Xanthotoxol (BioDeep_00000000359)

 

Secondary id: BioDeep_00000861007

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


9-hydroxy-7H-furo[3,2-g]chromen-7-one

化学式: C11H6O4 (202.0266)
中文名称: 花椒毒酚;8-羟基补骨脂素, 花椒毒醇, 黄嘌呤醇, 花椒毒酚
谱图信息: 最多检出来源 Homo sapiens(otcml) 39.25%

Reviewed

Last reviewed on 2024-10-24.

Cite this Page

Xanthotoxol. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/xanthotoxol (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000000359). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: c12c(c(c3c(c1)ccc(=O)o3)O)occ2
InChI: InChI=1S/C11H6O4/c12-8-2-1-6-5-7-3-4-14-10(7)9(13)11(6)15-8/h1-5,13H

描述信息

Isolated from Aegle marmelos (bael fruit), Angelica archangelica (angelica) and the seeds of Pastinaca sativa (parsnip). Xanthotoxol is found in many foods, some of which are fats and oils, green vegetables, herbs and spices, and fig.
Xanthotoxol is found in fats and oils. Xanthotoxol is isolated from Aegle marmelos (bael fruit), Angelica archangelica (angelica) and the seeds of Pastinaca sativa (parsnip
Xanthotoxol is an 8-hydroxyfurocoumarin.
Xanthotoxol is a natural product found in Citrus canaliculata, Prangos tschimganica, and other organisms with data available.
D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents > D011564 - Furocoumarins
Xanthotoxol (8-Hydroxypsoralen) is a biologically active linear furocoumarin, shows strong pharmacological activities as anti-inflammatory, antioxidant, 5-HT antagonistic, and neuroprotective effects.
Xanthotoxol (8-Hydroxypsoralen) It is a kind of fragrant bean substance, and it is a CYP450 inhibitor. Xanthotoxol has anti-inflammatory, anti-inflammatory, and 5-HT antagonistic and protective effects. Xanthotoxol inhibited CYP3A4 sum CYP1A2 IC50s separation 7.43 μM sum 27.82 μM. Xanthotoxol can pass through MAPK and NF-κB, inhibiting inflammation[1][2][3][4].
Xanthotoxol (8-Hydroxypsoralen) is a biologically active linear furocoumarin, shows strong pharmacological activities as anti-inflammatory, antioxidant, 5-HT antagonistic, and neuroprotective effects.

同义名列表

40 个代谢物同义名

2-Propenoic acid, 3-(6,7-dihydroxy-5-benzofuranyl)-, .delta.-lactone; InChI=1/C11H6O4/c12-8-2-1-6-5-7-3-4-14-10(7)9(13)11(6)15-8/h1-5,13; 6-(3,4-Dichlorophenyl)-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole; 2-Propenoic acid,7-dihydroxy-5-benzofuranyl)-, .delta.-lactone; 5-Benzofuranacrylic acid, 6,7-dihydroxy-, .delta.-lactone; 5-Benzofuranacrylic acid, 6,7-dihydroxy-, gamma-lactone; 6,7-Dihydroxy-5-benzofuranacrylic acid gamma-lactone; 9-Hydroxy-7H-furo[3,2-g][1]benzopyran-7-one, 9CI; 7H-Furo(3,2-g)(1)benzopyran-7-one, 9-hydroxy-; 7H-Furo[3,2-g][1]benzopyran-7-one, 9-hydroxy-; 5-19-06-00014 (Beilstein Handbook Reference); 7H-Furo[3,2-g][1]benzopyran-7-one,9-hydroxy-; 9-Hydroxy-7H-furo(3,2-g)(1)benzopyran-7-one; 9-Hydroxy-7H-furo[3,2-g][1]benzopyran-7-one; 9-Hydroxy-7H-furo[3,2-g]chromen-7-one #; 9-hydroxy-2H-furo[3,2-g]chromen-2-one; 9-Hydroxy-7H-furo[3,2-g]chromen-7-one; 9-hydroxy-furo[3,2-g]chromen-7-one; 9-hydroxyfuro[3,2-g]chromen-7-one; 8-hydroxyfuranocoumarins; an 8-hydroxyfurocoumarin; 8-Hydroxyfuranocoumarin; Xanthotol; Xanthotoxol; 8-hydroxyfurocoumarins; 8-hydroxyfurocoumarin; 7H-Furo[3, 9-hydroxy-; Psoralen, 8-hydroxy-; 8-Hydroxyanthotoxol; 8-hydroxy-psoralen; 8-Hydroxypsoralene; Xanthotoxol (6CI); 8-hydroxypsoralen; UNII-8RL486L8A5; Xanthotoxol; 8RL486L8A5; Xanthoxol; XANTHOTOL; Demethylmethoxsalen; Xanthotoxol; Xanthotoxol



数据库引用编号

20 个数据库交叉引用编号

分类词条

相关代谢途径

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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)

106 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 7 AKT1, CYP3A4, GRP, MAPK14, PIK3CA, PRPF19, PTGS2
Peripheral membrane protein 2 GORASP1, PTGS2
Endoplasmic reticulum membrane 9 CYP1A2, CYP3A4, PTGS2, UGT1A1, UGT1A10, UGT1A3, UGT1A6, UGT1A8, UGT2B7
Nucleus 3 AKT1, MAPK14, PRPF19
cytosol 3 AKT1, MAPK14, PIK3CA
nucleoplasm 3 AKT1, MAPK14, PRPF19
Cell membrane 3 AKT1, GRPR, TNF
Cytoplasmic side 1 GORASP1
lamellipodium 2 AKT1, PIK3CA
Multi-pass membrane protein 2 CACNA1I, GRPR
Golgi apparatus membrane 1 GORASP1
cell cortex 1 AKT1
cell surface 2 ICAM1, TNF
glutamatergic synapse 2 AKT1, MAPK14
Golgi apparatus 1 GORASP1
Golgi membrane 1 GORASP1
neuronal cell body 1 TNF
postsynapse 1 AKT1
plasma membrane 7 AKT1, CACNA1I, GRPR, ICAM1, PIK3CA, TNF, UGT1A1
Membrane 11 AKT1, CACNA1I, CYP3A4, ICAM1, PRPF19, UGT1A1, UGT1A10, UGT1A3, UGT1A6, UGT1A8, UGT2B7
caveola 1 PTGS2
extracellular exosome 1 ICAM1
endoplasmic reticulum 6 PTGS2, UGT1A1, UGT1A10, UGT1A3, UGT1A6, UGT1A8
extracellular space 3 GRP, ICAM1, TNF
perinuclear region of cytoplasm 2 PIK3CA, UGT1A1
intercalated disc 1 PIK3CA
mitochondrion 1 MAPK14
protein-containing complex 2 AKT1, PTGS2
intracellular membrane-bounded organelle 3 CYP1A2, CYP3A4, UGT1A6
Microsome membrane 3 CYP1A2, CYP3A4, PTGS2
Single-pass type I membrane protein 1 ICAM1
Secreted 1 GRP
extracellular region 4 DNAH9, GRP, MAPK14, TNF
Single-pass membrane protein 6 UGT1A1, UGT1A10, UGT1A3, UGT1A6, UGT1A8, UGT2B7
motile cilium 1 DNAH9
external side of plasma membrane 2 ICAM1, TNF
Secreted, extracellular space, extracellular matrix 1 GRP
microtubule cytoskeleton 1 AKT1
cell-cell junction 1 AKT1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 AKT1
Cytoplasm, perinuclear region 1 UGT1A1
Membrane raft 2 ICAM1, TNF
Cytoplasm, cytoskeleton, spindle 1 PRPF19
focal adhesion 1 ICAM1
microtubule 1 DNAH9
spindle 2 AKT1, PRPF19
cis-Golgi network 1 GORASP1
extracellular matrix 1 GRP
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
collagen-containing extracellular matrix 1 ICAM1
axoneme 1 DNAH9
nuclear speck 2 MAPK14, PRPF19
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Cell projection, neuron projection 1 GRP
neuron projection 2 GRP, PTGS2
ciliary basal body 1 AKT1
phagocytic cup 1 TNF
spindle pole 1 MAPK14
Cytoplasm, cytoskeleton, cilium axoneme 1 DNAH9
spliceosomal complex 1 PRPF19
site of double-strand break 1 PRPF19
Lipid droplet 1 PRPF19
Nucleus, nucleoplasm 1 PRPF19
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 2 GRP, MAPK14
endoplasmic reticulum lumen 1 PTGS2
voltage-gated calcium channel complex 1 CACNA1I
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GORASP1
immunological synapse 1 ICAM1
neuronal dense core vesicle 1 GRP
9+2 motile cilium 1 DNAH9
dynein complex 1 DNAH9
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
U2-type catalytic step 1 spliceosome 1 PRPF19
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
Cytoplasmic vesicle, secretory vesicle lumen 1 GRP
endoplasmic reticulum chaperone complex 1 UGT1A1
cytochrome complex 1 UGT1A1
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
outer dynein arm 1 DNAH9
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
distal portion of axoneme 1 DNAH9


文献列表

  • Xinyi Gao, Yayue Yang, Jianyu Zhu, Yuxin Zhang, Chenghao Wang, Zhifei Wang, Wenli Mi, Lixia Du. Xanthotoxol relieves itch in mice via suppressing spinal GRP/GRPR signaling. European journal of pharmacology. 2023 Oct; ?(?):176147. doi: 10.1016/j.ejphar.2023.176147. [PMID: 37871763]
  • L Zhu, S Sun, W Wu, Y Zhang, C Lin, L Ji. Xanthotoxol alleviates secondary brain injury after intracerebral hemorrhage by inhibiting microglia-mediated neuroinflammation and oxidative stress. Neuro-Chirurgie. 2023 Mar; 69(3):101426. doi: 10.1016/j.neuchi.2023.101426. [PMID: 36921390]
  • Xian Lin, Jingfeng Liu, Yujiao Zou, Cheng Tao, Jian Chen. Xanthotoxol suppresses non-small cell lung cancer progression and might improve patients' prognosis. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2022 Oct; 105(?):154364. doi: 10.1016/j.phymed.2022.154364. [PMID: 35932608]
  • 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]
  • Guiyuan He, Johanna Troberg, Xia Lv, Yang-Liu Xia, Liang-Liang Zhu, Jing Ning, Guang-Bo Ge, Moshe Finel, Ling Yang. Identification and characterization of human UDP-glucuronosyltransferases responsible for xanthotoxol glucuronidation. Xenobiotica; the fate of foreign compounds in biological systems. 2018 Feb; 48(2):109-116. doi: 10.1080/00498254.2017.1283719. [PMID: 28689454]
  • Lien Ngo, Phuong Tran, Seong-Ho Ham, Jung-Hee Cho, Hea-Young Cho, Yong-Bok Lee. Simultaneous determination of imperatorin and its metabolite xanthotoxol in rat plasma and urine by LC-MS/MS and its application to pharmacokinetic studies. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 Feb; 1044-1045(?):30-38. doi: 10.1016/j.jchromb.2016.12.037. [PMID: 28064067]
  • Vamshi K Manda, Bharathi Avula, Amar G Chittiboyina, Ikhlas A Khan, Larry A Walker, Shabana I Khan. Inhibition of CYP3A4 and CYP1A2 by Aegle marmelos and its constituents. Xenobiotica; the fate of foreign compounds in biological systems. 2016; 46(2):117-25. doi: 10.3109/00498254.2015.1053006. [PMID: 26247834]
  • Juan Zhang, Min Zhang, Shan Fu, Tao Li, Shuang Wang, Minmin Zhao, Weijing Ding, Chunying Wang, Qiao Wang. Simultaneous determination of imperatorin and its metabolite xanthotoxol in rat plasma by using HPLC-ESI-MS coupled with hollow fiber liquid phase microextraction. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Jan; 945-946(?):185-92. doi: 10.1016/j.jchromb.2013.11.050. [PMID: 24342512]
  • Stavros E Bariamis, Marilena Marin, Constantinos M Athanassopoulos, Christos Kontogiorgis, Zinovia Tsimali, Dionissios Papaioannou, Giovanni Sindona, Giovanni Romeo, Konstantinos Avgoustakis, Dimitra Hadjipavlou-Litina. Syntheses and evaluation of the antioxidant activity of novel methoxypsoralen derivatives. European journal of medicinal chemistry. 2013 Feb; 60(?):155-69. doi: 10.1016/j.ejmech.2012.11.043. [PMID: 23291118]
  • Zhao Chen, Jiajing Wang, Danxia Chen, Guorong Fan, Yutian Wu. Sodium desoxycholate-assisted capillary electrochromatography with methacrylate ester-based monolithic column on fast separation and determination of coumarin analogs in Angelica dahurica extract. Electrophoresis. 2012 Sep; 33(18):2884-91. doi: 10.1002/elps.201200120. [PMID: 22930555]
  • Aihong Zhao, Xiuwei Yang, Xinbao Yang, Jianxun Liu, Qiuling Wang, Wenquan Wang. [A new natural product from root of Angelica dahurica cv. Qibaizhi]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2012 Aug; 37(16):2400-7. doi: . [PMID: 23234138]
  • Amani S Awaad, Nabilah A Al-Jaber, Gamal A Soliman, Mounerah R Al-Outhman, Mohamed E Zain, John E Moses, Reham M El-Meligy. New biological activities of Casimiroa edulis leaf extract and isolated compounds. Phytotherapy research : PTR. 2012 Mar; 26(3):452-7. doi: 10.1002/ptr.3690. [PMID: 22173732]
  • Man Liu, Xiaowei Shi, Wei Yang, Songchen Liu, Na Wang, Rui Shi, Shi Qiao, Qiao Wang, Yongli Wang. Quantitative analysis of nine coumarins in rat urine and bile after oral administration of Radix Glehniae extract by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry. Biomedical chromatography : BMC. 2011 Jul; 25(7):783-93. doi: 10.1002/bmc.1517. [PMID: 20878664]
  • 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]
  • Winnie Lai Ting Kan, Bin Ma, Ge Lin. Sulfur fumigation processing of traditional chinese medicinal herbs: beneficial or detrimental?. Frontiers in pharmacology. 2011; 2(?):84. doi: 10.3389/fphar.2011.00084. [PMID: 22207851]
  • Bang-Le Zhang, Cheng-Qi Fan, Lei Dong, Fang-Dao Wang, Jian-Min Yue. Structural modification of a specific antimicrobial lead against Helicobacter pylori discovered from traditional Chinese medicine and a structure-activity relationship study. European journal of medicinal chemistry. 2010 Nov; 45(11):5258-64. doi: 10.1016/j.ejmech.2010.08.045. [PMID: 20832915]
  • Ying Xie, Weiquan Zhao, Tingting Zhou, Guorong Fan, Yutian Wu. An efficient strategy based on MAE, HPLC-DAD-ESI-MS/MS and 2D-prep-HPLC-DAD for the rapid extraction, separation, identification and purification of five active coumarin components from Radix Angelicae Dahuricae. Phytochemical analysis : PCA. 2010 Sep; 21(5):473-82. doi: 10.1002/pca.1222. [PMID: 20931624]
  • Guo-Qang Liu, Jing Dong, Hong Wang, Yuki Hashi, Shi-Zhong Chen. Differentiation of four pairs of furocoumarin isomers by electrospray ionization tandem mass spectrometry. European journal of mass spectrometry (Chichester, England). 2010; 16(2):215-20. doi: 10.1255/ejms.1070. [PMID: 20212330]
  • K Nagendra Prasad, Lye Yee Chew, Hock Eng Khoo, Kin Weng Kong, Azrina Azlan, Amin Ismail. Antioxidant capacities of peel, pulp, and seed fractions of Canarium odontophyllum Miq. fruit. Journal of biomedicine & biotechnology. 2010; 2010(?):. doi: 10.1155/2010/871379. [PMID: 20936182]
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  • 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]
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