precursor metabolite

Showing entry for Apigenin

Identification

PhytoHub ID
PHUB000861
Name
Apigenin
Systematic Name
Not Available
Synonyms
  • 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
  • 5,7,4'-Trihydroxyflavone
  • chamomile
  • versulin
CAS Number
520-36-5
Average Mass
270.24
Monoisotopic Mass
270.052823422
Chemical Formula
C15H10O5
IUPAC Name
5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
InChI Key
KZNIFHPLKGYRTM-UHFFFAOYSA-N
InChI Identifier
InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H
SMILES
OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1
Structure
Similar Structures

Calculated Properties

Solubility (ALOGPS)
1.18e-01 g/l
LogS (ALOGPS)
-3.36
LogP (ALOGPS)
3.07
Hydrogen Acceptors
5
Hydrogen Donors
3
Rotatable Bond Count
1
Polar Surface Area
86.99000000000001
Refractivity
72.91390000000001
Polarizability
26.7801790574094
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-5.381179969028222
pKa (strongest acidic)
6.574691761170129
Number of Rings
3
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Taxonomy as Food Phytochemical

Family
Polyphenols
Class
Flavonoids
Sub-class
Flavones

Taxonomy as Metabolite

Metabolite Family
(Poly)phenol metabolites
Metabolite Class
Flavonoid metabolites
Metabolite Sub-class
Flavones (parent and host metabolites)

Taxonomy of its Food Phytochemical Precursor(s)

Food PhytochemicalFamilyClassSub-class
ApigeninPolyphenolsFlavonoidsFlavonesShow Food Phytochemical
Apigenin 7-O-glucosidePolyphenolsFlavonoidsFlavonesShow Food Phytochemical
Apigenin 7-O-rutinosidePolyphenolsFlavonoidsFlavonesShow Food Phytochemical

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Flavonoids
Super-class
Phenylpropanoids and polyketides
Sub-class
Flavones
Direct Parent Name
Flavones
Alternative Parent Names
["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "4'-hydroxyflavonoids", "5-hydroxyflavonoids", "7-hydroxyflavonoids", "Benzene and substituted derivatives", "Chromones", "Heteroaromatic compounds", "Hydrocarbon derivatives", "Organic oxides", "Organooxygen compounds", "Oxacyclic compounds", "Pyranones and derivatives", "Vinylogous acids"]
External Descriptor Annotations
["Flavones and Flavonols", "flavones", "trihydroxyflavone"]
Substituent Names
["1-benzopyran", "1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "4'-hydroxyflavonoid", "5-hydroxyflavonoid", "7-hydroxyflavonoid", "Aromatic heteropolycyclic compound", "Benzenoid", "Benzopyran", "Chromone", "Flavone", "Heteroaromatic compound", "Hydrocarbon derivative", "Hydroxyflavonoid", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Phenol", "Pyran", "Pyranone", "Vinylogous acid"]

Spectra from Phytohub

Spectrum TypeInstrument TypeTechnologyIon ModeCollision EnergyView
GC-MSGC-MSNot AvailableNot AvailableNot AvailableView Spectrum
GC-MSGC-EI-TOFinstrument=Pegasus III TOF-MS system, Leco; GC 6890, Agilent TechnologiespositiveNot AvailableView Spectrum
GC-MSGC-EI-TOFinstrument=Pegasus III TOF-MS system, Leco; GC 6890, Agilent TechnologiespositiveNot AvailableView Spectrum
GC-MSGC-MSNot AvailableNot AvailableNot AvailableView Spectrum
Predicted GC-MSGC-MSPredicted by CFMID-EI, energy0PositiveNot AvailableView Spectrum
Predicted GC-MSGC-MSPredicted by CFMID-EI, Ionization energy 70 eV fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)C=C1)PositiveNot AvailableView Spectrum
Predicted GC-MSGC-MSPredicted by CFMID-EI, energy0EiNot AvailableView Spectrum
LC-MS/MSESI-TOFNot AvailableNegative30VView Spectrum
LC-MS/MSESI-TOFNot AvailableNegativeVView Spectrum
LC-MS/MSESI-TOFFrom Sumner LibraryNegative30VView Spectrum
LC-MS/MSESI-TOFFrom Sumner LibraryNegativeVView Spectrum
LC-MS/MSDI-ESI-qTofFrom GNPS LibraryNegativeVView Spectrum
LC-MS/MSDI-ESI-qTofFrom GNPS LibraryPositiveVView Spectrum
LC-MS/MSLC-ESI-qTofFrom GNPS LibraryPositiveVView Spectrum
LC-MS/MSLC-ESI-qTofFrom GNPS LibraryPositiveVView Spectrum
LC-MS/MSLC-ESI-QTOFinstrument=maXis (Bruker Daltonics)negativeVView Spectrum
LC-MS/MSLC-ESI-QTOFinstrument=maXis (Bruker Daltonics)negativeVView Spectrum
LC-MS/MSLC-ESI-QTOFinstrument=maXis (Bruker Daltonics)negativeVView Spectrum
LC-MS/MSLC-ESI-QTOFinstrument=maXis (Bruker Daltonics)negativeVView Spectrum
LC-MS/MSLC-ESI-QTOFinstrument=maXis (Bruker Daltonics)negativeVView Spectrum
LC-MS/MSLC-ESI-QTOFinstrument=UPLC Q-Tof Premier, WatersnegativeVView Spectrum
LC-MS/MSLC-ESI-QTOFinstrument=UPLC Q-Tof Premier, WatersnegativeVView Spectrum
LC-MS/MSLC-ESI-QTOFinstrument=UPLC Q-Tof Premier, WatersnegativeVView Spectrum
LC-MS/MSLC-ESI-QTOFinstrument=Agilent 1200 RRLC; Agilent 6520 QTOFnegativeVView Spectrum
LC-MS/MSLC-ESI-QTOFinstrument=Agilent 1200 RRLC; Agilent 6520 QTOFnegativeVView Spectrum
LC-MS/MSLC-ESI-QTOFinstrument=Agilent 1200 RRLC; Agilent 6520 QTOFnegativeVView Spectrum
Predicted LC-MS/MSNot AvailablePredicted by CFM-IDPositive10VView Spectrum
Predicted LC-MS/MSNot AvailablePredicted by CFM-IDPositive20VView Spectrum
Predicted LC-MS/MSNot AvailablePredicted by CFM-IDPositive40VView Spectrum
Predicted LC-MS/MSNot AvailablePredicted by CFM-IDNegative10VView Spectrum
Predicted LC-MS/MSNot AvailablePredicted by CFM-IDNegative20VView Spectrum
Predicted LC-MS/MSNot AvailablePredicted by CFM-IDNegative40VView Spectrum

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

Food PhytochemicalMetaboliteSpeciesBiofluidsOriginTMaxCMaxUrinary ExcretionFormulaMonoisotopic mass
Apigenin ApigeninhumanurineunchangedNo dataNo data<1%C15H10O5270.052823422 Publications
Apigenin Apigenin 7-O-glucuronidehumanplasma, urinehost metabolism1h-3h<20nmol/L<1%C21H18O11446.0849114 Detailed Intervention Studies Publications
Apigenin Apigenin 4'-O-glucuronidehumanplasma, urinehost metabolismNot AvailableNot Available<1%C21H18O11446.0849114 Publications
Apigenin 7-O-glucoside ApigeninhumanNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC15H10O5270.052823422
Apigenin 7-O-rutinoside ApigeninhumanNot AvailableNot AvailableNot AvailableNot AvailableNot AvailableC15H10O5270.052823422

Inter-Individual Variations in Metabolism

Food PhytochemicalMetaboliteEffectValue
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