Nigranoic acid (BioDeep_00000395574)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(2Z,6R)-6-[(1R,3aS,3bS,6S,6aR,7aS,9aR)-6a-(2-carboxyethyl)-3a,9a-dimethyl-6-(prop-1-en-2-yl)dodecahydro-1H-cyclopenta[a]cyclopropa[e]naphthalen-1-yl]-2-methylhept-2-enoic acid

化学式: C30H46O4 (470.3396)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C=C(C)[C@@H]1CC[C@@H]2[C@]3(CC[C@]4(C)[C@@H]([C@H](C)CC/C=C(/C)C(=O)O)CC[C@@]24C)C[C@]13CCC(=O)O
InChI: InChI=1S/C30H46O4/c1-19(2)22-10-11-24-28(6)14-12-23(20(3)8-7-9-21(4)26(33)34)27(28,5)16-17-30(24)18-29(22,30)15-13-25(31)32/h9,20,22-24H,1,7-8,10-18H2,2-6H3,(H,31,32)(H,33,34)/b21-9-/t20-,22+,23-,24+,27-,28+,29-,30+/m1/s1

描述信息

Nigranoic acid is a tetracyclic triterpenoid that is 3,4-secocycloarta-4(28),24-(Z)-diene substituted by carboxy groups at positions 3 and 26. Isolated from Schisandra henryi and Schisandra propinqua, it exhibits cytotoxic and anti-HIV activities. It has a role as a metabolite, an antineoplastic agent and a HIV-1 reverse transcriptase inhibitor. It is a tetracyclic triterpenoid and a dicarboxylic acid.
Nigranoic acid is a natural product found in Kadsura angustifolia, Kadsura heteroclita, and other organisms with data available.
A tetracyclic triterpenoid that is 3,4-secocycloarta-4(28),24-(Z)-diene substituted by carboxy groups at positions 3 and 26. Isolated from Schisandra henryi and Schisandra propinqua, it exhibits cytotoxic and anti-HIV activities.

同义名列表

5 个代谢物同义名

(2Z,6R)-6-[(1R,3aS,3bS,6S,6aR,7aS,9aR)-6a-(2-carboxyethyl)-3a,9a-dimethyl-6-(prop-1-en-2-yl)dodecahydro-1H-cyclopenta[a]cyclopropa[e]naphthalen-1-yl]-2-methylhept-2-enoic acid; (Z,6R)-6-(2-carboxyethyl-isopropenyl-dimethyl-[?]yl)-2-methyl-hept-2-enoic acid; 3,4-Secocycloarta-4(28),24-(Z)-diene-3,26-dioic acid; 3,4-secocycloarta-4(28),24(Z)-diene-3,26-dioic acid; Nigranoic acid



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)

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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)

24 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

  • Dong-Xuan Ni, Qi Wang, Yi-Ming Li, Yi-Man Cui, Tian-Ze Shen, Xiao-Li Li, Han-Dong Sun, Xing-Jie Zhang, Ruihan Zhang, Wei-Lie Xiao. Synthesis of nigranoic acid and manwuweizic acid derivatives as HDAC inhibitors and anti-inflammatory agents. Bioorganic chemistry. 2021 04; 109(?):104728. doi: 10.1016/j.bioorg.2021.104728. [PMID: 33636436]
  • MeiJun Han, Dan Qin, TianTian Ye, Xiao Yan, JunQi Wang, XiaoXiang Duan, JinYan Dong. An endophytic fungus from Trichoderma harzianum SWUKD3.1610 that produces nigranoic acid and its analogues. Natural product research. 2019 Jul; 33(14):2079-2087. doi: 10.1080/14786419.2018.1486311. [PMID: 29897270]
  • Dan Qin, Weiyun Shen, Junqi Wang, Meijun Han, Fangni Chai, Xiaoxiang Duan, Xiao Yan, Jiali Guo, Tiancong Gao, Shihao Zuo, Jinyan Dong. Enhanced production of unusual triterpenoids from Kadsura angustifolia fermented by a symbiont endophytic fungus, Penicillium sp. SWUKD4.1850. Phytochemistry. 2019 Feb; 158(?):56-66. doi: 10.1016/j.phytochem.2018.11.005. [PMID: 30476897]
  • Xiao-Xi Yuan, Li-Ping Yang, Zhong-Lin Yang, Wei-Lie Xiao, Han-Dong Sun, Gui-Sheng Wu, Huai-Rong Luo. Effect of nigranoic acid on Ca²⁺ influx and its downstream signal mechanism in NGF-differentiated PC12 cells. Journal of ethnopharmacology. 2014 May; 153(3):725-31. doi: 10.1016/j.jep.2014.03.038. [PMID: 24674947]
  • Cheng-Qin Liang, Rong-Hua Luo, Ju-Ming Yan, Yan Li, Xiao-Nian Li, Yi-Ming Shi, Shan-Zhai Shang, Zhong-Hua Gao, Liu-Meng Yang, Yong-Tang Zheng, Wei-Lie Xiao, Hong-Bin Zhang, Han-Dong Sun. Structure and bioactivity of triterpenoids from the stems of Schisandra sphenanthera. Archives of pharmacal research. 2014 Feb; 37(2):168-74. doi: 10.1007/s12272-013-0133-3. [PMID: 23703254]
  • Rong Sun, Hong-Chuan Song, Chun-Ren Wang, Kai-Ze Shen, Yao-Bo Xu, Yan-Xiu Gao, Ye-Gao Chen, Jin-Yan Dong. Compounds from Kadsura angustifolia with anti-HIV activity. Bioorganic & medicinal chemistry letters. 2011 Feb; 21(3):961-5. doi: 10.1016/j.bmcl.2010.12.055. [PMID: 21232955]
  • Zong-gen Peng, Li-jia Xu, Wen-cai Ye, Pei-gen Xiao, Hong-shan Chen. [Effective components against HIV-1 replicative enzymes isolated from plants]. Yao xue xue bao = Acta pharmaceutica Sinica. 2010 Feb; 45(2):235-40. doi: ". [PMID: 21351433]
  • Wei-Lie Xiao, Ren-Rong Tian, Jian-Xin Pu, Xian Li, Li Wu, Yang Lu, Sheng-Hong Li, Rong-Tao Li, Yong-Tang Zheng, Qi-Tai Zheng, Han-Dong Sun. Triterpenoids from Schisandra lancifolia with anti-HIV-1 activity. Journal of natural products. 2006 Feb; 69(2):277-9. doi: 10.1021/np0503303. [PMID: 16499331]
  • Y G Chen, G W Qin, L Cao, Y Leng, Y Y Xie. Triterpenoid acids from Schisandra propinqua with cytotoxic effect on rat luteal cells and human decidual cells in vitro. Fitoterapia. 2001 May; 72(4):435-7. doi: 10.1016/s0367-326x(01)00269-6. [PMID: 11395273]
  • H D Sun, S X Qiu, L Z Lin, Z Y Wang, Z W Lin, T Pengsuparp, J M Pezzuto, H H Fong, G A Cordell, N R Farnsworth. Nigranoic acid, a triterpenoid from Schisandra sphaerandra that inhibits HIV-1 reverse transcriptase. Journal of natural products. 1996 May; 59(5):525-7. doi: 10.1021/np960149h. [PMID: 8778243]