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Gluconapin (FDB017785)

Record Information
Version1.0
Creation date2010-04-08 22:13:18 UTC
Update date2019-11-26 03:15:13 UTC
Primary IDFDB017785
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGluconapin
DescriptionGluconapin belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. Gluconapin is an extremely weak basic (essentially neutral) compound (based on its pKa). Gluconapin has been detected, but not quantified in, several different foods, such as broccoli, cauliflowers, chinese mustards, white mustards, and horseradish. This could make gluconapin a potential biomarker for the consumption of these foods.
CAS Number19041-09-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility14.9 g/LALOGPS
logP-1.6ALOGPS
logP-2.7ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)-3.6ChemAxon
pKa (Strongest Basic)-0.33ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area166.11 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity79.3 m³·mol⁻¹ChemAxon
Polarizability34.28 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H19NO9S2
IUPAC name{[(E)-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}pent-4-en-1-ylidene)amino]oxy}sulfonic acid
InChI IdentifierInChI=1S/C11H19NO9S2/c1-2-3-4-7(12-21-23(17,18)19)22-11-10(16)9(15)8(14)6(5-13)20-11/h2,6,8-11,13-16H,1,3-5H2,(H,17,18,19)/b12-7+
InChI KeyPLYQBXHVYUJNQB-KPKJPENVSA-N
Isomeric SMILESOCC1OC(S\C(CCC=C)=N\OS(O)(=O)=O)C(O)C(O)C1O
Average Molecular Weight373.4
Monoisotopic Molecular Weight373.050122591
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 35.38%; H 5.13%; N 3.75%; O 38.56%; S 17.17%DFC
Melting PointMp 125° (K salt)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D -23.5 (c, 1.8 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGluconapin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0abc-9414000000-5fc2cd0542ac7b7dd56aSpectrum
Predicted GC-MSGluconapin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-5112139000-d223c4a7654df6d59c40Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-2749000000-92bf228af4bddfdeb0e42016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-4890000000-f6e580cbbdabc202356a2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-ef4e937cc29cf8b8d9e12016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-3591000000-5d7b33a7533ed3f5c0dc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-8910000000-0d5892023771dead4ac62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-020u-4900000000-8b0531fa199e0c5cda7b2016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC08415
Pubchem Compound ID656550
Pubchem Substance IDNot Available
ChEBI ID5411
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB38427
CRC / DFC (Dictionary of Food Compounds) IDLBB62-U:LBB62-U
EAFUS IDNot Available
Dr. Duke IDGLUCONAPIN
BIGG IDNot Available
KNApSAcK IDC00007586
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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
quinone-reductase inducerDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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.