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Botanical Name Plant's Common Name Plant Family   

   MMP-AC0109 : Butein

 
Compound Name  :
Butein		  
  Compound Class  : Flavonoid  
  Synonyms  : butein; 487-52-5; 2',3,4,4'-Tetrahydroxychalcone; 2',4',3,4-Tetrahydroxychalcone; 3,4,2',4'-Tetrahydroxychalcone;

  
  Compound Extracted from  : Butein is extracted / reported from 3 Plant(s) of Melghat Flora as below


 
 
Molecular Formula  :
C15H12O5		  
  Molecular Weight  : 272.25  
  InChi Key  :  
  IUPAC  :  
  InChi  :  
  Hydrogen Bond Donor count  : 4  
  Hydrogen Bond Acceptor count  : 5  
  Rotational Bond count  : 3  
  TPSA  : 98  
  LogP Value  :

 2.8

  
 
Lipinski Rule of Five  :
Yes		  
  Ghose Filter  : Yes  
  Veber Filter  : Yes  
  Muegge Filter  :

 Yes

  
 
PubChem CID  :
5281222		  
  Drugbank ID  : -  
  Super Natural  : 000487525  
  CTD  : C040918  
  HIT  : -  
  NCI-60 GI50 data  :

 -

  
 
Reference(s)  :
https://www.ncbi.nlm.nih.gov/pubmed/23318726

  

Compound_ID Cell Lines Cancer Type IC50 Value EC50 Value ED50 Value GI50 Value References
MMP-AC0109 HL-60 Haematopoietic and Lymphoid tissue 5 µM (cc-50) - - - 16158945
MMP-AC0109 HSG Salivary duct 188 µM (cc-50) - - - 16158945
MMP-AC0109 HSC-2 Head and Neck 26 µM (cc-50) - - - 16158945
MMP-AC0109 HSC-3 Oral 69 µM (cc-50) - - - 16158945
MMP-AC0109 RAW264 Haematopoietic and Lymphoid tissue 8±4 µM - - - 21372424

Compound_ID Target Gene_Name Gene_ID Cancer Cell_lines IC50 Value EC50 Value ED50 Value GI50 Value Remarks References
MMP-AC0109 BAX BCL2-associated X protein 581 Prostate Cancer LNCaP - - - - The deregulation of apoptosis is studied by the expression of Bax and Bcl2. Bax is proapoptotic protein, there was a significant increase in the protein expression of Bax with a dose-dependent on treatment of LNCaP and CWR22Rm1 cells with butein. 22114764
MMP-AC0109 BAX BCL2-associated X protein 581 Prostrate Carcinoma CWR22Rm1 - - - - The deregulation of apoptosis is studied by the expression of Bax and Bcl2. Bax is proapoptotic protein, there was a significant increase in the protein expression of Bax with a dose-dependent on treatment of LNCaP and CWR22Rm1 cells with butein. 22114764
MMP-AC0109 BAX BCL2-associated X protein 581 Human promyelocytic leukemia HL-60 - - - - The treatment of HL-60 cells with butein increased the expression of Bax protein 11393587
MMP-AC0109 BCL2 B-cell CLL/lymphoma 2 596 Prostate Cancer LNCaP - - - - The deregulation of apoptosis is studied by the expression of Bax and Bcl2. Bcl2 is anti-apoptotic, there was a significant decrease in the protein expression of Bcl2 on treatment of LNCaP and CWR22Rm1 cells with butein. 22114764
MMP-AC0109 BCL2 B-cell CLL/lymphoma 2 596 Prostrate Carcinoma CWR22Rm1 - - - - The deregulation of apoptosis is studied by the expression of Bax and Bcl2. Bcl2 is anti-apoptotic, there was a significant decrease in the protein expression of Bcl2 on treatment of LNCaP and CWR22Rm1 cells with butein. 22114764
MMP-AC0109 BCL2 B-cell CLL/lymphoma 2 596 Human promyelocytic leukemia HL-60 - - - - The treatment of HL-60 cells with butein decreased the expression of Bcl-2 protein 11393587
MMP-AC0109 CASP3 caspase 3, apoptosis-related cysteine peptidase 836 Human promyelocytic leukemia HL-60 - - - - The treatment of the cells with butein increased the caspase-3 activity 11393587
MMP-AC0109 CASP3 caspase 3, apoptosis-related cysteine peptidase 836 Prostate Cancer LNCaP - - - - Treatment of LNCaP cells with butein (10-30 µM) caused an increase in the activation of caspases-3, -8, and -9 dose dependently. 22114764
MMP-AC0109 CASP8 caspase 8, apoptosis-related cysteine peptidase 841 Prostate Cancer LNCaP - - - - Treatment of LNCaP cells with butein (10-30 µM) caused an increase in the activation of caspase-8 dose dependently. 22114764
MMP-AC0109 CASP9 caspase 9, apoptosis-related cysteine peptidase 842 Prostate Cancer LNCaP - - - - Treatment of LNCaP cells with butein (10-30 µM) caused an increase in the activation of caspase-9 dose dependently. 22114764
MMP-AC0109 CCND1 cyclin D1 595 Prostate Cancer LNCaP - - - - LNCaP cells with butein (10-30 µM; 48 h) caused a dose-dependent decrease in the protein expression of cyclinsD1 by using immunoblot analysis. Treatment of CWR22Rm1 cells with butein (10-30 µM; 48 h) also caused an inhibition of cyclin D1,suggesting that the effects of butein on prostrate cancer(PCa) cells are not limited for one-cell type. 22114764
MMP-AC0109 CCND1 cyclin D1 595 Prostrate Carcinoma CWR22Rm1 - - - - LNCaP cells with butein (10-30 µM; 48 h) caused a dose-dependent decrease in the protein expression of cyclinsD1 by using immunoblot analysis. Treatment of CWR22Rm1 cells with butein (10-30 µM; 48 h) also caused an inhibition of cyclin D1,suggesting that the effects of butein on prostrate cancer(PCa) cells are not limited for one-cell type. 22114764
MMP-AC0109 CCND2 Cyclin D2 894 Prostate Cancer LNCaP - - - - LNCaP cells with butein (10-30 µM; 48 h) caused a dose-dependent decrease in the protein expression of cyclin D2 by using immunoblot analysis. 22114764
MMP-AC0109 CCNE1 cyclin E1 898 Prostate Cancer LNCaP - - - - LNCaP cells with butein (10-30 µM; 48 h) caused a dose-dependent decrease in the protein expression of cyclin E by using immunoblot analysis. 22114764
MMP-AC0109 CDK2 cyclin-dependent kinase 2 1017 Prostate Cancer LNCaP - - - - LNCaP cells with butein (10-30 µM; 48 h) caused a dose-dependent decrease in the protein expression of cdk2 using immunoblot analysis. Treatment of CWR22Rm1 cells with butein (10-30 µM; 48 h) also caused an inhibition of cdk 2,suggesting that the effects of butein on prostrate cancer(PCa) cells are not limited for one-cell type. 22114764
MMP-AC0109 CDK2 cyclin-dependent kinase 2 1017 Prostrate Carcinoma CWR22Rm1 - - - - LNCaP cells with butein (10-30 µM; 48 h) caused a dose-dependent decrease in the protein expression of cdk2 using immunoblot analysis. Treatment of CWR22Rm1 cells with butein (10-30 µM; 48 h) also caused an inhibition of cdk 2,suggesting that the effects of butein on prostrate cancer(PCa) cells are not limited for one-cell type. 22114764
MMP-AC0109 CDK4 cyclin-dependent kinase 4 1019 Prostate Cancer LNCaP - - - - LNCaP cells with butein (10-30 µM; 48 h) caused a dose-dependent decrease in the protein expression of cdk4 using immunoblot analysis. 22114764
MMP-AC0109 CDK6 cyclin-dependent kinase 6 1021 Prostate Cancer LNCaP - - - - LNCaP cells with butein (10-30 µM; 48 h) caused a dose-dependent decrease in the protein expression of cdk4 using immunoblot analysis. 22114764
MMP-AC0109 CDKN1A cyclin-dependent kinase inhibitor 1A (p21, Cip1) 1026 Prostate Cancer LNCaP - - - - Treatment with butein resulted in an induction of WAF1/p21 even at the lowest concentration of 10 lM with a significant increase at the highest concentration of 30 µM. Treatment of CWR22Rm1 cells with butein (10-30 µM; 48 h) also caused an increase in WAF1/p21, suggesting that the effects of butein on prostrate cancer(PCa) cells are not limited for one-cell type. 22114764
MMP-AC0109 CDKN1B cyclin-dependent kinase inhibitor 1B (p27, Kip1) 1027 Prostate Cancer LNCaP - - - - Treatment with butein resulted in an induction of WAF1/p21 even at the lowest concentration of 10 lM with a significant increase at the highest concentration of 30 µM. Treatment of CWR22Rm1 cells with butein (10-30 µM; 48 h) also caused an increase in WAF1/p21, suggesting that the effects of butein on prostrate cancer(PCa) cells are not limited for one-cell type. 22114764
MMP-AC0109 CHUK conserved helix-loop-helix ubiquitous kinase 1147 Prostate Cancer LNCaP - - - - IKKalpha protein level was measured to evaluate the possible inhibitory mechanism of butein on IkBalpha protein degradation. Immunoblot analysis showed that pretreatment of LNCaP cells with butein inhibited IKKa in a dose-dependent manner. 22114764
MMP-AC0109 GRB2 growth factor receptor-bound protein 2 2885 Liver Carcinoma SK-HEP-1 - - - - Western blotting analysis indicated that butein decreased the levels of GRB2 in SK-HEP-1 cell. 21770460
MMP-AC0109 IL6 interleukin 6 3569 Murine monocyte/macrophage line derived from ascitic tumour induced with Abelson leukaemai virus Raw264 0.9 µM - - - IL-6 production in LPS-stimulated RAW264 cells was found to be suppressed by butein. 21372424
MMP-AC0109 JUN jun proto-oncogene 3725 Liver Carcinoma SK-HEP-1 - - - - Western blotting analysis indicated that butein decreased the levels of MMP-2, -7, and -9, uPA, Ras, Rho A, ROCK1, ERK1/2,JNK1/2, p-p38, and p-c-Jun in SK-HEP-1 cell. 21770460
MMP-AC0109 MAPK1 mitogen-activated protein kinase 1 5594 Liver Carcinoma SK-HEP-1 - - - - Western blotting analysis indicated that butein decreased the levels of p38 in SK-HEP-1 cells. And butein at 62.5 and 125 µM suppressed the p38 activity. 21770460
MMP-AC0109 MAPK8 mitogen-activated protein kinase 8 5599 Liver Carcinoma SK-HEP-1 - - - - Western blotting analysis indicated that butein decreased the levels of p38 in SK-HEP-1 cells. And butein at 62.5 and 125 µM suppressed the p38 activity. 21770460
MMP-AC0109 MMP9 matrix metallopeptidase 9 (gelatinase B, 92kDa gelatinase, 92kDa type IV collagenase) 4318 Liver Carcinoma SK-HEP-1 - - - - The gelatin zymography assay indicated that butein inhibited the activity of matrix metalloproteinases 2 (MMP-2). Gelationlytic activity of MMP-2 in the zymogram was inhibited by butein in a dose-dependent manner. Thus, MMP 2 was down-regulated in butein-treated SK-HEP-1 cells. 21770460
MMP-AC0109 MMP7 matrix metallopeptidase 7 (matrilysin, uterine) 4316 Carcinoma SK-HEP-1 - - - - The gelatin zymography assay indicated that butein inhibited the activity of matrix metalloproteinases 2 (MMP-2). Gelationlytic activity of MMP-2 in the zymogram was inhibited by butein in a dose-dependent manner. Thus, MMP 2 was down-regulated in butein-treated SK-HEP-1 cells. 21770460
MMP-AC0109 MMP-AC0109 nuclear factor of kappa light polypeptide gene enhancer in B-cells 1 4790 Liver Carcinoma SK-HEP-1 - - - - Butein at 50 µM might inhibit theNF-kB activity, which is able to involve cell migration and invasion of SK-HEP-1 cells. 21770460
MMP-AC0109 NFKBIA nuclear factor of kappa light polypeptide gene enhancer in B-cells inhibitor, alpha 4792 Prostate Cancer LNCaP - - - - A significant dose-dependent inhibition in the phosphorylation of IkBalpha protein on treatment of LNCaP cells with butein. 22114764
MMP-AC0109 NOS2 nitric oxide synthase 2, inducible 4843 Murine monocyte/macrophage line derived from ascitic tumour induced with Abelson leukaemai virus Raw264 5±2 µM - - - suppressed the TNF-a production in LPS-stimulated RAW264 cell. 21372424
MMP-AC0109 PARP1 poly (ADP-ribose) polymerase 1 142 Prostate Cancer LNCaP - - - - On treatment of LNCaP cells with butein, they found that there was an increase in the protein expression of the 85 KD fragment of PARP, while there was a decrease in the protein expression of full-size PARP (116 KD) protein. And PARP has several cellular functions including DNA recombination and repair, cellular proliferation, apoptosis in ischemic conditions, and necrotic cell deat. 22114764
MMP-AC0109 PLAU plasminogen activator, urokinase 5328 Liver Carcinoma SK-HEP-1 - - - - Western blotting analysis indicated that butein decreased the level of uPA in SK-HEP-1 cells. 21770460
MMP-AC0109 PTK2 PTK2 protein tyrosine kinase 2 5747 Liver Carcinoma SK-HEP-1 - - - - Western blotting analysis indicated that butein decreased the levels of FAK in SK-HEP-1 cell. 21770460
MMP-AC0109 RHOA ras homolog family member A 387 Liver Carcinoma SK-HEP-1 - - - - Western blotting analysis indicated that butein decreased the levels of Rho A in SK-HEP-1 cells. 21770460
MMP-AC0109 ROCK1 Rho-associated, coiled-coil containing protein kinase 1 6093 Liver Carcinoma SK-HEP-1 - - - - Western blotting analysis indicated that butein decreased the levels of Rho A in SK-HEP-1 cells. 21770460
MMP-AC0109 SOS1 son of sevenless homolog 1 (Drosophila) 6654 Liver Carcinoma SK-HEP-1 - - - - Western blotting analysis indicated that butein decreased the levels of SOS1 in SK-HEP-1 cells. 21770460
MMP-AC0109 VEGFA vascular endothelial growth factor A 7422 Liver Carcinoma SK-HEP-1 - - - - Western blotting analysis indicated that butein decreased the levels of SOS1 in SK-HEP-1 cells. 21770460
MMP-AC0109 TNF tumor necrosis factor 7124 Murine monocyte/macrophage line derived from ascitic tumour induced with Abelson leukaemai virus Raw264 8±4 µM - - - TNF-a suppressive alkaloids also inhibited NO production in RAW264 cell. 21372424