
Oxane
Monothioacetal
Organic sulfuric acid or derivatives
Secondary alcohol
Sulfoxide
Polyol
Oxacycle
Organoheterocyclic compound
Sulfinyl compound
Sulfenyl compound
Primary alcohol
Alcohol
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Organic anion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 32.94%; H 5.30%; N 3.20%; O 36.57%; S 21.99%	DFC
Melting Point	Not Available
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	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000j-1600900000-f3f9fa6852192847bc4e	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03fr-0839800000-31d730fcbc586a2de279	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9200000000-28c094a0eb7497b78b24	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dr-9000200000-fc0d0b71e5db7d627990	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-9100000000-fdd5a23ff9a3217253ec	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03l3-9600000000-de60554dc27b9a46e760	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

7827556

ChEMBL ID

Not Available

KEGG Compound ID

C08419

Pubchem Compound ID

9548633

Pubchem Substance ID

Not Available

ChEBI ID

5415

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB38404

CRC / DFC (Dictionary of Food Compounds) ID

KZZ63-M:KZZ67-Q

EAFUS ID

Not Available

Dr. Duke ID

GLUCORAPHANIN

BIGG ID

Not Available

KNApSAcK ID

C00007545

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

Not Available

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			DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

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).

Glucoraphanin (FDB017756)

Structure for FDB017756 (Glucoraphanin)