(R)-Oxypeucedanin (BioDeep_00000007831)

 

Secondary id: BioDeep_00001028362

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


7H-Furo[3,2-g][1]benzopyran-7-one, 4-((3,3-dimethyloxiranyl)methoxy)-, (S-)-

化学式: C16H14O5 (286.0841194)
中文名称: 氧化前胡素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 1.69%

分子结构信息

SMILES: CC1(C(O1)COC2=C3C=CC(=O)OC3=CC4=C2C=CO4)C
InChI: InChI=1S/C16H14O5/c1-16(2)13(21-16)8-19-15-9-3-4-14(17)20-12(9)7-11-10(15)5-6-18-11/h3-7,13H,8H2,1-2H3

描述信息

(r)-oxypeucedanin, also known as hishigado or phosphine, is a member of the class of compounds known as psoralens. Psoralens are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one (r)-oxypeucedanin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (r)-oxypeucedanin can be found in carrot, lemon, parsley, and wild carrot, which makes (r)-oxypeucedanin a potential biomarker for the consumption of these food products.
(R)-Oxypeucedanin is a member of psoralens.
4-[(3,3-Dimethyloxiran-2-yl)methoxy]furo[3,2-g]chromen-7-one is a natural product found in Prangos latiloba, Citrus medica, and other organisms with data available.
D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents > D011564 - Furocoumarins
(R)-Oxypeucedanin is found in herbs and spices. (R)-Oxypeucedanin is isolated from Angelica glauc
Oxypeucedanin is a furocoumarin derivative isolated from Angelica dahurica. Oxypeucedanin is a selective open-channel blocker, inhibits the hKv1.5 current with an IC50 value of 76 nM.?Oxypeucedanin prolongs cardiac action potential duration (APD), is a potential antiarrhythmic agent for atrial fibrillation[1]. Oxypeucedanin induces cell?apoptosis through inhibition of cancer cell migration[2].
Oxypeucedanin is a furocoumarin derivative isolated from Angelica dahurica. Oxypeucedanin is a selective open-channel blocker, inhibits the hKv1.5 current with an IC50 value of 76 nM.?Oxypeucedanin prolongs cardiac action potential duration (APD), is a potential antiarrhythmic agent for atrial fibrillation[1]. Oxypeucedanin induces cell?apoptosis through inhibition of cancer cell migration[2].

同义名列表

75 个代谢物同义名

7H-Furo[3,2-g][1]benzopyran-7-one, 4-((3,3-dimethyloxiranyl)methoxy)-, (S-)-; 7H-Furo[3,2-g][1]benzopyran-7-one, 4-[(3,3-dimethyl-2-oxiranyl)methoxy]-; 7H-FURO(3,2-G)(1)BENZOPYRAN-7-ONE, 4-((3,3-DIMETHYL-2-OXIRANYL)METHOXY)-; 4-((3,3-DIMETHYL-2-OXIRANYL)METHOXY)-7H-FURO(3,2-G)(1)BENZOPYRAN-7-ONE; 7H-Furo(3,2-g)(1)benzopyran-7-one, 4-((3,3-dimethyloxiranyl)methoxy)-; 4-(2,3-dihydroxy-3-methylbutoxy)-7H-furo(3,2-g)(1)benzopyran-7-one; 4-[[(2S)-3,3-dimethyloxiran-2-yl]methoxy]furo[3,2-g]chromen-7-one; 4-((3,3-Dimethyloxiran-2-yl)methoxy)-7H-furo[3,2-g]chromen-7-one; 4-[(3,3-dimethyloxiran-2-yl)methoxy]-7H-furo[3,2-g]chromen-7-one; 4-[(3,3-Dimethyloxiran-2-yl)methoxy]furo[3,2-g]chromen-7-one; 4-[(3,3-dimethyloxiran-2-yl)methoxy]uro[3,2-g]chromen-7-one; Common sense cockroach and rat preparations; PHOSPHORUS METAL, 99.999\\%, RED; 5-Epoxyisopentenyloxypsoralene; oxypeucadanin, (S)-(-)-isomer; oxypeucadanin, (R)-(+)-isomer; Bonide blue death rat killer; QTAGQHZOLRFCBU-UHFFFAOYSA-N; OXYPEUCEDANIN, (+/-)-; Phosphorus, amorphous; oxypeucadanin hydrate; Phosphine (fumigant); (+/-)-OXYPEUCEDANIN; (+-)-Oxypeucedanin; (RS)-Oxypeucedanin; (R)-Oxypeucedanin; Phosphorus, white; Black phosphorus; Hostaflam RP 614; Novaexcel ST 300; Hostaflam RP 622; Hostaflam RP 602; Hostaflam RP 654; FR-T 2 (Element); Exolit VPK-N 361; Novaexcel ST 140; Novaexcel ST 100; Phosphorus (red); Hishigado NP 10; UNII-AL8MV76MSB; Exolit LPKN 275; Novared 120ufa; Novared 120vfa; Amgard CPC 405; Exolit RP 652; Exolit RP 650; oxypeucadanin; Novaexcel 150; oxypeucedarin; Novaexcel F 5; Novaexcel 140; Exolit RP 654; Nova sol R 20; Novared 120uf; Exolit RP 605; Oxypeucedanin; Phosphorus-31; Novared C 120; Hishigado PL; Hishigado ap; Hishigado CP; Novared 140; Novared 280; Exolit LPKN; Novared F 5; Prangolarin; AL8MV76MSB; Exolit 385; Amgard CPC; Exolit 405; Phosphine; Hishigado; Gas-ex-b; ECO2fume; Rat-nip



数据库引用编号

24 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

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PharmGKB(0)

18 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

  • LuHuan Tang, YuMing Wang, JiaXuan Yang, LeXin Shu, Haoran Ding, Yaqi Yao, Yubo Li. Enantioseparation and determination of oxypeucedanin and its application to a stereoselective analysis in Angelica Dahuricae Radix and pharmacokinetic study of rats. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2022 Sep; 1207(?):123355. doi: 10.1016/j.jchromb.2022.123355. [PMID: 35839628]
  • Ming-Cong Zheng, Wen-Ting Tang, Lu-Lu Yu, Xun-Jia Qian, Jie Ren, Jie-Jia Li, Wei-Wei Rong, Jun-Xu Li, Qing Zhu. Preclinical Pharmacokinetics and Bioavailability of Oxypeucedanin in Rats after Single Intravenous and Oral Administration. Molecules (Basel, Switzerland). 2022 Jun; 27(11):. doi: 10.3390/molecules27113570. [PMID: 35684506]
  • Gulnur Sevin, Elif Alan, Serdar Demir, Gokay Albayrak, Tugce Demiroz, Gunay Yetik-Anacak, Sura Baykan. Comparative evaluation of relaxant effects of three prangos species on mouse corpus cavernosum: Chemical characterization and the relaxant mechanisms of action of P. pabularia and (+)-oxypeucedanin. Journal of ethnopharmacology. 2022 Feb; 284(?):114823. doi: 10.1016/j.jep.2021.114823. [PMID: 34775035]
  • Alice Nguvoko Kiyonga, Gyeongmin Hong, Hyun Su Kim, Young-Ger Suh, Kiwon Jung. Facile and Rapid Isolation of Oxypeucedanin Hydrate and Byakangelicin from Angelica dahurica by Using [Bmim]Tf2N Ionic Liquid. Molecules (Basel, Switzerland). 2021 Feb; 26(4):. doi: 10.3390/molecules26040830. [PMID: 33562719]
  • Baimei Shi, Jianghong Liu, Qian Zhang, Shixiang Wang, Pu Jia, Liujiao Bian, Xiaohui Zheng. Effect of co-administration of Acori Tatarinowii Rhizoma volatile oil on pharmacokinetic fate of xanthotoxol, oxypeucedanin hydrate, and byakangelicin from Angelicae Dahuricae Radix in rat. Journal of separation science. 2020 Jun; 43(12):2349-2362. doi: 10.1002/jssc.201901250. [PMID: 32222035]
  • Jianping Xiao, Ju Wang, Liang Yuan, Li Hao, Deguang Wang. Study on the mechanism and intervention strategy of sunitinib induced nephrotoxicity. European journal of pharmacology. 2019 Dec; 864(?):172709. doi: 10.1016/j.ejphar.2019.172709. [PMID: 31586633]
  • Saeed Tavakoli, Mohammad-Reza Delnavazi, Reza Hadjiaghaee, Saeedeh Jafari-Nodooshan, Farahnaz Khalighi-Sigaroodi, Maryam Akhbari, Abbas Hadjiakhoondi, Narguess Yassa. Bioactive coumarins from the roots and fruits of Ferulago trifida Boiss., an endemic species to Iran. Natural product research. 2018 Nov; 32(22):2724-2728. doi: 10.1080/14786419.2017.1375915. [PMID: 28954543]
  • Wei Dong, Zhen-Gen Liao, Guo-Wei Zhao, Xue-Jing Guan, Jing Zhang, Xin-Li Liang, Ming Yang. Reversal Effect of Oxypeucedanin on P-glycoprotein-mediated Drug Transport. Molecules (Basel, Switzerland). 2018 Jul; 23(8):. doi: 10.3390/molecules23081841. [PMID: 30042338]
  • 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]
  • Yong-Mei Guan, Wei-Feng Zhu, Xue-Jing Guan, Zheng-Gen Liao, Guo-Wei Zhao, Wei Dong, Xin-Li Liang. [Effect investigation of coumarin constituents in Angelica dahurica on pharmacokinetics of docetaxel by LC-MS]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2017 Dec; 42(24):4870-4874. doi: 10.19540/j.cnki.cjcmm.20170919.005. [PMID: 29493160]
  • Amila A Dissanayake, Baram A H Ameen, Muraleedharan G Nair. Lipid Peroxidation and Cyclooxygenase Enzyme Inhibitory Compounds from Prangos haussknechtii. Journal of natural products. 2017 09; 80(9):2472-2477. doi: 10.1021/acs.jnatprod.7b00322. [PMID: 28885836]
  • Jinmei Wang, Linna Peng, Mengjun Shi, Changqin Li, Yan Zhang, Wenyi Kang. Spectrum Effect Relationship and Component Knock-Out in Angelica Dahurica Radix by High Performance Liquid Chromatography-Q Exactive Hybrid Quadrupole-Orbitrap Mass Spectrometer. Molecules (Basel, Switzerland). 2017 Jul; 22(7):. doi: 10.3390/molecules22071231. [PMID: 28754032]
  • Isabella Pfeifer, Adele Murauer, Markus Ganzera. Determination of coumarins in the roots of Angelica dahurica by supercritical fluid chromatography. Journal of pharmaceutical and biomedical analysis. 2016 Sep; 129(?):246-251. doi: 10.1016/j.jpba.2016.07.014. [PMID: 27442886]
  • Seyed Mehdi Razavi, Ameneh Ravansalar, Shahabeddin Mirinejad. The investigation on phytochemicals from Ferulago angulata (Schlecht) Boiss, indigenous to central parts of Iran. Natural product research. 2015; 29(21):2037-40. doi: 10.1080/14786419.2015.1017725. [PMID: 25743037]
  • Gang Fan, Rui Deng, Lin Zhou, Xianli Meng, Tingting Kuang, Xianrong Lai, Jing Zhang, Yi Zhang. Development of a rapid resolution liquid chromatographic method combined with chemometrics for quality control of Angelicae dahuricae radix. Phytochemical analysis : PCA. 2012 Jul; 23(4):299-307. doi: 10.1002/pca.1358. [PMID: 21960288]
  • Joon-Seok Choi, Hyun-Young Shin, Ki-Sub Kwon, Seungwon Shin, Se-Young Choung, Yong-Soo Kwon, Jae-Won Lee, Bong-Hwan Choi, Cheol-Koo Lee. Effects of oxypeucedanin on global gene expression and MAPK signaling pathway in mouse neuroblastoma Neuro-2A cells. Planta medica. 2011 Sep; 77(13):1512-8. doi: 10.1055/s-0030-1270917. [PMID: 21425034]
  • 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]
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  • Ah Yeon Park, So-Young Park, Jaehyun Lee, Mihye Jung, Jinwoong Kim, Sam Sik Kang, Jeong-Rok Youm, Sang Beom Han. Simultaneous determination of five coumarins in Angelicae dahuricae Radix by HPLC/UV and LC-ESI-MS/MS. Biomedical chromatography : BMC. 2009 Oct; 23(10):1034-43. doi: 10.1002/bmc.1219. [PMID: 19402180]
  • Jaroslaw Widelski, Milena Popova, Konstantia Graikou, Kazimierz Glowniak, Ioanna Chinou. Coumarins from Angelica lucida L.--antibacterial activities. Molecules (Basel, Switzerland). 2009 Jul; 14(8):2729-34. doi: 10.3390/molecules14082729. [PMID: 19701119]
  • Tae Jin Kang, Sook Yeon Lee, Rana P Singh, Rajesh Agarwal, Dong Sool Yim. Anti-tumor activity of oxypeucedanin from Ostericum koreanum against human prostate carcinoma DU145 cells. Acta oncologica (Stockholm, Sweden). 2009; 48(6):895-900. doi: 10.1080/02841860902824925. [PMID: 19322700]
  • Ying Xie, Yi Chen, Mei Lin, Jun Wen, Guorong Fan, Yutian Wu. High-performance liquid chromatographic method for the determination and pharmacokinetic study of oxypeucedanin hydrate and byak-angelicin after oral administration of Angelica dahurica extracts in mongrel dog plasma. Journal of pharmaceutical and biomedical analysis. 2007 May; 44(1):166-72. doi: 10.1016/j.jpba.2007.02.002. [PMID: 17344014]
  • Wolfgang Feger, Herbert Brandauer, Paulina Gabris, Herta Ziegler. Nonvolatiles of commercial lime and grapefruit oils separated by high-speed countercurrent chromatography. Journal of agricultural and food chemistry. 2006 Mar; 54(6):2242-52. doi: 10.1021/jf052267t. [PMID: 16536603]
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  • Mengyue Wang, Minru Jia, Yuying Ma, Guihua Jiang, Shengwu Tang, Lu Xia. [Determination of coumarins content in Radix Angelicae dahuricae by HPLC and UV]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2004 Nov; 27(11):826-8. doi: . [PMID: 15810589]
  • Yong Yook Lee, Sanghyun Lee, Jing Ling Jin, Hye Sook Yun-Choi. Platelet anti-aggregatory effects of coumarins from the roots of Angelica genuflexa and A. gigas. Archives of pharmacal research. 2003 Sep; 26(9):723-6. doi: 10.1007/bf02976681. [PMID: 14560920]
  • Hyuncheol Oh, Ho-Sub Lee, Taewan Kim, Kyu-Yun Chai, Hun-Taeg Chung, Tae-Oh Kwon, Jung-Yang Jun, Ok-Sam Jeong, Youn-Chul Kim, Young-Gab Yun. Furocoumarins from Angelica dahurica with hepatoprotective activity on tacrine-induced cytotoxicity in Hep G2 cells. Planta medica. 2002 May; 68(5):463-4. doi: 10.1055/s-2002-32075. [PMID: 12058329]
  • Eun-Kyoung Seo, Kyeong Ho Kim, Min Ki Kim, Myung-Haing Cho, EunWook Choi, KiNam Kim, Woongchon Mar. Inhibitors of 5alpha -reductase type I in LNCaP cells from the roots of Angelica koreana. Planta medica. 2002 Feb; 68(2):162-3. doi: 10.1055/s-2002-20258. [PMID: 11859469]
  • K Ishihara, M Fukutake, T Asano, Y Mizuhara, Y Wakui, T Yanagisawa, H Kamei, S Ohmori, M Kitada. Simultaneous determination of byak-angelicin and oxypeucedanin hydrate in rat plasma by column-switching high-performance liquid chromatography with ultraviolet detection. Journal of chromatography. B, Biomedical sciences and applications. 2001 Apr; 753(2):309-14. doi: 10.1016/s0378-4347(00)00569-7. [PMID: 11334345]
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  • S X Deng. [Pharmacological studies on oxypeucedanin]. Zhong yao tong bao (Beijing, China : 1981). 1985 Dec; 10(12):36-8. doi: ". [PMID: 2940023]
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