Yangonin (BioDeep_00000000418)

   

human metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


5-Hydroxy-3-methoxy-7-(p-methoxyphenyl)-2,4,6-heptatrienoic acid .gamma.-lactone

化学式: C15H14O4 (258.0892)
中文名称: 甲氧醉椒素, 麻醉椒素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 57.14%

分子结构信息

SMILES: COC1=CC=C(C=C1)C=CC2=CC(=CC(=O)O2)OC
InChI: InChI=1S/C15H14O4/c1-17-12-6-3-11(4-7-12)5-8-13-9-14(18-2)10-15(16)19-13/h3-10H,1-2H3/b8-5+

描述信息

Yangonin is a member of 2-pyranones and an aromatic ether.
Yangonin is a natural product found in Piper methysticum, Ranunculus silerifolius, and Piper majusculum with data available.
See also: Piper methysticum root (part of).
Yangonin is found in beverages. Yangonin is found in kava root (Piper methysticum). FDA advises against use of kava in food due to potential risk of severe liver damage (2002).
Found in kava root (Piper methysticum). FDA advises against use of kava in food due to potential risk of severe liver damage (2002)
Yangonin exhibits affinity for the human recombinant cannabinoid CB1 receptor with an IC50 and a Ki of 1.79 μM and 0.72 μM, respectively.
Yangonin exhibits affinity for the human recombinant cannabinoid CB1 receptor with an IC50 and a Ki of 1.79 μM and 0.72 μM, respectively.

同义名列表

31 个代谢物同义名

5-Hydroxy-3-methoxy-7-(p-methoxyphenyl)-2,4,6-heptatrienoic acid .gamma.-lactone; 5-Hydroxy-3-methoxy-7-(p-methoxyphenyl)-2,4,6-heptatrienoic acid gamma-lactone; 2H-Pyran-2-one, 4-methoxy-6-(2-(4-methoxyphenyl)ethenyl)-, (E)-; 2H-Pyran-2-one, 4-methoxy-6-[2-(4-methoxyphenyl)ethenyl]-, (E)-; 2H-Pyran-2-one, 4-methoxy-6-[(1E)-2-(4-methoxyphenyl)ethenyl]-; 2H-PYRAN-2-ONE, 4-METHOXY-6-((1E)-2-(4-METHOXYPHENYL)ETHENYL)-; 4-Methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one #; 4-Methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one, 9CI; 4-Methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one; 4-methoxy-6-[(E)-2-(4-methoxyphenyl)vinyl]-2H-pyran-2-one; 4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]pyran-2-one; (E)-4-Methoxy-6-[2-(4-Methoxyphenyl)Ethenyl]Pyran-2-one; 4-Methoxy-6-[2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one; 4-METHOXY-6-((E)-2-(4-METHOXYPHENYL)ETHENYL)PYRAN-2-ONE; 4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-2-pyranone; 4-methoxy-6-[2-(4-methoxyphenyl)ethenyl]pyran-2-one; 4-Methoxy-6-(.beta.-(p-anisyl)vinyl)-.alpha.-pyrone; (E)-4-Methoxy-6-(4-methoxystyryl)-2H-pyran-2-one; 4-Methoxy-6-(beta-(p-anisyl)vinyl)-alpha-pyrone; 2H-PYRAN-2-ONE, 4-METHOXY-6-(p-METHOXYSTYRYL)-; 4-Methoxy-6-(p-methoxystyryl)-2H-pyran-2-one; 4-Methoxy-6-(4-methoxystyryl)-a-pyrone; Yangonin, analytical standard; XLHIYUYCSMZCCC-VMPITWQZSA-N; YANGONIN [MI]; Methoxyxerin; Tox21_202547; Yangonin; Demethoxyyangonin;5,6-Dehydrokavain; Yangonin; Yangonin



数据库引用编号

23 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)

47 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 6 ATG5, MAPK3, MTOR, RPS6, SULT2A1, TNFSF11
Peripheral membrane protein 2 ATG5, MTOR
Endoplasmic reticulum membrane 3 CYP7A1, CYP8B1, MTOR
Nucleus 6 FOS, HMGA1, MAPK3, MTOR, NR1H4, RPS6
autophagosome 1 ATG5
cytosol 9 ACACA, ACP5, ATG5, FOS, HMGA1, MAPK3, MTOR, RPS6, SULT2A1
dendrite 2 MTOR, RPS6
phagocytic vesicle 1 MTOR
nucleoplasm 6 FOS, HMGA1, MAPK3, MTOR, NR1H4, RPS6
RNA polymerase II transcription regulator complex 3 FOS, HMGA1, NR1H4
Cell membrane 3 SLC10A1, TNF, TNFSF11
Cytoplasmic side 1 MTOR
Multi-pass membrane protein 1 SLC10A1
Golgi apparatus membrane 1 MTOR
cell surface 1 TNF
glutamatergic synapse 2 ATG5, MAPK3
Golgi apparatus 1 MAPK3
Golgi membrane 2 INS, MTOR
lysosomal membrane 1 MTOR
neuronal cell body 1 TNF
postsynapse 1 ATG5
Cytoplasm, cytosol 1 ACACA
Lysosome 2 ACP5, MTOR
plasma membrane 4 MAPK3, SLC10A1, TNF, TNFSF11
Membrane 6 ACP5, ATG5, MTOR, RPS6, SLC10A1, TNFSF11
axon 2 ATG5, CCK
basolateral plasma membrane 1 SLC10A1
caveola 1 MAPK3
Lysosome membrane 1 MTOR
endoplasmic reticulum 2 FOS, RPS6
extracellular space 5 CCK, IL6, INS, TNF, TNFSF11
perinuclear region of cytoplasm 1 RPS6
Schaffer collateral - CA1 synapse 1 ATG5
mitochondrion 2 ACACA, MAPK3
protein-containing complex 1 ATG5
intracellular membrane-bounded organelle 1 CYP7A1
Microsome membrane 3 CYP7A1, CYP8B1, MTOR
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Secreted 4 CCK, IL6, INS, TNFSF11
extracellular region 5 CCK, IL6, INS, TNF, TNFSF11
Mitochondrion outer membrane 1 MTOR
Single-pass membrane protein 2 CYP7A1, CYP8B1
mitochondrial outer membrane 1 MTOR
transcription regulator complex 1 HMGA1
external side of plasma membrane 1 TNF
actin cytoskeleton 1 ACACA
nucleolus 1 RPS6
Early endosome 1 MAPK3
recycling endosome 1 TNF
Single-pass type II membrane protein 2 TNF, TNFSF11
Membrane raft 1 TNF
Cell junction, focal adhesion 1 MAPK3
focal adhesion 2 HMGA1, MAPK3
Nucleus, PML body 1 MTOR
PML body 1 MTOR
axoneme 1 ATG5
Late endosome 1 MAPK3
receptor complex 1 NR1H4
chromatin 3 FOS, HMGA1, NR1H4
phagocytic cup 1 TNF
phagocytic vesicle membrane 1 ATG5
Chromosome 1 HMGA1
cytoskeleton 1 MAPK3
[Isoform 3]: Nucleus 1 NR1H4
cytoplasmic ribonucleoprotein granule 1 RPS6
Nucleus, nucleolus 1 RPS6
fibrillar center 1 ACACA
nuclear envelope 2 MAPK3, MTOR
Endomembrane system 1 MTOR
endosome lumen 1 INS
Membrane, caveola 1 MAPK3
Preautophagosomal structure membrane 1 ATG5
Atg12-Atg5-Atg16 complex 1 ATG5
mitochondria-associated endoplasmic reticulum membrane contact site 1 ATG5
phagophore assembly site membrane 1 ATG5
euchromatin 1 NR1H4
cell body 1 RPS6
pseudopodium 1 MAPK3
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 IL6, INS, MAPK3
nuclear matrix 1 FOS
transport vesicle 1 INS
small-subunit processome 1 RPS6
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
[Isoform 2]: Cytoplasm 1 TNFSF11
[Tumor necrosis factor ligand superfamily member 11, soluble form]: Secreted 1 TNFSF11
ribonucleoprotein complex 1 RPS6
[Isoform 2]: Nucleus 1 NR1H4
[Isoform 1]: Nucleus 1 NR1H4
protein-DNA complex 1 FOS
Cytoplasmic vesicle, phagosome 1 MTOR
cytosolic ribosome 1 RPS6
[Isoform 4]: Nucleus 1 NR1H4
transferase complex 1 ATG5
ribosome 1 RPS6
transcription factor AP-1 complex 1 FOS
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
interleukin-6 receptor complex 1 IL6
cytosolic small ribosomal subunit 1 RPS6
senescence-associated heterochromatin focus 1 HMGA1
small ribosomal subunit 1 RPS6
phagophore 1 ATG5
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

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  • Philip W Melchert, Yuli Qian, Qingchen Zhang, Brandon O Klee, Chengguo Xing, John S Markowitz. In vitro inhibition of carboxylesterase 1 by Kava (Piper methysticum) Kavalactones. Chemico-biological interactions. 2022 Apr; 357(?):109883. doi: 10.1016/j.cbi.2022.109883. [PMID: 35278473]
  • Lina Kong, Renchao Dong, Kai Huang, Xiaohui Wang, Dalong Wang, Nan Yue, Changyuan Wang, Pengyuan Sun, Jiangning Gu, Haifeng Luo, Kexin Liu, Jingjing Wu, Huijun Sun, Qiang Meng. Yangonin modulates lipid homeostasis, ameliorates cholestasis and cellular senescence in alcoholic liver disease via activating nuclear receptor FXR. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2021 Sep; 90(?):153629. doi: 10.1016/j.phymed.2021.153629. [PMID: 34304130]
  • Antonio Celentano, Callisthenis Yiannis, Rita Paolini, Pangzhen Zhang, Camile S Farah, Nicola Cirillo, Tami Yap, Michael McCullough. Kava constituents exert selective anticancer effects in oral squamous cell carcinoma cells in vitro. Scientific reports. 2020 09; 10(1):15904. doi: 10.1038/s41598-020-73058-4. [PMID: 32985597]
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  • Xiaohui Wang, Ting Fu, Junqiao Wang, Changyuan Wang, Kexin Liu, Jingjing Wu, Huijun Sun, Xiaodong Ma, Pengyuan Sun, Qiang Meng. Hepatoprotection of yangonin against hepatic fibrosis in mice via farnesoid X receptor activation. International immunopharmacology. 2019 Oct; 75(?):105833. doi: 10.1016/j.intimp.2019.105833. [PMID: 31450152]
  • H M P Dilrukshi Herath, Sarah Preston, Abdul Jabbar, Jose Garcia-Bustos, Russell S Addison, Sasha Hayes, Topul Rali, Tao Wang, Anson V Koehler, Bill C H Chang, Andreas Hofmann, Rohan A Davis, Robin B Gasser. Selected α-pyrones from the plants Cryptocarya novoguineensis (Lauraceae) and Piper methysticum (Piperaceae) with activity against Haemonchus contortus in vitro. International journal for parasitology. Drugs and drug resistance. 2019 04; 9(?):72-79. doi: 10.1016/j.ijpddr.2018.12.006. [PMID: 30739078]
  • Renchao Dong, Xiaobo Yang, Changyuan Wang, Kexin Liu, Zhihao Liu, Xiaodong Ma, Huijun Sun, Xiaokui Huo, Ting Fu, Qiang Meng. Yangonin protects against non-alcoholic fatty liver disease through farnesoid X receptor. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Feb; 53(?):134-142. doi: 10.1016/j.phymed.2018.09.006. [PMID: 30668392]
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  • Alessia Ligresti, Rosaria Villano, Marco Allarà, István Ujváry, Vincenzo Di Marzo. Kavalactones and the endocannabinoid system: the plant-derived yangonin is a novel CB₁ receptor ligand. Pharmacological research. 2012 Aug; 66(2):163-9. doi: 10.1016/j.phrs.2012.04.003. [PMID: 22525682]
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  • Hideaki Matsuda, Noriko Hirata, Yoshiko Kawaguchi, Shunsuke Naruto, Takanobu Takata, Masayoshi Oyama, Munekazu Iinuma, Michinori Kubo. Melanogenesis stimulation in murine B16 melanoma cells by Kava (Piper methysticum) rhizome extract and kavalactones. Biological & pharmaceutical bulletin. 2006 Apr; 29(4):834-7. doi: 10.1248/bpb.29.834. [PMID: 16595931]
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  • Yuzhong Ma, Karuna Sachdeva, Jirong Liu, Michael Ford, Dongfang Yang, Ikhlas A Khan, Clinton O Chichester, Bingfang Yan. Desmethoxyyangonin and dihydromethysticin are two major pharmacological kavalactones with marked activity on the induction of CYP3A23. Drug metabolism and disposition: the biological fate of chemicals. 2004 Nov; 32(11):1317-24. doi: 10.1124/dmd.104.000786. [PMID: 15282211]
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