Natural Product (NP) Details
| General Information of the NP (ID: NP6465) | |||||
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| Name |
Ampelopsin
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| 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 | |||||
| Disease | Brain cancer [ICD-11: 2A00] | Investigative | [1] | ||
| Structure |
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Click to Download Mol2D MOL |
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| ADMET Property |
Absporption
Caco-2 Permeability
-6.389
MDCK Permeability
-4.958
PAMPA
+++
HIA
- -
Distribution
VDss
-0.325
PPB
92.9%
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
9.865
T1/2
2.101
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 |
C15H12O8
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| PubChem CID | |||||
| Canonical SMILES |
C1=C(C=C(C(=C1O)O)O)C2C(C(=O)C3=C(C=C(C=C3O2)O)O)O
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| 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
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| InChIKey |
KJXSIXMJHKAJOD-LSDHHAIUSA-N
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| CAS Number |
CAS 27200-12-0
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| ChEBI ID | |||||
| Herb ID | |||||
| SymMap ID | |||||
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| Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally | ||||||
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| 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
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| Molecule(s)
Regulation |
Up-regulation | Expression | CYBB | Molecule Info |
Pathway MAP
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| 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 | ||||
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| 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 | |||
