Natural Product (NP) Details

General Information of the NP (ID: NP8905)
Name
Astilbin
Synonyms
Astilbin; 29838-67-3; Isoastilbin; Taxifolin 3-O-rhamnoside; Neoisoastilbin; CHEBI:38200; (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)chroman-4-one; (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one; 4H-1-Benzopyran-4-one,3-[(6-deoxy-a-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-, (2R,3R)-; Dihydroquercitrin; 54081-48-0; CHEMBL486017; MEGxp0_000363; ACon1_000616; dihydroquercetin-3-O-alpha-LRhap; DTXSID501019948; AMY22307; HY-N0509; s3932; ZINC31156118; AKOS025402308; AC-8008; CCG-269236; MCULE-6234117773; NCGC00168909-01; (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3-dihydrochromen-4-one; BS-16813; CS-0009049; W1551; C17449; Astilbin from Engelhardtia roxburghiana, >=98%; Dihydroquercetin 3-O-.alpha.-L-rhamnopyranoside; Q-100379; Q4810880; (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-chromen-3-yl 6-deoxy-alpha-L-mannopyranoside; (2R,3R)-3-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one; (2R-trans)-3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one; 4H-1-Benzopyran-4-one, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-, (2R,3R)-; 4H-1-Benzopyran-4-one, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-, (2R-trans)-; 4H-1-Benzopyran-4-one, 3-[(6-deoxy-.alpha.-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-, (2R,3R)-; NCGC00168909-02!(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3-dihydrochromen-4-one
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Species Origin Smilax glabra ...     Click to Show/Hide
Smilax glabra
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Liliales
Family: Smilacaceae
Genus: Smilax
Species: Smilax glabra
Disease Osteoarthritis [ICD-11: FA00-FA05] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -6.411
 
MDCK Permeability
 -5.135
 
PAMPA
 +++
 
HIA
 -
 
Distribution
VDss
 -0.328
 
PPB
 80.5%
 
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
 4.173
 
T1/2
 3.738
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
C21H22O11
PubChem CID
119258
Canonical SMILES
CC1C(C(C(C(O1)OC2C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
InChI
1S/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19+,20-,21-/m0/s1
InChIKey
ZROGCCBNZBKLEL-MPRHSVQHSA-N
CAS Number
CAS 29838-67-3
ChEBI ID
CHEBI:38200
Herb ID
HBIN017200
SymMap ID
SMIT00209
TCMSP ID
MOL004575
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Methotrexate      Leukaemia     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		 Up-regulation Expression ERK1  Molecule Info 
Pathway MAP
Up-regulation Expression p105  Molecule Info 
Pathway MAP
Up-regulation Expression STAT1  Molecule Info 
Pathway MAP
                    In-vivo Model Specific-pathogen-free, eight-week-old male DBA/1J mice, and Eight-week-old C57BL/6 mice were used in this study.
                    Experimental
                    Result(s)		 Astilbin is a valuable candidate for low-dose MTX combined therapy in RA via increasing A2AAR/adenosine system and decreasing ERK/NFKappaB/STATs signals.
Target and Pathway
Target(s) Interleukin-10 (IL10)  Molecule Info  [3]
Tumor necrosis factor (TNF)  Molecule Info  [4]
KEGG Pathway MAPK signaling pathway Click to Show/Hide
2 Cytokine-cytokine receptor interaction
3 NF-kappa B signaling pathway
4 Sphingolipid signaling pathway
5 mTOR signaling pathway
6 Apoptosis
7 TGF-beta signaling pathway
8 Osteoclast differentiation
9 Antigen processing and presentation
10 Toll-like receptor signaling pathway
11 NOD-like receptor signaling pathway
12 RIG-I-like receptor signaling pathway
13 Hematopoietic cell lineage
14 Natural killer cell mediated cytotoxicity
15 T cell receptor signaling pathway
16 Fc epsilon RI signaling pathway
17 TNF signaling pathway
18 Adipocytokine signaling pathway
19 Type II diabetes mellitus
20 Non-alcoholic fatty liver disease (NAFLD)
21 Type I diabetes mellitus
22 Alzheimer's disease
23 Amyotrophic lateral sclerosis (ALS)
24 Pertussis
25 Legionellosis
26 Leishmaniasis
27 Chagas disease (American trypanosomiasis)
28 African trypanosomiasis
29 Malaria
30 Toxoplasmosis
31 Amoebiasis
32 Tuberculosis
33 Hepatitis C
34 Hepatitis B
35 Influenza A
36 HTLV-I infection
37 Herpes simplex infection
38 Proteoglycans in cancer
39 Asthma
40 Inflammatory bowel disease (IBD)
41 Systemic lupus erythematosus
42 Rheumatoid arthritis
43 Allograft rejection
44 Graft-versus-host disease
45 Hypertrophic cardiomyopathy (HCM)
46 Dilated cardiomyopathy
47 FoxO signaling pathway
48 Jak-STAT signaling pathway
49 Intestinal immune network for IgA production
50 Staphylococcus aureus infection
51 Epstein-Barr virus infection
52 Autoimmune thyroid disease
NetPath Pathway TCR Signaling Pathway Click to Show/Hide
2 IL2 Signaling Pathway
3 IL3 Signaling Pathway
4 IL4 Signaling Pathway
5 Leptin Signaling Pathway
6 RANKL Signaling Pathway
7 IL1 Signaling Pathway
8 BCR Signaling Pathway
Panther Pathway Apoptosis signaling pathway Click to Show/Hide
2 Wnt signaling pathway
3 Interleukin signaling pathway
Pathwhiz Pathway Fc Epsilon Receptor I Signaling in Mast Cells Click to Show/Hide
Pathway Interaction Database IL27-mediated signaling events Click to Show/Hide
2 Canonical NF-kappaB pathway
3 Calcineurin-regulated NFAT-dependent transcription in lymphocytes
4 Angiopoietin receptor Tie2-mediated signaling
5 Signaling events mediated by HDAC Class I
6 TNF receptor signaling pathway
7 Ceramide signaling pathway
8 amb2 Integrin signaling
9 RXR and RAR heterodimerization with other nuclear receptor
10 IL23-mediated signaling events
11 HIV-1 Nef: Negative effector of Fas and TNF-alpha
12 Caspase Cascade in Apoptosis
13 Cellular roles of Anthrax toxin
14 Downstream signaling in na&#xef
15
16 Regulation of nuclear SMAD2/3 signaling
17 IL4-mediated signaling events
18 AP-1 transcription factor network
Reactome Transcriptional regulation of white adipocyte differentiation Click to Show/Hide
2 TNFR1-induced proapoptotic signaling
3 Regulation of TNFR1 signaling
4 TNFR1-induced NFkappaB signaling pathway
5 TNFR1-mediated ceramide production
6 TNFR2 non-canonical NF-kB pathway
7 TNF signaling
WikiPathways Toll-like receptor signaling pathway Click to Show/Hide
2 Monoamine Transport
3 SIDS Susceptibility Pathways
4 TGF Beta Signaling Pathway
5 Cytokines and Inflammatory Response
6 MAPK Signaling Pathway
7 EV release from cardiac cells and their functional effects
8 FAS pathway and Stress induction of HSP regulation
9 Apoptosis-related network due to altered Notch3 in ovarian cancer
10 Cardiac Hypertrophic Response
11 Transcriptional Regulation of White Adipocyte Differentiation
12 Aryl Hydrocarbon Receptor
13 Apoptosis
14 Nanoparticle triggered regulated necrosis
15 Amyotrophic lateral sclerosis (ALS)
16 Adipogenesis
17 Allograft Rejection
18 TNF alpha Signaling Pathway
19 TWEAK Signaling Pathway
20 Extrinsic Pathway for Apoptosis
21 Folate Metabolism
22 MicroRNAs in cardiomyocyte hypertrophy
23 Vitamin B12 Metabolism
24 Selenium Micronutrient Network
25 Regulation of toll-like receptor signaling pathway
26 Matrix Metalloproteinases
References
Reference 1 Astilbin prevents osteoarthritis development through the TLR4/MD-2 pathway. J Cell Mol Med. 2020 Nov;24(22):13104-13114.
Reference 2 A novel combination of astilbin and low-dose methotrexate respectively targeting A 2A AR and its ligand adenosine for the treatment of collagen-induced arthritis. Biochem Pharmacol. 2018 Jul;153:269-281.
Reference 3 Astilbin inhibits contact hypersensitivity through negative cytokine regulation distinct from cyclosporin A. J Allergy Clin Immunol. 2005 Dec;116(6):1350-6.
Reference 4 Astilbin ameliorates cisplatin-induced nephrotoxicity through reducing oxidative stress and inflammation. Food Chem Toxicol. 2018 Apr;114:227-236.
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