Natural Product (NP) Details

General Information of the NP (ID: NP4620)
Name
Apigenin
Synonyms
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one; Chamomile; Versulin; Spigenin; Apigenol; 4',5,7-Trihydroxyflavone; Apigenine; C.I. Natural Yellow 1; 5,7,4'-Trihydroxyflavone; Pelargidenon 1449; 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone; 2-(p-Hydroxyphenyl)-5,7-dihydroxychromone; UCCF 031; NSC 83244; UNII-7V515PI7F6; 5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one; CCRIS 3789; CHEBI:18388; CHEMBL28; EINECS 208-292-3; 4H-1-Benzopyran-4-one, 5,7-di
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Species Origin Psilotum nudum ...     Click to Show/Hide
Psilotum nudum
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Polypodiopsida
Order: Psilotales
Family: Psilotaceae
Genus: Psilotum
Species: Psilotum nudum
Daucus carota
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Apiales
Family: Apiaceae
Genus: Daucus
Species: Daucus carota
Achillea millefolium
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Asterales
Family: Asteraceae
Genus: Achillea
Species: Achillea millefolium
Pogostemon cablin
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Lamiaceae
Genus: Pogostemon
Species: Pogostemon cablin
Chrysanthemum x morifolium
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Asterales
Family: Asteraceae
Genus: Chrysanthemum
Species: Chrysanthemum x morifolium
Astragalus sinicus
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Astragalus
Species: Astragalus sinicus
Juniperus chinensis
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Pinopsida
Family: Cupressaceae
Genus: Juniperus
Species: Juniperus chinensis
Trachelospermum jasminoides
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Gentianales
Family: Apocynaceae
Genus: Trachelospermum
Species: Trachelospermum jasminoides
Agrimonia pilosa
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Rosales
Family: Rosaceae
Genus: Agrimonia
Species: Agrimonia pilosa
Campsis radicans
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Bignoniaceae
Genus: Campsis
Species: Campsis radicans
Saussurea medusa
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Asterales
Family: Asteraceae
Genus: Saussurea
Species: Saussurea medusa
Causonis japonica
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Vitales
Family: Vitaceae
Genus: Causonis
Species: Causonis japonica
Clerodendrum japonicum
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Lamiaceae
Genus: Clerodendrum
Species: Clerodendrum japonicum
Indigofera tinctoria
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Indigofera
Species: Indigofera tinctoria
Saussurea stella
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Asterales
Family: Asteraceae
Genus: Saussurea
Species: Saussurea stella
Acanthus ilicifolius
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Acanthaceae
Genus: Acanthus
Species: Acanthus ilicifolius
Siphonostegia chinensis
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Orobanchaceae
Genus: Siphonostegia
Species: Siphonostegia chinensis
Thunbergia grandiflora
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Acanthaceae
Genus: Thunbergia
Species: Thunbergia grandiflora
Lespedeza thunbergii
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Lespedeza
Species: Lespedeza thunbergii
Phlomoides rotata
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Lamiaceae
Genus: Phlomoides
Species: Phlomoides rotata
Clinopodium gracile
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Lamiaceae
Genus: Clinopodium
Species: Clinopodium gracile
Daphne genkwa
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Malvales
Family: Thymelaeaceae
Genus: Daphne
Species: Daphne genkwa
Disease Candidosis [ICD-11: 1F23] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -5.129
 
MDCK Permeability
 -4.759
 
PAMPA
 +
 
HIA
 - - -
 
Distribution
VDss
 -0.463
 
PPB
 96.5%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 +++
CYP1A2 substrate
 -
CYP2C19 inhibitor
 - -
CYP2C19 substrate
 - - -
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 +
CYP2D6 inhibitor
 +++
CYP2D6 substrate
 +++
CYP3A4 inhibitor
 +++
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 - -
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 +++
HLM Stability
 +
 
Excretion
CLplasma
 5.939
 
T1/2
 1.203
Toxicity
DILI
 ++
 
Rat Oral Acute Toxicity
 +
 
FDAMDD
 ++
 
Respiratory
 ++
 
Human Hepatotoxicity
 -
 
Ototoxicity
 - - -
 
Drug-induced Nephrotoxicity
 - - -
 
Drug-induced Neurotoxicity
 - - -
 
Hematotoxicity
 - - -
 
Genotoxicity
 +++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C15H10O5
PubChem CID
5280443
Canonical SMILES
C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O
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
InChIKey
KZNIFHPLKGYRTM-UHFFFAOYSA-N
CAS Number
CAS 520-36-5
Herb ID
HBIN016408
ETMC ID
372
SymMap ID
SMIT00003
TCMSP ID
MOL000008
TTD Drug ID
D00RIX
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    Î±. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          ABT-263      Chronic lymphocytic leukaemia     Click to Show/Hide the Molecular Data of This Drug
                 Augmenting Drug Sensitivity     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Phosphorylation AKT1  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation ERK1  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation ERK2  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation FOXO3  Molecule Info 
Pathway MAP
                    In-vitro Model NCI-H1975 CVCL_1511 Lung adenocarcinoma Homo sapiens
HCC827 CVCL_2063 Lung adenocarcinoma Homo sapiens
NCI-H1650 CVCL_1483 Lung adenocarcinoma Homo sapiens
NCI-H3255 CVCL_6831 Lung adenocarcinoma Homo sapiens
SK-MEL-28 CVCL_0526 Cutaneous melanoma Homo sapiens
                    Experimental
                    Result(s)		 Apigenin upregulated the expression of Noxa in EGFRm tumor cells by targeting the AKT-FoxO3a pathway, thereby synergizing with ABT-263 to suppress tumor cell growth and proliferation in vitro and in vivo.
          HA14-1      Colon cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression CAPN1  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP8  Molecule Info 
Pathway MAP
Down-regulation Expression EGFR  Molecule Info 
Pathway MAP
Down-regulation Expression VEGFA  Molecule Info 
Pathway MAP
                    Biological
                    Regulation		 Up-regulation Ratio of Bax to Bcl-2
Up-regulation Cytochrome c release
                    In-vitro Model SK-N-DZ CVCL_1701 Neuroblastoma Homo sapiens
SH-SY5Y CVCL_0019 Neuroblastoma Homo sapiens
IMR-32 CVCL_0346 Neuroblastoma Homo sapiens
                    Experimental
                    Result(s)		 Bcl-2 inhibitor and apigenin worked synergistically in human malignant neuroblastoma cell lines and increased apoptosis with activation of extrinsic and intrinsic pathways.
          Cetuximab      Colorectal cancer     Click to Show/Hide the Molecular Data of This Drug
                 Augmenting Drug Sensitivity     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Phosphorylation AKT1  Molecule Info 
Pathway MAP
Down-regulation Expression CCND1  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation EGFR  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation STAT3  Molecule Info 
Pathway MAP
                    Biological
                    Regulation		 Induction Cell cycle arrest in G2/M phase
                    In-vitro Model HONE-1 CVCL_8706 Nasopharyngeal carcinoma Homo sapiens
CNE-2 CVCL_6889 Human nasopharyngeal carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Apigenin enhances the antitumor effects of cetuximab in nasopharyngeal carcinoma by inhibiting EGFR signaling.
          Abivertinib      Lung cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Phosphorylation GSK-3B  Molecule Info 
Pathway MAP
                    In-vitro Model U-2932 CVCL_1896 B-cell lymphoma Homo sapiens
OCI-Ly10 CVCL_8795 B-cell lymphoma Homo sapiens
                    Experimental
                    Result(s)		 Apigenin can synergize with Abivertinib in treating DLBCL visa synergistically inducing apoptosis and inhibiting the p-GS3K-beta and its downstream targets.
          Gefitinib      Lung cancer     Click to Show/Hide the Molecular Data of This Drug
                 Augmenting Drug Sensitivity     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [6]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Up-regulation Expression BCL2L11  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Down-regulation Expression CYB5R2  Molecule Info 
Pathway MAP
Down-regulation Expression CYM  Molecule Info 
Pathway MAP
Down-regulation Expression HIF-1A  Molecule Info 
Pathway MAP
Down-regulation Expression MYC  Molecule Info 
Pathway MAP
Up-regulation Cleavage PARP1  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation PRKAA1  Molecule Info 
Pathway MAP
Down-regulation Expression SLC2A1  Molecule Info 
Pathway MAP
Down-regulation Expression SLC2A3  Molecule Info 
Pathway MAP
Down-regulation Expression SLC2A4  Molecule Info 
Pathway MAP
                    Biological
                    Regulation		 Down-regulation Autophagy flux
Induction Cell cycle arrest in G0/G1 phase
                    In-vitro Model NCI-H1975 CVCL_1511 Lung adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Apigenin combined with gefitinib blocks autophagy flux and induces apoptotic cell death through inhibition of HIF-1alpha, c-Myc, p-EGFR, and glucose metabolism in EGFR L858R+T790M-mutated H1975 Cells.
          TRAIL/Apo2L      Lung cancer     Click to Show/Hide the Molecular Data of This Drug
                 Augmenting Drug Sensitivity     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [7]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression SLC25A5  Molecule Info 
Pathway MAP
Up-regulation Expression TRAIL-R2  Molecule Info 
Pathway MAP
                    In-vitro Model DU145 CVCL_0105 Prostate carcinoma Homo sapiens
LNCaP CVCL_0395 Prostate carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Apigenin sensitizes prostate cancer cells to Apo2L/TRAIL by targeting adenine nucleotide translocase-2.
          Sorafenib      Renal cell carcinoma     Click to Show/Hide the Molecular Data of This Drug
                 Augmenting Drug Sensitivity     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [8]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression BID  Molecule Info 
Pathway MAP
Up-regulation Expression CASP10  Molecule Info 
Pathway MAP
Up-regulation Expression CASP3  Molecule Info 
Pathway MAP
Up-regulation Expression CASP8  Molecule Info 
Pathway MAP
Up-regulation Expression CDKN1A  Molecule Info 
Pathway MAP
Up-regulation Expression CDKN2A  Molecule Info 
Pathway MAP
                    In-vitro Model Hep-G2 CVCL_0027 Hepatocellular carcinoma Homo sapiens
                    Experimental
                    Result(s)		 The combination of apigenin and sorafenib arrested cell cycle and increased apoptotic gene expressions more than single treatment groups.
          5-fluorouracil      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [9]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Up-regulation Cleavage PARP1  Molecule Info 
Pathway MAP
                    Biological
                    Regulation		 Up-regulation ROS generation
Down-regulation Loss of mitochondrial membrane potential
                    In-vitro Model SK-HEP-1 CVCL_0525 Hepatocellular carcinoma Homo sapiens
BEL-7402 CVCL_5492 Human hepatocellular carcinoma Homo sapiens
                    In-vivo Model SK-Hep-1 cells (5*106 cells per mice) were suspended in 100 L of serum-free RPMI-1640 medium, then subcutaneously injected into the left flank of nude mice (Male, 4-6 weeks old).
                    Experimental
                    Result(s)		 Apigenin may potentiate the cytotoxicity of 5-FU in HCC via inhibition of ROS-mediated drug resistance and concurrent activation of the mitochondrial pathways of apoptosis.
          Gemcitabine      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Augmenting Drug Sensitivity     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [10]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression AKT1  Molecule Info 
Pathway MAP
Down-regulation Expression p105  Molecule Info 
Pathway MAP
                    In-vitro Model MIA PaCa-2 CVCL_0428 Pancreatic ductal adenocarcinoma Homo sapiens
AsPC-1 CVCL_0152 Pancreatic ductal adenocarcinoma Homo sapiens
                    In-vivo Model Male BALB/c nude mice were subcutaneously inoculated with MiaPaca-2 cells (1*106 cells/mouse) cells in 1 mL of Matrigel.
                    Experimental
                    Result(s)		 The combination of gemcitabine and apigenin enhanced anti-tumor efficacy through Akt and NF-kappa B activity suppression and apoptosis induction.
          TNF-related apoptosis inducing ligand      Lung cancer     Click to Show/Hide the Molecular Data of This Drug
                 Augmenting Drug Sensitivity     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [11]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model LNCaP CVCL_0395 Prostate carcinoma Homo sapiens
DU145 CVCL_0105 Prostate carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Apigenin markedly augmented TRAIL-mediated apoptosis in prostate cancer cells .
    Î². A List of Drug(s) Whose Adverse Effect can be Decreased by This NP
          Cisplatin      Bladder cancer     Click to Show/Hide the Molecular Data of This Drug
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [12]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression CASP3  Molecule Info 
Pathway MAP
Down-regulation Expression IL19  Molecule Info 
Pathway MAP
Down-regulation Expression IL6  Molecule Info 
Pathway MAP
Down-regulation Expression TNF  Molecule Info 
Pathway MAP
                    In-vivo Model Adult female Wistar Albino mice weighing 10-12g were used in this study.
                    Experimental
                    Result(s)		 Apigenin and myricetin exhibited a protective and promising preventive strategy against cisplatin-induced nephrotoxicity due to their antioxidant and anti-inflammatory effects.
Target and Pathway
Target(s) Aldose reductase (AKR1B1)  Molecule Info  [13]
Androgen receptor (AR)  Molecule Info  [14]
Aromatase (CYP19A1)  Molecule Info  [15]
Casein kinase II alpha (CSNK2A1)  Molecule Info  [16]
Cyclin-dependent kinase 6 (CDK6)  Molecule Info  [17]
Cytochrome P450 1B1 (CYP1B1)  Molecule Info  [18]
Estradiol 17 beta-dehydrogenase 1 (17-beta-HSD1)  Molecule Info  [19]
Influenza Neuraminidase (Influ NA)  Molecule Info  [20]
Plasmodium CDK Pfmrk (Malaria Pfmrk)  Molecule Info  [21]
BioCyc Methylglyoxal degradation III Click to Show/Hide
2 Acetone degradation I (to methylglyoxal)
3 Superpathway of steroid hormone biosynthesis
4 Estradiol biosynthesis II
5 Estradiol biosynthesis I
6 Superpathway of tryptophan utilization
7 Superpathway of melatonin degradation
8 Melatonin degradation I
KEGG Pathway Oocyte meiosis Click to Show/Hide
2 Pathways in cancer
3 Prostate cancer
4 Cell cycle
5 p53 signaling pathway
6 PI3K-Akt signaling pathway
7 Hepatitis B
8 Measles
9 Viral carcinogenesis
10 MicroRNAs in cancer
11 Pancreatic cancer
12 Glioma
13 Melanoma
14 Chronic myeloid leukemia
15 Small cell lung cancer
16 Non-small cell lung cancer
17 Pentose and glucuronate interconversions
18 Fructose and mannose metabolism
19 Galactose metabolism
20 Glycerolipid metabolism
21 Metabolic pathways
22 Steroid hormone biosynthesis
23 Ovarian steroidogenesis
24 Tryptophan metabolism
25 Metabolism of xenobiotics by cytochrome P450
26 Chemical carcinogenesis
27 Ribosome biogenesis in eukaryotes
28 NF-kappa B signaling pathway
29 Wnt signaling pathway
30 Adherens junction
31 Tight junction
32 Herpes simplex infection
33 Epstein-Barr virus infection
34 Other glycan degradation
NetPath Pathway EGFR1 Signaling Pathway Click to Show/Hide
2 AndrogenReceptor Signaling Pathway
3 FSH Signaling Pathway
4 TGF_beta_Receptor Signaling Pathway
5 IL1 Signaling Pathway
6 TSH Signaling Pathway
7 IL4 Signaling Pathway
Panther Pathway Androgen/estrogene/progesterone biosynthesis Click to Show/Hide
Pathwhiz Pathway Fructose and Mannose Degradation Click to Show/Hide
2 Pyruvate Metabolism
3 Pterine Biosynthesis
4 Glycerolipid Metabolism
5 Galactose Metabolism
6 Androgen and Estrogen Metabolism
Pathway Interaction Database Regulation of nuclear SMAD2/3 signaling Click to Show/Hide
2 Coregulation of Androgen receptor activity
3 Regulation of Androgen receptor activity
4 Nongenotropic Androgen signaling
5 Regulation of nuclear beta catenin signaling and target gene transcription
6 FOXA1 transcription factor network
7 Notch-mediated HES/HEY network
8 p73 transcription factor network
9 C-MYB transcription factor network
10 IL2 signaling events mediated by STAT5
11 Regulation of retinoblastoma protein
12 BCR signaling pathway
13 Atypical NF-kappaB pathway
14 DNA-PK pathway in nonhomologous end joining
15 Presenilin action in Notch and Wnt signaling
16 Role of Calcineurin-dependent NFAT signaling in lymphocytes
17 E-cadherin signaling in the nascent adherens junction
18 Lissencephaly gene (LIS1) in neuronal migration and development
19 PDGFR-alpha signaling pathway
20 Signaling mediated by p38-alpha and p38-beta
21 Alpha-synuclein signaling
Reactome Nuclear Receptor transcription pathway Click to Show/Hide
2 Activated PKN1 stimulates transcription of AR (androgen receptor) regulated genes KLK2 and KLK3
3 Oxidative Stress Induced Senescence
4 Senescence-Associated Secretory Phenotype (SASP)
5 Oncogene Induced Senescence
6 Cyclin D associated events in G1
7 Endogenous sterols
8 Condensation of Prometaphase Chromosomes
9 The canonical retinoid cycle in rods (twilight vision)
WikiPathways SIDS Susceptibility Pathways Click to Show/Hide
2 Integrated Pancreatic Cancer Pathway
3 Prostate Cancer
4 Integrated Breast Cancer Pathway
5 Nuclear Receptors
6 Androgen receptor signaling pathway
7 DNA Damage Response
8 G1 to S cell cycle control
9 Wnt Signaling Pathway Netpath
10 Retinoblastoma (RB) in Cancer
11 Signaling Pathways in Glioblastoma
12 Metastatic brain tumor
13 miR-targeted genes in muscle cell - TarBase
14 miR-targeted genes in lymphocytes - TarBase
15 miR-targeted genes in leukocytes - TarBase
16 miR-targeted genes in epithelium - TarBase
17 Mitotic G1-G1/S phases
18 Cell Cycle
19 miRNAs involved in DNA damage response
20 miRNA Regulation of DNA Damage Response
21 Metapathway biotransformation
22 Polyol Pathway
23 Metabolism of steroid hormones and vitamin D
24 Tryptophan metabolism
25 Oxidation by Cytochrome P450
26 Ovarian Infertility Genes
27 FSH signaling pathway
28 Phase 1 - Functionalization of compounds
29 Estrogen metabolism
30 Benzo(a)pyrene metabolism
31 Tamoxifen metabolism
32 Nuclear Receptors Meta-Pathway
33 Estrogen Receptor Pathway
34 Sulindac Metabolic Pathway
35 Arylhydrocarbon receptor (AhR) signaling pathway
36 miR-targeted genes in adipocytes - TarBase
37 Mitotic Prometaphase
38 BDNF signaling pathway
39 TNF alpha Signaling Pathway
40 L1CAM interactions
41 Steroid Biosynthesis
References
Reference 1 Apigenin induces cell shrinkage in Candida albicans by membrane perturbation. FEMS Yeast Res. 2018 Feb 1;18(1).
Reference 2 BH3 mimetic ABT-263 enhances the anticancer effects of apigenin in tumor cells with activating EGFR mutation. Cell Biosci. 2019 Jul 23;9:60.
Reference 3 Bcl-2 inhibitor and apigenin worked synergistically in human malignant neuroblastoma cell lines and increased apoptosis with activation of extrinsic and intrinsic pathways. Biochem Biophys Res Commun. 2009 Oct 30;388(4):705-10.
Reference 4 Apigenin enhances the antitumor effects of cetuximab in nasopharyngeal carcinoma by inhibiting EGFR signaling. Biomed Pharmacother. 2018 Jun;102:681-688.
Reference 5 Apigenin and Abivertinib, a novel BTK inhibitor synergize to inhibit diffuse large B-cell lymphoma in vivo and vitro. J Cancer. 2020 Feb 3;11(8):2123-2132.
Reference 6 Apigenin Combined With Gefitinib Blocks Autophagy Flux and Induces Apoptotic Cell Death Through Inhibition of HIF-1alpha, c-Myc, p-EGFR, and Glucose Metabolism in EGFR L858R+T790M-Mutated H1975 Cells. Front Pharmacol. 2019 Mar 22;10:260.
Reference 7 Apigenin sensitizes prostate cancer cells to Apo2L/TRAIL by targeting adenine nucleotide translocase-2. PLoS One. 2013;8(2):e55922.
Reference 8 Investigation of possible effects of apigenin, sorafenib and combined applications on apoptosis and cell cycle in hepatocellular cancer cells. Gene. 2020 May 5;737:144428.
Reference 9 5-Fluorouracil combined with apigenin enhances anticancer activity through mitochondrial membrane potential mediated apoptosis in hepatocellular carcinoma. Clin Exp Pharmacol Physiol. 2015 Feb;42(2):146-53.
Reference 10 Enhanced anti-tumor effect of combination therapy with gemcitabine and apigenin in pancreatic cancer. Cancer Lett. 2008 Jan 18;259(1):39-49.
Reference 11 Ethanolic Extract of Propolis Augments TRAIL-Induced Apoptotic Death in Prostate Cancer Cells. Evid Based Complement Alternat Med. 2011;2011:535172.
Reference 12 Protective effects of apigenin and myricetin against cisplatin-induced nephrotoxicity in mice. Pharm Biol. 2017 Dec;55(1):766-774.
Reference 13 Erigeroflavanone, a flavanone derivative from the flowers of Erigeron annuus with protein glycation and aldose reductase inhibitory activity. J Nat Prod. 2008 Apr;71(4):713-5.
Reference 14 Effect of flavonoids on androgen and glucocorticoid receptors based on in vitro reporter gene assay. Bioorg Med Chem Lett. 2009 Aug 15;19(16):4706-10.
Reference 15 Pharmacophore modeling strategies for the development of novel nonsteroidal inhibitors of human aromatase (CYP19). Bioorg Med Chem Lett. 2010 May 15;20(10):3050-64.
Reference 16 Structural insight into human CK2alpha in complex with the potent inhibitor ellagic acid. Bioorg Med Chem Lett. 2009 Jun 1;19(11):2920-3.
Reference 17 Crystal structure of a human cyclin-dependent kinase 6 complex with a flavonol inhibitor, fisetin. J Med Chem. 2005 Feb 10;48(3):737-43.
Reference 18 Selective inhibition of methoxyflavonoids on human CYP1B1 activity. Bioorg Med Chem. 2010 Sep 1;18(17):6310-5.
Reference 19 Discovery of nonsteroidal 17beta-hydroxysteroid dehydrogenase 1 inhibitors by pharmacophore-based screening of virtual compound libraries. J Med Chem. 2008 Jul 24;51(14):4188-99.
Reference 20 Neuraminidase inhibitory activities of flavonols isolated from Rhodiola rosea roots and their in vitro anti-influenza viral activities. Bioorg Med Chem. 2009 Oct 1;17(19):6816-23.
Reference 21 A three-dimensional in silico pharmacophore model for inhibition of Plasmodium falciparum cyclin-dependent kinases and discovery of different class... J Med Chem. 2004 Oct 21;47(22):5418-26.
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