Natural Product (NP) Details

General Information of the NP (ID: NP9241)
Name
Amentoflavone
Synonyms
Amentoflavone; 1617-53-4; Didemethyl-ginkgetin; 3',8''-Biapigenin; Amenthoflavone; UNII-9I1VC79L77; I3,II8-biapigenin; MLS000574827; CHEBI:2631; 9I1VC79L77; MFCD00017470; 8-[5-(5,7-dihydroxy-4-oxo-chromen-2-yl)-2-hydroxy-phenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one; SMR000156235; 4H-1-Benzopyran-4-one, 8-[5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-; 8-(5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 8-(5-(5,7-Dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one; 8-[5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one; Tridemethylsciadopitysin; SR-01000721725; 4H-1-Benzopyran-4-one, 8-(5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-; NSC 295677; BIDD:PXR0028; SCHEMBL312563; MEGxp0_000924; med.21724, Compound 138; DTXSID20167225; Amentoflavone, analytical standard; BDBM429466; HMS2228B12; HMS3343J17; HMS3885A08; BCP13255; HY-N0662; ZINC3984030; Amentoflavone, >=99.0% (HPLC); LMPK12040009; MFCD20275041; NSC295677; s3833; (4-hydroxyphenyl)-4H-chromen-4-one; AKOS015896819; CCG-269950; CS-4945; NSC-295677; 3',8-Bi[4',5,7-trihydroxyflavone]; NCGC00247542-01; 8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one; AK167966; BS-15502; DB-043499; FT-0622262; N2268; W1536; C10018; 617A534; A810291; 8-(5-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2; Q-100192; Q4742425; SR-01000721725-2; SR-01000721725-3; 4',5,7-Trihydroxyflavone(3'->8)-4',5,7-trihydroxyflavone; 4',4''',5,5'',7,7''-Hexahydroxy-3''',8-biflavone, 8CI; 5,5',7,7'-Tetrahydroxy-2,2'-bis(4-hydroxyphenyl)-[3,8'-bi-4H-1-benzopyran]-4,4'-dione; 4H-1-Benzopyran-4-one, 8-[5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl); 8-[5-(5,7-dihydroxy-4-oxo-1-benzopyran-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-1-benzopyran-4-one; 8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one.; 8-[5-[5,7-bis(oxidanyl)-4-oxidanylidene-chromen-2-yl]-2-oxidanyl-phenyl]-2-(4-hydroxyphenyl)-5,7-bis(oxidanyl)chromen-4-one
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Species Origin Gingko biloba ...     Click to Show/Hide
Gingko biloba
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Ginkgoopsida
Order: Ginkgoales
Family: Ginkgoaceae
Genus: Ginkgo
Species: Gingko biloba
Disease Epilepsy/seizure [ICD-11: 8A60] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -5.458
 
MDCK Permeability
 -4.799
 
PAMPA
 ++
 
HIA
 - - -
 
Distribution
VDss
 -0.463
 
PPB
 96.6%
 
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
 1.96
 
T1/2
 2.065
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
C30H18O10
PubChem CID
5281600
Canonical SMILES
C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4=C(C=CC(=C4)C5=CC(=O)C6=C(C=C(C=C6O5)O)O)O)O
InChI
1S/C30H18O10/c31-15-4-1-13(2-5-15)24-12-23(38)29-21(36)10-20(35)27(30(29)40-24)17-7-14(3-6-18(17)33)25-11-22(37)28-19(34)8-16(32)9-26(28)39-25/h1-12,31-36H
InChIKey
YUSWMAULDXZHPY-UHFFFAOYSA-N
CAS Number
CAS 1617-53-4
ChEBI ID
CHEBI:2631
Herb ID
HBIN015834
SymMap ID
SMIT04353
TCMSP ID
MOL002037
TTD Drug ID
D06HRX
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Cisplatin      Bladder 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		 Up-regulation Expression BAK  Molecule Info 
Pathway MAP
Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP9  Molecule Info 
Pathway MAP
                    In-vitro Model SAS CVCL_1675 Tongue squamous cell carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Inactivation of NF-KappaB and induction of apoptosis through intrinsic caspase-dependent and independent apoptotic pathways are associated with amentoflavone enhanced anti-OSCC efficacy of cisplatin.
          Sorafenib      Renal cell carcinoma     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 [3]
                    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 CASP9  Molecule Info 
Pathway MAP
Down-regulation Expression CFLAR  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation ERK1  Molecule Info 
Pathway MAP
Down-regulation Expression MCL1  Molecule Info 
Pathway MAP
Down-regulation Expression XIAP  Molecule Info 
Pathway MAP
                    In-vivo Model To establish the animal model, 1*107 SK-Hep1 cells were suspended in 150 ul mix-ture of serum-free DMEM and matrigel (2: 1) and inoculated subcutaneously in the right legs of nude mice.
                    Experimental
                    Result(s)		 Amentoflavone boosts therapeutic efficacy of sorafenib through blockage of anti-apoptotic potential and induction of apoptosis in HCC in vivo.
          Ampicillin      Bacterial infection     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 [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Enterococcus faecium ATCC 19434 Microorganism model Enterococcus faecium
Staphylococcus aureus ATCC 25923 Microorganism model Staphylococcus aureus
Streptococcus mutans ATCC 3065 Microorganism model Streptococcus mutans
Escherichia coli ATCC 43895 Microorganism model Escherichia coli
Escherichia coli ATCC 25922 Microorganism model Escherichia coli
Pseudomonas aeruginosa ATCC 27853 Microorganism model Pseudomonas aeruginosa
                    Experimental
                    Result(s)		 Amentoflavone had a considerable antibacterial effect and synergistic interaction with antibiotics against various bacterial strains. The formation of hydroxyl radical would be a cause of the synergistic effect and that this oxidative stress originated from a transient NADH depletion. .
          Cefotaxime      Bacterial infection     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 [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Enterococcus faecium ATCC 19434 Microorganism model Enterococcus faecium
Staphylococcus aureus ATCC 25923 Microorganism model Staphylococcus aureus
Streptococcus mutans ATCC 3065 Microorganism model Streptococcus mutans
Escherichia coli ATCC 43895 Microorganism model Escherichia coli
Escherichia coli ATCC 25922 Microorganism model Escherichia coli
Pseudomonas aeruginosa ATCC 27853 Microorganism model Pseudomonas aeruginosa
                    Experimental
                    Result(s)		 Amentoflavone had a considerable antibacterial effect and synergistic interaction with antibiotics against various bacterial strains. The formation of hydroxyl radical would be a cause of the synergistic effect and that this oxidative stress originated from a transient NADH depletion. .
          Chloramphenicol      Bacterial infection     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 [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Enterococcus faecium ATCC 19434 Microorganism model Enterococcus faecium
Staphylococcus aureus ATCC 25923 Microorganism model Staphylococcus aureus
Streptococcus mutans ATCC 3065 Microorganism model Streptococcus mutans
Escherichia coli ATCC 43895 Microorganism model Escherichia coli
Escherichia coli ATCC 25922 Microorganism model Escherichia coli
Pseudomonas aeruginosa ATCC 27853 Microorganism model Pseudomonas aeruginosa
                    Experimental
                    Result(s)		 Amentoflavone had a considerable antibacterial effect and synergistic interaction with antibiotics against various bacterial strains. The formation of hydroxyl radical would be a cause of the synergistic effect and that this oxidative stress originated from a transient NADH depletion. .
    β. A List of Drug(s) Whose Adverse Effect can be Decreased by This NP
          Gamma-ray irradiation      Brain metastases     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 [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression TNFAIP2  Molecule Info 
Pathway MAP
                    In-vivo Model Male C57BL/6 mice(18-22g) were exposed to 60Co Gamma-irradiation at a dose of 7.5 Gy or 3 Gy and the dose rate was 1.58 Gy/min
                    Experimental
                    Result(s)		 AMF is a potential protective agent against radiation injury.
Target and Pathway
Target(s) Bcl-2-like protein 3 (MCL1)  Molecule Info  [6]
Gamma-aminobutyric acid receptor (GAR)  Molecule Info  [7]
Xanthine dehydrogenase/oxidase (XDH)  Molecule Info  [8]
BioCyc Purine nucleotides degradation Click to Show/Hide
2 Urate biosynthesis/inosine 5'-phosphate degradation
3 Guanosine nucleotides degradation
4 Adenosine nucleotides degradation
5 Retinoate biosynthesis II
KEGG Pathway PI3K-Akt signaling pathway Click to Show/Hide
2 MicroRNAs in cancer
3 Purine metabolism
4 Caffeine metabolism
5 Drug metabolism - other enzymes
6 Metabolic pathways
7 Peroxisome
NetPath Pathway TCR Signaling Pathway Click to Show/Hide
Panther Pathway Apoptosis signaling pathway Click to Show/Hide
2 CCKR signaling map ST
3 Adenine and hypoxanthine salvage pathway
4 Purine metabolism
Pathwhiz Pathway Caffeine Metabolism Click to Show/Hide
2 Purine Metabolism
Pathway Interaction Database E2F transcription factor network Click to Show/Hide
2 Direct p53 effectors
3 IL6-mediated signaling events
4 HIF-1-alpha transcription factor network
Reactome Purine catabolism Click to Show/Hide
WikiPathways Apoptosis Click to Show/Hide
2 miR-targeted genes in muscle cell - TarBase
3 miR-targeted genes in lymphocytes - TarBase
4 miR-targeted genes in leukocytes - TarBase
5 Apoptosis Modulation and Signaling
6 Oxidative Stress
7 Effects of Nitric Oxide
8 Metabolism of nucleotides
9 Selenium Micronutrient Network
References
Reference 1 Amentoflavone Affects Epileptogenesis and Exerts Neuroprotective Effects by Inhibiting NLRP3 Inflammasome. Front Pharmacol. 2019 Jul 30;10:856.
Reference 2 Anticancer Efficacy and Mechanism of Amentoflavone for Sensitizing Oral Squamous Cell Carcinoma to Cisplatin. Anticancer Res. 2020 Dec;40(12):6723-6732.
Reference 3 Amentoflavone Enhances the Therapeutic Efficacy of Sorafenib by Inhibiting Anti-apoptotic Potential and Potentiating Apoptosis in Hepatocellular Carcinoma In Vivo. Anticancer Res. 2018 Apr;38(4):2119-2125.
Reference 4 Antibacterial effect of amentoflavone and its synergistic effect with antibiotics. J Microbiol Biotechnol. 2013;23(7):953-8.
Reference 5 Amentoflavone protects the hematopoietic system of mice against Gamma-irradiation. Arch Pharm Res. 2019 Nov;42(11):1021-1029.
Reference 6 In silico identification and biochemical evaluation of novel inhibitors of NRH:quinone oxidoreductase 2 (NQO2). Bioorg Med Chem Lett. 2010 Dec 15;20(24):7331-6.
Reference 7 Semisynthetic preparation of amentoflavone: A negative modulator at GABA(A) receptors. Bioorg Med Chem Lett. 2003 Jul 21;13(14):2281-4.
Reference 8 Inhibition of cow's milk xanthine oxidase by flavonoids. J Nat Prod. 1988 Mar-Apr;51(2):345-8.
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