Record Information
Version1.0
Creation date2010-04-08 22:06:19 UTC
Update date2019-11-26 03:00:06 UTC
Primary IDFDB004597
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlucocapangulin
DescriptionGlucocapangulin, also known as anthraglycoside b, is a member of the class of compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. Thus, glucocapangulin is considered to be an aromatic polyketide lipid molecule. Glucocapangulin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Glucocapangulin can be found in capers, which makes glucocapangulin a potential biomarker for the consumption of this food product.
CAS Number38840-23-2
Structure
Thumb
Synonyms
SynonymSource
1-beta-D-Glucopyranosyloxy-3-methyl-6-hydroxy-8-hydroxy-9,10-anthraquinoneKegg
1-b-D-Glucopyranosyloxy-3-methyl-6-hydroxy-8-hydroxy-9,10-anthraquinoneGenerator
1-Β-D-glucopyranosyloxy-3-methyl-6-hydroxy-8-hydroxy-9,10-anthraquinoneGenerator
Anthraglycoside bMeSH
4-Oxoheptyl glucosinolatebiospider
Glucocapangulinbiospider
Glucopangulinbiospider
Predicted Properties
PropertyValueSource
Water Solubility2.23 g/LALOGPS
logP0.71ALOGPS
logP0.9ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)7.24ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area173.98 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity104.28 m³·mol⁻¹ChemAxon
Polarizability41.98 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H20O10
IUPAC name1,6-dihydroxy-3-methyl-8-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dihydroanthracene-9,10-dione
InChI IdentifierInChI=1S/C21H20O10/c1-7-2-9-14(11(24)3-7)18(27)15-10(16(9)25)4-8(23)5-12(15)30-21-20(29)19(28)17(26)13(6-22)31-21/h2-5,13,17,19-24,26,28-29H,6H2,1H3/t13-,17-,19+,20-,21-/m1/s1
InChI KeyHSWIRQIYASIOBE-JNHRPPPUSA-N
Isomeric SMILES[H][C@]1(CO)O[C@@]([H])(OC2=CC(O)=CC3=C2C(=O)C2=C(C=C(C)C=C2O)C3=O)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O
Average Molecular Weight432.381
Monoisotopic Molecular Weight432.105646844
Classification
Description Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassAnthraquinones
Direct ParentHydroxyanthraquinones
Alternative Parents
Substituents
  • Hydroxyanthraquinone
  • Phenolic glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monosaccharide
  • Oxane
  • Vinylogous acid
  • Ketone
  • Secondary alcohol
  • Acetal
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00e9-0191800000-ebf37a14fedac4b63fed2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0290000000-92379afb999b434d91c42016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-3690000000-4c3ee4eacd5d479913c82016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00lr-1151900000-597373f9305a657904c92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1190200000-c22ce117bfbdd567259f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-4490000000-34c4c5de7d2aa7d545a62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090300000-64e9c7f3218b77c623082021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-eb51ce64fd59d84bfdd02021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-7291000000-b77a4f115437a814e8cf2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0030900000-7bf60e1db72182ebd0f42021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1090200000-618b298bb6ef4ae896882021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0090000000-654126b482d5f9a07e752021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDGLUCOCAPANGULIN
BIGG IDNot Available
KNApSAcK IDC00007848
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 / BioactivitiesNot Available
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).