Natural Product (NP) Details

General Information of the NP (ID: NP0258)
Name
Wogonoside
Synonyms
Wogonoside; Oroxindin; 51059-44-0; Wogonin 7-O-glucuronide; UNII-ETX4944Z3R; CHEBI:61282; 5,7-dihydroxy-8-methoxyflavone 7-O-beta-D-glucuronide; CHEMBL464732; ETX4944Z3R; wogonin 7-O-beta-D-glucuronide; MFCD08704808; 5-hydroxy-8-methoxy-4-oxo-2-phenyl-4H-chromen-7-yl beta-D-glucopyranosiduronic acid; (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(5-hydroxy-8-methoxy-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid; wogonin 7-O-beta-glucuronine methyl ester; MEGxp0_000537; ACon1_000851; DTXSID80199062; HY-N0399; BDBM50478452; s9115; ZINC28537647; AKOS015897144; CCG-269333; MCULE-2705236589; Wogonoside, >=95% (LC/MS-ELSD); NCGC00169296-01; CS-0008934; Q3356626; W-202920; BRD-K72010518-001-01-0; (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-((5-hydroxy-8-methoxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid; NCGC00169296-02!(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(5-hydroxy-8-methoxy-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid
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Species Origin Scutellaria baicalensis ...     Click to Show/Hide
Scutellaria baicalensis
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Lamiaceae
Genus: Scutellaria
Species: Scutellaria baicalensis
Disease Colitis [ICD-11: 1A40] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -6.033
 
MDCK Permeability
 -5.23
 
PAMPA
 +++
 
HIA
 - - -
 
Distribution
VDss
 -0.454
 
PPB
 89.6%
 
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
 1.762
 
T1/2
 3.923
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
C22H20O11
PubChem CID
3084961
Canonical SMILES
COC1=C(C=C(C2=C1OC(=CC2=O)C3=CC=CC=C3)O)OC4C(C(C(C(O4)C(=O)O)O)O)O
InChI
1S/C22H20O11/c1-30-18-13(32-22-17(27)15(25)16(26)20(33-22)21(28)29)8-11(24)14-10(23)7-12(31-19(14)18)9-5-3-2-4-6-9/h2-8,15-17,20,22,24-27H,1H3,(H,28,29)/t15-,16-,17+,20-,22+/m0/s1
InChIKey
LNOHXHDWGCMVCO-NTKSAMNMSA-N
CAS Number
CAS 51059-44-0
ChEBI ID
CHEBI:61282
Herb ID
HBIN048376
SymMap ID
SMIT18228
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Adverse Effect can be Decreased by This NP
          Dextran sulfate sodium      Human immunodeficiency virus disease     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 [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression IL6  Molecule Info 
Pathway MAP
Down-regulation Expression NLRP3  Molecule Info 
Pathway MAP
Down-regulation Expression NOS2  Molecule Info 
Pathway MAP
Down-regulation Expression p105  Molecule Info 
Pathway MAP
                    In-vitro Model THP-1 CVCL_0006 Childhood acute monocytic leukemia Homo sapiens
                    In-vivo Model Acute colitis was induced by administration of DSS in drinking water in 35-40 days old female BALB/c mice, weighing 18-22 g,
                    Experimental
                    Result(s)		 Wogonoside may exert its anti-inflammatory effect via dual inhibition of NF-KappaB and NLRP3 inflammasome, suggesting that wogonoside might be a potential effective drug for inflammatory bowel diseases.
Target and Pathway
Target(s) IP3 receptor isoform 1 (ITPR1)  Molecule Info  [3]
Proto-oncogene c-Myc (MYC)  Molecule Info  [3]
Sodium/potassium-transporting ATPase alpha-3 (PLSCR1)  Molecule Info  [4]
TNF receptor-associated factor 2 (TRAF2)  Molecule Info  [5]
Vascular endothelial growth factor A (VEGFA)  Molecule Info  [6]
Zinc finger protein GLI1 (Gli1)  Molecule Info  [6]
KEGG Pathway Ras signaling pathway Click to Show/Hide
2 Rap1 signaling pathway
3 Cytokine-cytokine receptor interaction
4 HIF-1 signaling pathway
5 mTOR signaling pathway
6 PI3K-Akt signaling pathway
7 VEGF signaling pathway
8 Focal adhesion
9 Pathways in cancer
10 Proteoglycans in cancer
11 MicroRNAs in cancer
12 Renal cell carcinoma
13 Pancreatic cancer
14 Bladder cancer
15 Rheumatoid arthritis
16 MAPK signaling pathway
17 ErbB signaling pathway
18 Cell cycle
19 Wnt signaling pathway
20 TGF-beta signaling pathway
21 Hippo signaling pathway
22 Signaling pathways regulating pluripotency of stem cells
23 Jak-STAT signaling pathway
24 Thyroid hormone signaling pathway
25 Hepatitis B
26 HTLV-I infection
27 Epstein-Barr virus infection
28 Transcriptional misregulation in cancer
29 Colorectal cancer
30 Endometrial cancer
31 Thyroid cancer
32 Chronic myeloid leukemia
33 Acute myeloid leukemia
34 Small cell lung cancer
35 Central carbon metabolism in cancer
NetPath Pathway IL2 Signaling Pathway Click to Show/Hide
2 EGFR1 Signaling Pathway
3 TGF_beta_Receptor Signaling Pathway
4 TSH Signaling Pathway
5 Leptin Signaling Pathway
6 FSH Signaling Pathway
7 IL9 Signaling Pathway
8 TCR Signaling Pathway
9 IL4 Signaling Pathway
10 Notch Signaling Pathway
11 Wnt Signaling Pathway
Panther Pathway Angiogenesis Click to Show/Hide
2 VEGF signaling pathway
3 Interleukin signaling pathway
4 Oxidative stress response
5 PDGF signaling pathway
6 Wnt signaling pathway
7 p53 pathway feedback loops 2
8 CCKR signaling map ST
Pathway Interaction Database Glypican 1 network Click to Show/Hide
2 HIF-2-alpha transcription factor network
3 Beta3 integrin cell surface interactions
4 S1P3 pathway
5 Signaling events mediated by TCPTP
6 S1P1 pathway
7 Alpha9 beta1 integrin signaling events
8 Integrins in angiogenesis
9 VEGFR1 specific signals
10 HIF-1-alpha transcription factor network
11 Regulation of nuclear SMAD2/3 signaling
12 Notch signaling pathway
13 p73 transcription factor network
14 E2F transcription factor network
15 CD40/CD40L signaling
16 Validated targets of C-MYC transcriptional activation
17 Presenilin action in Notch and Wnt signaling
18 LKB1 signaling events
19 Regulation of Telomerase
20 IL2-mediated signaling events
21 C-MYC pathway
22 IL2 signaling events mediated by PI3K
23 Ceramide signaling pathway
24 AP-1 transcription factor network
25 FOXM1 transcription factor network
26 IL6-mediated signaling events
27 PDGFR-beta signaling pathway
28 C-MYB transcription factor network
29 Validated nuclear estrogen receptor alpha network
30 Regulation of nuclear beta catenin signaling and target gene transcription
31 IL2 signaling events mediated by STAT5
32 Validated targets of C-MYC transcriptional repression
Reactome Platelet degranulation Click to Show/Hide
2 Regulation of gene expression by Hypoxia-inducible Factor
3 VEGF ligand-receptor interactions
4 VEGF binds to VEGFR leading to receptor dimerization
5 NOTCH1 Intracellular Domain Regulates Transcription
6 SMAD2/SMAD3:SMAD4 heterotrimer regulates transcription
7 Constitutive Signaling by NOTCH1 PEST Domain Mutants
8 Constitutive Signaling by NOTCH1 HD+PEST Domain Mutants
9 Binding of TCF/LEF:CTNNB1 to target gene promoters
10 MAPK6/MAPK4 signaling
11 Cyclin E associated events during G1/S transition
12 Cyclin A:Cdk2-associated events at S phase entry
WikiPathways SIDS Susceptibility Pathways Click to Show/Hide
2 Hypertrophy Model
3 Endochondral Ossification
4 Focal Adhesion
5 Differentiation Pathway
6 Bladder Cancer
7 Regulation of Hypoxia-inducible Factor (HIF) by Oxygen
8 Nifedipine Activity
9 Aryl Hydrocarbon Receptor
10 Quercetin and Nf-kB/ AP-1 Induced Cell Apoptosis
11 Integrated Pancreatic Cancer Pathway
12 Oncostatin M Signaling Pathway
13 Allograft Rejection
14 Integrated Breast Cancer Pathway
15 Signaling by VEGF
16 Heart Development
17 Angiogenesis
18 DNA Damage Response (only ATM dependent)
19 DNA Damage Response
20 ErbB Signaling Pathway
21 Notch Signaling Pathway
22 IL-2 Signaling Pathway
23 G1 to S cell cycle control
24 Wnt Signaling Pathway
25 p38 MAPK Signaling Pathway
26 Wnt Signaling Pathway and Pluripotency
27 MAPK Signaling Pathway
28 TGF beta Signaling Pathway
29 Wnt Signaling Pathway Netpath
30 PPAR Alpha Pathway
31 Ectoderm Differentiation
32 Hair Follicle Development: Organogenesis (Part 2 of 3)
33 Mammary gland development pathway - Involution (Stage 4 of 4)
34 Hair Follicle Development: Induction (Part 1 of 3)
35 S Phase
36 Transcriptional activity of SMAD2/SMAD3:SMAD4 heterotrimer
37 Signaling by NOTCH1
38 Structural Pathway of Interleukin 1 (IL-1)
39 Polycystic Kidney Disease Pathway
40 Apoptosis
41 Retinoblastoma (RB) in Cancer
42 Spinal Cord Injury
43 Gastric cancer network 2
44 B Cell Receptor Signaling Pathway
45 Prostate Cancer
46 Metastatic brain tumor
47 TSLP Signaling Pathway
48 Neural Crest Differentiation
49 IL-7 Signaling Pathway
50 TSH signaling pathway
51 Integrated Cancer pathway
52 Mitotic G1-G1/S phases
53 TP53 Network
54 miRNAs involved in DNA damage response
55 miRNA Regulation of DNA Damage Response
56 IL-5 Signaling Pathway
References
Reference 1 Wogonoside alleviates colitis by improving intestinal epithelial barrier function via the MLCK/pMLC2 pathway. Phytomedicine. 2020 Mar;68:153179.
Reference 2 Wogonoside protects against dextran sulfate sodium-induced experimental colitis in mice by inhibiting NF-KappaB and NLRP3 inflammasome activation. Biochem Pharmacol. 2015 Mar 15;94(2):142-54.
Reference 3 Wogonoside induces cell cycle arrest and differentiation by affecting expression and subcellular localization of PLSCR1 in AML cells. Blood. 2013 May 2;121(18):3682-91.
Reference 4 PLSCR1/IP3R1/Ca(2+) axis contributes to differentiation of primary AML cells induced by wogonoside. Cell Death Dis. 2017 May 11;8(5):e2768.
Reference 5 Wogonoside inhibits invasion and migration through suppressing TRAF2/4 expression in breast cancer. J Exp Clin Cancer Res. 2017 Aug 3;36(1):103.
Reference 6 A Systems Pharmacology Approach Uncovers Wogonoside as an Angiogenesis Inhibitor of Triple-Negative Breast Cancer by Targeting Hedgehog Signaling. Cell Chem Biol. 2019 Aug 15;26(8):1143-1158.e6.
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