Isopimpinellin (BioDeep_00000000214)

 

Secondary id: BioDeep_00000402939, BioDeep_00000862403

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


InChI=1/C13H10O5/c1-15-10-7-3-4-9(14)18-12(7)13(16-2)11-8(10)5-6-17-11/h3-6H,1-2H3

化学式: C13H10O5 (246.052821)
中文名称: 异茴芹内酯, 异虎耳草素, 异茴芹灵
谱图信息: 最多检出来源 Homo sapiens(blood) 0.18%

分子结构信息

SMILES: COC1=C2C=COC2=C(C3=C1C=CC(=O)O3)OC
InChI: InChI=1S/C13H10O5/c1-15-10-7-3-4-9(14)18-12(7)13(16-2)11-8(10)5-6-17-11/h3-6H,1-2H3

描述信息

Isopimpinellin is a member of psoralens.
Isopimpinellin is a natural product found in Zanthoxylum mayu, Zanthoxylum ovalifolium, and other organisms with data available.
Isopimpinellin is found in angelica. Isopimpinellin is present in the seeds of Pastinaca sativa (parsnip) Isopimpinellin belongs to the family of Furanocoumarins. These are polycyclic aromatic compounds containing a furan ring fused to a coumarin moeity.
See also: Angelica keiskei top (part of).
Present in the seeds of Pastinaca sativa (parsnip). Isopimpinellin is found in many foods, some of which are carrot, anise, celery stalks, and fennel.
Isopimpinellin is found in angelica. Isopimpinellin is present in the seeds of Pastinaca sativa (parsnip
D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents > D011564 - Furocoumarins
Isopimpinellin, an orally active compound isolated from Glomerella cingulata. Isopimpinellin blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene. Isopimpinellin possesses anti-leishmania effect[1].
Isopimpinellin, an orally active compound isolated from Glomerella cingulata. Isopimpinellin blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene. Isopimpinellin possesses anti-leishmania effect[1].

同义名列表

50 个代谢物同义名

InChI=1/C13H10O5/c1-15-10-7-3-4-9(14)18-12(7)13(16-2)11-8(10)5-6-17-11/h3-6H,1-2H3; 5,8-Dimethoxypsoralen; 4,9-dimethoxyfuro[3,2-g]chromen-7-one; 7H-Furo(3,2-g)(1)benzopyran-7-one, 4,9-dimethoxy- (8CI); 4,9-Dimethoxy-7H-furo[3,2-g][1]benzopyran-7-one, 9CI; 7H-Furo(3,2-g)(1)benzopyran-7-one, 4,9-dimethoxy-; Isopimpinellin - Angelica archangelica (angelica); 7H-Furo[3,2-g][1]benzopyran-7-one, 4,9-dimethoxy-; 4,9-Dimethoxy-7H-furo(3,2-G) (1)benzopyran-7-one; 4,9-Dimethoxy-7H-furo(3,2-g)(1)benzopyran-7-one; 4,9-Dimethoxy-7H-furo[3,2-g][1]benzopyran-7-one; 4,9-Dimethoxy-7H-furo[3,2-g]chromen-7-one #; 4,9-Dimethoxy-7H-furo[3,2-g]chromen-7-one; 5,9-dimethoxy-2H-furo[3,2-g]chromen-2-one; 4,9-dimethoxy-7H-furo(3,2-g)chromen-7-one; 4,9-Dimethoxyfuro[3,2-g]benzopyran-7-one; Isopimpinellin (4,9-Dimethoxypsoralen); 4,9-Dimethoxy-furo[3,2-g]chromen-7-one; 4,9-Dimethoxy-7-oxofuro[3,2-g]chromene; 4,9-dimethoxyfuro[3,2-g]chromen-7-one; Isopimpinellin, analytical standard; 5,8-Dimethoxy-6,7-furanocoumarin; DFMAXQKDIGCMTL-UHFFFAOYSA-N; DFMAXQKDIGCMTL-UHFFFAOYSA-; 7H-Furo[3, 4,9-dimethoxy-; 5, 8-Dimethoxypsoralene; 5,8-Dimethoxypsoralene; 5,8-dimethoxypsoralen; 4,9-dimethoxypsoralen; 5-METHOXYXANTHOTOXIN; 8-METHOXYBERGAPTEN; Dimethylpsoralen; Spectrum3_001232; Spectrum4_001442; Spectrum5_000023; Spectrum2_000308; ISO-PIMPINELLIN; UNII-20GCF755G6; Isopimpinellin; Oprea1_593894; DivK1c_006250; MEGxp0_000706; Oprea1_132007; ACon1_002361; NCI60_003765; KBio3_002204; KBio2_003672; KBio2_006240; KBio1_001194; KBio2_001104; 20GCF755G6



数据库引用编号

19 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)

107 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

  • Piseth Nhoek, Sungjin Ahn, Pisey Pel, Young-Mi Kim, Jungmoo Huh, Hyun Woo Kim, Minsoo Noh, Young-Won Chin. Alkaloids and Coumarins with Adiponectin-Secretion-Promoting Activities from the Leaves of Orixa japonica. Journal of natural products. 2023 01; 86(1):138-148. doi: 10.1021/acs.jnatprod.2c00844. [PMID: 36529937]
  • Wenya Ma, Iftikhar Ali, Yali Li, Hidayat Hussain, Huanzhu Zhao, Xuan Sun, Lei Xie, Li Cui, Daijie Wang. A Simple and Efficient Two-Dimensional High-Speed Counter-Current Chromatography Linear Gradient and Isocratic Elution Modes for the Preparative Separation of Coumarins from Roots of Toddalia asiatica (Linn.) Lam. Molecules (Basel, Switzerland). 2021 Oct; 26(19):. doi: 10.3390/molecules26195986. [PMID: 34641527]
  • Prashant Joshi, Vinay R Sonawane, Ibidapo S Williams, Glen J P McCann, Linda Gatchie, Rajni Sharma, Naresh Satti, Bhabatosh Chaudhuri, Sandip B Bharate. Identification of karanjin isolated from the Indian beech tree as a potent CYP1 enzyme inhibitor with cellular efficacy via screening of a natural product repository. MedChemComm. 2018 Feb; 9(2):371-382. doi: 10.1039/c7md00388a. [PMID: 30108931]
  • Marie Fomani, Emmanuel Ngeufa Happi, Achille Nouga Bisoue, Jean Claude Ndom, Alain François Kamdem Waffo, Norbert Sewald, Jean Duplex Wansi. Oxidative burst inhibition, cytotoxicity and antibacterial acriquinoline alkaloids from Citrus reticulate (Blanco). Bioorganic & medicinal chemistry letters. 2016 Jan; 26(2):306-309. doi: 10.1016/j.bmcl.2015.12.028. [PMID: 26711890]
  • Fatima Zerargui, Sabah Boumerfeg, Noureddine Charef, Abderrahmane Baghiani, Meriem Djarmouni, Seddik Khennouf, Lekhmici Arrar, Musa H Abu Zarga, Mohammad S Mubarak. Antioxidant Potentials and Xanthine Oxidase Inhibitory Effect of Two Furanocoumarins Isolated from Tamus communis L. Medicinal chemistry (Shariqah (United Arab Emirates)). 2015; 11(5):506-13. doi: 10.2174/1573406411666150130145246. [PMID: 25633370]
  • Jing Li, Bo Ma, Qi Zhang, Xiaojing Yang, Jingjing Sun, Bowen Tang, Guangbo Cui, Di Yao, Lei Liu, Guiying Gu, Jianwei Zhu, Ping Wei, Pingkai Ouyang. Simultaneous determination of osthole, bergapten and isopimpinellin in rat plasma and tissues by liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Nov; 970(?):77-85. doi: 10.1016/j.jchromb.2014.06.014. [PMID: 25240925]
  • Henrique D de Menezes, Ana C Pereira, Guilherme T P Brancini, Helton Carlos de Leão, Nelson S Massola Júnior, Luciano Bachmann, Mark Wainwright, Jairo Kenupp Bastos, Gilberto U L Braga. Furocoumarins and coumarins photoinactivate Colletotrichum acutatum and Aspergillus nidulans fungi under solar radiation. Journal of photochemistry and photobiology. B, Biology. 2014 Feb; 131(?):74-83. doi: 10.1016/j.jphotobiol.2014.01.008. [PMID: 24509069]
  • Taryn O'Neill, John A Johnson, Duncan Webster, Christopher A Gray. The Canadian medicinal plant Heracleum maximum contains antimycobacterial diynes and furanocoumarins. Journal of ethnopharmacology. 2013 May; 147(1):232-7. doi: 10.1016/j.jep.2013.03.009. [PMID: 23501157]
  • Zhan-Chang Wang, Dan-Qing Feng, Cai-Huan Ke. Coumarins from the Herb Cnidium monnieri and chemically modified derivatives as antifoulants against Balanus albicostatus and Bugula neritina larvae. International journal of molecular sciences. 2013 Jan; 14(1):1197-206. doi: 10.3390/ijms14011197. [PMID: 23303279]
  • Věra Schulzová, Luboš Babička, Jana Hajšlová. Furanocoumarins in celeriac from different farming systems: a 3-year study. Journal of the science of food and agriculture. 2012 Nov; 92(14):2849-54. doi: 10.1002/jsfa.5629. [PMID: 22407843]
  • Nallely E Sandoval-Montemayor, Abraham García, Elizabeth Elizondo-Treviño, Elvira Garza-González, Laura Alvarez, María del Rayo Camacho-Corona. Chemical composition of hexane extract of Citrus aurantifolia and anti-Mycobacterium tuberculosis activity of some of its constituents. Molecules (Basel, Switzerland). 2012 Sep; 17(9):11173-84. doi: 10.3390/molecules170911173. [PMID: 22992784]
  • Ahmed Abbaskhan, Muhammed Iqbal Choudhary, Mohammed Nabeel Ghayur, Zeba Parween, Farzana Shaheen, Anwar-ul-Hassan Gilani, Takuro Maruyama, Kiran Iqbal, Yoshisuke Tsuda. Biological activities of Indian celery, Seseli diffusum (Roxb. ex Sm.) Sant. & Wagh. Phytotherapy research : PTR. 2012 May; 26(5):783-6. doi: 10.1002/ptr.3600. [PMID: 22095902]
  • Krystyna Skalicka-Woźniak, Kazimierz Głowniak. Pressurized liquid extraction of coumarins from fruits of Heracleum leskowii with application of solvents with different polarity under increasing temperature. Molecules (Basel, Switzerland). 2012 Apr; 17(4):4133-41. doi: 10.3390/molecules17044133. [PMID: 22481536]
  • Heyuan Qiu, Xiaohua Xiao, Gongke Li. Separation and purification of furanocoumarins from Toddalia asiatica (L.) Lam. using microwave-assisted extraction coupled with high-speed counter-current chromatography. Journal of separation science. 2012 Apr; 35(7):901-6. doi: 10.1002/jssc.201100995. [PMID: 22532360]
  • Zhigang Liu, Minyan Jiang, Xiumei Lu, Feng Qin, Yang Song, Jing Wen, Famei Li. Simultaneous determination of pimpinellin, isopimpinellin and phellopterin in rat plasma by a validated UPLC-MS/MS and its application to a pharmacokinetic study after administration of Toddalia asiatica extract. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Apr; 891-892(?):102-8. doi: 10.1016/j.jchromb.2012.02.022. [PMID: 22418072]
  • Pius S Fasinu, Patrick J Bouic, Bernd Rosenkranz. An overview of the evidence and mechanisms of herb-drug interactions. Frontiers in pharmacology. 2012; 3(?):69. doi: 10.3389/fphar.2012.00069. [PMID: 22557968]
  • Ah-Young Kang, Lindsay R Young, Carlus Dingfelder, Sabrina Peterson. Effects of furanocoumarins from apiaceous vegetables on the catalytic activity of recombinant human cytochrome P-450 1A2. The protein journal. 2011 Oct; 30(7):447-56. doi: 10.1007/s10930-011-9350-0. [PMID: 21847668]
  • Helge Joa, Sylvia Vogl, Atanas G Atanasov, Martin Zehl, Thomas Nakel, Nanang Fakhrudin, Elke H Heiss, Paolo Picker, Ernst Urban, Christoph Wawrosch, Johannes Saukel, Gottfried Reznicek, Brigitte Kopp, Verena M Dirsch. Identification of ostruthin from Peucedanum ostruthium rhizomes as an inhibitor of vascular smooth muscle cell proliferation. Journal of natural products. 2011 Jun; 74(6):1513-6. doi: 10.1021/np200072a. [PMID: 21627108]
  • Guglielmina Froldi, Riccardo Bertin, Enrico Secchi, Giuseppe Zagotto, Mariano Martínez-Vázquez, Aída García-Argaéz. Vasorelaxation by extracts of Casimiroa spp. in rat resistance vessels and pharmacological study of cellular mechanisms. Journal of ethnopharmacology. 2011 Apr; 134(3):637-43. doi: 10.1016/j.jep.2011.01.008. [PMID: 21236328]
  • Eunjin Shin, Chul Lee, Sang Hyun Sung, Young Choong Kim, Bang Yeon Hwang, Mi Kyeong Lee. Antifibrotic activity of coumarins from Cnidium monnieri fruits in HSC-T6 hepatic stellate cells. Journal of natural medicines. 2011 Apr; 65(2):370-4. doi: 10.1007/s11418-010-0485-7. [PMID: 21082271]
  • Yuma Iwai, Kouki Murakami, Yasuyuki Gomi, Toshihiro Hashimoto, Yoshinori Asakawa, Yoshinobu Okuno, Toyokazu Ishikawa, Dai Hatakeyama, Noriko Echigo, Takashi Kuzuhara. Anti-influenza activity of marchantins, macrocyclic bisbibenzyls contained in liverworts. PloS one. 2011; 6(5):e19825. doi: 10.1371/journal.pone.0019825. [PMID: 21625478]
  • Christiane Lohr, Nicole Raquet, Dieter Schrenk. Application of the concept of relative photomutagenic potencies to selected furocoumarins in V79 cells. Toxicology in vitro : an international journal published in association with BIBRA. 2010 Mar; 24(2):558-66. doi: 10.1016/j.tiv.2009.10.017. [PMID: 19883747]
  • Wei Yang, Chao Feng, Dezhi Kong, Xiaowei Shi, Yang Cui, Man Liu, Qiao Wang, Yongli Wang, Lantong Zhang. Simultaneous and sensitive determination of xanthotoxin, psoralen, isoimpinellin and bergapten in rat plasma by liquid chromatography-electrospray ionization mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Feb; 878(5-6):575-82. doi: 10.1016/j.jchromb.2009.12.035. [PMID: 20116347]
  • Takuro Maruyama, Ahmed Abbaskhan, Muhammad Iqbal Choudhary, Yoshisuke Tsuda, Yukihiro Goda, Michel Farille, Jean-Pierre Reduron. Botanical origin of Indian celery seed (fruit). Journal of natural medicines. 2009 Jul; 63(3):248-53. doi: 10.1007/s11418-009-0321-0. [PMID: 19214654]
  • Kailan Zhou, Bing Wu, Yulei Zhuang, Liqin Ding, Zhihui Liu, Feng Qiu. [Chemical constituents of fresh celery]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2009 Jun; 34(12):1512-5. doi: . [PMID: 19777835]
  • Maria Fâni Dolabela, Salma G Oliveira, José Maria Nascimento, José Maria Peres, Hildebert Wagner, Marinete Marins Póvoa, Alaíde Braga de Oliveira. In vitro antiplasmodial activity of extract and constituents from Esenbeckia febrifuga, a plant traditionally used to treat malaria in the Brazilian Amazon. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2008 May; 15(5):367-72. doi: 10.1016/j.phymed.2008.02.001. [PMID: 18337075]
  • Aleksandra Orlita, Matylda Sidwa-Gorycka, Jolanta Kumirska, Edmund Maliński, Ewa M Siedlecka, Jerzy Gajdus, Ewa Lojkowska, Piotr Stepnowski. Identification of Ruta graveolens L. metabolites accumulated in the presence of abiotic elicitors. Biotechnology progress. 2008 Jan; 24(1):128-33. doi: 10.1021/bp070261d. [PMID: 18052337]
  • Xiu-wei Yang, Bo Xu, Fu-xiang Ran, Rui-qing Wang, Jun Wu, Jing-rong Cui. [Inhibitory effects of 11 coumarin compounds against growth of human bladder carcinoma cell line E-J in vitro]. Zhong xi yi jie he xue bao = Journal of Chinese integrative medicine. 2007 Jan; 5(1):56-60. doi: 10.3736/jcim20070111. [PMID: 17214937]
  • Ya-li Zong, Yu-ping Lin, Qiong-e Ding, Hui He, Gao-xiong Rao. [Studies on the chemical constituents of the aerial parts of Seseli mairei]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2007 Jan; 30(1):42-4. doi: . [PMID: 17539301]
  • Yuan-Yan Liu, Cun Zhang, Li Li, Yong-Qing Xiao. [Studies on chemical constituents in roots of Heracleum rapula]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 Feb; 31(4):309-11. doi: . [PMID: 16706022]
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  • Hideaki Matsuda, Noriko Hirata, Yoshiko Kawaguchi, Miho Yamazaki, Shunsuke Naruto, Makio Shibano, Masahiko Taniguchi, Kimiye Baba, Michinori Kubo. Melanogenesis stimulation in murine b16 melanoma cells by umberiferae plant extracts and their coumarin constituents. Biological & pharmaceutical bulletin. 2005 Jul; 28(7):1229-33. doi: 10.1248/bpb.28.1229. [PMID: 15997104]
  • Annette Baumgart, Melanie Schmidt, Hans-Joachim Schmitz, Dieter Schrenk. Natural furocoumarins as inducers and inhibitors of cytochrome P450 1A1 in rat hepatocytes. Biochemical pharmacology. 2005 Feb; 69(4):657-67. doi: 10.1016/j.bcp.2004.11.017. [PMID: 15670584]
  • Xiao-Yan Hao, Xiao-Hong Cao, Yan Liang, Yue-Mao Shen. [Quantification of isopimpinellin in root of Toddalia asiatica by HPLC]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2004 Aug; 29(8):768-9. doi: ". [PMID: 15506290]
  • Manu Eeva, Jussi-Pekka Rauha, Pia Vuorela, Heikki Vuorela. Computer-assisted, high-performance liquid chromatography with mass spectrometric detection for the analysis of coumarins in Peucedanum palustre and Angelica archangelica. Phytochemical analysis : PCA. 2004 May; 15(3):167-74. doi: 10.1002/pca.764. [PMID: 15202601]
  • Ling-Ling Yang, Min-Chieh Wang, Lih-Geeng Chen, Ching-Chiung Wang. Cytotoxic activity of coumarins from the fruits of Cnidium monnieri on leukemia cell lines. Planta medica. 2003 Dec; 69(12):1091-5. doi: 10.1055/s-2003-45188. [PMID: 14750023]
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  • Zhao-Yang Tao, Wan-Sheng Chen, Wei-Dong Zhang, Lian-Na Sun, Shui-Qing Zheng, Liang You, Chuan-Zhuo Qiao. [Studies on the coumarins in the root of Zanthoxylum dimorphophyllum]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2003 Apr; 28(4):344-6. doi: ". [PMID: 15139146]
  • William N Setzer, Bernhard Vogler, Robert B Bates, Jennifer M Schmidt, Christopher W Dicus, Pichaya Nakkiew, William A Haber. HPLC-NMR/HPLC-MS analysis of the bark extract of Stauranthus perforatus. Phytochemical analysis : PCA. 2003 Jan; 14(1):54-9. doi: 10.1002/pca.687. [PMID: 12597256]
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  • Heather E Kleiner, Suryanarayana V Vulimiri, Matthew F Starost, Melissa J Reed, John DiGiovanni. Oral administration of the citrus coumarin, isopimpinellin, blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene in SENCAR mice. Carcinogenesis. 2002 Oct; 23(10):1667-75. doi: 10.1093/carcin/23.10.1667. [PMID: 12376476]
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  • W N Setzer, M C Setzer, J M Schmidt, D M Moriarity, B Vogler, S Reeb, A M Holmes, W A Haber. Cytotoxic components from the bark of Stauranthus perforatus from Monteverde, Costa Rica. Planta medica. 2000 Jun; 66(5):493-4. doi: 10.1055/s-2000-8595. [PMID: 10909280]
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  • Y Yoke Marchant, M Turjman, T Flynn, F Balza, J C Mitchell, G H Towers. Identification of psoralen, 8-methoxypsoralen, isopimpinellin, and 5,7-dimethoxycoumarin in Pelea anisata H. Mann. Contact dermatitis. 1985 Apr; 12(4):196-9. doi: 10.1111/j.1600-0536.1985.tb01105.x. [PMID: 4017567]