AP-10 (BioDeep_00000229982)

 

Secondary id: BioDeep_00000266927

PANOMIX_OTCML-2023


代谢物信息卡片


4-[(E)-2-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]-2H-furan-5-one

化学式: C20H28O4 (332.19874880000003)
中文名称: 14-去氧-11,12-二去氢穿心莲内酯, 14-脱氧-11,12-二去氢穿心莲内酯, 14-脱氧-11,12-二氢穿心莲内酯, 穿心莲内酯
谱图信息: 最多检出来源 Viridiplantae(plant) 1.31%

分子结构信息

SMILES: CC12CCC(C(C1CCC(=C)C2C=CC3=CCOC3=O)(C)CO)O
InChI: InChI=1S/C20H28O4/c1-13-4-7-16-19(2,10-8-17(22)20(16,3)12-21)15(13)6-5-14-9-11-24-18(14)23/h5-6,9,15-17,21-22H,1,4,7-8,10-12H2,2-3H3/b6-5+/t15-,16+,17-,19+,20+/m1/s1

描述信息

14-Deoxy-11,12-didehydroandrographolide is a diterpene lactone. It has a role as a metabolite.
14-Deoxy-11,12-didehydroandrographolide is a natural product found in Andrographis paniculata, Andrographis affinis, and other organisms with data available.
A natural product found in Andrographis paniculata.
14-Deoxy-11,12-didehydroandrographolide is an analogue of Andrographolide. 14-Deoxy-11,12-didehydroandrographolide inhibits NF-κB activation.
14-Deoxy-11,12-didehydroandrographolide is an analogue of Andrographolide. 14-Deoxy-11,12-didehydroandrographolide inhibits NF-κB activation.

同义名列表

18 个代谢物同义名

4-[(E)-2-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethenyl]-2H-furan-5-one; 2(5H)-Furanone, 3-((1E)-2-((1R,4aS,5R,6R,8aR)-decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethenyl)-; 3-{(E)-2-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidenedecahydronaphthalen-1-yl]ethenyl}furan-2(5H)-one; 14-DEOXY-11,12-DEHYDROANDROGRAPHOLIDE (CONSTITUENT OF ANDROGRAPHIS) [DSC]; 14-Deoxy-11,12-didehydroandrographolide, analytical standard; 14-Deoxy-11,12-didehydroandrographolide;AP10; 14-Deoxy-11,12-didehydro andrographolide; 14-Deoxy-11,12-didehydroandrographolide; 11,12-Didehydro-14-deoxyandrographolide; 14-Deoxy-11,12-dehydroandrographolide; 14-dehydro Andrographolide;AP10; 14-dehydro Andrographolide; UNII-5S0X4YZJ0E; MEGxp0_000982; 5S0X4YZJ0E; A1-06836; AP-10; AP10



数据库引用编号

8 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)

2 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。



文献列表

  • Wentao Cai, Haimei Wen, Qinyang Zhou, Lei Wu, Yong Chen, Hongbo Zhou, Meilin Jin. 14-Deoxy-11,12-didehydroandrographolide inhibits apoptosis in influenza A(H5N1) virus-infected human lung epithelial cells via the caspase-9-dependent intrinsic apoptotic pathway which contributes to its antiviral activity. Antiviral research. 2020 09; 181(?):104885. doi: 10.1016/j.antiviral.2020.104885. [PMID: 32702348]
  • Chih-Ching Yen, Yun-Ta Liu, Ying-Jyan Lin, Ya-Chen Yang, Chien-Chih Chen, Hsien-Tsung Yao, Haw-Wen Chen, Chong-Kuei Lii. Bioavailability of the diterpenoid 14-deoxy-11,12-didehydroandrographolide in rats and up-regulation of hepatic drug-metabolizing enzyme and drug transporter expression. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Aug; 61(?):152841. doi: 10.1016/j.phymed.2019.152841. [PMID: 31035043]
  • Hung-Chih Lin, Chien-Chun Li, Ya-Chen Yang, Tzu-Hsuan Chiu, Kai-Li Liu, Chong-Kuei Lii, Haw-Wen Chen. Andrographis paniculata diterpenoids and ethanolic extract inhibit TNFα-induced ICAM-1 expression in EA.hy926 cells. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Jan; 52(?):157-167. doi: 10.1016/j.phymed.2018.09.205. [PMID: 30599895]
  • Chien-Chun Li, Chih-Ching Yen, Ciou-Ting Fan, Wei-Ting Chuang, Chin-Shiu Huang, Haw-Wen Chen, Chong-Kuei Lii. 14-Deoxy-11,12-didehydroandrographolide suppresses adipogenesis of 3 T3-L1 preadipocytes by inhibiting CCAAT/enhancer-binding protein β activation and AMPK-mediated mitotic clonal expansion. Toxicology and applied pharmacology. 2018 11; 359(?):82-90. doi: 10.1016/j.taap.2018.09.028. [PMID: 30248417]
  • Sudarat Sombut, Rada Bunthawong, Uthaiwan Sirion, Teerapich Kasemsuk, Pawinee Piyachaturawat, Kanoknetr Suksen, Apichart Suksamrarn, Rungnapha Saeeng. Synthesis of 14-deoxy-11,12-didehydroandrographolide analogues as potential cytotoxic agents for cholangiocarcinoma. Bioorganic & medicinal chemistry letters. 2017 12; 27(23):5139-5143. doi: 10.1016/j.bmcl.2017.10.063. [PMID: 29097170]
  • Wentao Cai, Sunrui Chen, Yongtao Li, Anding Zhang, Hongbo Zhou, Huanchun Chen, Meilin Jin. 14-Deoxy-11,12-didehydroandrographolide attenuates excessive inflammatory responses and protects mice lethally challenged with highly pathogenic A(H5N1) influenza viruses. Antiviral research. 2016 09; 133(?):95-105. doi: 10.1016/j.antiviral.2016.07.020. [PMID: 27476045]
  • J C-W Lim, F-Y Goh, S-R Sagineedu, A C-H Yong, S M Sidik, N H Lajis, W S F Wong, J Stanslas. A semisynthetic diterpenoid lactone inhibits NF-κB signalling to ameliorate inflammation and airway hyperresponsiveness in a mouse asthma model. Toxicology and applied pharmacology. 2016 07; 302(?):10-22. doi: 10.1016/j.taap.2016.04.004. [PMID: 27089844]
  • Hao Chen, Yun-Bao Ma, Xiao-Yan Huang, Chang-An Geng, Yong Zhao, Li-Jun Wang, Rui-Hua Guo, Wen-Juan Liang, Xue-Mei Zhang, Ji-Jun Chen. Synthesis, structure-activity relationships and biological evaluation of dehydroandrographolide and andrographolide derivatives as novel anti-hepatitis B virus agents. Bioorganic & medicinal chemistry letters. 2014 May; 24(10):2353-9. doi: 10.1016/j.bmcl.2014.03.060. [PMID: 24731274]
  • Rahul Raghavan, Sanith Cheriyamundath, Joseph Madassery. 14-Deoxy-11,12-didehydroandrographolide inhibits proliferation and induces GSH-dependent cell death of human promonocytic leukemic cells. Journal of natural medicines. 2014 Apr; 68(2):387-94. doi: 10.1007/s11418-014-0815-2. [PMID: 24458985]
  • Alireza Valdiani, Daryush Talei, Soon Guan Tan, Mihdzar Abdul Kadir, Mahmood Maziah, Mohd Yusop Rafii, Sreenivasa Rao Sagineedu. A classical genetic solution to enhance the biosynthesis of anticancer phytochemicals in Andrographis paniculata Nees. PloS one. 2014; 9(2):e87034. doi: 10.1371/journal.pone.0087034. [PMID: 24586262]
  • Daryush Talei, Alireza Valdiani, Mahmood Maziah, Sreenivasa Rao Sagineedu, Mohd Said Saad. Analysis of the anticancer phytochemicals in Andrographis paniculata Nees. under salinity stress. BioMed research international. 2013; 2013(?):319047. doi: 10.1155/2013/319047. [PMID: 24371819]
  • Mei Lan Tan, Heng Kean Tan, Chern Ein Oon, Masanori Kuroyanagi, Tengku Sifzizul Tengku Muhammad. Identification of genes involved in the regulation of 14-deoxy-11,12-didehydroandrographolide-induced toxicity in T-47D mammary cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2012 Feb; 50(2):431-44. doi: 10.1016/j.fct.2011.11.001. [PMID: 22101062]
  • Waranya Chatuphonprasert, Tawun Remsungnen, Nobuo Nemoto, Kanokwan Jarukamjorn. Different AhR binding sites of diterpenoid ligands from Andrographis paniculata caused differential CYP1A1 induction in primary culture in mouse hepatocytes. Toxicology in vitro : an international journal published in association with BIBRA. 2011 Dec; 25(8):1757-63. doi: 10.1016/j.tiv.2011.09.004. [PMID: 21963808]
  • Shou-Ping Guan, Li-Ren Kong, Chang Cheng, Jonathan C W Lim, W S Fred Wong. Protective role of 14-deoxy-11,12-didehydroandrographolide, a noncytotoxic analogue of andrographolide, in allergic airway inflammation. Journal of natural products. 2011 Jun; 74(6):1484-90. doi: 10.1021/np2002572. [PMID: 21598983]
  • Chantana Aromdee, Supawadee Suebsasana, Tipaya Ekalaksananan, Chamsai Pientong, Sasithorn Thongchai. Stage of action of naturally occurring andrographolides and their semisynthetic analogues against herpes simplex virus type 1 in vitro. Planta medica. 2011 Jun; 77(9):915-21. doi: 10.1055/s-0030-1250659. [PMID: 21259187]
  • Meng-Jen Lee, Yerra Koteswara Rao, Keru Chen, Yi-Ching Lee, Yi-Shuan Chung, Yew-Min Tzeng. Andrographolide and 14-deoxy-11,12-didehydroandrographolide from Andrographis paniculata attenuate high glucose-induced fibrosis and apoptosis in murine renal mesangeal cell lines. Journal of ethnopharmacology. 2010 Nov; 132(2):497-505. doi: 10.1016/j.jep.2010.07.057. [PMID: 20813180]
  • Petra H Pfisterer, Judith M Rollinger, Lilianna Schyschka, Anita Rudy, Angelika M Vollmar, Hermann Stuppner. Neoandrographolide from Andrographis paniculata as a potential natural chemosensitizer. Planta medica. 2010 Oct; 76(15):1698-700. doi: 10.1055/s-0030-1249876. [PMID: 20446243]
  • G A Akowuah, I Zhari, A Mariam, M F Yam. Absorption of andrographolides from Andrographis paniculata and its effect on CCl(4)-induced oxidative stress in rats. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2009 Sep; 47(9):2321-6. doi: 10.1016/j.fct.2009.06.022. [PMID: 19540299]
  • Suresh R Naik, Amolkumar Hule. Evaluation of immunomodulatory activity of an extract of andrographolides from Andographis paniculata. Planta medica. 2009 Jun; 75(8):785-91. doi: 10.1055/s-0029-1185398. [PMID: 19263340]
  • Hai-Wei Xu, Gui-Fu Dai, Gai-Zhi Liu, Jun-Feng Wang, Hong-Min Liu. Synthesis of andrographolide derivatives: a new family of alpha-glucosidase inhibitors. Bioorganic & medicinal chemistry. 2007 Jun; 15(12):4247-55. doi: 10.1016/j.bmc.2007.03.063. [PMID: 17428667]
  • Nattaporn Yoopan, Piengpen Thisoda, Nuchanart Rangkadilok, Somjed Sahasitiwat, Nanthanit Pholphana, Somsak Ruchirawat, Jutamaad Satayavivad. Cardiovascular effects of 14-deoxy-11,12-didehydroandrographolide and Andrographis paniculata extracts. Planta medica. 2007 Jun; 73(6):503-11. doi: 10.1055/s-2007-967181. [PMID: 17650544]
  • Piengpen Thisoda, Nuchanart Rangkadilok, Nanthanit Pholphana, Luksamee Worasuttayangkurn, Somsak Ruchirawat, Jutamaad Satayavivad. Inhibitory effect of Andrographis paniculata extract and its active diterpenoids on platelet aggregation. European journal of pharmacology. 2006 Dec; 553(1-3):39-45. doi: 10.1016/j.ejphar.2006.09.052. [PMID: 17081514]
  • Yun-Heng Shen, Rong-Tao Li, Wei-Lie Xiao, Gang Xu, Zhong-Wen Lin, Qin-Shi Zhao, Han-Dong Sun. ent-Labdane diterpenoids from Andrographis paniculata. Journal of natural products. 2006 Mar; 69(3):319-22. doi: 10.1021/np050160u. [PMID: 16562826]
  • Nanthanit Pholphana, Nuchanart Rangkadilok, Sanit Thongnest, Somsak Ruchirawat, Mathuros Ruchirawat, Jutamaad Satayavivad. Determination and variation of three active diterpenoids in Andrographis paniculata (Burm.f.) Nees. Phytochemical analysis : PCA. 2004 Nov; 15(6):365-71. doi: 10.1002/pca.789. [PMID: 15595451]
  • Srinivas Nanduri, Vijay Kumar Nyavanandi, Siva Sanjeeva Rao Thunuguntla, Sridevi Kasu, Mahesh Kumar Pallerla, P Sai Ram, Sriram Rajagopal, R Ajaya Kumar, Rajagopalan Ramanujam, J Moses Babu, Krishnamurthi Vyas, A Sivalakshmi Devi, G Om Reddy, Venkateswarlu Akella. Synthesis and structure-activity relationships of andrographolide analogues as novel cytotoxic agents. Bioorganic & medicinal chemistry letters. 2004 Sep; 14(18):4711-7. doi: 10.1016/j.bmcl.2004.06.090. [PMID: 15324893]