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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:34:55 UTC
Update Date2022-03-07 02:55:42 UTC
HMDB IDHMDB0038297
Secondary Accession Numbers
  • HMDB38297
Metabolite Identification
Common NameApigenin 7-[p-coumaroyl-(->2)-[glucuronyl-(1->3)]-glucuronyl-(1->2)-glucuronide]
DescriptionApigenin 7-[p-coumaroyl-(->2)-[glucuronyl-(1->3)]-glucuronyl-(1->2)-glucuronide] belongs to the class of organic compounds known as flavonoid o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid. Based on a literature review very few articles have been published on Apigenin 7-[p-coumaroyl-(->2)-[glucuronyl-(1->3)]-glucuronyl-(1->2)-glucuronide].
Structure
Data?1563863174
Synonyms
ValueSource
6-({2-carboxy-6-[(6-carboxy-4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-3-yl)oxy]-3-hydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}oxan-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylateHMDB
Chemical FormulaC42H40O25
Average Molecular Weight944.752
Monoisotopic Molecular Weight944.18586683
IUPAC Name6-({2-carboxy-6-[(6-carboxy-4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-3-yl)oxy]-3-hydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}oxan-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name6-({2-carboxy-6-[(6-carboxy-4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxan-3-yl)oxy]-3-hydroxy-5-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}oxan-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC1C(OC2C(O)C(OC(OC3C(OC4=CC(O)=C5C(=O)C=C(OC5=C4)C4=CC=C(O)C=C4)OC(C(O)C3O)C(O)=O)C2OC(=O)\C=C\C2=CC=C(O)C=C2)C(O)=O)OC(C(O)C1O)C(O)=O
InChI Identifier
InChI=1S/C42H40O25/c43-16-6-1-14(2-7-16)3-10-23(47)62-36-31(63-40-29(52)25(48)26(49)32(64-40)37(54)55)30(53)34(39(58)59)66-42(36)67-35-28(51)27(50)33(38(56)57)65-41(35)60-18-11-19(45)24-20(46)13-21(61-22(24)12-18)15-4-8-17(44)9-5-15/h1-13,25-36,40-45,48-53H,(H,54,55)(H,56,57)(H,58,59)/b10-3+
InChI KeyXBLARMNPRFOJOC-XCVCLJGOSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid O-glucuronides
Alternative Parents
Substituents
  • Flavonoid-4p-o-glucuronide
  • 5-hydroxyflavonoid
  • 7-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
  • Phenol ether
  • Anisole
  • Phenoxy compound
  • Methoxybenzene
  • Beta-hydroxy acid
  • Pyranone
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Pyran
  • Oxane
  • Benzenoid
  • Fatty acyl
  • Hydroxy acid
  • Alpha,beta-unsaturated carboxylic ester
  • Vinylogous acid
  • Enoate ester
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxylic acid ester
  • Ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Carboxylic acid
  • Oxacycle
  • Acetal
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • 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 Point203 - 204 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.55 g/LALOGPS
logP1.74ALOGPS
logP0.59ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)2.43ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area401.95 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity211.04 m³·mol⁻¹ChemAxon
Polarizability89.41 ųChemAxon
Number of Rings7ChemAxon
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]+283.48630932474
DeepCCS[M-H]-281.59130932474
DeepCCS[M-2H]-315.53230932474
DeepCCS[M+Na]+289.62230932474
AllCCS[M+H]+273.432859911
AllCCS[M+H-H2O]+273.932859911
AllCCS[M+NH4]+272.932859911
AllCCS[M+Na]+272.832859911
AllCCS[M-H]-271.532859911
AllCCS[M+Na-2H]-276.332859911
AllCCS[M+HCOO]-281.632859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-[p-coumaroyl-(->2)-[glucuronyl-(1->3)]-glucuronyl-(1->2)-glucuronide] 10V, Positive-QTOFsplash10-00fs-0370901706-387c2309bb65560d02392016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-[p-coumaroyl-(->2)-[glucuronyl-(1->3)]-glucuronyl-(1->2)-glucuronide] 20V, Positive-QTOFsplash10-00di-0290401200-e8cbd8ded11b5698f41d2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-[p-coumaroyl-(->2)-[glucuronyl-(1->3)]-glucuronyl-(1->2)-glucuronide] 40V, Positive-QTOFsplash10-00di-0391301010-91f19b23dfd875503df22016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-[p-coumaroyl-(->2)-[glucuronyl-(1->3)]-glucuronyl-(1->2)-glucuronide] 10V, Negative-QTOFsplash10-02vm-0761811985-c0c092f10ffbd6e7ff162016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-[p-coumaroyl-(->2)-[glucuronyl-(1->3)]-glucuronyl-(1->2)-glucuronide] 20V, Negative-QTOFsplash10-02t9-0971500312-ebe3896c2c003b4a91f02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-[p-coumaroyl-(->2)-[glucuronyl-(1->3)]-glucuronyl-(1->2)-glucuronide] 40V, Negative-QTOFsplash10-02ta-0951200000-5b63d3d68501347697da2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-[p-coumaroyl-(->2)-[glucuronyl-(1->3)]-glucuronyl-(1->2)-glucuronide] 10V, Negative-QTOFsplash10-014l-0090000006-173ca2d19db1b537eff72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-[p-coumaroyl-(->2)-[glucuronyl-(1->3)]-glucuronyl-(1->2)-glucuronide] 20V, Negative-QTOFsplash10-014i-0090000000-0f9cf513153f5787dba62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-[p-coumaroyl-(->2)-[glucuronyl-(1->3)]-glucuronyl-(1->2)-glucuronide] 40V, Negative-QTOFsplash10-014i-0090000000-74726919fa50baee16372021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-[p-coumaroyl-(->2)-[glucuronyl-(1->3)]-glucuronyl-(1->2)-glucuronide] 10V, Positive-QTOFsplash10-00dj-0090000004-031f3ddfcbc79c849ca62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-[p-coumaroyl-(->2)-[glucuronyl-(1->3)]-glucuronyl-(1->2)-glucuronide] 20V, Positive-QTOFsplash10-00di-0090000000-60b322ff74af8a7655802021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Apigenin 7-[p-coumaroyl-(->2)-[glucuronyl-(1->3)]-glucuronyl-(1->2)-glucuronide] 40V, Positive-QTOFsplash10-00di-0090000000-60b322ff74af8a7655802021-09-24Wishart 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 IDFDB017626
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752327
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.. .