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Natural Product (NP) Details

General Information of the NP (ID: NP4127)
Name
Daidzein
Synonyms
4',7-Dihydroxyisoflavone; Daidzeol; 7,4'-Dihydroxyisoflavone; 7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one; 4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-; 7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 7-hydroxy-3-(4-hydroxyphenyl)chromen-4-one; 7-Hydroxy-3-(4-hydroxyphenyl)-4-benzopyrone; UNII-6287WC5J2L; CCRIS 7600; K 251b; 4,7-Dihydroxyisoflavone; EINECS 207-635-4; BRN 0231523; CHEMBL8145; 4',7-Dihydroxy-iso-flavone; d-(+)-alpha-methylbenzylamine; ,7-Dihydroxyisoflavone; 7,4'-dihydroxyisoflavone; DIADZEIN; 486-66-8
    Click to Show/Hide
Species Origin Erythrina latissima ...     Click to Show/Hide
Erythrina latissima
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Erythrina
Species: Erythrina latissima
Glycine max
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Glycine
Species: Glycine max
Medicago sativa
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Medicago
Species: Medicago sativa
Trifolium repens
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Trifolium
Species: Trifolium repens
Trifolium pratense
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Trifolium
Species: Trifolium pratense
Epimedium pubescens
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Ranunculales
Family: Berberidaceae
Genus: Epimedium
Species: Epimedium pubescens
Pueraria calycina
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Pueraria
Species: Pueraria calycina
Pueraria edulis
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Fabales
Family: Fabaceae
Genus: Pueraria
Species: Pueraria edulis
Disease Diabetic retinopathy [ICD-11: 9B71] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C15H10O4
PubChem CID
5281708
Canonical SMILES
C1=CC(=CC=C1C2=COC3=C(C2=O)C=CC(=C3)O)O
InChI
1S/C15H10O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-8,16-17H
InChIKey
ZQSIJRDFPHDXIC-UHFFFAOYSA-N
CAS Number
CAS 486-66-8
Herb ID
HBIN022577
ETMC ID
2578
SymMap ID
SMIT00036
TCMSP ID
MOL000390
TTD Drug ID
D0SY2M
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Topotecan      Ovarian 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 [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Down-regulation Expression ABCG2  Molecule Info 
Pathway MAP
Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
                    In-vitro Model MCF-7 CVCL_0031 Invasive breast carcinoma Homo sapiens
                    In-vivo Model Adult female athymic nude mice (six-week-old) were injected with MCF7 cells (5*106 cells/mouse) to construct subcutaneous breast cancer xenografts.
                    Experimental
                    Result(s)
Daidzein enhances the anticancer effect of topotecan and reverses BCRP-mediated drug resistance in breast cancer.
    β. A List of Drug(s) Whose Resistance can be Reversed by This NP
          TNF-related apoptosis inducing ligand      Lung cancer     Click to Show/Hide the Molecular Data of This Drug
                 Reversing Drug Resistance     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
Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
                    In-vitro Model NCH89 CVCL_S823 Glioblastoma Homo sapiens
LN-229 CVCL_0393 Glioblastoma Homo sapiens
                    Experimental
                    Result(s)
Daidzein overcomes TRAIL-resistance in malignant glioma cells by modulating the expression of the intrinsic apoptotic inhibitor, bcl-2.
Target and Pathway
Target(s) Aldose reductase (AKR1B1)  Molecule Info  [4]
Estrogen receptor (ESR)  Molecule Info  [5]
Estrogen-related receptor (ESRR)  Molecule Info  [6]
Transient receptor potential channel 5 (TRPC5)  Molecule Info  [7]
BioCyc Methylglyoxal degradation III Click to Show/Hide
2 Acetone degradation I (to methylglyoxal)
KEGG Pathway Pentose and glucuronate interconversions Click to Show/Hide
2 Fructose and mannose metabolism
3 Galactose metabolism
4 Glycerolipid metabolism
5 Metabolic pathways
6 Estrogen signaling pathway
7 Prolactin signaling pathway
8 Thyroid hormone signaling pathway
9 Endocrine and other factor-regulated calcium reabsorption
10 Proteoglycans in cancer
NetPath Pathway IL1 Signaling Pathway Click to Show/Hide
2 TGF_beta_Receptor Signaling Pathway
3 FSH Signaling Pathway
4 EGFR1 Signaling Pathway
5 RANKL Signaling Pathway
Panther Pathway Alzheimer disease-presenilin pathway 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
Pathway Interaction Database Regulation of nuclear SMAD2/3 signaling Click to Show/Hide
2 Signaling events mediated by HDAC Class II
3 Plasma membrane estrogen receptor signaling
4 LKB1 signaling events
5 Regulation of Telomerase
6 ATF-2 transcription factor network
7 AP-1 transcription factor network
8 FOXM1 transcription factor network
9 Validated nuclear estrogen receptor alpha network
10 Signaling mediated by p38-alpha and p38-beta
11 FOXA1 transcription factor network
Reactome Nuclear signaling by ERBB4 Click to Show/Hide
2 Nuclear Receptor transcription pathway
3 TRP channels
4 Role of second messengers in netrin-1 signaling
WikiPathways Metapathway biotransformation Click to Show/Hide
2 Polyol Pathway
3 Metabolism of steroid hormones and vitamin D
4 Estrogen signaling pathway
5 Nuclear Receptors Meta-Pathway
6 Estrogen Receptor Pathway
7 Signaling by ERBB4
8 JAK/STAT
9 Integrated Pancreatic Cancer Pathway
10 Leptin signaling pathway
11 miR-targeted genes in muscle cell - TarBase
12 Integrated Breast Cancer Pathway
13 Nuclear Receptors
14 Netrin-1 signaling
References
Reference 1 Daidzein ameliorates diabetic retinopathy in experimental animals. Life Sci. 2021 Jan 15;265:118779.
Reference 2 Functional daidzein enhances the anticancer effect of topotecan and reverses BCRP-mediated drug resistance in breast cancer. Pharmacol Res. 2019 Sep;147:104387.
Reference 3 Daidzein overcomes TRAIL-resistance in malignant glioma cells by modulating the expression of the intrinsic apoptotic inhibitor, bcl-2. Neurosci Lett. 2009 May 1;454(3):223-8.
Reference 4 1-Benzopyran-4-one antioxidants as aldose reductase inhibitors. J Med Chem. 1999 Jun 3;42(11):1881-93.
Reference 5 Isolation and structure elucidation of an isoflavone and a sesterterpenoic acid from Henriettella fascicularis. J Nat Prod. 2002 Dec;65(12):1749-53.
Reference 6 Flavone and isoflavone phytoestrogens are agonists of estrogen-related receptors. Mol Cancer Res. 2003 Nov;1(13):981-91.
Reference 7 URL: 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. (Target id: 490).
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Cite NPCDR
Visitor Map
Correspondence

X. N. Sun, Y. T. Zhang, Y. Zhou, X. C. Lian, L. L. Yan, T. Pan, T. Jin, H. Xie, Z. M. Liang, W. Q. Qiu, J. X. Wang, Z. R. Li, F. Zhu*, X. B. Sui*. NPCDR: natural product-based drug combination and its disease-specific molecular regulation. Nucleic Acids Research. 50(D1): 1324-1333 (2020). PMID: 34664659

Prof. Feng ZHU  (zhufeng@zju.edu.cn)

College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China


Prof. Xinbing SUI  (hzzju@hznu.edu.cn)

School of Pharmacy and Department of Medical Oncology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou, China