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 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

Spectra from Phytohub

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-0000900000-b6d7fc88c039e719d1642014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-0433900000-b411d851fccc9f228d842017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-03xv-1913500000-be46740b1210f9e106ee2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-0000900000-b6d7fc88c039e719d1642017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fu-0390000000-746c7fa7b11e53e272352017-07-27View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0229-4222900000-fe657c625506c272a0362017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0940000000-eb8b08c7beca627dc7282017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0090000000-3fea3046af52ea21ae282017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-014i-0940000000-eb8b08c7beca627dc7282017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0090000000-3fea3046af52ea21ae282017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-014i-0890000000-c8366acac0c0d42ae2e82017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0udi-0920000000-812a3ee12823ec0b20252017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-003r-0194000200-b2908d4b21e6769c5a082017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-3970000000-5a23944b045cfe1763b12017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0090000000-0f608530bf761944dbf32017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0090000000-0c659ac43b543480168b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0690000000-e19eed49b8311d9cd3392017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0910000000-57a56bfe2cce55357a112017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-b8799a618cff0ac84ddb2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0490000000-f9a416c79166c84ca7732017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-1499c7f2bceeb3e13f522017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0490000000-413a7da79773bc92a1122017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0090000000-8f4d30104539ae85cd502017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0290000000-32e8793c17b364eee1272017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0uea-0900000000-52147353f7af35162dab2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-7c7c531f383cbaad5b232016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0090000000-bb93867833cf83cbdb012016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-7890000000-ef384ab54a966e53fb232016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-31e5cabfee91b72de2962016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-12d2a0ddf52acf6dc93a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gdi-3960000000-847553cbcf5b653a90592016-08-03View 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
Back