Bromadiolone (BioDeep_00000001766)

   


代谢物信息卡片


Bromadiolone

化学式: C30H23BrO4 (526.078)
中文名称: 溴敌隆
谱图信息: 最多检出来源 Viridiplantae(plant) 2.44%

分子结构信息

SMILES: C(C=1C(c(c5)cccc5)CC(O)c(c4)ccc(c4)c(c3)ccc(Br)c3)(=O)Oc(c2)c(ccc2)C1O
InChI: InChI=1S/C30H23BrO4/c31-23-16-14-20(15-17-23)19-10-12-22(13-11-19)26(32)18-25(21-6-2-1-3-7-21)28-29(33)24-8-4-5-9-27(24)35-30(28)34/h1-17,25-26,32-33H,18H2

描述信息

D006401 - Hematologic Agents > D000925 - Anticoagulants > D015110 - 4-Hydroxycoumarins
D010575 - Pesticides > D012378 - Rodenticides
D016573 - Agrochemicals
CONFIDENCE standard compound; EAWAG_UCHEM_ID 3656

同义名列表

2 个代谢物同义名

Bromadiolone; Bromadiolone



数据库引用编号

23 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)

0 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 9 ALB, CASP3, CAT, CYP2E1, CYP3A4, EXOSC6, MYL2, NQO1, PRPH
Peripheral membrane protein 4 ACHE, CYP1B1, CYP2E1, MBP
Endosome membrane 1 TF
Endoplasmic reticulum membrane 6 CALU, CYP1B1, CYP2E1, CYP3A4, HSP90B1, VKORC1
Nucleus 7 ACHE, ALB, CASP3, EXOSC6, HSP90B1, MBP, NQO1
cytosol 9 ALB, CASP3, CAT, EXOSC6, GSR, HSP90B1, MBP, MYL2, NQO1
dendrite 1 NQO1
centrosome 1 ALB
nucleoplasm 2 CASP3, EXOSC6
Cell membrane 2 ACHE, CASR
Cytoplasmic side 1 MBP
Cell projection, axon 1 PRPH
Multi-pass membrane protein 4 CASR, MT-CYB, PRPH, VKORC1
Synapse 3 ACHE, MBP, NQO1
cell surface 4 ACHE, CASR, MBP, TF
glutamatergic synapse 2 CASP3, CASR
Golgi apparatus 3 ACHE, ALB, CALU
mitochondrial inner membrane 2 CYP2E1, MT-CYB
neuromuscular junction 1 ACHE
neuronal cell body 4 CASP3, CASR, MBP, NQO1
presynaptic membrane 1 CASR
smooth endoplasmic reticulum 1 HSP90B1
Cytoplasm, cytosol 1 NQO1
plasma membrane 6 ACHE, CASR, F7, MBP, PRPH, TF
Membrane 10 ACHE, CALU, CASR, CAT, CYP1B1, CYP3A4, HSP90B1, MT-CYB, NQO1, PRPH
apical plasma membrane 2 CASR, TF
axon 1 PRPH
basolateral plasma membrane 1 CASR
extracellular exosome 7 ALB, CAT, GSR, HSP90B1, MBP, PRPH, TF
endoplasmic reticulum 4 ALB, CALU, HSP90B1, VKORC1
extracellular space 4 ACHE, ALB, F7, TF
perinuclear region of cytoplasm 3 ACHE, HSP90B1, TF
mitochondrion 4 CAT, CYP1B1, GSR, MT-CYB
protein-containing complex 4 ALB, CAT, HSP90B1, MBP
intracellular membrane-bounded organelle 4 CAT, CYP1B1, CYP2E1, CYP3A4
Microsome membrane 3 CYP1B1, CYP2E1, CYP3A4
postsynaptic density 1 CASP3
Secreted 5 ACHE, ALB, CALU, F7, TF
extracellular region 8 ACHE, ALB, CALU, CAT, F7, HSP90B1, MBP, TF
basal part of cell 1 TF
mitochondrial matrix 2 CAT, GSR
Extracellular side 1 ACHE
anchoring junction 1 ALB
photoreceptor inner segment 1 PRPH
photoreceptor outer segment 1 PRPH
external side of plasma membrane 1 GSR
perikaryon 1 PRPH
cytoplasmic vesicle 1 TF
nucleolus 1 EXOSC6
midbody 1 HSP90B1
Early endosome 1 TF
clathrin-coated pit 1 TF
recycling endosome 1 TF
vesicle 2 F7, TF
Mitochondrion inner membrane 2 CYP2E1, MT-CYB
Cytoplasm, cytoskeleton 1 PRPH
focal adhesion 2 CAT, HSP90B1
Peroxisome 1 CAT
basement membrane 1 ACHE
myofibril 1 MYL2
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 3 F7, HSP90B1, MBP
intermediate filament 1 PRPH
Late endosome 1 TF
sarcomere 1 MYL2
ciliary basal body 1 ALB
cell periphery 1 MBP
cytoskeleton 1 MYL2
[Isoform 3]: Nucleus 1 MBP
centriole 1 ALB
Cell projection, cilium, photoreceptor outer segment 1 PRPH
Nucleus, nucleolus 1 EXOSC6
spindle pole 1 ALB
blood microparticle 2 ALB, TF
Lipid-anchor, GPI-anchor 1 ACHE
myosin complex 1 MYL2
Melanosome 2 CALU, HSP90B1
side of membrane 1 ACHE
myelin sheath 1 MBP
sperm plasma membrane 1 HSP90B1
basal plasma membrane 1 TF
cytoplasmic exosome (RNase complex) 1 EXOSC6
ficolin-1-rich granule lumen 2 CAT, MBP
secretory granule lumen 2 CAT, TF
HFE-transferrin receptor complex 1 TF
Golgi lumen 1 F7
endoplasmic reticulum lumen 5 ALB, CALU, F7, HSP90B1, TF
platelet alpha granule lumen 1 ALB
axon terminus 1 CASR
endocytic vesicle 1 TF
transport vesicle 1 MBP
clathrin-coated endocytic vesicle membrane 1 TF
respiratory chain complex III 1 MT-CYB
Sarcoplasmic reticulum lumen 2 CALU, HSP90B1
A band 1 MYL2
synaptic cleft 1 ACHE
death-inducing signaling complex 1 CASP3
exosome (RNase complex) 1 EXOSC6
vesicle coat 1 TF
type III intermediate filament 1 PRPH
endocytic vesicle lumen 1 HSP90B1
cardiac myofibril 1 MYL2
compact myelin 1 MBP
internode region of axon 1 MBP
catalase complex 1 CAT
endoplasmic reticulum chaperone complex 1 HSP90B1
serine-type peptidase complex 1 F7
Cytoplasm, myofibril, sarcomere, A band 1 MYL2
[Bone marrow proteoglycan]: Secreted 1 MBP
[Isoform H]: Cell membrane 1 ACHE
ciliary transition fiber 1 ALB
Myelin membrane 1 MBP
dense body 1 TF
nuclear exosome (RNase complex) 1 EXOSC6
nucleolar exosome (RNase complex) 1 EXOSC6


文献列表

  • Javier Fernandez-de-Simon, Francisco Díaz-Ruiz, Daniel Jareño, Julio C Domínguez, José F Lima-Barbero, Noelia de Diego, Ana E Santamaría, Marta Herrero-Villar, Pablo R Camarero, Pedro P Olea, Jesús T García, Rafael Mateo, Javier Viñuela. Weasel exposure to the anticoagulant rodenticide bromadiolone in agrarian landscapes of southwestern Europe. The Science of the total environment. 2022 Sep; 838(Pt 1):155914. doi: 10.1016/j.scitotenv.2022.155914. [PMID: 35569667]
  • Thomas Chetot, Marjorie Mouette-Bonnet, Shira Taufana, Isabelle Fourel, Sebastien Lefebvre, Etienne Benoit, Virginie Lattard. Differences in teratogenicity of some vitamin K antagonist substances used as human therapeutic or rodenticide are due to major differences in their fate after an oral administration. Toxicology letters. 2020 Oct; 333(?):71-79. doi: 10.1016/j.toxlet.2020.07.034. [PMID: 32768651]
  • Douglas L Feinstein, Daniel G Nosal, Swetha Ramanathan, Jifang Zhou, Luying Chen, Ronald C Hershow, Richard B van Breemen, Erik Wright, John W Hafner, Israel Rubinstein. Effects of vitamin K1 treatment on plasma concentrations of long-acting anticoagulant rodenticide enantiomers following inhalation of contaminated synthetic cannabinoids. Clinical toxicology (Philadelphia, Pa.). 2020 07; 58(7):716-724. doi: 10.1080/15563650.2019.1687903. [PMID: 31736367]
  • S F Jiang, Y T Zhang, J Sun, J Zhang, H S Zhang. [Study on the pharmacokinetics of bromadiolone in oral poisoning rabbits]. Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases. 2020 Jun; 38(6):444-446. doi: 10.3760/cma.j.cn121094-20190927-00395. [PMID: 32629576]
  • Kristin Opdal Seljetun, Vigdis Vindenes, Elisabeth Leere Øiestad, Gerd-Wenche Brochmann, Elin Eliassen, Lars Moe. Determination of anticoagulant rodenticides in faeces of exposed dogs and in a healthy dog population. Acta veterinaria Scandinavica. 2020 Jun; 62(1):30. doi: 10.1186/s13028-020-00531-5. [PMID: 32546243]
  • Daniel G Nosal, Douglas L Feinstein, Luying Chen, Richard B van Breemen. Separation and Quantification of Superwarfarin Rodenticide Diastereomers-Bromadiolone, Difenacoum, Flocoumafen, Brodifacoum, and Difethialone-in Human Plasma. Journal of AOAC International. 2020 Jun; 103(3):770-778. doi: 10.1093/jaoacint/qsaa007. [PMID: 33241367]
  • Wei Zuo, Xiao Zhang, Jian-Bo Chang, Wen-Bin Ma, Jun-Ji Wei. Bromadiolone poisoning leading to subarachnoid haemorrhage: A case report and review of the literature. Journal of clinical pharmacy and therapeutics. 2019 Dec; 44(6):958-962. doi: 10.1111/jcpt.13005. [PMID: 31556967]
  • Javier Fernandez-de-Simon, Michael Coeurdassier, Geoffroy Couval, Isabelle Fourel, Patrick Giraudoux. Do bromadiolone treatments to control grassland water voles (Arvicola scherman) affect small mustelid abundance?. Pest management science. 2019 Apr; 75(4):900-907. doi: 10.1002/ps.5194. [PMID: 30175431]
  • Amar H Kelkar, Nichole A Smith, Annia Martial, Harsha Moole, Michael D Tarantino, Jonathan C Roberts. An Outbreak of Synthetic Cannabinoid-Associated Coagulopathy in Illinois. The New England journal of medicine. 2018 09; 379(13):1216-1223. doi: 10.1056/nejmoa1807652. [PMID: 30280655]
  • Isabelle Fourel, Mickaël Sage, Etienne Benoit, Virginie Lattard. Liver and fecal samples suggest differential exposure of red fox (Vulpes vulpes) to trans- and cis-bromadiolone in areas from France treated with plant protection products. The Science of the total environment. 2018 May; 622-623(?):924-929. doi: 10.1016/j.scitotenv.2017.12.053. [PMID: 29227943]
  • Veronika Doubková, Petr Maršálek, Vladimír Večerek. The rapid determination of bromadiolone in liver and blood plasma by in-injector pyrolysis gas chromatography - Ion trap tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 Dec; 1070(?):117-120. doi: 10.1016/j.jchromb.2017.10.027. [PMID: 29107732]
  • Mingsheng Ma, Mengqi Zhang, Xiaoyan Tang, Zhenghong Li. Massive neonatal intracranial hemorrhage caused by bromadiolone: A case report. Medicine. 2017 Nov; 96(45):e8506. doi: 10.1097/md.0000000000008506. [PMID: 29137047]
  • Tanja Šćepović, Goran Jokić, Alexandra Esther, Dragan Kataranovski, Petar Vukša, Suzana Đedović, Marina Vukša. VKOR variant and sex are the main influencing factors on bromadiolone tolerance of the house mouse (Mus musculus L.). Pest management science. 2016 Mar; 72(3):574-9. doi: 10.1002/ps.4027. [PMID: 25904314]
  • Jing Liu, Kang Xiong, Xiaoqing Ye, Jianyun Zhang, Ye Yang, Li Ji. Toxicity and bioaccumulation of bromadiolone to earthworm Eisenia fetida. Chemosphere. 2015 Sep; 135(?):250-6. doi: 10.1016/j.chemosphere.2015.04.058. [PMID: 25965004]
  • Karel Ondracek, Hana Bandouchova, Klara Hilscherova, Veronika Kovacova, Petr Linhart, Miroslava Miksikova, Veronika Mlcakova, Jitka Osickova, Miroslav Pohanka, Hana Skochova, Jiri Pikula. Mixture toxicity of microcystin-LR, paraoxon and bromadiolone in Xenopus laevis embryos. Neuro endocrinology letters. 2015; 36 Suppl 1(?):114-9. doi: . [PMID: 26757121]
  • Anke Geduhn, Jens Jacob, Detlef Schenke, Barbara Keller, Sven Kleinschmidt, Alexandra Esther. Relation between Intensity of Biocide Practice and Residues of Anticoagulant Rodenticides in Red Foxes (Vulpes vulpes). PloS one. 2015; 10(9):e0139191. doi: 10.1371/journal.pone.0139191. [PMID: 26418154]
  • Michael Coeurdassier, Romain Riols, Anouk Decors, Aymeric Mionnet, Fabienne David, Thomas Quintaine, Denis Truchetet, Renaud Scheifler, Patrick Giraudoux. Unintentional wildlife poisoning and proposals for sustainable management of rodents. Conservation biology : the journal of the Society for Conservation Biology. 2014 Apr; 28(2):315-21. doi: 10.1111/cobi.12230. [PMID: 24405288]
  • Jens Jacob, Stefan Endepols, Hans-Joachim Pelz, Engelbert Kampling, Trevor G Cooper, Ching Hei Yeung, Klaus Redmann, Stefan Schlatt. Vitamin K requirement and reproduction in bromadiolone-resistant Norway rats. Pest management science. 2012 Mar; 68(3):378-85. doi: 10.1002/ps.2273. [PMID: 21919186]
  • Zhao-hui Fu, Quan-kai Wang, Wen-lan Yu, Jian Wang, An-na Wang, Jian-ning Xu. [Determination of brodifacoum in rat plasma by HPLC]. Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases. 2012 Feb; 30(2):135-6. doi: NULL. [PMID: 22808549]
  • Robert A Middleberg, Joseph Homan. Qualitative identification of rodenticide anticoagulants by LC-MS/MS. Methods in molecular biology (Clifton, N.J.). 2012; 902(?):139-48. doi: 10.1007/978-1-61779-934-1_12. [PMID: 22767114]
  • Karel Ondracek, Hana Bandouchova, Veronika Damkova, Klara Hilscherova, Jiri Kral, Jitka Osickova, Veronika Mlcakova, Miroslav Pohanka, Hana Skochova, Frantisek Vitula, Frantisek Treml, Jiri Pikula. Risk of combined exposure of birds to cyanobacterial biomass containing microcystins, acetylcholinesterase inhibitor and anticoagulant. Neuro endocrinology letters. 2012; 33 Suppl 3(?):155-60. doi: . [PMID: 23353860]
  • Jae-chul Jung, Hyung-in Moon. Larvicidal activity of 4-hydroxycoumarin derivatives against Aedes aegypti. Pharmaceutical biology. 2011 Feb; 49(2):190-3. doi: 10.3109/13880209.2010.507769. [PMID: 21043993]
  • Mario Giorgi, Grazia Mengozzi. An HPLC method for the determination of bromadiolone plasma kinetics and its residues in hen eggs. Journal of chromatographic science. 2010 Oct; 48(9):714-20. doi: 10.1093/chromsci/48.9.714. [PMID: 20875232]
  • Mickaël Sage, Isabelle Fourel, Michaël Cœurdassier, Jacques Barrat, Philippe Berny, Patrick Giraudoux. Determination of bromadiolone residues in fox faeces by LC/ESI-MS in relationship with toxicological data and clinical signs after repeated exposure. Environmental research. 2010 Oct; 110(7):664-74. doi: 10.1016/j.envres.2010.07.009. [PMID: 20692656]
  • Isabelle Fourel, Christophe Hugnet, Isabelle Goy-Thollot, Philippe Berny. Validation of a new liquid chromatography- tandem mass spectrometry ion-trap technique for the simultaneous determination of thirteen anticoagulant rodenticides, drugs, or natural products. Journal of analytical toxicology. 2010 Mar; 34(2):95-102. doi: 10.1093/jat/34.2.95. [PMID: 20223102]
  • V Vandenbroucke, A Bousquet-Melou, P De Backer, S Croubels. Pharmacokinetics of eight anticoagulant rodenticides in mice after single oral administration. Journal of veterinary pharmacology and therapeutics. 2008 Oct; 31(5):437-45. doi: 10.1111/j.1365-2885.2008.00979.x. [PMID: 19000263]
  • Vanessa M H Lo, C K Ching, Albert Y W Chan, Tony W L Mak. Bromadiolone toxicokinetics: diagnosis and treatment implications. Clinical toxicology (Philadelphia, Pa.). 2008 Sep; 46(8):703-10. doi: 10.1080/15563650701504366. [PMID: 19238731]
  • Vigdis Vindenes, Ritva Karinen, Inger Hasvold, Jean-Paul Bernard, Jørg G Mørland, Asbjørg S Christophersen. Bromadiolone poisoning: LC-MS method and pharmacokinetic data. Journal of forensic sciences. 2008 Jul; 53(4):993-6. doi: 10.1111/j.1556-4029.2008.00737.x. [PMID: 18482378]
  • Virginie Vandenbroucke, Noël Desmet, Patrick De Backer, Siska Croubels. Multi-residue analysis of eight anticoagulant rodenticides in animal plasma and liver using liquid chromatography combined with heated electrospray ionization tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 Jun; 869(1-2):101-10. doi: 10.1016/j.jchromb.2008.05.011. [PMID: 18502701]
  • Thomas Grobosch, Boris Angelow, Lena Schönberg, Dagmar Lampe. Acute bromadiolone intoxication. Journal of analytical toxicology. 2006 May; 30(4):281-6. doi: 10.1093/jat/30.4.281. [PMID: 16803669]
  • Philippe J Berny, Laurent Alves de Oliveira, Bernadette Videmann, Stéphanie Rossi. Assessment of ruminal degradation, oral bioavailability, and toxic effects of anticoagulant rodenticides in sheep. American journal of veterinary research. 2006 Feb; 67(2):363-71. doi: 10.2460/ajvr.67.2.363. [PMID: 16454646]
  • K Revathi, M Yogananda. Effect of bromadiolone on haematology, liver and kidney in Mus musculus. Journal of environmental biology. 2006 Jan; 27(1):135-40. doi: NULL. [PMID: 16850891]
  • Subbiah Deepa, Ashok K Mishra. Fluorescence spectroscopic study of serum albumin-bromadiolone interaction: fluorimetric determination of bromadiolone. Journal of pharmaceutical and biomedical analysis. 2005 Jul; 38(3):556-63. doi: 10.1016/j.jpba.2005.01.023. [PMID: 15925260]
  • Barbara E Watt, Alex T Proudfoot, Sally M Bradberry, J Allister Vale. Anticoagulant rodenticides. Toxicological reviews. 2005; 24(4):259-69. doi: 10.2165/00139709-200524040-00005. [PMID: 16499407]
  • E A Kuijpers, J den Hartigh, T J Savelkoul, F A de Wolff. A method for the simultaneous identification and quantitation of five superwarfarin rodenticides in human serum. Journal of analytical toxicology. 1995 Nov; 19(7):557-62. doi: 10.1093/jat/19.7.557. [PMID: 8577178]
  • P J Berny, T Buronfosse, G Lorgue. Anticoagulant poisoning in animals: a simple new high-performance thin-layer chromatographic (HPTLC) method for the simultaneous determination of eight anticoagulant rodenticides in liver samples. Journal of analytical toxicology. 1995 Nov; 19(7):576-80. doi: 10.1093/jat/19.7.576. [PMID: 8577181]
  • A Y Jeantet, M Truchet, G Naulleau, R Martoja. [Effects of bromadiolone on some organs and tissues (liver, kidney, spleen, blood) of coypu (Myocastor coypus)]. Comptes rendus de l'Academie des sciences. Serie III, Sciences de la vie. 1991; 312(4):149-56. doi: . [PMID: 1901755]
  • N Kamil. Kinetics of bromadiolone, anticoagulant rodenticide, in the Norway rat (Rattus norvegicus). Pharmacological research communications. 1987 Nov; 19(11):767-75. doi: 10.1016/0031-6989(87)90011-7. [PMID: 3444841]
  • K Nahas. [Analysis of bromadiolone (an anticoagulant rodenticide) in plasma, liver and kidney of the rat]. Journal of chromatography. 1986 Nov; 369(2):445-8. doi: 10.1016/s0021-9673(00)90156-0. [PMID: 3805211]
  • F P Rowe, C J Plant, A Bradfield. Trials of the anticoagulant rodenticides bromadiolone and difenacoum against the house mouse (Mus musculus L.). The Journal of hygiene. 1981 Oct; 87(2):171-7. doi: 10.1017/s0022172400069370. [PMID: 7288171]