ononin (BioDeep_00000270227)

Main id: BioDeep_00000003338

 

natural product PANOMIX_OTCML-2023


代谢物信息卡片


3-(4-methoxyphenyl)-7-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]-4-chromenone

化学式: C22H22O9 (430.1264)
中文名称: 芒柄花苷
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: c(c1)c(ccc1C(C(=O)4)=COc(c42)cc(O[C@@H]([C@@H](O)3)OC(CO)[C@H](O)[C@@H]3O)cc2)OC
InChI: InChI=1S/C22H22O9/c1-28-12-4-2-11(3-5-12)15-10-29-16-8-13(6-7-14(16)18(15)24)30-22-21(27)20(26)19(25)17(9-23)31-22/h2-8,10,17,19-23,25-27H,9H2,1H3

描述信息

Origin: Plant; Formula(Parent): C22H22O9; Bottle Name:Ononin; PRIME Parent Name:Formononetin-7-O-glucoside; PRIME in-house No.:S0305, Pyrans
Annotation level-1
Ononin is an isoflavone that inhibits the growth of Pluchea lanceolata in soil.
Ononin is an isoflavone that inhibits the growth of Pluchea lanceolata in soil.

同义名列表

27 个代谢物同义名

3-(4-methoxyphenyl)-7-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]-4-chromenone; 3-(4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one; 3-(4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-chromen-4-one; 3-(4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl]oxy-chromone; 3-(4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one; 4H-1-Benzopyran-4-one, 7-(beta-D-glucopyranosyloxy)-3-(4-methoxyphenyl)-; 3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl beta-D-glucopyranoside; Formononetin-7-O-beta-D-glucopyranoside; Formononetin 7-O-glucoside; Formononetin-7-glucoside; Formononetin glucoside; MEGxp0_000395; STOCK1N-14986; ACon1_000463; ZINC01081322; 75375_FLUKA; CHEBI:7775; 486-62-4; ononin; C10509; Fmnn-7-Glc; FORMONONETIN 7-O-beta-D-GLUCOSIDE; formononetin-7-O-glucoside; 7- (beta-D-Glucopyranosyloxy) -3- (4-methoxyphenyl) -4H-1-benzopyran-4-one; Ononoside; Formononetin 7-O-β-D-glucopyranoside; Ononin



数据库引用编号

37 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

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)

276 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 16 AIMP2, BCL2, BDNF, CASP3, EGFR, HIF1A, MAPK3, MAPK8, MTOR, MYD88, NLRP3, PIK3CA, PTGS2, RELA, STAT3, VEGFA
Peripheral membrane protein 2 MTOR, PTGS2
Endosome membrane 2 EGFR, MYD88
Endoplasmic reticulum membrane 4 BCL2, EGFR, MTOR, PTGS2
Nucleus 13 AIMP2, BCL2, CASP3, EGFR, HIF1A, MAPK3, MAPK8, MTOR, MYD88, NLRP3, RELA, STAT3, VEGFA
cytosol 12 AIMP2, BCL2, CASP3, HIF1A, MAPK3, MAPK8, MTOR, MYD88, NLRP3, PIK3CA, RELA, STAT3
dendrite 2 BDNF, MTOR
nuclear body 1 HIF1A
phagocytic vesicle 1 MTOR
nucleoplasm 7 CASP3, HIF1A, MAPK3, MAPK8, MTOR, RELA, STAT3
RNA polymerase II transcription regulator complex 2 HIF1A, STAT3
Cell membrane 2 EGFR, TNF
Cytoplasmic side 1 MTOR
lamellipodium 1 PIK3CA
ruffle membrane 1 EGFR
Early endosome membrane 1 EGFR
Golgi apparatus membrane 2 MTOR, NLRP3
Synapse 1 MAPK8
cell junction 1 EGFR
cell surface 4 EGFR, MYD88, TNF, VEGFA
glutamatergic synapse 4 CASP3, EGFR, MAPK3, RELA
Golgi apparatus 2 MAPK3, VEGFA
Golgi membrane 4 EGFR, INS, MTOR, NLRP3
lysosomal membrane 1 MTOR
neuronal cell body 2 CASP3, TNF
synaptic vesicle 1 BDNF
Cytoplasm, cytosol 2 AIMP2, NLRP3
Lysosome 1 MTOR
endosome 1 EGFR
plasma membrane 6 EGFR, MAPK3, MYD88, PIK3CA, STAT3, TNF
Membrane 7 AIMP2, BCL2, BDNF, EGFR, MTOR, NLRP3, VEGFA
apical plasma membrane 1 EGFR
axon 2 BDNF, MAPK8
basolateral plasma membrane 1 EGFR
caveola 2 MAPK3, PTGS2
extracellular exosome 1 MMP9
Lysosome membrane 1 MTOR
endoplasmic reticulum 4 BCL2, NLRP3, PTGS2, VEGFA
extracellular space 7 BDNF, EGFR, IL6, INS, MMP9, TNF, VEGFA
perinuclear region of cytoplasm 3 BDNF, EGFR, PIK3CA
adherens junction 1 VEGFA
intercalated disc 1 PIK3CA
mitochondrion 3 BCL2, MAPK3, NLRP3
protein-containing complex 5 BCL2, EGFR, HIF1A, MYD88, PTGS2
Microsome membrane 2 MTOR, PTGS2
postsynaptic density 1 CASP3
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 1 EGFR
Secreted 5 BDNF, IL6, INS, NLRP3, VEGFA
extracellular region 7 BDNF, IL6, INS, MMP9, NLRP3, TNF, VEGFA
Mitochondrion outer membrane 2 BCL2, MTOR
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 2 BCL2, MTOR
transcription regulator complex 2 RELA, STAT3
motile cilium 1 HIF1A
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 2 BCL2, EGFR
external side of plasma membrane 1 TNF
Secreted, extracellular space, extracellular matrix 2 MMP9, VEGFA
axon cytoplasm 1 HIF1A
Early endosome 1 MAPK3
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Membrane raft 2 EGFR, TNF
pore complex 1 BCL2
Cell junction, focal adhesion 1 MAPK3
focal adhesion 2 EGFR, MAPK3
extracellular matrix 1 VEGFA
intracellular vesicle 1 EGFR
Nucleus, PML body 1 MTOR
PML body 1 MTOR
collagen-containing extracellular matrix 1 MMP9
secretory granule 1 VEGFA
nuclear speck 1 HIF1A
Cytoplasm, cytoskeleton, microtubule organizing center 1 NLRP3
Inflammasome 1 NLRP3
interphase microtubule organizing center 1 NLRP3
NLRP3 inflammasome complex 1 NLRP3
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Late endosome 1 MAPK3
receptor complex 1 EGFR
neuron projection 1 PTGS2
chromatin 3 HIF1A, RELA, STAT3
phagocytic cup 1 TNF
cytoskeleton 1 MAPK3
nuclear envelope 2 MAPK3, MTOR
Endomembrane system 2 MTOR, NLRP3
endosome lumen 1 INS
Membrane, caveola 1 MAPK3
microtubule organizing center 1 NLRP3
Nucleus speckle 1 HIF1A
euchromatin 1 HIF1A
myelin sheath 1 BCL2
pseudopodium 1 MAPK3
basal plasma membrane 1 EGFR
synaptic membrane 1 EGFR
ficolin-1-rich granule lumen 1 MMP9
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 5 BDNF, IL6, INS, MAPK3, PTGS2
platelet alpha granule lumen 1 VEGFA
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
tertiary granule lumen 1 MMP9
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
clathrin-coated endocytic vesicle membrane 1 EGFR
extrinsic component of cytoplasmic side of plasma membrane 1 MYD88
basal dendrite 1 MAPK8
death-inducing signaling complex 1 CASP3
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
Cytoplasmic vesicle, phagosome 1 MTOR
extrinsic component of plasma membrane 1 MYD88
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
interleukin-6 receptor complex 1 IL6
BAD-BCL-2 complex 1 BCL2
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
NF-kappaB p50/p65 complex 1 RELA
NF-kappaB complex 1 RELA
[Neurotrophic factor BDNF precursor form]: Secreted 1 BDNF
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Yi-Ming Zhang, Zhi-Ming Miao, Ya-Ping Chen, Zhang-Bo Song, Yang-Yang Li, Zhi-Wei Liu, Gu-Cheng Zhou, Jing Li, Liang-Liang Shi, Yan Chen, Shang-Zu Zhang, Xiaohui Xu, Jin-Peng He, Ju-Fang Wang, Li-Ying Zhang, Yong-Qi Liu. Ononin promotes radiosensitivity in lung cancer by inhibiting HIF-1α/VEGF pathway. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2023 Dec; 125(?):155290. doi: 10.1016/j.phymed.2023.155290. [PMID: 38308918]
  • Yu-Zhu Yang, Tao Wang, Qi-Lei Chen, Hu-Biao Chen, Qian-Song He, Ya-Zhou Zhang. Identification of the Metabolites of Both Formononetin in Rat Hepatic S9 and Ononin in Rat Urine Samples and Preliminary Network Pharmacology Evaluation of Their Main Metabolites. Molecules (Basel, Switzerland). 2023 Nov; 28(21):. doi: 10.3390/molecules28217451. [PMID: 37959870]
  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Liangliang Du, Douyun Zeng, Xian Hu, Xi Ren, Dazhi He. Ononin Relieves the Thyroid Cancer Progression through Targeting the Caspase 3 and CD274 Expression Levels. Biological & pharmaceutical bulletin. 2023; 46(8):1041-1048. doi: 10.1248/bpb.b22-00796. [PMID: 37532555]
  • Wan Xu, Feiye Zhou, Qin Zhu, Mengyao Bai, Tiancheng Luo, Libin Zhou, Ruyuan Deng. Calycosin-7-O-β-D-glucoside attenuates palmitate-induced lipid accumulation in hepatocytes through AMPK activation. European journal of pharmacology. 2022 Jun; 925(?):174988. doi: 10.1016/j.ejphar.2022.174988. [PMID: 35490724]
  • Jiao Guan, Liming Wang, Yuan Ji, Tianyi Zhang, Ye Sang, Sheng Chang, Bo Feng, Heyun Zhu. UHPLC-MS/MS Method for Quantifying Fangchinoline, Tetrandrine and Calycosin-7-O-β-D-Glucoside of Fangji Huangqi Decoction in Rat Plasma and Its Application to a Pharmacokinetic Study. Journal of chromatographic science. 2022 Jun; 60(5):458-464. doi: 10.1093/chromsci/bmab116. [PMID: 34734235]
  • Zhen Yang, Xiaoping Tan, Zhiqiang Zhang, Jing Han, Shenye Qu, Tianqiang Liu, Gaoxue Wang. Ononin: A candidate anti-parasitic drug isolated from Spatholobi caulis against infections of Dactylogyrus intermedius (Monogenea). Parasitology international. 2022 Jun; 88(?):102535. doi: 10.1016/j.parint.2021.102535. [PMID: 34995771]
  • Saveta G Mladenova, Martina S Savova, Andrey S Marchev, Claudio Ferrante, Giustino Orlando, Martin Wabitsch, Milen I Georgiev. Anti-adipogenic activity of maackiain and ononin is mediated via inhibition of PPARγ in human adipocytes. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2022 May; 149(?):112908. doi: 10.1016/j.biopha.2022.112908. [PMID: 35367764]
  • Fang Xu, Liang-Jun Zhao, Ting Liao, Zhao-Cong Li, Lei-Lei Wang, Pan-Yu Lin, Rui Jiang, Qing-Jun Wei. Ononin ameliorates inflammation and cartilage degradation in rat chondrocytes with IL-1β-induced osteoarthritis by downregulating the MAPK and NF-κB pathways. BMC complementary medicine and therapies. 2022 Jan; 22(1):25. doi: 10.1186/s12906-022-03504-5. [PMID: 35086536]
  • Kyung-Ran Park, Ji Eun Park, Bomi Kim, Il Keun Kwon, Jin Tae Hong, Hyung-Mun Yun. Calycosin-7-O-β-Glucoside Isolated from Astragalus membranaceus Promotes Osteogenesis and Mineralization in Human Mesenchymal Stem Cells. International journal of molecular sciences. 2021 Oct; 22(21):. doi: 10.3390/ijms222111362. [PMID: 34768792]
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  • Liyu Luo, Junyi Zhou, Haiyu Zhao, Miaoxuan Fan, Wenyuan Gao. The anti-inflammatory effects of formononetin and ononin on lipopolysaccharide-induced zebrafish models based on lipidomics and targeted transcriptomics. Metabolomics : Official journal of the Metabolomic Society. 2019 11; 15(12):153. doi: 10.1007/s11306-019-1614-2. [PMID: 31768751]
  • Yunru Yu, Zhenhao Li, Rui Guo, Jing Qian, Han Zhang, Junhua Zhang, Xiaoping Zhao, Shufang Wang, Yi Wang. Ononin, sec-O-β-d-glucosylhamaudol and astragaloside I: antiviral lead compounds identified via high throughput screening and biological validation from traditional Chinese medicine Zhongjing formulary. Pharmacological research. 2019 07; 145(?):104248. doi: 10.1016/j.phrs.2019.04.032. [PMID: 31082475]
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  • Xiao-ya Liu, Ji-ping Li, Xin-yue Chen, Ya-li Chen, Yan Hong, Shi-lan Feng. [Determination of eight active components in Radix Hedysari by HPLC and its cluster analysis]. Yao xue xue bao = Acta pharmaceutica Sinica. 2016 05; 51(5):786-91. doi: . [PMID: 29878726]
  • Jian-Qing Ruan, Shang Li, Ya-Ping Li, Wen-Jin Wu, Simon Ming-Yuen Lee, Ru Yan. The Presystemic Interplay between Gut Microbiota and Orally Administered Calycosin-7-O-β-D-Glucoside. Drug metabolism and disposition: the biological fate of chemicals. 2015 Oct; 43(10):1601-11. doi: 10.1124/dmd.115.065094. [PMID: 26101224]
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  • Yue-Hua Jiang, Wei Sun, Wei Li, Hong-Zhen Hu, Le Zhou, Hui-Hui Jiang, Jing-Xin Xu. Calycosin-7-O-β-D-glucoside promotes oxidative stress-induced cytoskeleton reorganization through integrin-linked kinase signaling pathway in vascular endothelial cells. BMC complementary and alternative medicine. 2015 Sep; 15(?):315. doi: 10.1186/s12906-015-0839-5. [PMID: 26346982]
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  • Bingrui Liu, Kenneth T Kongstad, Sun Qinglei, Nils T Nyberg, Anna K Jäger, Dan Staerk. Dual high-resolution α-glucosidase and radical scavenging profiling combined with HPLC-HRMS-SPE-NMR for identification of minor and major constituents directly from the crude extract of Pueraria lobata. Journal of natural products. 2015 Feb; 78(2):294-300. doi: 10.1021/np5009416. [PMID: 25679337]
  • Rui Zhang, Shouyu Wang, Ming Lu, Zhen Zhang, Xiliang Tian, Decheng Lv. Simultaneous determination and pharmacokinetic study of three isoflavones from Trifolium pratense extract in rat plasma by LC-MS/MS. Biomedical chromatography : BMC. 2015 Feb; 29(2):210-9. doi: 10.1002/bmc.3261. [PMID: 24898405]
  • Xiao-Li Zhao, Ling Liu, Liu-Qing Di, Jun-Song Li, An Kang. [Studies on effects of calycosin-7-O-β-D-glucoside on prim-O-glucosylcimifugin and cimifugin in vivo pharmacokinetics]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2014 Dec; 39(23):4669-74. doi: . [PMID: 25911821]
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