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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:26:52 UTC
Update Date2022-03-07 02:54:09 UTC
HMDB IDHMDB0034571
Secondary Accession Numbers
  • HMDB34571
Metabolite Identification
Common NameChrysophanol 1-triglucoside
DescriptionChrysophanol 1-triglucoside belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. Chrysophanol 1-triglucoside has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, herbs and spices, pulses, and robusta coffees (Coffea canephora). This could make chrysophanol 1-triglucoside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Chrysophanol 1-triglucoside.
Structure
Data?1563862583
SynonymsNot Available
Chemical FormulaC33H40O19
Average Molecular Weight740.6593
Monoisotopic Molecular Weight740.216379098
IUPAC Name1-{[6-({[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-8-hydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione
Traditional Name1-{[6-({[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-8-hydroxy-3-methylanthracene-9,10-dione
CAS Registry Number120181-07-9
SMILES
CC1=CC2=C(C(=O)C3=C(C=CC=C3O)C2=O)C(OC2OC(COC3OC(CO)C(O)C(OC4OC(CO)C(O)C(O)C4O)C3O)C(O)C(O)C2O)=C1
InChI Identifier
InChI=1S/C33H40O19/c1-10-5-12-19(24(41)18-11(20(12)37)3-2-4-13(18)36)14(6-10)48-32-27(44)26(43)22(39)17(51-32)9-47-31-29(46)30(23(40)16(8-35)49-31)52-33-28(45)25(42)21(38)15(7-34)50-33/h2-6,15-17,21-23,25-36,38-40,42-46H,7-9H2,1H3
InChI KeySOWISUOFXLRAML-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentOligosaccharides
Alternative Parents
Substituents
  • Oligosaccharide
  • 9,10-anthraquinone
  • Anthraquinone
  • Phenolic glycoside
  • Anthracene
  • Glycosyl compound
  • O-glycosyl compound
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Oxane
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Organic oxide
  • Primary alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point284 - 286 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility11.1 g/LALOGPS
logP-0.82ALOGPS
logP-2.3ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)9.39ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area312.05 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity167.12 m³·mol⁻¹ChemAxon
Polarizability71.56 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+264.4531661259
DarkChem[M-H]-250.04931661259
DeepCCS[M+H]+261.50230932474
DeepCCS[M-H]-259.35930932474
DeepCCS[M-2H]-292.59830932474
DeepCCS[M+Na]+267.41430932474
AllCCS[M+H]+251.032859911
AllCCS[M+H-H2O]+250.832859911
AllCCS[M+NH4]+251.232859911
AllCCS[M+Na]+251.332859911
AllCCS[M-H]-244.332859911
AllCCS[M+Na-2H]-247.732859911
AllCCS[M+HCOO]-251.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Chrysophanol 1-triglucosideCC1=CC2=C(C(=O)C3=C(C=CC=C3O)C2=O)C(OC2OC(COC3OC(CO)C(O)C(OC4OC(CO)C(O)C(O)C4O)C3O)C(O)C(O)C2O)=C15422.5Standard polar33892256
Chrysophanol 1-triglucosideCC1=CC2=C(C(=O)C3=C(C=CC=C3O)C2=O)C(OC2OC(COC3OC(CO)C(O)C(OC4OC(CO)C(O)C(O)C4O)C3O)C(O)C(O)C2O)=C15378.6Standard non polar33892256
Chrysophanol 1-triglucosideCC1=CC2=C(C(=O)C3=C(C=CC=C3O)C2=O)C(OC2OC(COC3OC(CO)C(O)C(OC4OC(CO)C(O)C(O)C4O)C3O)C(O)C(O)C2O)=C16379.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_1_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_1_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chrysophanol 1-triglucoside GC-MS (TMS_2_14) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 1-triglucoside 10V, Positive-QTOFsplash10-0c00-0191180800-017418bbb2b0cf93ae982016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 1-triglucoside 20V, Positive-QTOFsplash10-0a4i-0191130000-abb7aa45ed840248b74a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 1-triglucoside 40V, Positive-QTOFsplash10-0a4i-0591020000-c98bdfe7a0ea35bd5b212016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 1-triglucoside 10V, Negative-QTOFsplash10-0uki-0393331800-d06bd9df477f6382ebc72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 1-triglucoside 20V, Negative-QTOFsplash10-0udi-1392020100-34b8459118f246de21332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 1-triglucoside 40V, Negative-QTOFsplash10-0udi-2490000000-d1a4997cefe01c6ee8f12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 1-triglucoside 10V, Negative-QTOFsplash10-000i-0030000900-df8ed3df8186d3f7ecc92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 1-triglucoside 20V, Negative-QTOFsplash10-0uy0-3191218500-5b5f9b967d6e0d144faa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 1-triglucoside 40V, Negative-QTOFsplash10-0udi-3290001000-92f48e1b53c5538df4bd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 1-triglucoside 10V, Positive-QTOFsplash10-0a4i-0090100100-e6a7b07e9e2601a8b6682021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 1-triglucoside 20V, Positive-QTOFsplash10-0a4i-0290000000-4d9c80ade4ad23b462362021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysophanol 1-triglucoside 40V, Positive-QTOFsplash10-0a4r-2290000000-bbb80788daaafd80d1a42021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
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
FooDB IDFDB013084
KNApSAcK IDC00054110
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14213506
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .