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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:51:16 UTC
Update Date2018-03-12 21:56:50 UTC
HMDB IDHMDB0034070
Secondary Accession Numbers
  • HMDB34070
Metabolite Identification
Common NameSinigrin
DescriptionSinigrin 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).
Structure
Thumb
Synonyms
ValueSource
1-thio-b-D-Glucopyranose 1-[N-(sulfooxy)-3-butenimidate], 9ciHMDB
2-Phenylethyl glucosinolateHMDB
Allyl glucosinolateHMDB
MyronateHMDB
Myronic acidHMDB
Sinigrin, monopotassium saltMeSH
Chemical FormulaC10H17NO9S2
Average Molecular Weight359.373
Monoisotopic Molecular Weight359.034472527
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
CAS Registry Number534-69-0
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 KeyPHZOWSSBXJXFOR-PTGZALFTSA-N
Chemical Taxonomy
DescriptionThis compound 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point125 - 127 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9423000000-7647c2c4ab14297fbb5cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-001i-5212139000-44f0f7f5b1e1360d77d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ow-2917000000-1e5e9dddb7150c7f6ba9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gxt-6980000000-b9e4cac65ffb45350417View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-8e04e4b3fd539b9910cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-3910000000-82262583417df5e92578View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-8900000000-c5ab479eb8b63e48f693View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03k9-5900000000-6402ab08001a62f077deView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012319
KNApSAcK IDC00001488
Chemspider ID5288338
KEGG Compound IDC08427
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSinigrin
METLIN IDNot Available
PubChem Compound6911854
PDB IDNot Available
ChEBI ID9162
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .