Natural Product (NP) Details

General Information of the NP (ID: NP8210)
Name
Galangin
Synonyms
Norizalpinin; 3,5,7-Trihydroxyflavone; 3,5,7-Trihydroxy-2-phenyl-4H-chromen-4-one; 3,5,7-triOH-Flavone; UNII-142FWE6ECS; 3,5,7-Trihydroxy-2-phenyl-4-benzopyrone; 4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-phenyl-; EINECS 208-960-4; NSC407229; FLAVONE, 3,5,7-TRIHYDROXY-; NSC 407229; NSC-407229; 4H-Benzopyran-4-one, 3,5,7-trihydroxy-2-phenyl-; BRN 0272179; 142FWE6ECS; 3,5,7-trihydroxy-2-phenylchromen-4-one; CHEBI:5262; CHEMBL309490; VCCRNZQBSJXYJD-UHFFFAOYSA-N; 3,5,7-trihydroxy-2-phenyl-4H-benzopyran-4-one; 548-83-4
    Click to Show/Hide
Species Origin Plantago major ...     Click to Show/Hide
Plantago major
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Plantaginaceae
Genus: Plantago
Species: Plantago major
Alpinia galanga
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Zingiberales
Family: Zingiberaceae
Genus: Alpinia
Species: Alpinia galanga
Disease Brain cancer [ICD-11: 2A00] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -5.353
 
MDCK Permeability
 -4.833
 
PAMPA
 -
 
HIA
 - - -
 
Distribution
VDss
 -0.52
 
PPB
 98.2%
 
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
 4.635
 
T1/2
 1.052
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.
    Click to Show/Hide
    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C15H10O5
PubChem CID
5281616
Canonical SMILES
C1=CC=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O
InChI
1S/C15H10O5/c16-9-6-10(17)12-11(7-9)20-15(14(19)13(12)18)8-4-2-1-3-5-8/h1-7,16-17,19H
InChIKey
VCCRNZQBSJXYJD-UHFFFAOYSA-N
CAS Number
CAS 548-83-4
Herb ID
HBIN027003
ETMC ID
2251
SymMap ID
SMIT04781
TCMSP ID
MOL002563
TTD Drug ID
D0Y7HG
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 BAX  Molecule Info 
Pathway MAP
Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Up-regulation Expression BID  Molecule Info 
Pathway MAP
Down-regulation Expression RELA  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation STAT3  Molecule Info 
Pathway MAP
                    In-vitro Model A-549 CVCL_0023 Lung adenocarcinoma Homo sapiens
                    In-vivo Model A549/DDP cells were harvested, 5 * 106 cells were in jected subcutaneously into the right oxter of mice.
                    Experimental
                    Result(s)		 Galangin (GG) combined with cisplatin (DDP) to suppress human lung cancer by inhibition of STAT3-regulated NF-KappaB and Bcl-2/Bax signaling pathways.
          TNF-related apoptosis inducing ligand      Lung 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 [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Down-regulation Expression CFLAR  Molecule Info 
Pathway MAP
Down-regulation Expression MCL1  Molecule Info 
Pathway MAP
Down-regulation Expression p105  Molecule Info 
Pathway MAP
                    In-vitro Model Caki-1 CVCL_0234 Clear cell renal cell carcinoma Homo sapiens
ACHN CVCL_1067 Papillary renal cell carcinoma Homo sapiens
A-498 CVCL_1056 Renal cell carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Galangin sensitizes TRAIL-induced apoptosis through down-regulation of anti-apoptotic proteins in renal carcinoma Caki cells.
          Imatinib      Mantle cell lymphoma     Click to Show/Hide the Molecular Data of This Drug
                 Augmenting Drug Sensitivity     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
                    Molecule(s)
                    Regulation		 Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
                    In-vitro Model K-562 CVCL_0004 Chronic myelogenous leukemia Homo sapiens
KCL-22 CVCL_2091 Chronic myelogenous leukemia Homo sapiens
                    Experimental
                    Result(s)		 Galangin caused a decrease in Bcl-2 levels and markedly increased the apoptotic activity of imatinib both in sensitive or imatinib-resistant Bcr-Abl+ cell lines.
Target and Pathway
Target(s) Adenosine A2a receptor (ADORA2A)  Molecule Info  [5]
Adenosine A3 receptor (ADORA3)  Molecule Info  [6]
Cytochrome P450 1B1 (CYP1B1)  Molecule Info  [7]
BioCyc Superpathway of tryptophan utilization Click to Show/Hide
2 Superpathway of melatonin degradation
3 Melatonin degradation I
KEGG Pathway Rap1 signaling pathway Click to Show/Hide
2 Calcium signaling pathway
3 cAMP signaling pathway
4 Neuroactive ligand-receptor interaction
5 Vascular smooth muscle contraction
6 Parkinson's disease
7 Alcoholism
8 Steroid hormone biosynthesis
9 Tryptophan metabolism
10 Metabolism of xenobiotics by cytochrome P450
11 Ovarian steroidogenesis
12 Chemical carcinogenesis
13 MicroRNAs in cancer
NetPath Pathway TSH Signaling Pathway Click to Show/Hide
2 IL4 Signaling Pathway
3 TGF_beta_Receptor Signaling Pathway
Pathwhiz Pathway Intracellular Signalling Through Adenosine Receptor A2a and Adenosine Click to Show/Hide
Pathway Interaction Database HIF-2-alpha transcription factor network Click to Show/Hide
Reactome NGF-independant TRKA activation Click to Show/Hide
2 Adenosine P1 receptors
3 G alpha (s) signalling events
4 Surfactant metabolism
5 G alpha (i) signalling events
6 Endogenous sterols
WikiPathways Nucleotide GPCRs Click to Show/Hide
2 Monoamine Transport
3 GPCRs, Class A Rhodopsin-like
4 NGF signalling via TRKA from the plasma membrane
5 GPCR ligand binding
6 GPCR downstream signaling
7 GPCRs, Other
8 Metapathway biotransformation
9 Estrogen metabolism
10 Benzo(a)pyrene metabolism
11 Tamoxifen metabolism
12 Tryptophan metabolism
13 Oxidation by Cytochrome P450
14 Nuclear Receptors Meta-Pathway
15 Estrogen Receptor Pathway
16 Sulindac Metabolic Pathway
17 Arylhydrocarbon receptor (AhR) signaling pathway
18 miR-targeted genes in muscle cell - TarBase
19 miR-targeted genes in lymphocytes - TarBase
20 miR-targeted genes in epithelium - TarBase
21 miR-targeted genes in adipocytes - TarBase
22 Phase 1 - Functionalization of compounds
References
Reference 1 The Natural Flavonoid Galangin Elicits Apoptosis, Pyroptosis, and Autophagy in Glioblastoma. Front Oncol. 2019 Sep 27;9:942.
Reference 2 Galangin (GG) combined with cisplatin (DDP) to suppress human lung cancer by inhibition of STAT3-regulated NF-KappaB and Bcl-2/Bax signaling pathways. Biomed Pharmacother. 2018 Jan;97:213-224.
Reference 3 Galangin sensitizes TRAIL-induced apoptosis through down-regulation of anti-apoptotic proteins in renal carcinoma Caki cells. Sci Rep. 2016 Jan 4;6:18642.
Reference 4 Galangin increases the cytotoxic activity of imatinib mesylate in imatinib-sensitive and imatinib-resistant Bcr-Abl expressing leukemia cells. Cancer Lett. 2008 Jul 8;265(2):289-97.
Reference 5 Mutagenesis reveals structure-activity parallels between human A2A adenosine receptors and biogenic amine G protein-coupled receptors. J Med Chem. 1997 Aug 1;40(16):2588-95.
Reference 6 Interactions of flavonoids and other phytochemicals with adenosine receptors. J Med Chem. 1996 Feb 2;39(3):781-8.
Reference 7 Selective inhibition of methoxyflavonoids on human CYP1B1 activity. Bioorg Med Chem. 2010 Sep 1;18(17):6310-5.
 Download Picture         KEGG Link      
 Download Picture         KEGG Link      
 Download Picture         KEGG Link      
 Download Picture         KEGG Link      
 Download Picture         KEGG Link      
 Download Picture         KEGG Link      
 Download Picture         KEGG Link      
 Download Picture         KEGG Link