Isatidine (BioDeep_00000002342)

 

Secondary id: BioDeep_00000396796

PANOMIX_OTCML-2023


代谢物信息卡片


retrorsine

化学式: C18H25NO6 (351.1682)
中文名称: 倒千里光碱
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 77.21%

分子结构信息

SMILES: C/C=C1/C[C@H](C)[C@](O)(CO)C(=O)OCC2=CCN3CC[C@@H](OC1=O)[C@@H]23
InChI: InChI=1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3

描述信息

Origin: Plant; SubCategory_DNP: Alkaloids derived from ornithine, Pyrrolizidine alkaloids
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.363
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.358
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.361
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2325
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 177
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 117
INTERNAL_ID 147; CONFIDENCE Reference Standard (Level 1)
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 147
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 137
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 157
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 167
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 127
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 107
D000970 - Antineoplastic Agents
Retrorsine is a naturally occurring toxic pyrrolizidine alkaloid. Retrorsine can bind with DNA and inhibits the proliferative capacity of hepatocytes. Retrorsine can be used for the research of hepatocellular injury[1][2].
Retrorsine is a naturally occurring toxic pyrrolizidine alkaloid. Retrorsine can bind with DNA and inhibits the proliferative capacity of hepatocytes. Retrorsine can be used for the research of hepatocellular injury[1][2].

同义名列表

3 个代谢物同义名

retrorsine; Isatidine; Retrorsine



数据库引用编号

82 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)

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 6 AFP, ALB, CCND1, CYP2B6, CYP3A4, HPGDS
Peripheral membrane protein 2 CYP1B1, CYP2B6
Endoplasmic reticulum membrane 4 CYP1A2, CYP1B1, CYP2B6, CYP3A4
Nucleus 3 ALB, CCND1, PCNA
cytosol 5 ALB, CCND1, GPT, HPGDS, KRT19
dendrite 1 THY1
nuclear body 1 PCNA
centrosome 3 ALB, CCND1, PCNA
nucleoplasm 3 CCND1, HPGDS, PCNA
Cell membrane 5 DPP4, PTPRC, SLC10A1, SLC22A1, THY1
lamellipodium 1 DPP4
Multi-pass membrane protein 2 SLC10A1, SLC22A1
Synapse 1 PTPRC
cell junction 1 DPP4
cell surface 4 DPP4, EPCAM, PTPRC, THY1
glutamatergic synapse 1 THY1
Golgi apparatus 1 ALB
growth cone 1 THY1
lysosomal membrane 2 DPP4, EGF
postsynapse 1 THY1
sarcolemma 1 KRT19
Presynapse 2 SLC22A1, THY1
plasma membrane 8 DPP4, EGF, EPCAM, KRT19, PTPRC, SLC10A1, SLC22A1, THY1
Membrane 8 CYP1B1, CYP3A4, DPP4, EGF, HGF, PTPRC, SLC10A1, SLC22A1
apical plasma membrane 4 DPP4, EPCAM, SLC22A1, THY1
basolateral plasma membrane 3 EPCAM, SLC10A1, SLC22A1
extracellular exosome 9 ALB, DPP4, EGF, EPCAM, GPT, KRT19, PCNA, PTPRC, THY1
endoplasmic reticulum 2 ALB, THY1
extracellular space 5 AFP, ALB, EGF, HGF, IL6
Cell junction, tight junction 1 EPCAM
apicolateral plasma membrane 1 KRT19
bicellular tight junction 2 CCND1, EPCAM
intercellular canaliculus 1 DPP4
mitochondrion 1 CYP1B1
protein-containing complex 1 ALB
intracellular membrane-bounded organelle 5 CYP1A2, CYP1B1, CYP2B6, CYP3A4, HPGDS
Microsome membrane 4 CYP1A2, CYP1B1, CYP2B6, CYP3A4
Single-pass type I membrane protein 2 EPCAM, PTPRC
Secreted 4 AFP, ALB, DPP4, IL6
extracellular region 6 ALB, DPP4, EGF, HGF, IL6, THY1
cytoplasmic side of plasma membrane 1 PTPRC
Single-pass membrane protein 1 DPP4
neuronal cell body membrane 1 THY1
anchoring junction 2 ALB, DPP4
Nucleus membrane 1 CCND1
nuclear membrane 1 CCND1
external side of plasma membrane 2 PTPRC, THY1
Z disc 1 KRT19
Single-pass type II membrane protein 1 DPP4
Apical cell membrane 2 DPP4, SLC22A1
Membrane raft 3 DPP4, PTPRC, THY1
focal adhesion 3 DPP4, PTPRC, THY1
axolemma 1 THY1
intermediate filament 1 KRT19
lateral plasma membrane 2 EPCAM, SLC22A1
ciliary basal body 1 ALB
chromatin 1 PCNA
cell periphery 1 KRT19
cytoskeleton 1 KRT19
centriole 1 ALB
spindle pole 1 ALB
nuclear replication fork 1 PCNA
chromosome, telomeric region 1 PCNA
blood microparticle 1 ALB
Basolateral cell membrane 1 SLC22A1
Lipid-anchor, GPI-anchor 1 THY1
Endomembrane system 1 DPP4
side of membrane 1 THY1
replication fork 1 PCNA
basal plasma membrane 1 SLC22A1
secretory granule membrane 1 PTPRC
endoplasmic reticulum lumen 3 AFP, ALB, IL6
transcription repressor complex 1 CCND1
male germ cell nucleus 1 PCNA
platelet alpha granule lumen 3 ALB, EGF, HGF
endocytic vesicle 1 DPP4
nuclear lamina 1 PCNA
clathrin-coated endocytic vesicle membrane 1 EGF
costamere 1 KRT19
Basal cell membrane 1 SLC22A1
Lateral cell membrane 2 EPCAM, SLC22A1
dendrite membrane 1 THY1
terminal web 1 KRT19
membrane microdomain 1 PTPRC
cyclin-dependent protein kinase holoenzyme complex 2 CCND1, PCNA
bleb 1 PTPRC
lamellipodium membrane 1 DPP4
Cell projection, lamellipodium membrane 1 DPP4
interleukin-6 receptor complex 1 IL6
Cell projection, invadopodium membrane 1 DPP4
cyclin D1-CDK4 complex 1 CCND1
PCNA complex 1 PCNA
PCNA-p21 complex 1 PCNA
replisome 1 PCNA
cyclin D1-CDK6 complex 1 CCND1
[Dipeptidyl peptidase 4 soluble form]: Secreted 1 DPP4
ciliary transition fiber 1 ALB


文献列表

  • Yongguo Dai, Qi Guo, Kequan Xu, Zheng Gong, Shuaikai Qiu, Xiaoxiang Sun, Jie Liu, Yuxi Wang, Zhixin Yang, Hui Wang, Yu Guo. Lactational retrorsine exposure changes maternal milk components and disturbs metabolism homeostasis of offspring rats. The Science of the total environment. 2023 Jun; ?(?):164929. doi: 10.1016/j.scitotenv.2023.164929. [PMID: 37329908]
  • Weiwei Li, Ting Cheng, Tingting Jiang, Mengyue Zhou, Bowen Gong, Guode Zhao, Jing Li, Rong Tan, Xiaojing Yang, Kandarp Joshi, Ying Peng, Maosheng Cheng, Ting Liu, Dan Ohtan Wang, Jiang Zheng. Hepatic RNA adduction derived from metabolic activation of retrorsine in vitro and in vivo. Chemico-biological interactions. 2022 Sep; 365(?):110047. doi: 10.1016/j.cbi.2022.110047. [PMID: 35917946]
  • Lin Zhu, Junyi Xue, Yisheng He, Qingsu Xia, Peter P Fu, Ge Lin. Correlation Investigation between Pyrrole-DNA and Pyrrole-Protein Adducts in Male ICR Mice Exposed to Retrorsine, a Hepatotoxic Pyrrolizidine Alkaloid. Toxins. 2022 05; 14(6):. doi: 10.3390/toxins14060377. [PMID: 35737038]
  • Feifei Lin, Yan Ma, Anni Pan, Yang Ye, Jia Liu. Quantification of Usaramine and its N-Oxide Metabolite in Rat Plasma Using Liquid Chromatography-Tandem Mass Spectrometry. Journal of analytical toxicology. 2022 May; 46(5):512-518. doi: 10.1093/jat/bkab060. [PMID: 34086913]
  • Jing Li, Mengyue Zhou, Xiaoqiong Lai, Yang Wang, Ying Zou, Kunna Li, Weiwei Li, Jiang Zheng. Toxicokinetic and bioavailability studies on retrorsine in mice, and ketoconazole-induced alteration in toxicokinetic properties. Biomedical chromatography : BMC. 2022 Feb; 36(2):e5270. doi: 10.1002/bmc.5270. [PMID: 34727371]
  • Jiang Ma, Chunyuan Zhang, Yisheng He, Xinmeng Chen, Ge Lin. Fasting augments pyrrolizidine alkaloid-induced hepatotoxicity. Archives of toxicology. 2022 02; 96(2):639-651. doi: 10.1007/s00204-021-03193-y. [PMID: 34792613]
  • Anne-Margarethe Enge, Florian Kaltner, Christoph Gottschalk, Angelina Kin, Michael Kirstgen, Joachim Geyer, Anja These, Helen Hammer, Oliver Pötz, Albert Braeuning, Stefanie Hessel-Pras. Organic Cation Transporter I and Na+ /taurocholate Co-Transporting Polypeptide are Involved in Retrorsine- and Senecionine-Induced Hepatotoxicity in HepaRG cells. Molecular nutrition & food research. 2022 01; 66(2):e2100800. doi: 10.1002/mnfr.202100800. [PMID: 34826203]
  • Lin Zhu, Chunyuan Zhang, Wei Zhang, Qingsu Xia, Jiang Ma, Xin He, Yisheng He, Peter P Fu, Wei Jia, Yuzheng Zhuge, Ge Lin. Developing urinary pyrrole-amino acid adducts as non-invasive biomarkers for identifying pyrrolizidine alkaloids-induced liver injury in human. Archives of toxicology. 2021 10; 95(10):3191-3204. doi: 10.1007/s00204-021-03129-6. [PMID: 34390356]
  • Li Guo, Li Zhang, Haiman Xu, Pei Yu, Zhigang Wang, Danyi Lu, Min Chen, Baojian Wu. Diurnal hepatic CYP3A11 contributes to chronotoxicity of the pyrrolizidine alkaloid retrorsine in mice. Xenobiotica; the fate of foreign compounds in biological systems. 2021 Sep; 51(9):1019-1028. doi: 10.1080/00498254.2021.1950867. [PMID: 34311664]
  • Xiaoyan Pang, Chongzhuang Tang, Peng Cao, Lei Zhou, Xiaoyan Chen. Metabolic Activation of Retrorsine may Disrupt Bile Acid Homeostasis in Mice through the Nrf2 Pathway. Current drug metabolism. 2021; 22(11):870-881. doi: 10.2174/1389200222666210427124332. [PMID: 33906588]
  • Xiaoyan Pang, Chongzhuang Tang, Fandi Kong, Meixia Chen, Xiaoyan Chen. CYP2C and CYP2B Mediated Metabolic Activation of Retrorsine in Cyp3a Knockout Mice. Current drug metabolism. 2020; 21(13):1040-1051. doi: 10.2174/1389200221666201202101715. [PMID: 33267758]
  • Yu Guo, Di Xiao, Xiaojing Yang, Jiang Zheng, Shuwei Hu, Panfeng Wu, Xiaoxia Li, Hao Kou, Hui Wang. Prenatal exposure to pyrrolizidine alkaloids induced hepatotoxicity and pulmonary injury in fetal rats. Reproductive toxicology (Elmsford, N.Y.). 2019 04; 85(?):34-41. doi: 10.1016/j.reprotox.2019.02.006. [PMID: 30771476]
  • Xiaojie Liu, Klaas Vrieling, Peter G L Klinkhamer. Phytochemical Background Mediates Effects of Pyrrolizidine Alkaloids on Western Flower Thrips. Journal of chemical ecology. 2019 Feb; 45(2):116-127. doi: 10.1007/s10886-018-1009-2. [PMID: 30221331]
  • Xiaojing Yang, Weiwei Li, Hui Li, Xu Wang, Yan Chen, Xiucai Guo, Ying Peng, Jiang Zheng. A Difference in Internal Exposure Makes Newly Weaned Mice More Susceptible to the Hepatotoxicity of Retrorsine Than Adult Mice. Chemical research in toxicology. 2018 12; 31(12):1348-1355. doi: 10.1021/acs.chemrestox.8b00220. [PMID: 30427168]
  • Yao Lu, Jiang Ma, Zijing Song, Yang Ye, Peter P Fu, Ge Lin. The role of formation of pyrrole-ATP synthase subunit beta adduct in pyrrolizidine alkaloid-induced hepatotoxicity. Archives of toxicology. 2018 11; 92(11):3403-3414. doi: 10.1007/s00204-018-2309-6. [PMID: 30244272]
  • Xiu-Ren Hu, Gui-Xin Chou, Cheng-Gang Zhang. Flavonoids, alkaloids from the seeds of Crotalaria pallida and their cytotoxicity and anti-inflammatory activities. Phytochemistry. 2017 Nov; 143(?):64-71. doi: 10.1016/j.phytochem.2017.07.010. [PMID: 28777979]
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  • Lin Zhu, Junyi Xue, Qingsu Xia, Peter P Fu, Ge Lin. The long persistence of pyrrolizidine alkaloid-derived DNA adducts in vivo: kinetic study following single and multiple exposures in male ICR mice. Archives of toxicology. 2017 Feb; 91(2):949-965. doi: 10.1007/s00204-016-1713-z. [PMID: 27125825]
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  • Damjan Janeš, Samo Kreft. TLC densitometric method for screening of lycopsamine in comfrey root (Symphytum officinale L.) extracts using retrorsine as a reference compound. Acta pharmaceutica (Zagreb, Croatia). 2014 Dec; 64(4):503-8. doi: 10.2478/acph-2014-0031. [PMID: 25531790]
  • Gonzalo J Diaz, Leidy X Almeida, Dale R Gardner. Effects of dietary Crotalaria pallida seeds on the health and performance of laying hens and evaluation of residues in eggs. Research in veterinary science. 2014 Oct; 97(2):297-303. doi: 10.1016/j.rvsc.2014.06.011. [PMID: 25062989]
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  • Dandan Cheng, Heather Kirk, Klaas Vrieling, Patrick P J Mulder, Peter G L Klinkhamer. The relationship between structurally different pyrrolizidine alkaloids and western flower thrips resistance in F(2) hybrids of Jacobaea vulgaris and Jacobaea aquatica. Journal of chemical ecology. 2011 Oct; 37(10):1071-80. doi: 10.1007/s10886-011-0021-6. [PMID: 21969251]
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  • Jiayin Han, Aihu Liang, Yan Yi. [Developmental toxicity of retrorsine on mouse embryos in vitro]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Jul; 36(14):1901-4. doi: NULL. [PMID: 22016956]
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  • Biao Zhang, Mitsuhiro Inagaki, Bojian Jiang, Masaaki Miyakoshi, Jun Arikura, Katsuhiro Ogawa, Shinichi Kasai. Effects of bone marrow and hepatocyte transplantation on liver injury. The Journal of surgical research. 2009 Nov; 157(1):71-80. doi: 10.1016/j.jss.2008.12.013. [PMID: 19345373]
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  • Walber Toma, José Roberto Trigo, Ana Cláudia Bensuaski de Paula, Alba Regina Monteiro Souza Brito. Modulation of gastrin and epidermal growth factor by pyrrolizidine alkaloids obtained from Senecio brasiliensis in acute and chronic induced gastric ulcers. Canadian journal of physiology and pharmacology. 2004 May; 82(5):319-25. doi: 10.1139/y04-023. [PMID: 15213731]
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