2-Hydroxychalcone (BioDeep_00000405671)

 

Secondary id: BioDeep_00000003657, BioDeep_00000402759, BioDeep_00000865017

natural product PANOMIX_OTCML-2023


代谢物信息卡片


2-Propen-1-one,1-(2-hydroxyphenyl)-3-phenyl-, (2E)-

化学式: C15H12O2 (224.0837)
中文名称: (E)-2′-羟基查耳酮, 2-羟基查尔酮, (E)-2-羟基查耳酮, 2-羟基查酮, 2'-羟基查尔酮
谱图信息: 最多检出来源 Viridiplantae(plant) 10.65%

分子结构信息

SMILES: C1=CC=C(C=C1)C(=O)C=CC2=CC=CC=C2O
InChI: InChI=1S/C15H12O2/c16-14-9-5-4-8-13(14)10-11-15(17)12-6-2-1-3-7-12/h1-11,16H/b11-10+

描述信息

2-hydroxychalcone, a natural flavonoid, is a potent antioxidant, inhibiting lipid peroxidation. 2-Hydroxychalcone induces apoptosis by Bcl-2 downregulation. 2-Hydroxychalcone inhibits the activation of NF-kB[1][2][3].
2-hydroxychalcone, a natural flavonoid, is a potent antioxidant, inhibiting lipid peroxidation. 2-Hydroxychalcone induces apoptosis by Bcl-2 downregulation. 2-Hydroxychalcone inhibits the activation of NF-kB[1][2][3].

同义名列表

5 个代谢物同义名

2-Propen-1-one,1-(2-hydroxyphenyl)-3-phenyl-, (2E)-; 2-Hydroxychalcone; 2-Propen-1-one,3-(2-hydroxyphenyl)-1-phenyl-, (2E)-; 2-Hydroxychalcone; 2'-Hydroxychalcone



数据库引用编号

36 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 10 AIMP2, ANXA5, CAMKK2, CASP9, HPGDS, NFKB1, PIK3C3, PRKX, PTGS2, SOD1
Peripheral membrane protein 2 ANXA5, PTGS2
Endosome membrane 1 ATP6V0A2
Endoplasmic reticulum membrane 2 HMOX1, PTGS2
Cytoplasmic vesicle, autophagosome 1 PIK3C3
Nucleus 9 AIMP2, CAMKK2, CASP9, HMOX1, JUN, JUND, NFKB1, PRKX, SOD1
autophagosome 1 PIK3C3
cytosol 10 AIMP2, ANXA5, CAMKK2, CASP9, HMOX1, HPGDS, NFKB1, PIK3C3, PRKCQ, SOD1
phosphatidylinositol 3-kinase complex, class III 1 PIK3C3
nucleoplasm 8 CAMKK2, HMOX1, HPGDS, JUN, JUND, NFKB1, PRKX, SOD1
RNA polymerase II transcription regulator complex 2 JUN, JUND
Cell membrane 2 SELE, TNF
Cytoplasmic side 1 HMOX1
Multi-pass membrane protein 2 ATP6V0A2, SLC45A2
cell surface 1 TNF
glutamatergic synapse 1 PIK3C3
Golgi membrane 1 ATP6V0A2
lysosomal membrane 1 ATP6V0A2
neuronal cell body 2 SOD1, TNF
sarcolemma 1 ANXA5
Cytoplasm, cytosol 1 AIMP2
acrosomal vesicle 1 ATP6V0A2
endosome 1 PIK3C3
plasma membrane 5 ATP6V0A2, BCHE, PRKCQ, SELE, TNF
Membrane 6 AIMP2, ANXA5, ATP6V0A2, HMOX1, PIK3C3, SLC45A2
caveola 2 PTGS2, SELE
extracellular exosome 2 ANXA5, SOD1
endoplasmic reticulum 2 HMOX1, PTGS2
extracellular space 6 BCHE, CXCL8, HMOX1, SELE, SOD1, TNF
perinuclear region of cytoplasm 3 ATP6V0A2, HMOX1, SELE
mitochondrion 3 CASP9, NFKB1, SOD1
protein-containing complex 3 CASP9, PTGS2, SOD1
intracellular membrane-bounded organelle 2 ATP6V0A2, HPGDS
Microsome membrane 1 PTGS2
Single-pass type I membrane protein 1 SELE
Secreted 2 BCHE, CXCL8
extracellular region 6 ANXA5, BCHE, CXCL8, NFKB1, SOD1, TNF
mitochondrial outer membrane 1 HMOX1
mitochondrial matrix 1 SOD1
transcription regulator complex 3 JUN, JUND, NFKB1
centriolar satellite 1 PRKCQ
external side of plasma membrane 3 ANXA5, SELE, TNF
cytoplasmic vesicle 1 SOD1
axon cytoplasm 1 SOD1
Melanosome membrane 1 SLC45A2
midbody 1 PIK3C3
clathrin-coated pit 1 SELE
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Membrane raft 2 SELE, TNF
focal adhesion 2 ANXA5, ATP6V0A2
GABA-ergic synapse 1 PIK3C3
Peroxisome 2 PIK3C3, SOD1
mitochondrial intermembrane space 1 SOD1
collagen-containing extracellular matrix 1 ANXA5
axoneme 1 PIK3C3
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
dendrite cytoplasm 1 SOD1
Late endosome 1 PIK3C3
Cell projection, neuron projection 1 CAMKK2
Zymogen granule membrane 1 ANXA5
neuron projection 2 CAMKK2, PTGS2
chromatin 3 JUN, JUND, NFKB1
phagocytic cup 1 TNF
phagocytic vesicle membrane 2 ATP6V0A2, PIK3C3
nuclear chromosome 1 JUN
blood microparticle 1 BCHE
phagophore assembly site 1 PIK3C3
phosphatidylinositol 3-kinase complex, class III, type I 1 PIK3C3
phosphatidylinositol 3-kinase complex, class III, type II 1 PIK3C3
euchromatin 1 JUN
secretory granule lumen 1 NFKB1
endoplasmic reticulum lumen 2 BCHE, PTGS2
transcription repressor complex 1 JUND
specific granule lumen 1 NFKB1
immunological synapse 1 PRKCQ
presynaptic endosome 1 PIK3C3
aggresome 1 PRKCQ
Single-pass type IV membrane protein 1 HMOX1
nuclear envelope lumen 1 BCHE
apoptosome 1 CASP9
vesicle membrane 1 ANXA5
proton-transporting V-type ATPase, V0 domain 1 ATP6V0A2
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
proton-transporting V-type ATPase complex 1 ATP6V0A2
vacuolar proton-transporting V-type ATPase complex 1 ATP6V0A2
vacuolar proton-transporting V-type ATPase, V0 domain 1 ATP6V0A2
postsynaptic endosome 1 PIK3C3
transcription factor AP-1 complex 2 JUN, JUND
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
cortical cytoskeleton 1 SELE
Autolysosome 1 PIK3C3
endothelial microparticle 1 ANXA5
[Nuclear factor NF-kappa-B p105 subunit]: Cytoplasm 1 NFKB1
[Nuclear factor NF-kappa-B p50 subunit]: Nucleus 1 NFKB1
I-kappaB/NF-kappaB complex 1 NFKB1
NF-kappaB p50/p65 complex 1 NFKB1
caspase complex 1 CASP9
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Ioanna Kostopoulou, Andromachi Tzani, Nestor-Ioannis Polyzos, Maria-Anna Karadendrou, Eftichia Kritsi, Eleni Pontiki, Thalia Liargkova, Dimitra Hadjipavlou-Litina, Panagiotis Zoumpoulakis, Anastasia Detsi. Exploring the 2'-Hydroxy-Chalcone Framework for the Development of Dual Antioxidant and Soybean Lipoxygenase Inhibitory Agents. Molecules (Basel, Switzerland). 2021 May; 26(9):. doi: 10.3390/molecules26092777. [PMID: 34066803]
  • Haleema Sadia Malik, Aishah Bilal, Rahim Ullah, Maheen Iqbal, Sardraz Khan, Ishtiaq Ahmed, Karsten Krohn, Rahman Shah Zaib Saleem, Hidayat Hussain, Amir Faisal. Natural and Semisynthetic Chalcones as Dual FLT3 and Microtubule Polymerization Inhibitors. Journal of natural products. 2020 10; 83(10):3111-3121. doi: 10.1021/acs.jnatprod.0c00699. [PMID: 32975953]
  • Zhaodi Xie, Xiaoting Luo, Zhuan Zou, Xiao Zhang, Feifei Huang, Ruishan Li, Shijie Liao, Yun Liu. Synthesis and evaluation of hydroxychalcones as multifunctional non-purine xanthine oxidase inhibitors for the treatment of hyperuricemia. Bioorganic & medicinal chemistry letters. 2017 08; 27(15):3602-3606. doi: 10.1016/j.bmcl.2017.01.053. [PMID: 28655421]
  • Neera Raghav, Shweta Garg, Indu Ravish. Conversion of 2'-substituted chalcones in the presence of BSA as evidenced by ¹H NMR studies. International journal of biological macromolecules. 2016 Apr; 85(?):23-8. doi: 10.1016/j.ijbiomac.2015.12.060. [PMID: 26723247]
  • Santosh N Mokale, Manjusha C Nevase, Nikhil S Sakle, Pritam N Dube, Vishakha R Shelke, Swati A Bhavale, Afreen Begum. Synthesis and in-vivo hypolipidemic activity of some novel substituted phenyl isoxazol phenoxy acetic acid derivatives. Bioorganic & medicinal chemistry letters. 2014 May; 24(9):2155-8. doi: 10.1016/j.bmcl.2014.03.030. [PMID: 24703232]
  • Soon Young Shin, Hyeryoung Jung, Seunghyun Ahn, Doseok Hwang, Hyuk Yoon, Jiye Hyun, Yeonjoong Yong, Hi Jae Cho, Dongsoo Koh, Young Han Lee, Yoongho Lim. Polyphenols bearing cinnamaldehyde scaffold showing cell growth inhibitory effects on the cisplatin-resistant A2780/Cis ovarian cancer cells. Bioorganic & medicinal chemistry. 2014 Mar; 22(6):1809-20. doi: 10.1016/j.bmc.2014.01.058. [PMID: 24565968]
  • Lei Ma, Zhengyi Yang, Chenjing Li, Zhiyuan Zhu, Xu Shen, Lihong Hu. Design, synthesis and SAR study of hydroxychalcone inhibitors of human β-secretase (BACE1). Journal of enzyme inhibition and medicinal chemistry. 2011 Oct; 26(5):643-8. doi: 10.3109/14756366.2010.543420. [PMID: 21222511]
  • Mauricio Cabrera, Macarena Simoens, Gabriela Falchi, M Laura Lavaggi, Oscar E Piro, Eduardo E Castellano, Anabel Vidal, Amaia Azqueta, Antonio Monge, Adela López de Ceráin, Gabriel Sagrera, Gustavo Seoane, Hugo Cerecetto, Mercedes González. Synthetic chalcones, flavanones, and flavones as antitumoral agents: biological evaluation and structure-activity relationships. Bioorganic & medicinal chemistry. 2007 May; 15(10):3356-67. doi: 10.1016/j.bmc.2007.03.031. [PMID: 17383189]
  • Hadil Abuarqoub, Roberta Foresti, Colin J Green, Roberto Motterlini. Heme oxygenase-1 mediates the anti-inflammatory actions of 2'-hydroxychalcone in RAW 264.7 murine macrophages. American journal of physiology. Cell physiology. 2006 Apr; 290(4):C1092-9. doi: 10.1152/ajpcell.00380.2005. [PMID: 16291820]
  • Roberta Foresti, Martha Hoque, Diego Monti, Colin J Green, Roberto Motterlini. Differential activation of heme oxygenase-1 by chalcones and rosolic acid in endothelial cells. The Journal of pharmacology and experimental therapeutics. 2005 Feb; 312(2):686-93. doi: 10.1124/jpet.104.074153. [PMID: 15537827]
  • Jan F Stevens, Cristobal L Miranda, Balz Frei, Donald R Buhler. Inhibition of peroxynitrite-mediated LDL oxidation by prenylated flavonoids: the alpha,beta-unsaturated keto functionality of 2'-hydroxychalcones as a novel antioxidant pharmacophore. Chemical research in toxicology. 2003 Oct; 16(10):1277-86. doi: 10.1021/tx020100d. [PMID: 14565769]
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  • S Sogawa, Y Nihro, H Ueda, A Izumi, T Miki, H Matsumoto, T Satoh. 3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors. Journal of medicinal chemistry. 1993 Nov; 36(24):3904-9. doi: 10.1021/jm00076a019. [PMID: 8254620]
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