Natural Product (NP) Details

General Information of the NP (ID: NP9120)
Name
Chrysin
Synonyms
5,7-Dihydroxyflavone; Chrysine; 5,7-Dihydroxy-2-phenyl-4H-chromen-4-one; Crysin; 5,7-dihydroxy-2-phenylchromen-4-one; 4H-1-Benzopyran-4-one, 5,7-dihydroxy-2-phenyl-; UNII-3CN01F5ZJ5; NSC-407436; FLAVONE, 5,7-DIHYDROXY-; EINECS 207-549-7; NSC407436; 5,7-Dihydroxy-2-phenyl-4H-1-benzopyran-4-one; CHEMBL117; NSC 407436; 5,7-Dihydroxy-2-phenyl-chromen-4-one; BRN 0233276; 3CN01F5ZJ5; CHEBI:75095; RTIXKCRFFJGDFG-UHFFFAOYSA-N; 5,7-Dihydroxy-2-phenyl-4H-benzo(b)pyran-4-one; MFCD00006834; Chrysin, 99+%; CAS-480-40-0
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Species Origin Tripterygium wilfordii ...     Click to Show/Hide
Tripterygium wilfordii
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Celastrales
Family: Celastraceae
Genus: Tripterygium
Species: Tripterygium wilfordii
Disease Atopic dermatitis [ICD-11: EA80] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -4.98
 
MDCK Permeability
 -4.768
 
PAMPA
 - -
 
HIA
 - - -
 
Distribution
VDss
 -0.168
 
PPB
 97.8%
 
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
 4.667
 
T1/2
 0.967
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
C15H10O4
PubChem CID
5281607
Canonical SMILES
C1=CC=C(C=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O)O
InChI
1S/C15H10O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-8,16-17H
InChIKey
RTIXKCRFFJGDFG-UHFFFAOYSA-N
CAS Number
CAS 480-40-0
Herb ID
HBIN020447
ETMC ID
2248
SymMap ID
SMIT00508
TCMSP ID
MOL002560
TTD Drug ID
D01UYI
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          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 [2]
                    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 CASP8  Molecule Info 
Pathway MAP
Down-regulation Expression PARP1  Molecule Info 
Pathway MAP
                    In-vitro Model HCT 116 CVCL_0291 Colon carcinoma Homo sapiens
HeLa CVCL_0030 Endocervical adenocarcinoma Homo sapiens
Hep-G2 CVCL_0027 Hepatocellular carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Chrysin can enhance the apoptosis induced by TRAIL, and the apoptosis is caspase-dependent and related to the activation of caspase 8.
          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 [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Phosphorylation ERK1  Molecule Info 
Pathway MAP
Up-regulation Phosphorylation ERK2  Molecule Info 
Pathway MAP
                    In-vitro Model Hep-G2 CVCL_0027 Hepatocellular carcinoma Homo sapiens
Hep 3B2.1-7 CVCL_0326 Childhood hepatocellular carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Chrysin-induced ERK1/2 phosphorylation enhances the sensitivity of human gepatocellular carcinoma cells to sorafenib.
          5-fluorouracil      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 [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 CCNB1  Molecule Info 
Pathway MAP
Up-regulation Expression CDK6  Molecule Info 
Pathway MAP
Up-regulation Expression CDKN1A  Molecule Info 
Pathway MAP
Down-regulation Expression POLD1  Molecule Info 
Pathway MAP
                    In-vitro Model AGS CVCL_0139 Gastric adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Chrysin potentiated the chemotherapeutic effect of 5-FU in gastric cancer AGS and AGS/FR cells via cell cycle arrest.
          Cisplatin      Bladder 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 [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model U-87MG ATCC CVCL_0022 Glioblastoma Homo sapiens
                    Experimental
                    Result(s)		 Chrysin additively potentiates the antiproliferative, cell cycle arrest and apoptotic activity of cisplatin in human glioma cancer (U87) cells.
          Epirubicin      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 [6]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model MDA-MB-231 CVCL_0062 Breast adenocarcinoma Homo sapiens
L5178 Mouse leukemia Rattus norvegicus
                    Experimental
                    Result(s)		 Chrysin synergistically enhanced the effect of epirubicin.
Target and Pathway
Target(s) Aldose reductase (AKR1B1)  Molecule Info  [7]
Aromatase (CYP19A1)  Molecule Info  [8]
Cyclin-dependent kinase 6 (CDK6)  Molecule Info  [9]
Cytochrome P450 1B1 (CYP1B1)  Molecule Info  [10]
Plasmodium 3-oxoacyl-acyl-carrier reductase (Malaria fabG)  Molecule Info  [11]
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 Cell cycle Click to Show/Hide
2 p53 signaling pathway
3 PI3K-Akt signaling pathway
4 Hepatitis B
5 Measles
6 Pathways in cancer
7 Viral carcinogenesis
8 MicroRNAs in cancer
9 Pancreatic cancer
10 Glioma
11 Melanoma
12 Chronic myeloid leukemia
13 Small cell lung cancer
14 Non-small cell lung cancer
15 Pentose and glucuronate interconversions
16 Fructose and mannose metabolism
17 Galactose metabolism
18 Glycerolipid metabolism
19 Metabolic pathways
20 Steroid hormone biosynthesis
21 Ovarian steroidogenesis
22 Tryptophan metabolism
23 Metabolism of xenobiotics by cytochrome P450
24 Chemical carcinogenesis
NetPath Pathway TGF_beta_Receptor Signaling Pathway Click to Show/Hide
2 IL1 Signaling Pathway
3 FSH Signaling Pathway
4 TSH Signaling Pathway
5 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 p73 transcription factor network Click to Show/Hide
2 Coregulation of Androgen receptor activity
3 C-MYB transcription factor network
4 IL2 signaling events mediated by STAT5
5 Regulation of retinoblastoma protein
Reactome Oxidative Stress Induced Senescence Click to Show/Hide
2 Senescence-Associated Secretory Phenotype (SASP)
3 Oncogene Induced Senescence
4 Cyclin D associated events in G1
5 Endogenous sterols
WikiPathways DNA Damage Response Click to Show/Hide
2 G1 to S cell cycle control
3 Wnt Signaling Pathway Netpath
4 Retinoblastoma (RB) in Cancer
5 Signaling Pathways in Glioblastoma
6 Metastatic brain tumor
7 miR-targeted genes in muscle cell - TarBase
8 miR-targeted genes in lymphocytes - TarBase
9 miR-targeted genes in leukocytes - TarBase
10 miR-targeted genes in epithelium - TarBase
11 Mitotic G1-G1/S phases
12 Cell Cycle
13 miRNAs involved in DNA damage response
14 miRNA Regulation of DNA Damage Response
15 Metapathway biotransformation
16 Polyol Pathway
17 Metabolism of steroid hormones and vitamin D
18 Tryptophan metabolism
19 Oxidation by Cytochrome P450
20 Ovarian Infertility Genes
21 FSH signaling pathway
22 Integrated Breast Cancer Pathway
23 Phase 1 - Functionalization of compounds
24 Estrogen metabolism
25 Benzo(a)pyrene metabolism
26 Tamoxifen metabolism
27 Nuclear Receptors Meta-Pathway
28 Estrogen Receptor Pathway
29 Sulindac Metabolic Pathway
30 Arylhydrocarbon receptor (AhR) signaling pathway
31 miR-targeted genes in adipocytes - TarBase
References
Reference 1 Chrysin attenuates atopic dermatitis by suppressing inflammation of keratinocytes. Food Chem Toxicol. 2017 Dec;110:142-150.
Reference 2 Chrysin promotes tumor necrosis factor (TNF)-related apoptosis-inducing ligand (TRAIL) induced apoptosis in human cancer cell lines. Toxicol In Vitro. 2011 Apr;25(3):630-5.
Reference 3 Chrysin-induced ERK1/2 Phosphorylation Enhances the Sensitivity of Human Hepatocellular Carcinoma Cells to Sorafenib. Anticancer Res. 2019 Feb;39(2):695-701.
Reference 4 Potentiating activities of chrysin in the therapeutic efficacy of 5-fluorouracil in gastric cancer cells. Oncol Lett. 2021 Jan;21(1):24.
Reference 5 Additive anticancer effects of chrysin and low dose cisplatin in human malignant glioma cell (U87) proliferation and evaluation of the mechanistic pathway. J BUON. Sep-Oct 2015;20(5):1327-36.
Reference 6 In vitro search for synergy between flavonoids and epirubicin on multidrug-resistant cancer cells. In Vivo. Mar-Apr 2005;19(2):367-74.
Reference 7 Synthesis, characterization and vasculoprotective effects of nitric oxide-donating derivatives of chrysin. Bioorg Med Chem. 2010 May 1;18(9):3020-5.
Reference 8 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 9 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 10 Selective inhibition of methoxyflavonoids on human CYP1B1 activity. Bioorg Med Chem. 2010 Sep 1;18(17):6310-5.
Reference 11 Inhibition of Plasmodium falciparum fatty acid biosynthesis: evaluation of FabG, FabZ, and FabI as drug targets for flavonoids. J Med Chem. 2006 Jun 1;49(11):3345-53.
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