Botanical Name Plant's Common Name Plant Family   

   MMP-AC0022 : Naringenin

 
Compound Name  :

Naringenin
 
  Compound Class  : Flavonoid  
  Synonyms  : naringenin; 67604-48-2; Naringenine; 4',5,7-Trihydroxyflavanone; (+/-)-Naringenin; 480-41-1; naringetol; salipurpol; (-)-Naringenin; NARIGENIN; Salipurol; 93602-28-9; 5,7,4'-Trihydroxyflavanone; NSC 34875; CHEMBL32571; MLS000028739; MLS000738094; CHEBI:50202;

 
  Compound Extracted from  : Naringenin is extracted / reported from 10 Plant(s) of Melghat Flora as below


 
 
Molecular Formula  :

C15H12O5
 
  Molecular Weight  : 272.256  
  InChi Key  :  
  IUPAC  :  
  InChi  :  
  Hydrogen Bond Donor count  : 3  
  Hydrogen Bond Acceptor count  : 5  
  Rotational Bond count  : 1  
  TPSA  : 87  
  LogP Value  :

2.4

 
 
Lipinski Rule of Five  :

Yes
 
  Ghose Filter  : Yes  
  Veber Filter  : Yes  
  Muegge Filter  :

Yes

 
 
PubChem CID  :

932
 
  Drugbank ID  : DB03467  
  Super Natural  : 000480411  
  CTD  : C005273  
  HIT  : C0352  
  NCI-60 GI50 data  :

-

 
 
Reference(s)  :

https://www.ncbi.nlm.nih.gov/pubmed/25455453


 

Compound_ID Cell Lines Cancer Type IC50 Value EC50 Value ED50 Value GI50 Value References
MMP-AC0022 MCF-7 Breast - 240±23 µM - - 15744083
MMP-AC0022 MDA-MB-231 Breast - 267±59 µM - - 15744083
MMP-AC0022 HeLa Cervix - 243±22 µM - - 15744083
MMP-AC0022 Hela-TG Cervix - 223±47 µM - - 15744083
MMP-AC0022 Caco-2 Colon - 557±48 µM - - 15744083
MMP-AC0022 CCRF-HSB-2 Haematopoietic and Lymphoid tissue >40 µM - - - 10380632
MMP-AC0022 HL-60 Haematopoietic and Lymphoid tissue - 153±15 µM - - 15744083
MMP-AC0022 Jurkat Haematopoietic and Lymphoid tissue - 206±50 µM - - 15744083
MMP-AC0022 NALM-6 Haematopoietic and Lymphoid tissue - 157±16 µM - - 15744083
MMP-AC0022 U-937 Haematopoietic and Lymphoid tissue - 190±50 µM - - 15744083
MMP-AC0022 Hep G2 Liver - 340±92 µM - - 15744083
MMP-AC0022 Hep-3B Liver - 230±51 µM - - 15744083
MMP-AC0022 HUH7 Liver - 350±68 µM - - 15744083
MMP-AC0022 A549 Lung >40 µM - - - 10380632
MMP-AC0022 PK-1 Pancreas - 237±43 µM - - 15744083
MMP-AC0022 B16 melanoma 4A5 Skin >40 µM - - - 10380632
MMP-AC0022 KATO-III Stomach - 407±58 µM - - 15744083
MMP-AC0022 MKN-7 Stomach - 320±40 µM - - 15744083
MMP-AC0022 TGBC11TKB Stomach >40 µM - - - 10380632

Compound_ID Target Gene_Name Gene_ID Cancer Cell_lines IC50 Value EC50 Value ED50 Value GI50 Value Remarks References
MMP-AC0022 BAX BCL2-associated X protein 581 Gastric Cancer AGS - - - - Western blot results showed that expression level of Bax was increased in a dose-dependent manner. 22194772
MMP-AC0022 BCL2L1 BCL2-like 1 598 Gastric Cancer AGS - - - - Western blot results showed that expression level of Bcl-xL was decreased in a dose-dependent manner. 22194772
MMP-AC0022 CASP3 caspase 3, apoptosis-related cysteine peptidase 836 Gastric Cancer AGS - - - - Flavonoids caused downregulation of procaspase-3 which consequently increased the activity of caspase-3. 22194772
MMP-AC0022 CCNB1 cyclin B1 891 Gastric Cancer AGS - - - - It reduces the protein level of cyclin B1 in a dose-dependent manner.Decrease of cyclin B1 expression might be a molecular mechanism through which flavonoids induce G2/M arrest. 22194772
MMP-AC0022 CDC25C cell division cycle 25 homolog C (S. pombe) 995 Gastric Cancer AGS - - - - It reduces the protein level of cdc 25c in a dose-dependent manner.Decrease of cdc 25c expression might be a molecular mechanism through which flavonoids induce G2/M arrest. 22194772
MMP-AC0022 CDK1 cyclin-dependent kinase 1 983 Gastric Cancer AGS - - - - It reduces the protein level of cdc 2 in a dose-dependent manner.Decrease of cdc 2 expression might be a molecular mechanism through which flavonoids induce G2/M arrest. 22194772
MMP-AC0022 COX-1 cytochrome c oxidase subunit I 4512 Murine monocyte/macrophage line derived from ascitic tumour induced with Abelson leukaemai virus RAW264.7 164.6 µM - - - It inhibits cyclooxygenase 1 (Cox-1) activity and it is an anti-inflammatory mechanism. Phytochemistry Reviews 1: 369-377, 2002
MMP-AC0022 CYP19A1 cytochrome P450, family 19, subfamily A, polypeptide 1 1588 Breast adenocarcinoma MCF-7 2 µM - - - Naringenin inhibited aromatase activity with IC50 value of about 2µM. 22209285
MMP-AC0022 CYP19A1 cytochrome P450, family 19, subfamily A, polypeptide 1 1588 Adrenocortical Carcinoma H295R 85 µM - - - The first inhibitory effects on aromatase activity in vitro in H295R cells were observed at concentrations above 10 mM for naringenin and above 1 mM for chrysin and apigenin. 15319488
MMP-AC0022 CYPIA1 cytochrome P450, family 1, subfamily A, polypeptide 1 1543 Murine monocyte/macrophage line derived from ascitic tumour induced with Abelson leukaemai virus RAW264.7 0.2 µM - - - Naringenin potently inhibited Cyp1A activity with an IC50 of 0.2 µM. Cyp1A, which is e.g. involved in the activation of carcinogens from grilled meat, as a model phase 1 enzyme, and measured the potential of beer constituents to inhibit its enzymatic activity. Phytochemistry Reviews 1: 369-377, 2002
MMP-AC0022 NOS2 nitric oxide synthase 2, inducible 4843 Murine monocyte/macrophage line derived from ascitic tumour induced with Abelson leukaemai virus RAW264.7 12.9 µM - - - Nitric oxide (NO) synthase (iNOS) and consequently, enhance the generation of NO. Generally, NO is an important signaling molecule, long-term elevated levels of NO, however, have been linked to early steps in carcinogenesis.It cause inhibition of lipopolysaccharide (LPS)-mediated induction of inducible nitric oxide synthase , which is an anti-inflammatory mechanis. Phytochemistry Reviews 1: 369-377, 2002
MMP-AC0022 NQO1 NAD(P)H dehydrogenase, quinone 1 1728 Murine monocyte/macrophage line derived from ascitic tumour induced with Abelson leukaemai virus RAW264.7 >50 µM - - - It induces the QR activity.Induction of phases 2 enzymes contributes to chemopreventive activity. QR is not catalyzing a conjugation reaction, but it is induced co-ordinately with other phase 2 enzymes and contributes to detoxification by reduction of reactive quinones to less reactive hydroquinones. Phytochemistry Reviews 1: 369-377, 2002
MMP-AC0022 PARP1 poly (ADP-ribose) polymerase 1 142 Gastric Cancer AGS - - - - During apoptosis, caspases induce PARP cleavage and inactivation and cleavage of PARP helps cellular disassembly and is a marker of cells undergoing apoptosis. 22194772