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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:28:34 UTC
Update Date2022-03-07 02:56:24 UTC
HMDB IDHMDB0039932
Secondary Accession Numbers
  • HMDB39932
Metabolite Identification
Common NameChrysoeriol 7-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide]
DescriptionChrysoeriol 7-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide] belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position. Chrysoeriol 7-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide] has been detected, but not quantified in, alfalfas (Medicago sativa) and pulses. This could make chrysoeriol 7-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide] a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Chrysoeriol 7-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide].
Structure
Data?1563863463
Synonyms
ValueSource
5-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 2-O-[2-O-[(2E)-3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]-beta-D-glucopyranuronosyl]-beta-D-glucopyranosiduronic acidHMDB
Chrysoeriol 7-(2'''-feruloylglucuronosyl)-(1->2)-glucuronideHMDB
6-[(6-Carboxy-4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-3-yl)oxy]-3,4-dihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}oxane-2-carboxylateGenerator
Chemical FormulaC38H36O21
Average Molecular Weight828.6798
Monoisotopic Molecular Weight828.174908214
IUPAC Name6-[(6-carboxy-4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-3-yl)oxy]-3,4-dihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}oxane-2-carboxylic acid
Traditional Name6-[(6-carboxy-4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxan-3-yl)oxy]-3,4-dihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}oxane-2-carboxylic acid
CAS Registry Number380468-53-1
SMILES
COC1=C(O)C=CC(\C=C\C(=O)OC2C(OC3C(OC4=CC(O)=C5C(=O)C=C(OC5=C4)C4=CC(OC)=C(O)C=C4)OC(C(O)C3O)C(O)=O)OC(C(O)C2O)C(O)=O)=C1
InChI Identifier
InChI=1S/C38H36O21/c1-52-22-9-14(3-6-17(22)39)4-8-25(43)56-33-29(46)27(44)32(36(50)51)58-38(33)59-34-30(47)28(45)31(35(48)49)57-37(34)54-16-11-19(41)26-20(42)13-21(55-24(26)12-16)15-5-7-18(40)23(10-15)53-2/h3-13,27-34,37-41,44-47H,1-2H3,(H,48,49)(H,50,51)/b8-4+
InChI KeyCQSOKHCNRZFEOH-XBXARRHUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glucuronides
Alternative Parents
Substituents
  • Flavonoid-7-o-glucuronide
  • Flavonoid-7-o-glycoside
  • 3p-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Chromone
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Methoxyphenol
  • Tricarboxylic acid or derivatives
  • Styrene
  • Anisole
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Fatty acid ester
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Hydroxy acid
  • Fatty acyl
  • Oxane
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Enoate ester
  • Heteroaromatic compound
  • Vinylogous acid
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Acetal
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • 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 Point235 - 236 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
logP2.37ALOGPS
logP1.72ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)2.6ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area324.19 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity191.68 m³·mol⁻¹ChemAxon
Polarizability79.42 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
DeepCCS[M+H]+273.5630932474
DeepCCS[M-H]-271.72930932474
DeepCCS[M-2H]-305.76430932474
DeepCCS[M+Na]+279.85230932474
AllCCS[M+H]+265.632859911
AllCCS[M+H-H2O]+265.632859911
AllCCS[M+NH4]+265.632859911
AllCCS[M+Na]+265.632859911
AllCCS[M-H]-265.832859911
AllCCS[M+Na-2H]-270.032859911
AllCCS[M+HCOO]-274.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Chrysoeriol 7-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide]COC1=C(O)C=CC(\C=C\C(=O)OC2C(OC3C(OC4=CC(O)=C5C(=O)C=C(OC5=C4)C4=CC(OC)=C(O)C=C4)OC(C(O)C3O)C(O)=O)OC(C(O)C2O)C(O)=O)=C19314.4Standard polar33892256
Chrysoeriol 7-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide]COC1=C(O)C=CC(\C=C\C(=O)OC2C(OC3C(OC4=CC(O)=C5C(=O)C=C(OC5=C4)C4=CC(OC)=C(O)C=C4)OC(C(O)C3O)C(O)=O)OC(C(O)C2O)C(O)=O)=C16196.4Standard non polar33892256
Chrysoeriol 7-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide]COC1=C(O)C=CC(\C=C\C(=O)OC2C(OC3C(OC4=CC(O)=C5C(=O)C=C(OC5=C4)C4=CC(OC)=C(O)C=C4)OC(C(O)C3O)C(O)=O)OC(C(O)C2O)C(O)=O)=C17433.6Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoeriol 7-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide] 10V, Positive-QTOFsplash10-0ufr-0409803150-7e63785b44e0bef03c522016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoeriol 7-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide] 20V, Positive-QTOFsplash10-0udi-0229400000-c3525d8f3af2399ee6192016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoeriol 7-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide] 40V, Positive-QTOFsplash10-0udi-0549200000-3a98f5d1d5135fe5b5e52016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoeriol 7-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide] 10V, Negative-QTOFsplash10-005d-0795725660-2af38a208b2389142d012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoeriol 7-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide] 20V, Negative-QTOFsplash10-002e-0973500110-7783337fd653de8feffa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoeriol 7-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide] 40V, Negative-QTOFsplash10-0037-1961100000-ca6b211d4e6ed045bb772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoeriol 7-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide] 10V, Positive-QTOFsplash10-0ufr-0009000040-6e6ed549a2b939a413582021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoeriol 7-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide] 20V, Positive-QTOFsplash10-0udi-0009000000-545fc7c692e0abcd79662021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoeriol 7-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide] 40V, Positive-QTOFsplash10-0udi-0009000000-545fc7c692e0abcd79662021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoeriol 7-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide] 10V, Negative-QTOFsplash10-002b-0090000060-1909b3bd154ea0d3dc852021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoeriol 7-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide] 20V, Negative-QTOFsplash10-0002-0090000000-59b41aa66498f4767d562021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chrysoeriol 7-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide] 40V, Negative-QTOFsplash10-0002-0090000000-8037a8afc84ba87df8592021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB019594
KNApSAcK IDC00013680
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752760
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.. .