Drug Information

Drug General Information
Drug ID
D00RIX
Former ID
DNC004714
Drug Name
APIGENIN
Drug Type
Small molecular drug
Indication Discovery agent Investigative [1]
Structure
Download
2D MOL

3D MOL
Formula
C15H10O5
InChI
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
PubChem Compound ID
5280443
PubChem Substance ID
4649, 121464, 597182, 3157885, 7548407, 7985171, 8143786, 8149149, 8616271, 10319029, 10321674, 10852035, 11108249, 11110728, 11110729, 11113975, 11120256, 11120744, 11121232, 11335973, 11361212, 11372984, 11375697, 11446182, 11462184, 11466442, 11467562, 11484152, 11486043, 11488244, 11491697, 11493813, 11537389, 14750506, 17389511, 17404628, 24278212, 24846790, 25622500, 26613049, 26679908, 26747161, 26747162, 26752115, 26752116, 26758236, 29203847, 39289566, 46500336, 46501293
Target and Pathway
Target(s) Neuraminidase Target Info Inhibitor [2]
Casein kinase II, alpha chain Target Info Inhibitor [3]
Aldose reductase Target Info Inhibitor [4]
Cytochrome P450 1B1 Target Info Inhibitor [5]
Cytochrome P450 19 Target Info Inhibitor [6]
mRNA of androgen receptor Target Info Inhibitor [7]
Cyclin-dependent protein kinase Pfmrk Target Info Inhibitor [8]
Cell division protein kinase 6 Target Info Inhibitor [9]
Estradiol 17 beta-dehydrogenase 1 Target Info Inhibitor [10]
BioCyc Pathway Methylglyoxal degradation III
Acetone degradation I (to methylglyoxal)PWY66-401:Superpathway of tryptophan utilization
Superpathway of melatonin degradation
Melatonin degradation IPWY-7305:Superpathway of steroid hormone biosynthesis
Estradiol biosynthesis II
Estradiol biosynthesis IPWY-7305:Superpathway of steroid hormone biosynthesis
Estradiol biosynthesis I
KEGG Pathway Other glycan degradationhsa03008:Ribosome biogenesis in eukaryotes
NF-kappa B signaling pathway
Wnt signaling pathway
Adherens junction
Tight junction
Measles
Herpes simplex infection
Epstein-Barr virus infectionhsa00040:Pentose and glucuronate interconversions
Fructose and mannose metabolism
Galactose metabolism
Glycerolipid metabolism
Metabolic pathwayshsa00140:Steroid hormone biosynthesis
Tryptophan metabolism
Metabolism of xenobiotics by cytochrome P450
Ovarian steroidogenesis
Chemical carcinogenesis
MicroRNAs in cancerhsa00140:Steroid hormone biosynthesis
Metabolic pathways
Ovarian steroidogenesishsa04114:Oocyte meiosis
Pathways in cancer
Prostate cancerhsa04110:Cell cycle
p53 signaling pathway
PI3K-Akt signaling pathway
Hepatitis B
Viral carcinogenesis
MicroRNAs in cancer
Pancreatic cancer
Glioma
Melanoma
Chronic myeloid leukemia
Small cell lung cancer
Non-small cell lung cancerhsa00140:Steroid hormone biosynthesis
NetPath Pathway FSH Signaling PathwayNetPath_13:IL1 Signaling Pathway
TGF_beta_Receptor Signaling PathwayNetPath_23:TSH Signaling Pathway
IL4 Signaling Pathway
TGF_beta_Receptor Signaling PathwayNetPath_25:FSH Signaling PathwayNetPath_4:EGFR1 Signaling Pathway
AndrogenReceptor Signaling Pathway
FSH Signaling PathwayNetPath_7:TGF_beta_Receptor Signaling PathwayNetPath_25:FSH Signaling Pathway
PANTHER Pathway Androgen/estrogene/progesterone biosynthesisP02727:Androgen/estrogene/progesterone biosynthesis
Pathway Interaction Database BCR signaling pathway
Atypical NF-kappaB pathway
DNA-PK pathway in nonhomologous end joining
Presenilin action in Notch and Wnt signaling
Role of Calcineurin-dependent NFAT signaling in lymphocytes
E-cadherin signaling in the nascent adherens junction
Lissencephaly gene (LIS1) in neuronal migration and development
PDGFR-alpha signaling pathway
Signaling mediated by p38-alpha and p38-beta
Alpha-synuclein signalingsmad2_3nuclearpathway:Regulation of nuclear SMAD2/3 signaling
Coregulation of Androgen receptor activity
Regulation of Androgen receptor activity
Nongenotropic Androgen signaling
Regulation of nuclear beta catenin signaling and target gene transcription
FOXA1 transcription factor network
Notch-mediated HES/HEY networkp73pathway:p73 transcription factor network
C-MYB transcription factor network
IL2 signaling events mediated by STAT5
Regulation of retinoblastoma protein
PathWhiz Pathway Fructose and Mannose Degradation
Pyruvate Metabolism
Pterine Biosynthesis
Glycerolipid Metabolism
Galactose MetabolismPW000045:Androgen and Estrogen MetabolismPW000045:Androgen and Estrogen Metabolism
Reactome Condensation of Prometaphase ChromosomesR-HSA-211976:Endogenous sterolsR-HSA-211976:Endogenous sterolsR-HSA-383280:Nuclear Receptor transcription pathway
Activated PKN1 stimulates transcription of AR (androgen receptor) regulated genes KLK2 and KLK3R-HSA-2559580:Oxidative Stress Induced Senescence
Senescence-Associated Secretory Phenotype (SASP)
Oncogene Induced Senescence
Cyclin D associated events in G1R-HSA-2453902:The canonical retinoid cycle in rods (twilight vision)
WikiPathways Mitotic Prometaphase
BDNF signaling pathway
TNF alpha Signaling Pathway
L1CAM interactionsWP702:Metapathway biotransformation
Polyol Pathway
Metabolism of steroid hormones and vitamin DWP702:Metapathway biotransformation
Estrogen metabolism
Benzo(a)pyrene metabolism
Tamoxifen metabolism
Tryptophan metabolism
Oxidation by Cytochrome P450
Nuclear Receptors Meta-Pathway
Estrogen Receptor Pathway
Sulindac Metabolic Pathway
Arylhydrocarbon receptor (AhR) signaling pathway
miR-targeted genes in muscle cell - TarBase
miR-targeted genes in lymphocytes - TarBase
miR-targeted genes in epithelium - TarBase
miR-targeted genes in adipocytes - TarBase
Phase 1 - Functionalization of compoundsWP702:Metapathway biotransformation
Ovarian Infertility Genes
Metabolism of steroid hormones and vitamin D
FSH signaling pathway
Integrated Breast Cancer Pathway
Phase 1 - Functionalization of compoundsWP706:SIDS Susceptibility Pathways
Integrated Pancreatic Cancer Pathway
Prostate Cancer
Nuclear Receptors
Androgen receptor signaling pathwayWP707:DNA Damage Response
G1 to S cell cycle control
Wnt Signaling Pathway Netpath
Retinoblastoma (RB) in Cancer
Signaling Pathways in Glioblastoma
Metastatic brain tumor
miR-targeted genes in leukocytes - TarBase
Mitotic G1-G1/S phases
Cell Cycle
miRNAs involved in DNA damage response
miRNA Regulation of DNA Damage ResponseWP496:Steroid Biosynthesis
References
REF 1(http://www.guidetopharmacology.org/) Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4136).
REF 2Bioorg Med Chem. 2009 Oct 1;17(19):6816-23. Epub 2009 Aug 21.Neuraminidase inhibitory activities of flavonols isolated from Rhodiola rosea roots and their in vitro anti-influenza viral activities.
REF 3Bioorg Med Chem Lett. 2009 Jun 1;19(11):2920-3. Epub 2009 Apr 22.Structural insight into human CK2alpha in complex with the potent inhibitor ellagic acid.
REF 4J Nat Prod. 2008 Apr;71(4):713-5. Epub 2008 Feb 26.Erigeroflavanone, a flavanone derivative from the flowers of Erigeron annuus with protein glycation and aldose reductase inhibitory activity.
REF 5Bioorg Med Chem. 2010 Sep 1;18(17):6310-5. Epub 2010 Jul 13.Selective inhibition of methoxyflavonoids on human CYP1B1 activity.
REF 6Bioorg Med Chem Lett. 2010 May 15;20(10):3050-64. Epub 2010 Apr 8.Pharmacophore modeling strategies for the development of novel nonsteroidal inhibitors of human aromatase (CYP19).
REF 7Bioorg Med Chem Lett. 2009 Aug 15;19(16):4706-10. Epub 2009 Jun 23.Effect of flavonoids on androgen and glucocorticoid receptors based on in vitro reporter gene assay.
REF 8J Med Chem. 2004 Oct 21;47(22):5418-26.A three-dimensional in silico pharmacophore model for inhibition of Plasmodium falciparum cyclin-dependent kinases and discovery of different classes of novel Pfmrk specific inhibitors.
REF 9J Med Chem. 2005 Feb 10;48(3):737-43.Crystal structure of a human cyclin-dependent kinase 6 complex with a flavonol inhibitor, fisetin.
REF 10J Med Chem. 2008 Jul 24;51(14):4188-99. Epub 2008 Jun 6.Discovery of nonsteroidal 17beta-hydroxysteroid dehydrogenase 1 inhibitors by pharmacophore-based screening of virtual compound libraries.

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