ContaminantDB: Sinigrin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 00:16:28 UTC

Update Date

2016-11-09 01:18:38 UTC

Accession Number

CHEM028182

Identification

Common Name

Sinigrin

Class

Small Molecule

Description

Sinigrin is found in brassicas. Sinigrin is isolated from seeds of black mustard (Brassica nigra) and cabbage, as K salt. Sinigrin is present in many crucifers, major glucosinolate in Brussels sprouts (Brassica oleraceae).

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-thio-b-D-Glucopyranose 1-[N-(sulfooxy)-3-butenimidate], 9ci	HMDB
2-Phenylethyl glucosinolate	HMDB
Allyl glucosinolate	HMDB
Myronate	HMDB
Myronic acid	HMDB
Sinigrin, monopotassium salt	MeSH, HMDB
{[(e)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino]oxy}sulfonate	Generator
{[(e)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}but-3-en-1-ylidene)amino]oxy}sulphonate	Generator
{[(e)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}but-3-en-1-ylidene)amino]oxy}sulphonic acid	Generator
Sinigrin	MeSH

Chemical Formula

C₁₀H₁₇NO₉S₂

Average Molecular Mass

359.373 g/mol

Monoisotopic Mass

359.034 g/mol

CAS Registry Number

534-69-0

IUPAC Name

{[(E)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino]oxy}sulfonic acid

Traditional Name

[(E)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino]oxysulfonic acid

SMILES

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

InChI Identifier

InChI=1S/C10H17NO9S2/c1-2-3-6(11-20-22(16,17)18)21-10-9(15)8(14)7(13)5(4-12)19-10/h2,5,7-10,12-15H,1,3-4H2,(H,16,17,18)/b11-6+/t5-,7-,8+,9-,10+/m1/s1

InChI Key

PHZOWSSBXJXFOR-PTGZALFTSA-N

Chemical Taxonomy

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
Polyol
Oxacycle
Organoheterocyclic compound
Sulfenyl compound
Alcohol
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Organic oxide
Primary alcohol
Organic nitrogen compound
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	22.6 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-3.2	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	-3.6	ChemAxon
pKa (Strongest Basic)	-0.49	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	166.11 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	74.7 m³·mol⁻¹	ChemAxon
Polarizability	32.49 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9423000000-7647c2c4ab14297fbb5c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-001i-5212139000-44f0f7f5b1e1360d77d3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ow-2917000000-1e5e9dddb7150c7f6ba9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gxt-6980000000-b9e4cac65ffb45350417	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-8e04e4b3fd539b9910cd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-3910000000-82262583417df5e92578	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-8900000000-c5ab479eb8b63e48f693	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03k9-5900000000-6402ab08001a62f077de	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0009000000-25d4cebfa4dd0d0d7c6a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ikc-2595000000-e11c08f1fe56eef4efef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gi0-9720000000-9e0bb14e5e2fa4101e43	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bta-0908000000-b7abdde860347283b8af	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06s2-4912000000-1e889da8b56a1c237bc5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03ea-9800000000-66c017ed4ac7af48e6f1	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum