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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-23 20:46:30 UTC
Update Date2021-09-23 20:46:30 UTC
HMDB IDHMDB0302800
Secondary Accession NumbersNone
Metabolite Identification
Common NameApigenin 7-di-O-xyloside
Description5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-{[(2S,3R,4S,5S,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4H-chromen-4-one belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Based on a literature review very few articles have been published on 5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-{[(2S,3R,4S,5S,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4H-chromen-4-one.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC25H26O15
Average Molecular Weight566.4649
Monoisotopic Molecular Weight566.127170162
IUPAC Name5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-{[(2S,3R,4S,5S,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-4H-chromen-4-one
Traditional Name5-hydroxy-2-(4-hydroxyphenyl)-7-{[(2R,3R,4R,5S,6R)-3,4,5-trihydroxy-6-{[(2S,3R,4S,5S,6S)-3,4,5,6-tetrahydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}chromen-4-one
CAS Registry NumberNot Available
SMILES
O[C@H]1O[C@@H](O[C@H]2O[C@@H](OC3=CC4=C(C(O)=C3)C(=O)C=C(O4)C3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C25H26O15/c26-9-3-1-8(2-4-9)13-7-12(28)15-11(27)5-10(6-14(15)37-13)36-23-20(33)17(30)21(34)25(39-23)40-24-19(32)16(29)18(31)22(35)38-24/h1-7,16-27,29-35H/t16-,17+,18-,19+,20+,21-,22-,23+,24-,25+/m0/s1
InChI KeyAYWNPQYSGVEBBX-DXIOFANKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-7-o-glycoside
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Phenolic glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Chromone
  • Disaccharide
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Oxane
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Vinylogous acid
  • Heteroaromatic compound
  • Hemiacetal
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP-0.22ALOGPS
logP-0.8ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)8.3ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area245.29 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity127.61 m³·mol⁻¹ChemAxon
Polarizability53 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+224.39832859911
AllCCS[M+H-H2O]+222.86832859911
AllCCS[M+Na]+226.17532859911
AllCCS[M+NH4]+225.78332859911
AllCCS[M-H]-218.4832859911
AllCCS[M+Na-2H]-220.1432859911
AllCCS[M+HCOO]-222.11232859911
DeepCCS[M+H]+225.22230932474
DeepCCS[M-H]-223.12830932474
DeepCCS[M-2H]-256.79430932474
DeepCCS[M+Na]+231.14630932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Apigenin 7-di-O-xyloside,3TMS,isomer #47C[Si](C)(C)OC1=CC(O[C@@H]2O[C@H](O[C@@H]3O[C@H](O)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O24878.2Semi standard non polar33892256
Apigenin 7-di-O-xyloside,3TMS,isomer #47C[Si](C)(C)OC1=CC(O[C@@H]2O[C@H](O[C@@H]3O[C@H](O)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O24572.0Standard non polar33892256
Apigenin 7-di-O-xyloside,3TMS,isomer #47C[Si](C)(C)OC1=CC(O[C@@H]2O[C@H](O[C@@H]3O[C@H](O)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O26630.6Standard polar33892256
Apigenin 7-di-O-xyloside,4TMS,isomer #19C[Si](C)(C)OC1=CC(O[C@@H]2O[C@H](O[C@@H]3O[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O24745.5Semi standard non polar33892256
Apigenin 7-di-O-xyloside,4TMS,isomer #19C[Si](C)(C)OC1=CC(O[C@@H]2O[C@H](O[C@@H]3O[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O24557.4Standard non polar33892256
Apigenin 7-di-O-xyloside,4TMS,isomer #19C[Si](C)(C)OC1=CC(O[C@@H]2O[C@H](O[C@@H]3O[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O26196.1Standard polar33892256
Apigenin 7-di-O-xyloside,4TMS,isomer #55C[Si](C)(C)O[C@@H]1[C@@H](O[C@@H]2O[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)O[C@@H](OC2=CC(O)=C3C(=O)C=C(C4=CC=C(O)C=C4)OC3=C2)[C@H](O)[C@H]1O4761.0Semi standard non polar33892256
Apigenin 7-di-O-xyloside,4TMS,isomer #55C[Si](C)(C)O[C@@H]1[C@@H](O[C@@H]2O[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)O[C@@H](OC2=CC(O)=C3C(=O)C=C(C4=CC=C(O)C=C4)OC3=C2)[C@H](O)[C@H]1O4560.7Standard non polar33892256
Apigenin 7-di-O-xyloside,4TMS,isomer #55C[Si](C)(C)O[C@@H]1[C@@H](O[C@@H]2O[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)O[C@@H](OC2=CC(O)=C3C(=O)C=C(C4=CC=C(O)C=C4)OC3=C2)[C@H](O)[C@H]1O6180.5Standard polar33892256
Apigenin 7-di-O-xyloside,4TMS,isomer #79C[Si](C)(C)OC1=CC(O[C@@H]2O[C@H](O[C@@H]3O[C@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]3O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O24715.1Semi standard non polar33892256
Apigenin 7-di-O-xyloside,4TMS,isomer #79C[Si](C)(C)OC1=CC(O[C@@H]2O[C@H](O[C@@H]3O[C@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]3O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O24564.1Standard non polar33892256
Apigenin 7-di-O-xyloside,4TMS,isomer #79C[Si](C)(C)OC1=CC(O[C@@H]2O[C@H](O[C@@H]3O[C@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]3O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O26151.1Standard polar33892256
Apigenin 7-di-O-xyloside,4TMS,isomer #85C[Si](C)(C)OC1=CC(O[C@@H]2O[C@H](O[C@@H]3O[C@H](O)[C@@H](O)[C@H](O)[C@H]3O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O24733.4Semi standard non polar33892256
Apigenin 7-di-O-xyloside,4TMS,isomer #85C[Si](C)(C)OC1=CC(O[C@@H]2O[C@H](O[C@@H]3O[C@H](O)[C@@H](O)[C@H](O)[C@H]3O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O24567.7Standard non polar33892256
Apigenin 7-di-O-xyloside,4TMS,isomer #85C[Si](C)(C)OC1=CC(O[C@@H]2O[C@H](O[C@@H]3O[C@H](O)[C@@H](O)[C@H](O)[C@H]3O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O26179.7Standard polar33892256
Apigenin 7-di-O-xyloside,4TMS,isomer #88C[Si](C)(C)OC1=CC(O[C@@H]2O[C@H](O[C@@H]3O[C@H](O)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O24762.3Semi standard non polar33892256
Apigenin 7-di-O-xyloside,4TMS,isomer #88C[Si](C)(C)OC1=CC(O[C@@H]2O[C@H](O[C@@H]3O[C@H](O)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O24529.3Standard non polar33892256
Apigenin 7-di-O-xyloside,4TMS,isomer #88C[Si](C)(C)OC1=CC(O[C@@H]2O[C@H](O[C@@H]3O[C@H](O)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)=CC2=C1C(=O)C=C(C1=CC=C(O)C=C1)O26192.3Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-di-O-xyloside 10V, Positive-QTOFsplash10-0gi1-0960630000-9bbc6fdd4b695ee695372016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-di-O-xyloside 20V, Positive-QTOFsplash10-00di-0490200000-0159825d802ec28ea2652016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-di-O-xyloside 40V, Positive-QTOFsplash10-00di-2590000000-89baaecca7831820176a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-di-O-xyloside 10V, Negative-QTOFsplash10-014i-6884690000-c2ca6b252e15bade4bdf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-di-O-xyloside 20V, Negative-QTOFsplash10-014i-3892110000-920b7e85a2549106a2f52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-di-O-xyloside 40V, Negative-QTOFsplash10-014i-2290000000-9330f7170e34e346a4e62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-di-O-xyloside 10V, Positive-QTOFsplash10-014i-0000090000-d60878680e83e295d49a2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-di-O-xyloside 20V, Positive-QTOFsplash10-014i-0000090000-d60878680e83e295d49a2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-di-O-xyloside 40V, Positive-QTOFsplash10-014j-0600960000-d4f9bdbcc85a7bf176032021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-di-O-xyloside 10V, Negative-QTOFsplash10-014i-0000090000-a40d02f5d0de9ee71e592021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-di-O-xyloside 20V, Negative-QTOFsplash10-014i-0000090000-90db245beb3b8a9f227d2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-di-O-xyloside 40V, Negative-QTOFsplash10-0a4j-0900630000-907e61a136a11a7740d22021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDFDB006304
KNApSAcK IDNot Available
Chemspider ID59696397
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
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 ReferencesNot Available