Record Information
Version1.0
Creation date2010-04-08 22:10:06 UTC
Update date2019-11-26 03:06:34 UTC
Primary IDFDB012319
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSinigrin
DescriptionSinigrin, also known as myronate or myronic acid, belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. Sinigrin is an extremely weak basic (essentially neutral) compound (based on its pKa). Sinigrin is a bitter tasting compound. Sinigrin has been detected, but not quantified in, several different foods, such as cabbages, white cabbages, horseradish, wasabis, and capers. This could make sinigrin a potential biomarker for the consumption of these foods.
CAS Number534-69-0
Structure
Thumb
Synonyms
SynonymSource
1-Thio-b-D-glucopyranose 1-[N-(sulfooxy)-3-butenimidate], 9ciHMDB
2-Phenylethyl glucosinolateHMDB
Allyl glucosinolateHMDB
MyronateHMDB
Myronic acidHMDB
Sinigrin, monopotassium saltHMDB
{[(e)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino]oxy}sulfonateGenerator
{[(e)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}but-3-en-1-ylidene)amino]oxy}sulphonateGenerator
{[(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 acidGenerator
SinigrinMeSH
1-Thio-b-D-glucopyranose 1-[N-(sulfooxy)-3-butenimidate], 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility22.6 g/LALOGPS
logP-1.7ALOGPS
logP-3.2ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)-3.6ChemAxon
pKa (Strongest Basic)-0.49ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area166.11 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity74.7 m³·mol⁻¹ChemAxon
Polarizability32.49 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H17NO9S2
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
InChI IdentifierInChI=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 KeyPHZOWSSBXJXFOR-PTGZALFTSA-N
Isomeric SMILESOC[C@H]1O[C@@H](S\C(=N\OS(O)(=O)=O)CC=C)[C@H](O)[C@@H](O)[C@@H]1O
Average Molecular Weight359.373
Monoisotopic Molecular Weight359.034472527
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAlkylglucosinolates
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 FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 33.42%; H 4.77%; N 3.90%; O 40.07%; S 17.85%DFC
Melting PointMp 125-127° (K salt)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]28D -17 (c, 0.2 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9423000000-7647c2c4ab14297fbb5cJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-001i-5212139000-44f0f7f5b1e1360d77d3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ow-2917000000-1e5e9dddb7150c7f6ba9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gxt-6980000000-b9e4cac65ffb45350417JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-8e04e4b3fd539b9910cdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-3910000000-82262583417df5e92578JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-8900000000-c5ab479eb8b63e48f693JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03k9-5900000000-6402ab08001a62f077deJSpectraViewer
ChemSpider ID5288338
ChEMBL IDNot Available
KEGG Compound IDC08427
Pubchem Compound ID6911854
Pubchem Substance IDNot Available
ChEBI ID9162
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34070
CRC / DFC (Dictionary of Food Compounds) IDHGH51-L:HGH51-L
EAFUS IDNot Available
Dr. Duke IDSINIGRIN
BIGG IDNot Available
KNApSAcK IDC00001488
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDSinigrin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti feedantDUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
larvicideDUKE
mutagenicDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phagocytoticDUKE
quinone-reductase inducerDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. 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
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.