(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 (286.0841)
中文名称: 氧化前胡素
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 67.47%

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

76 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; Oxypeucedanin



数据库引用编号

27 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。

Reactome(0)

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。

亚细胞结构定位 关联基因列表
Cytoplasm 15 ABCB1, BCL2, CASP3, CCNB1, CDC25C, CYP2B6, CYP2D6, CYP3A4, MAPK1, MARVELD1, MDM2, PIK3CA, PRPF19, PTGS2, TYR
Peripheral membrane protein 3 ACHE, CYP2B6, PTGS2
Endoplasmic reticulum membrane 5 BCL2, CYP2B6, CYP2D6, CYP3A4, PTGS2
Nucleus 10 ACHE, BCL2, CASP3, CCNB1, CDC25C, MAPK1, MARVELD1, MDM2, MPO, PRPF19
cytosol 7 BCL2, CASP3, CCNB1, CDC25C, MAPK1, MDM2, PIK3CA
centrosome 2 CCNB1, MAPK1
nucleoplasm 7 CASP3, CCNB1, CDC25C, MAPK1, MDM2, MPO, PRPF19
Cell membrane 5 ABCB1, ACHE, CLDN3, MARVELD1, TNF
lamellipodium 1 PIK3CA
Multi-pass membrane protein 3 ABCB1, CLDN3, MARVELD1
Synapse 2 ACHE, MAPK1
cell surface 3 ABCB1, ACHE, TNF
glutamatergic synapse 2 CASP3, MDM2
Golgi apparatus 2 ACHE, MAPK1
neuromuscular junction 1 ACHE
neuronal cell body 2 CASP3, TNF
Lysosome 2 MPO, TYR
plasma membrane 8 ABCB1, ACHE, CLDN3, MAPK1, MARVELD1, MDM2, PIK3CA, TNF
Membrane 9 ABCB1, ACHE, BCL2, CCNB1, CLDN3, CYP2D6, CYP3A4, MARVELD1, PRPF19
apical plasma membrane 1 ABCB1
caveola 2 MAPK1, PTGS2
extracellular exosome 2 ABCB1, MPO
endoplasmic reticulum 3 BCL2, CYP2D6, PTGS2
extracellular space 3 ACHE, MPO, TNF
perinuclear region of cytoplasm 4 ACHE, CDC25C, PIK3CA, TYR
Cell junction, tight junction 1 CLDN3
apicolateral plasma membrane 1 CLDN3
bicellular tight junction 1 CLDN3
intercalated disc 1 PIK3CA
mitochondrion 3 BCL2, CYP2D6, MAPK1
protein-containing complex 4 BCL2, CLDN3, MDM2, PTGS2
intracellular membrane-bounded organelle 5 CYP2B6, CYP2D6, CYP3A4, MPO, TYR
Microsome membrane 4 CYP2B6, CYP2D6, CYP3A4, PTGS2
postsynaptic density 2 CASP3, MDM2
Single-pass type I membrane protein 1 TYR
Secreted 1 ACHE
extracellular region 4 ACHE, MAPK1, MPO, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 2 BCL2, CYP2D6
mitochondrial outer membrane 1 BCL2
mitochondrial matrix 1 CCNB1
Extracellular side 1 ACHE
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 MAPK1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 TNF
nucleolus 1 MDM2
Melanosome membrane 1 TYR
Early endosome 1 MAPK1
cell-cell junction 1 CLDN3
Golgi-associated vesicle 1 TYR
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Apical cell membrane 1 ABCB1
Membrane raft 1 TNF
pore complex 1 BCL2
Cell junction, focal adhesion 1 MAPK1
Cytoplasm, cytoskeleton 1 MARVELD1
Cytoplasm, cytoskeleton, spindle 2 MAPK1, PRPF19
focal adhesion 1 MAPK1
spindle 2 MAPK1, PRPF19
basement membrane 1 ACHE
mitochondrial intermembrane space 1 CDC25C
secretory granule 1 MPO
lateral plasma membrane 1 CLDN3
nuclear speck 1 PRPF19
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Late endosome 1 MAPK1
neuron projection 1 PTGS2
phagocytic cup 1 TNF
mitotic spindle 1 MAPK1
cytoskeleton 2 MAPK1, MARVELD1
Nucleus, nucleolus 1 MDM2
spindle pole 1 CCNB1
Lipid-anchor, GPI-anchor 1 ACHE
spliceosomal complex 1 PRPF19
site of double-strand break 1 PRPF19
Lipid droplet 1 PRPF19
Membrane, caveola 1 MAPK1
Nucleus, nucleoplasm 2 MDM2, PRPF19
Melanosome 1 TYR
side of membrane 1 ACHE
myelin sheath 1 BCL2
pseudopodium 1 MAPK1
azurophil granule 1 MPO
ficolin-1-rich granule lumen 1 MAPK1
endoplasmic reticulum lumen 2 MAPK1, PTGS2
transcription repressor complex 1 MDM2
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
endocytic vesicle membrane 1 MDM2
tight junction 1 CLDN3
azurophil granule lumen 2 MAPK1, MPO
outer kinetochore 1 CCNB1
phagocytic vesicle lumen 1 MPO
synaptic cleft 1 ACHE
U2-type catalytic step 1 spliceosome 1 PRPF19
external side of apical plasma membrane 1 ABCB1
death-inducing signaling complex 1 CASP3
apical junction complex 1 CLDN3
catalytic step 2 spliceosome 1 PRPF19
Prp19 complex 1 PRPF19
U2-type catalytic step 2 spliceosome 1 PRPF19
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
cyclin B1-CDK1 complex 1 CCNB1
BAD-BCL-2 complex 1 BCL2
[Isoform H]: Cell membrane 1 ACHE
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


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]
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  • 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]
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  • 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]
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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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