Zosimin (BioDeep_00000229970)

 

Secondary id: BioDeep_00000227970

PANOMIX_OTCML-2023


代谢物信息卡片


2-Butenoic acid, 2-methyl-, 1-(8,9-dihydro-2-oxo-2H-furo(2,3-h)-1-benzopyran-8-yl)-1-methylet- hyl ester, (S-(Z))-

化学式: C19H20O5 (328.13106700000003)
中文名称: 二氢欧山芹醇当归酸酯, 二氢欧山芹当归酸酯, 二氢欧山芹醇当归酸酯
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 45.45%

分子结构信息

SMILES: C/C=C(C)\C(OC(C)([C@@H]1CC2=C(O3)C(C=CC3=O)=CC=C2O1)C)=O
InChI: InChI=1S/C19H20O5/c1-5-11(2)18(21)24-19(3,4)15-10-13-14(22-15)8-6-12-7-9-16(20)23-17(12)13/h5-9,15H,10H2,1-4H3/b11-5-/t15-/m0/s1

描述信息

Columbianadin is an alpha,beta-unsaturated carboxylic ester obtained by formal condensation of the carboxy group of angelic acid with the hydroxy group of 2-[(8S)-2-oxo-8,9-dihydro-2H-furo[2,3-h][1]benzopyran-8-yl]propan-2-ol. It has a role as an anti-inflammatory agent, an apoptosis inducer, a hepatoprotective agent, an antineoplastic agent, a rat metabolite and a plant metabolite. It is a furanocoumarin and an alpha,beta-unsaturated carboxylic ester. It is functionally related to an angelic acid.
Columbianadin is a natural product found in Heracleum candolleanum, Peucedanum palustre, and other organisms with data available.
An alpha,beta-unsaturated carboxylic ester obtained by formal condensation of the carboxy group of angelic acid with the hydroxy group of 2-[(8S)-2-oxo-8,9-dihydro-2H-furo[2,3-h][1]benzopyran-8-yl]propan-2-ol.
Columbianadin, a natural coumarin from Heracleum hemsleyanum, is known to have various biological activities including anti-inflammatory and anti-cancer effects.
Columbianadin, a natural coumarin from Heracleum hemsleyanum, is known to have various biological activities including anti-inflammatory and anti-cancer effects.

同义名列表

20 个代谢物同义名

2-Butenoic acid, 2-methyl-, 1-(8,9-dihydro-2-oxo-2H-furo(2,3-h)-1-benzopyran-8-yl)-1-methylet- hyl ester, (S-(Z))-; 2-Butenoic acid, 2-methyl-, 1-(8,9-dihydro-2-oxo-2H-furo(2,3-h)-1-benzopyran-8-yl)-1-methylethyl ester, (S-(Z))-; (S)-8-[1-[(Z)-2-Methyl-2-butenoyloxy]-1-methylethyl]-8,9-dihydro-2H-furo[2,3-h]-1-benzopyran-2-one; (Z)-2-Methylbut-2-enoic Acid (S)-2-(2-Oxo-8,9-dihydro-2H-furo[2,3-h]chromen-8-yl)propan-2-yl Ester; 2-[(8S)-2-oxo-8,9-dihydro-2H-furo[2,3-h][1]benzopyran-8-yl]propan-2-yl (2Z)-2-methylbut-2-enoate; [1-methyl-1-[(8S)-2-oxo-8,9-dihydrofuro[2,3-h]chromen-8-yl]ethyl] (Z)-2-methylbut-2-enoate; (S)-2-(2-oxo-8,9-dihydro-2H-furo[2,3-h]chromen-8-yl)propan-2-yl (Z)-2-methylbut-2-enoate; (S,Z)-2-(2-oxo-8,9-dihydro-2H-furo[2,3-h]chromen-8-yl)propan-2-yl 2-methylbut-2-enoate; 2-[(8S)-2-oxo-8,9-dihydrofuro[2,3-h]chromen-8-yl]propan-2-yl (Z)-2-methylbut-2-enoate; Columbianadin; Zosimin; (Z)-2-methylbut-2-enoic acid [1-[(8S)-2-keto-8,9-dihydrofuro[5,4-h]chromen-8-yl]-1-methyl-ethyl] ester; (Z)-2-methylbut-2-enoic acid [1-methyl-1-[(8S)-2-oxo-8,9-dihydrofuro[5,4-h]chromen-8-yl]ethyl] ester; [1-methyl-1-[(8S)-2-oxo-8,9-dihydrofuro[5,4-h]chromen-8-yl]ethyl] (Z)-2-methylbut-2-enoate; 2-[(8S)-2-oxo-8,9-dihydrofuro[5,4-h]chromen-8-yl]propan-2-yl (Z)-2-methylbut-2-enoate; MLS000574825; SMR000156217; AIDS-071122; AIDS071122; 5058-13-9



数据库引用编号

9 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)

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

  • Shujing Chen, Yuan Wang, Lei Zhang, Yuli Han, Chunxiao Liang, Shuangqi Wang, Lina Qi, Xiaoli Pang, Jin Li, Yanxu Chang. Therapeutic effects of columbianadin from Angelicae Pubescentis radix on the progression of collagen-induced rheumatoid arthritis by regulating inflammation and oxidative stress. Journal of ethnopharmacology. 2023 Nov; 316(?):116727. doi: 10.1016/j.jep.2023.116727. [PMID: 37277080]
  • Shujing Chen, Yun Bai, Yuan Wang, Chunxiao Liang, Kunze Du, Shuangqi Wang, Jin Li, Yan-Xu Chang. Immunosuppressive effect of Columbianadin on maturation, migration, allogenic T cell stimulation and phagocytosis capacity of TNF-α induced dendritic cells. Journal of ethnopharmacology. 2022 Mar; 285(?):114918. doi: 10.1016/j.jep.2021.114918. [PMID: 34919989]
  • Yanmei Feng, Qian Li, Lan Yang, Yu Zhang, Daiyu Qiu. The Use of 1H-qNMR Method for Simultaneous Determination of Osthol, Columbianadin, and Isoimperatorin in Angelicae Pubescentis Radix. Journal of AOAC International. 2020 Jun; 103(3):851-856. doi: 10.1093/jaoacint/qsz031. [PMID: 33241377]
  • Yuqiao Yang, Ruichao Zhu, Jin Li, Xuejing Yang, Jun He, Hui Wang, Yanxu Chang. Separation and Enrichment of Three Coumarins from Angelicae Pubescentis Radix by Macroporous Resin with Preparative HPLC and Evaluation of Their Anti-Inflammatory Activity. Molecules (Basel, Switzerland). 2019 Jul; 24(14):. doi: 10.3390/molecules24142664. [PMID: 31340484]
  • Chao Zhang, Alan Chen-Yu Hsu, He Pan, Yinuo Gu, Xu Zuo, Bing Dong, Ziyan Wang, Jingtong Zheng, Junying Lu, Ruipeng Zheng, Fang Wang. Columbianadin Suppresses Lipopolysaccharide (LPS)-Induced Inflammation and Apoptosis through the NOD1 Pathway. Molecules (Basel, Switzerland). 2019 Feb; 24(3):. doi: 10.3390/molecules24030549. [PMID: 30717343]
  • Ruili Li, Chao Zhao, Minna Yao, Ying Song, Yin Wu, Aidong Wen. Analgesic effect of coumarins from Radix angelicae pubescentis is mediated by inflammatory factors and TRPV1 in a spared nerve injury model of neuropathic pain. Journal of ethnopharmacology. 2017 Jan; 195(?):81-88. doi: 10.1016/j.jep.2016.11.046. [PMID: 27915078]
  • You-Bo Zhang, Xiu-Wei Yang. Tissue distribution study of columbianadin and its active metabolite columbianetin in rats. Biomedical chromatography : BMC. 2016 Feb; 30(2):256-62. doi: 10.1002/bmc.3543. [PMID: 26115176]
  • Hun Jai Lim, Ju Hee Lee, Jae Sue Choi, Sang Kook Lee, Yeong Shik Kim, Hyun Pyo Kim. Inhibition of airway inflammation by the roots of Angelica decursiva and its constituent, columbianadin. Journal of ethnopharmacology. 2014 Sep; 155(2):1353-61. doi: 10.1016/j.jep.2014.07.033. [PMID: 25068578]
  • You-Bo Zhang, Wei Li, Xiu-Wei Yang. Biotransformation of columbianadin by rat hepatic microsomes and inhibition of biotransformation products on NO production in RAW 264.7 cells in vitro. Phytochemistry. 2012 Sep; 81(?):109-16. doi: 10.1016/j.phytochem.2012.06.015. [PMID: 22784551]
  • Li Liu, Hongyue Ma, Yuping Tang, Wenxing Chen, Yin Lu, Jianming Guo, Jin-Ao Duan. Discovery of estrogen receptor α modulators from natural compounds in Si-Wu-Tang series decoctions using estrogen-responsive MCF-7 breast cancer cells. Bioorganic & medicinal chemistry letters. 2012 Jan; 22(1):154-63. doi: 10.1016/j.bmcl.2011.11.041. [PMID: 22137340]
  • You-Bo Zhang, Xiu-Wei Yang. A simple RP-HPLC method for quantification of columbianadin in rat plasma and its application to pharmacokinetic study. Biomedical chromatography : BMC. 2010 Apr; 24(4):433-7. doi: 10.1002/bmc.1310. [PMID: 19662622]
  • Xiu-wei Yang, Qing-mei Guo, Ying Wang. [Absorption and transport of 6 coumarins isolated from the roots of Angelica pubescens f. biserrata in human Caco-2 cell monolayer model]. Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine. 2008 Apr; 6(4):392-8. doi: 10.3736/jcim20080413. [PMID: 18405608]
  • Ya-Na Wu, Li-Biao Luan. [In situ rats single pass perfusion intestinal absorption of the effectivein components in Radix Angelicae Pubescentis]. Yao xue xue bao = Acta pharmaceutica Sinica. 2008 Jan; 43(1):102-7. doi: . [PMID: 18357742]
  • J F Xu, L Y Kong. [Studies on chemical constituents from the herb of Peucedanum decursivum (Miq.) Maxim]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2001 Mar; 26(3):178-80. doi: . [PMID: 12525036]