ContaminantDB: Apigenin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (9)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:20:57 UTC

Update Date

2026-03-27 01:49:21 UTC

Accession Number

CHEM003844

Identification

Common Name

Apigenin

Class

Small Molecule

Description

Apigenin is a plant-derived flavonoid that has significant promise as a skin cancer chemopreventive agent. Apigenin inhibits the expression of involucrin (hINV), a marker of keratinocyte differentiation, is increased by differentiating agents via a protein kinase Cdelta (PKCdelta), Ras, MEKK1, MEK3 cascade that increases AP1 factor level and AP1 factor binding to DNA elements in the hINV promoter. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter and the increase in hINV promoter activity. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311. Activation of hINV promoter activity by the green tea polyphenol, (-)-epigellocathecin-3-gallate, is also inhibited by apigenin, suggesting that the two chemopreventive agents can produce opposing actions in keratinocytes. (1). Apigenin, a flavone abundantly found in fruits and vegetables, exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. This flavonoid provides selective activity to promote caspase-dependent-apoptosis of leukemia cells and uncover an essential role of PKCdelta during the induction of apoptosis by apigenin. (2). Apigenin markedly induces the expression of death receptor 5 (DR5) and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) to induce apoptosis in malignant tumor cells. On the other hand, apigenin-mediated induction of DR5 expression is not observed in normal human peripheral blood mononuclear cells. Moreover, apigenin does not sensitize normal human peripheral blood mononuclear cells to TRAIL-induced apoptosis. (3).

Contaminant Sources

FooDB Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Drug
Ester
Food Toxin
Household Toxin
Metabolite
Natural Compound
Organic Compound
Plant Toxin

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
2-(p-Hydroxyphenyl)-5,7-dihydroxychromone	ChEBI
4',5,7-Trihydroxyflavone	ChEBI
5,7,4'-Trihydroxyflavone	ChEBI
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone	ChEBI
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
C.I. natural yellow 1	ChEBI
Chamomile	ChEBI
Spigenin	ChEBI
Versulin	ChEBI
4',5,7-Trihydroxy-flavone	HMDB
4,5, 7-Trihydroxyflavone	HMDB
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one	HMDB
Apigenol	HMDB
4’,5,7-Trihydroxyflavone	PhytoBank
5,7,4’-Trihydroxyflavone	PhytoBank
5,7-Dihydroxy-2-(4-Hydroxyphenyl)chromen-4-one	PhytoBank
5,7-Dihydroxy-2-p-hydroxyphenyl-4-chromenone	PhytoBank
Apegenin	PhytoBank
Apigenin	PhytoBank
Apigenine	PhytoBank

Chemical Formula

C₁₅H₁₀O₅

Average Molecular Mass

270.237 g/mol

Monoisotopic Mass

270.053 g/mol

CAS Registry Number

520-36-5

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

chamomile

SMILES

OC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(O)C=C2O1

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

InChI Key

KZNIFHPLKGYRTM-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavones

Alternative Parents

Substituents

4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

trihydroxyflavone (CHEBI:18388 )
flavones (C01477 )
Flavones and Flavonols (C01477 )
Flavones and Flavonols (LMPK12110005 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	347.5 °C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	3.07	ALOGPS
logP	2.71	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.57	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.91 m³·mol⁻¹	ChemAxon
Polarizability	26.78 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-00di-0000900000-b6d7fc88c039e719d164	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-0433900000-b411d851fccc9f228d84	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-03xv-1913500000-be46740b1210f9e106ee	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-0000900000-b6d7fc88c039e719d164	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00fu-0390000000-746c7fa7b11e53e27235	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0229-4222900000-fe657c625506c272a036	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-014i-0940000000-eb8b08c7beca627dc728	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0090000000-3fea3046af52ea21ae28	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-014i-0940000000-eb8b08c7beca627dc728	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0090000000-3fea3046af52ea21ae28	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-014i-0890000000-c8366acac0c0d42ae2e8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-0udi-0920000000-812a3ee12823ec0b2025	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-003r-0194000200-b2908d4b21e6769c5a08	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-00di-3970000000-5a23944b045cfe1763b1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0090000000-0f608530bf761944dbf3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0090000000-0c659ac43b543480168b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0690000000-e19eed49b8311d9cd339	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0910000000-57a56bfe2cce55357a11	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-b8799a618cff0ac84ddb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0490000000-f9a416c79166c84ca773	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0900000000-1499c7f2bceeb3e13f52	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0490000000-413a7da79773bc92a112	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0090000000-8f4d30104539ae85cd50	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0290000000-32e8793c17b364eee127	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0uea-0900000000-52147353f7af35162dab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-7c7c531f383cbaad5b23	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0090000000-bb93867833cf83cbdb01	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-7890000000-ef384ab54a966e53fb23	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-31e5cabfee91b72de296	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0090000000-12d2a0ddf52acf6dc93a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gdi-3960000000-847553cbcf5b653a9059	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

HMDB ID

FooDB ID

Phenol Explorer ID

KNApSAcK ID

BiGG ID

Not Available

BioCyc ID

CPD-431

METLIN ID

3397

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Chen, Xin; Li, Ping. Processes for the preparation of apigenin from naringin via rhoifolin or naringenin intermediate. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 9 pp

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23304222

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23344191

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23354402

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23359392

5. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217

6. Chen, Xin; Li, Ping. Processes for the preparation of apigenin from naringin via rhoifolin or naringenin intermediate. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 9 pp

7. Chen, Xin; Li, Ping. Processes for the preparation of apigenin from naringin via rhoifolin or naringenin intermediate. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 9 pp

8. Balasubramanian S, Zhu L, Eckert RL: Apigenin inhibition of involucrin gene expression is associated with a specific reduction in phosphorylation of protein kinase Cdelta Tyr311. J Biol Chem. 2006 Nov 24;281(47):36162-72. Epub 2006 Sep 18.

9. Vargo MA, Voss OH, Poustka F, Cardounel AJ, Grotewold E, Doseff AI: Apigenin-induced-apoptosis is mediated by the activation of PKCdelta and caspases in leukemia cells. Biochem Pharmacol. 2006 Sep 14;72(6):681-92. Epub 2006 Jul 17.

10. Horinaka M, Yoshida T, Shiraishi T, Nakata S, Wakada M, Sakai T: The dietary flavonoid apigenin sensitizes malignant tumor cells to tumor necrosis factor-related apoptosis-inducing ligand. Mol Cancer Ther. 2006 Apr;5(4):945-51.

Apigenin (CHEM003844)

Structure for CHEM003844: Apigenin