Myricanol (BioDeep_00000232272)

   

natural product PANOMIX_OTCML-2023


代谢物信息卡片


NCGC00380288-01_C21H26O5_Tricyclo[12.3.1.1~2,6~]nonadeca-1(18),2,4,6(19),14,16-hexaene-3,9,15-triol, 16,17-dimethoxy-

化学式: C21H26O5 (358.178)
中文名称: 杨梅醇, 肉豆蔻醇
谱图信息: 最多检出来源 Viridiplantae(plant) 72.22%

分子结构信息

SMILES: COC1=C(O)C2=CC(=C1OC)C1=C(O)C=CC(CCC(O)CCCC2)=C1
InChI: InChI=1S/C21H26O5/c1-25-20-17-12-14(19(24)21(20)26-2)5-3-4-6-15(22)9-7-13-8-10-18(23)16(17)11-13/h8,10-12,15,22-24H,3-7,9H2,1-2H3

描述信息

Myricanol is a member of the class of compounds known as meta,meta-bridged biphenyls. Meta,meta-bridged biphenyls are cyclic diarylheptanoids where the two aryl groups are linked to each other by an ether group conjugated to their 3-position. Myricanol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Myricanol can be found in anise, which makes myricanol a potential biomarker for the consumption of this food product.
Myricanol is a natural product found in Myrica nagi, Morella rubra, and other organisms with data available.

同义名列表

10 个代谢物同义名

Myricanol; NCGC00380288-01_C21H26O5_Tricyclo[12.3.1.1~2,6~]nonadeca-1(18),2,4,6(19),14,16-hexaene-3,9,15-triol, 16,17-dimethoxy-; Tricyclo[12.3.1.12,6]nonadeca-1(18),2,4,6(19),14,16-hexaene-3,9,15-triol, 16,17-dimethoxy-, (9R)-; (9R)-16,17-Dimethoxytricyclo[12.3.1.12,6]nonadeca-1(17),2,4,6(19),14(18),15-hexaene-3,9,15-triol; Tricyclo(12.3.1.12,6)nonadeca-1(18),2,4,6(19),14,16-hexaene-3,9,15-triol, 16,17-dimethoxy-, (R)-; 16,17-Dimethoxytricyclo[12.3.1.1~2,6~]nonadeca-1(18),2(19),3,5,14,16-hexaene-3,9,15-triol; (R)-15,16-Dimethoxy-1,2(1,3)-dibenzenacyclononaphane-14,26,5-triol; SBGBAZQAEOWGFT-OAHLLOKOSA-N; (-)-Myricanol; Myricanol



数据库引用编号

12 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)

0 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


文献列表

  • Peng Lyu, Shengrong Li, Ying Han, Shengnan Shen, Zheling Feng, Piliang Hao, Zhengqiu Li, Ligen Lin. Affinity-based protein profiling-driven discovery of myricanol as a Nampt activator. Bioorganic chemistry. 2023 04; 133(?):106435. doi: 10.1016/j.bioorg.2023.106435. [PMID: 36841049]
  • Corinne Vanucci-Bacqué, Florence Bedos-Belval. Anti-inflammatory activity of naturally occuring diarylheptanoids - A review. Bioorganic & medicinal chemistry. 2021 02; 31(?):115971. doi: 10.1016/j.bmc.2020.115971. [PMID: 33422907]
  • Shengnan Shen, Qiwen Liao, Tian Zhang, Ruile Pan, Ligen Lin. Myricanol modulates skeletal muscle-adipose tissue crosstalk to alleviate high-fat diet-induced obesity and insulin resistance. British journal of pharmacology. 2019 10; 176(20):3983-4001. doi: 10.1111/bph.14802. [PMID: 31339170]
  • Shengnan Shen, Qiwen Liao, Jingxin Liu, Ruile Pan, Simon Ming-Yuen Lee, Ligen Lin. Myricanol rescues dexamethasone-induced muscle dysfunction via a sirtuin 1-dependent mechanism. Journal of cachexia, sarcopenia and muscle. 2019 04; 10(2):429-444. doi: 10.1002/jcsm.12393. [PMID: 30793539]
  • Shengnan Shen, Qiwen Liao, Yu Feng, Jingxin Liu, Ruile Pan, Simon Ming-Yuen Lee, Ligen Lin. Myricanol mitigates lipid accumulation in 3T3-L1 adipocytes and high fat diet-fed zebrafish via activating AMP-activated protein kinase. Food chemistry. 2019 Jan; 270(?):305-314. doi: 10.1016/j.foodchem.2018.07.117. [PMID: 30174051]
  • Guan-Hai Dai, Chen-Jie Fan, Ze-Ming Ren, Xuan Chen, Ye-Ling Tong, Zhen-Hua Li, Xiao-Jing Nie, Ke-Qun Chai. The mechanistic antitumor study of myricanol 5-fluorobenzyloxy ether in human leukemic cell HL-60. Future medicinal chemistry. 2017 12; 9(18):2117-2127. doi: 10.4155/fmc-2017-0165. [PMID: 28819994]
  • Guanhai Dai, Yeling Tong, Xuan Chen, Zeming Ren, Xuhua Ying, Feng Yang, Kequn Chai. Myricanol induces apoptotic cell death and anti-tumor activity in non-small cell lung carcinoma in vivo. International journal of molecular sciences. 2015 Jan; 16(2):2717-31. doi: 10.3390/ijms16022717. [PMID: 25629230]
  • G H Dai, G M Meng, Y L Tong, X Chen, Z M Ren, K Wang, F Yang. Growth-inhibiting and apoptosis-inducing activities of Myricanol from the bark of Myrica rubra in human lung adenocarcinoma A549 cells. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2014 Sep; 21(11):1490-6. doi: 10.1016/j.phymed.2014.04.025. [PMID: 24939078]
  • Ya-Chih Ting, Horng-Huey Ko, Hui-Chun Wang, Chien-Fang Peng, Hsun-Shuo Chang, Pei-Chen Hsieh, Ih-Sheng Chen. Biological evaluation of secondary metabolites from the roots of Myrica adenophora. Phytochemistry. 2014 Jul; 103(?):89-98. doi: 10.1016/j.phytochem.2014.04.003. [PMID: 24810013]
  • Morio Yoshimura, Saori Yamakami, Yoshiaki Amakura, Takashi Yoshida. Diarylheptanoid sulfates and related compounds from Myrica rubra bark. Journal of natural products. 2012 Oct; 75(10):1798-802. doi: 10.1021/np300212c. [PMID: 23066712]
  • Jeffrey R Jones, Matthew D Lebar, Umesh K Jinwal, Jose F Abisambra, John Koren, Laura Blair, John C O'Leary, Zachary Davey, Justin Trotter, Amelia G Johnson, Edwin Weeber, Christopher B Eckman, Bill J Baker, Chad A Dickey. The diarylheptanoid (+)-aR,11S-myricanol and two flavones from bayberry (Myrica cerifera) destabilize the microtubule-associated protein tau. Journal of natural products. 2011 Jan; 74(1):38-44. doi: 10.1021/np100572z. [PMID: 21141876]
  • Jing Tao, Toshio Morikawa, Iwao Toguchida, Shin Ando, Hisashi Matsuda, Masayuki Yoshikawa. Inhibitors of nitric oxide production from the bark of Myrica rubra: structures of new biphenyl type diarylheptanoid glycosides and taraxerane type triterpene. Bioorganic & medicinal chemistry. 2002 Dec; 10(12):4005-12. doi: 10.1016/s0968-0896(02)00314-0. [PMID: 12413852]