Natural Product (NP) Details

General Information of the NP (ID: NP6465)
Name
Ampelopsin
Synonyms
Dihydromyricetin; Ampelopsin; 27200-12-0; Ampeloptin; (+)-Dihydromyricetin; (+)-Ampelopsin; (2r,3r)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-4-one; UNII-KD8QND6427; 4H-1-Benzopyran-4-one, 2,3-dihydro-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-, (2R-trans)-; KD8QND6427; CHEBI:28429; (2R,3R)-2,3-dihydro-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one; (2R,3R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydrochromen-4-one; 4H-1-Benzopyran-4-one, 2,3-dihydro-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-, (2R,3R)-; (2R,3R)-3,5,7,3',4',5'-hexahydroxyflavanone; Ampelopsin (flavanol); (2R,3R)-3,3',4',5,5',7-hexahydroxy-2,3-dihydroflavanonol; dihydro-myricetin; (2R,3R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-4H-chromen-4-one; Flavanone, 3,3',4',5,5',7-hexahydroxy-; 3,3',4',5,5',7-Hexahydroxy-2,3-dihydroflavanonol; (2r,3r)-dihydromyricetin; Dihydromyricetin (diH-Myr); (2R-trans)-2,3-Dihydro-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one; Dihydromyricetin (Ampeloptin); Dihydromyricetin - Ampeloptin; SCHEMBL723736; CHEMBL3348861; DTXSID50181676; BDBM212434; HMS3884B17; Dihydromyricetin, >=98% (HPLC); HY-N0112; Dihydromyricetin, analytical standard; CD0156; MFCD00189451; s2399; AKOS022168215; ZINC100037633; AC-8004; CCG-267699; CS-3809; NCGC00346604-01; AS-71702; AB0020621; SW219328-1; V1568; C02906; M-1204; Q422305; 2B89FBAC-4DD1-44C9-BE2A-9D0C173BDFD8; Q-100341; (2R,3R)-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
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Species Origin Ampelopsis cordata ...     Click to Show/Hide
Ampelopsis cordata
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Vitales
Family: Vitaceae
Genus: Ampelopsis
Species: Ampelopsis cordata
Disease Brain cancer [ICD-11: 2A00] Investigative [1]
Structure
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2D MOL

3D MOL

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Formula
C15H12O8
PubChem CID
161557
Canonical SMILES
C1=C(C=C(C(=C1O)O)O)C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O
InChI
1S/C15H12O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,14-20,22H/t14-,15+/m0/s1
InChIKey
KJXSIXMJHKAJOD-LSDHHAIUSA-N
CAS Number
CAS 27200-12-0
ChEBI ID
CHEBI:28429
Herb ID
HBIN015890
SymMap ID
SMIT00329
TCMSP ID
MOL013374
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Resistance can be Reversed by This NP
          Erlotinib      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 [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression CYBB  Molecule Info 
Pathway MAP
                    In-vitro Model NCI-H1975 CVCL_1511 Lung adenocarcinoma Homo sapiens
NCI-H1650 CVCL_1483 Lung adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 The combination of erlotinib and ampelopsin induces cell death via the Nox2-ROS-Bim pathway, and ampelopsin could be used as a novel anti-cancer agent combined with EGFR-TKI to overcome resistance to erlotinib in EGFR-mutant NSCLC.
Target and Pathway
Target(s) Collagen alpha-2 XI (COL11A2)  Molecule Info  [3]
Sphingosine kinase 1 (SPHK1)  Molecule Info  [3]
BioCyc Sphingosine and sphingosine-1-phosphate metabolism Click to Show/Hide
KEGG Pathway Sphingolipid metabolism Click to Show/Hide
2 Metabolic pathways
3 Calcium signaling pathway
4 Sphingolipid signaling pathway
5 VEGF signaling pathway
6 Fc gamma R-mediated phagocytosis
7 Tuberculosis
NetPath Pathway TCR Signaling Pathway Click to Show/Hide
2 TNFalpha Signaling Pathway
Panther Pathway Angiogenesis Click to Show/Hide
2 VEGF signaling pathway
Pathway Interaction Database Fc-epsilon receptor I signaling in mast cells Click to Show/Hide
2 Beta3 integrin cell surface interactions
3 S1P1 pathway
4 Sphingosine 1-phosphate (S1P) pathway
5 PDGFR-beta signaling pathway
Reactome Sphingolipid de novo biosynthesis Click to Show/Hide
2 VEGFR2 mediated cell proliferation
WikiPathways Signal Transduction of S1P Receptor Click to Show/Hide
2 Protein folding
3 Sphingolipid Metabolism
References
Reference 1 Ampelopsin inhibits human glioma through inducing apoptosis and autophagy dependent on ROS generation and JNK pathway. Biomed Pharmacother. 2019 Aug;116:108524.
Reference 2 Combination treatment with erlotinib and ampelopsin overcomes erlotinib resistance in NSCLC cells via the Nox2-ROS-Bim pathway. Lung Cancer. 2017 Apr;106:115-124.
Reference 3 Resveratrol dimers are novel sphingosine kinase 1 inhibitors and affect sphingosine kinase 1 expression and cancer cell growth and survival. Br J Pharmacol. 2012 Jul;166(5):1605-16.
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