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Showing Compound Sinigrin (FDB012319)

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 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 a bitter tasting compound. Sinigrin is found, on average, in the highest concentration within brussel sprouts (Brassica oleracea var. gemmifera) and cauliflowers (Brassica oleracea var. botrytis). Sinigrin has also been detected, but not quantified in, several different foods, such as mustard, chinese mustards (Brassica juncea), horseradishes (Armoracia rusticana), broccolis (Brassica oleracea var. italica), and radishes (Raphanus sativus). This could make sinigrin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Sinigrin.
CAS Number534-69-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1-thio-b-D-Glucopyranose 1-[N-(sulfooxy)-3-butenimidate], 9ciHMDB
2-Phenylethyl glucosinolateHMDB
Allyl glucosinolateHMDB
MyronateHMDB
Myronic acidHMDB
Sinigrin, monopotassium saltMeSH, 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}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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSSinigrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-9423000000-7647c2c4ab14297fbb5cSpectrum
Predicted GC-MSSinigrin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-5212139000-44f0f7f5b1e1360d77d3Spectrum
Predicted GC-MSSinigrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ow-2917000000-1e5e9dddb7150c7f6ba92016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gxt-6980000000-b9e4cac65ffb453504172016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-8e04e4b3fd539b9910cd2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-3910000000-82262583417df5e925782016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-8900000000-c5ab479eb8b63e48f6932016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03k9-5900000000-6402ab08001a62f077de2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-25d4cebfa4dd0d0d7c6a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ikc-2595000000-e11c08f1fe56eef4efef2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gi0-9720000000-9e0bb14e5e2fa4101e432021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bta-0908000000-b7abdde860347283b8af2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06s2-4912000000-1e889da8b56a1c237bc52021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03ea-9800000000-66c017ed4ac7af48e6f12021-09-23View Spectrum
NMRNot Available
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 feedantA substance that inhibits normal feeding behavior, found in certain plants, deterring insects and animals from consuming them. Its therapeutic applications include pest control, while key medical uses involve managing insect-borne diseases and reducing crop damage.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
LarvicideAn insecticide that targets the larval life stage of insects, preventing their development into adults. Its biological role is to control insect populations, and its therapeutic applications include managing mosquito-borne diseases such as malaria and dengue fever, as well as controlling pest infestations in agriculture and public health.DUKE
MutagenicAn agent that induces genetic mutations, altering DNA sequences. It plays a biological role in evolution and adaptation. Therapeutically, mutagenic agents are used in cancer treatment, such as chemotherapy, and in gene therapy to introduce beneficial traits. Key medical uses include oncology and genetic research.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
PhagocytoticAn agent that engulfs and internalizes solid particles or cells through phagocytosis, playing a key role in immune defense. Therapeutically, it aids in removing pathogens and debris, with medical applications in treating infections and inflammatory disorders.DUKE
Quinone-reductase inducerAn 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
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.