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

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 Online Resources

Record IDSourceDescriptionView
BML00404MassBankLC-ESI-QTOF Spectrum - 10 ev, unspecifiedView Spectra
BML00418MassBankLC-ESI-QTOF Spectrum - 20 ev, unspecifiedView Spectra
BML00444MassBankLC-ESI-QTOF Spectrum - 10 ev, unspecifiedView Spectra
BML00454MassBankLC-ESI-QTOF Spectrum - 20 ev, unspecifiedView Spectra
BML00464MassBankLC-ESI-QTOF Spectrum - 40 ev, unspecifiedView Spectra
BML80760MassBankLC-ESI-QTOF Spectrum - -, unspecifiedView Spectra
BML80761MassBankLC-ESI-QTOF Spectrum - -, unspecifiedView Spectra
FIO00006MassBankLC-ESI-QTOF Spectrum - 10 eV, unspecifiedView Spectra
FIO00007MassBankLC-ESI-QTOF Spectrum - 20 eV, unspecifiedView Spectra
FIO00008MassBankLC-ESI-QTOF Spectrum - 30 eV, unspecifiedView Spectra
FIO00009MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
FIO00010MassBankLC-ESI-QTOF Spectrum - 50 eV, unspecifiedView Spectra
FIO00011MassBankLC-ESI-QTOF Spectrum - 10 eV, unspecifiedView Spectra
FIO00012MassBankLC-ESI-QTOF Spectrum - 20 eV, unspecifiedView Spectra
FIO00013MassBankLC-ESI-QTOF Spectrum - 30 eV, unspecifiedView Spectra
FIO00014MassBankLC-ESI-QTOF Spectrum - 40 eV, unspecifiedView Spectra
FIO00015MassBankLC-ESI-QTOF Spectrum - 50 eV, unspecifiedView Spectra
ML002601MassBankLC-ESI-ITFT Spectrum - 50 % (nominal), unspecifiedView Spectra
OUF00116MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
OUF00117MassBankGC-EI-TOF Spectrum - -, unspecifiedView Spectra
PR040001MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 eV, [M-H]-View Spectra
PR040002MassBankLC-ESI-QTOF Spectrum - 30 eV, [M-H]-View Spectra
PR040003MassBankLC-ESI-QTOF Spectrum - 30 eV, [M+H]+View Spectra
PR040004MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 eV, [M+H]+View Spectra
PR100223MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PR100224MassBankLC-ESI-QTOF Spectrum - 30 V, unspecifiedView Spectra
PR100634MassBankLC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecifiedView Spectra
PS039301ReSpectN/A Spectrum - 10, [M+H]+View Spectra
PS039302ReSpectN/A Spectrum - 20, [M+H]+View Spectra
PS039303ReSpectN/A Spectrum - 30, [M+H]+View Spectra
PS039304ReSpectN/A Spectrum - 40, [M+H]+View Spectra
PS039307ReSpectN/A Spectrum - 10, [M-H]-View Spectra
PS039308ReSpectN/A Spectrum - 20, [M-H]-View Spectra
PS039309ReSpectN/A Spectrum - 30, [M-H]-View Spectra
TY000119MassBankLC-ESI-ITTOF Spectrum - -, [M+H]+View Spectra

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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