Acetylhydrazine (BioDeep_00000006497)

 

Secondary id: BioDeep_00001868005

human metabolite Endogenous blood metabolite


代谢物信息卡片


Acetylhydrazine, (e)-2-fumarate (1:1)

化学式: C2H6N2O (74.048)
中文名称: 乙酰肼
谱图信息: 最多检出来源 Viridiplantae(lipidsearch) 10.41%

分子结构信息

SMILES: CC(=O)NN
InChI: InChI=1S/C2H6N2O/c1-2(5)4-3/h3H2,1H3,(H,4,5)

描述信息

The acetylhydrazine metabolite was found to be much less cytotoxic than hydrazine in this hepatocyte inflammation model. (PMID: 18295292) In the pathogenesis of isoniazid-induced hepatic injury, cytochrome P450-dependent metabolic activation of the metabolite, acetylhydrazine (AcHz), is the crucial step. (PMID: 8852701) The mechanism of action of acetylphosphabenzide is likely to involve the formation of acetylhydrazine, capable of producing active electrophiles attacking DNA. (PMID: 9589859)
D009676 - Noxae > D002273 - Carcinogens

同义名列表

18 个代谢物同义名

Acetylhydrazine, (e)-2-fumarate (1:1); Acetylhydrazine monohydrochloride; Ethanehydrazonic acid; Acetic acid hydrazide; Monoacetyl hydrazine; Monoacetylhydrazine; Ethanehydrazonate; N-Acetylhydrazine; Acetate hydrazide; Acetyl hydrazide; Acetic hydrazide; Acetylhydrazine; Acetylhydrazide; acetohydrazide; Acethydrazide; Acethydrazine; Acetylhydrazine; Acethydrazide



数据库引用编号

12 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)

2 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 8 ANXA5, ASL, CYP2E1, NAT2, PMP2, PRDX5, PTGS2, STAT3
Peripheral membrane protein 4 ANXA5, CYP2E1, GORASP1, PTGS2
Endoplasmic reticulum membrane 3 CD4, CYP2E1, PTGS2
Nucleus 6 MPO, NAT2, PARP1, PMP2, PRDX5, STAT3
cytosol 10 ADSL, ANXA5, ASL, GPT, NAT2, PARP1, PMP2, PRDX5, STAT3, TYMP
nuclear body 1 PARP1
nucleoplasm 4 GLDC, MPO, PARP1, STAT3
RNA polymerase II transcription regulator complex 1 STAT3
Cell membrane 3 CD4, NAT2, TNF
Cytoplasmic side 1 GORASP1
Multi-pass membrane protein 2 NAT2, SLC34A2
Golgi apparatus membrane 1 GORASP1
cell surface 2 TNF, TNR
glutamatergic synapse 1 TNR
Golgi apparatus 1 GORASP1
Golgi membrane 2 GORASP1, INS
mitochondrial inner membrane 1 CYP2E1
neuronal cell body 2 NAT2, TNF
sarcolemma 1 ANXA5
Cytoplasm, cytosol 1 PARP1
Lysosome 1 MPO
plasma membrane 6 CD4, GLDC, NAT2, SLC34A2, STAT3, TNF
Membrane 4 ANXA5, NAT2, PARP1, SLC34A2
apical plasma membrane 1 SLC34A2
axon 1 NAT2
basolateral plasma membrane 1 NAT2
brush border 1 SLC34A2
caveola 1 PTGS2
extracellular exosome 7 ANXA5, ASL, GPT, MPO, NAT2, PMP2, PRDX5
endoplasmic reticulum 1 PTGS2
extracellular space 5 INS, MPO, PRDX5, TNF, TNR
perinuclear region of cytoplasm 1 PRDX5
Schaffer collateral - CA1 synapse 1 TNR
mitochondrion 3 GLDC, PARP1, PRDX5
protein-containing complex 3 ADSL, PARP1, PTGS2
intracellular membrane-bounded organelle 3 CYP2E1, MPO, PRDX5
Microsome membrane 2 CYP2E1, PTGS2
Single-pass type I membrane protein 1 CD4
Secreted 1 INS
extracellular region 5 ANXA5, INS, MPO, TNF, TNR
mitochondrial matrix 2 GLDC, PRDX5
transcription regulator complex 3 NAT2, PARP1, STAT3
external side of plasma membrane 3 ANXA5, CD4, TNF
Secreted, extracellular space, extracellular matrix 1 TNR
cytoplasmic vesicle 1 PRDX5
nucleolus 1 PARP1
Early endosome 1 CD4
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 SLC34A2
Apical cell membrane 1 SLC34A2
Mitochondrion inner membrane 1 CYP2E1
Membrane raft 3 CD4, TNF, TNR
focal adhesion 1 ANXA5
cis-Golgi network 1 GORASP1
Peroxisome 1 PRDX5
Peroxisome matrix 1 PRDX5
peroxisomal matrix 1 PRDX5
collagen-containing extracellular matrix 2 ANXA5, TNR
secretory granule 1 MPO
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Zymogen granule membrane 1 ANXA5
neuron projection 1 PTGS2
chromatin 2 PARP1, STAT3
phagocytic cup 1 TNF
Chromosome 1 PARP1
brush border membrane 1 SLC34A2
Nucleus, nucleolus 1 PARP1
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
site of double-strand break 1 PARP1
nuclear envelope 1 PARP1
endosome lumen 1 INS
myelin sheath 1 PMP2
azurophil granule 1 MPO
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 CD4, INS, PTGS2
transport vesicle 1 INS
azurophil granule lumen 1 MPO
Endoplasmic reticulum-Golgi intermediate compartment membrane 2 GORASP1, INS
perineuronal net 1 TNR
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
vesicle membrane 1 ANXA5
clathrin-coated endocytic vesicle membrane 1 CD4
phagocytic vesicle lumen 1 MPO
protein-DNA complex 1 PARP1
external side of apical plasma membrane 1 NAT2
site of DNA damage 1 PARP1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
T cell receptor complex 1 CD4
[Isoform Mitochondrial]: Mitochondrion 1 PRDX5
endothelial microparticle 1 ANXA5
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
tenascin complex 1 TNR
glycine cleavage complex 1 GLDC
[Isoform Cytoplasmic+peroxisomal]: Cytoplasm 1 PRDX5
NatA complex 1 NAT2
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Mahmoud F Ismail, Amira A El-Sayed, Eslam M Hosni, Aya I Hassaballah. Synthesis and evaluation of larvicidal efficacy against C. pipiens of some new heterocyclic compounds emanated from 2-cyano-N'-(2-(2,4-dichlorophenoxy)acetyl)acetohydrazide. Chemistry & biodiversity. 2024 Feb; 21(2):e202301560. doi: 10.1002/cbdv.202301560. [PMID: 38251927]
  • Suhail Razak, Tayyaba Afsar, Nousheen Bibi, Mahmoud Abulmeaty, Mashooq Ahmad Bhat, Anam Inam, Janeen H Trembley, Ali Almajwal, Maria Shabbir, Nawaf W Alruwaili, Abdulrahman Algarni. Sulindac acetohydrazide derivative attenuates against cisplatin induced organ damage by modulation of antioxidant and inflammatory signaling pathways. Scientific reports. 2022 07; 12(1):11749. doi: 10.1038/s41598-022-15950-9. [PMID: 35817806]
  • Xiaobin Wang, Mengqi Wang, Ling Han, Fei Jin, Jian Jiao, Min Chen, Chunlong Yang, Wei Xue. Novel Pyrazole-4-acetohydrazide Derivatives Potentially Targeting Fungal Succinate Dehydrogenase: Design, Synthesis, Three-Dimensional Quantitative Structure-Activity Relationship, and Molecular Docking. Journal of agricultural and food chemistry. 2021 Aug; 69(33):9557-9570. doi: 10.1021/acs.jafc.1c03399. [PMID: 34382800]
  • Fouzia Naz, Kanwal, Mehreen Latif, Uzma Salar, Khalid Mohammed Khan, Mariya Al-Rashida, Irfan Ali, Basharat Ali, Muhammad Taha, Shahnaz Perveen. 4-Oxycoumarinyl linked acetohydrazide Schiff bases as potent urease inhibitors. Bioorganic chemistry. 2020 12; 105(?):104365. doi: 10.1016/j.bioorg.2020.104365. [PMID: 33091669]
  • Tanveer A Wani, Ahmed H Bakheit, Seema Zargar, Mashooq A Bhat, Abdulrahman A Al-Majed. Molecular docking and experimental investigation of new indole derivative cyclooxygenase inhibitor to probe its binding mechanism with bovine serum albumin. Bioorganic chemistry. 2019 08; 89(?):103010. doi: 10.1016/j.bioorg.2019.103010. [PMID: 31132602]
  • Raghu Ramanathan, Karthikeyan Sivanesan. Investigations on the Influence of Zidovudine in the Pharmacokinetics of Isoniazid and Its Hepatotoxic Metabolites in Rats. Journal of pharmacy practice. 2019 Feb; 32(1):9-18. doi: 10.1177/0897190017735424. [PMID: 29017426]
  • Lu Song, Dan Gao, Shangfu Li, Yanwei Wang, Hongxia Liu, Yuyang Jiang. Simultaneous quantitation of hydrazine and acetylhydrazine in human plasma by high performance liquid chromatography-tandem mass spectrometry after derivatization with p-tolualdehyde. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 Sep; 1063(?):189-195. doi: 10.1016/j.jchromb.2017.08.036. [PMID: 28881295]
  • Getnet Yimer, Nobuhisa Ueda, Abiy Habtewold, Wondwossen Amogne, Akira Suda, Klaus-Dieter Riedel, Jürgen Burhenne, Getachew Aderaye, Lars Lindquist, Eyasu Makonnen, Eleni Aklillu. Pharmacogenetic & pharmacokinetic biomarker for efavirenz based ARV and rifampicin based anti-TB drug induced liver injury in TB-HIV infected patients. PloS one. 2011; 6(12):e27810. doi: 10.1371/journal.pone.0027810. [PMID: 22162992]
  • A H M Viswanatha Swamy, Rucha V Kulkarni, A H M Thippeswamy, B C Koti, Aparna Gore. Evaluation of hepatoprotective activity of Cissus quadrangularis stem extract against isoniazid-induced liver damage in rats. Indian journal of pharmacology. 2010 Dec; 42(6):397-400. doi: 10.4103/0253-7613.71920. [PMID: 21189914]
  • Masaaki Toyoda, Hisashi Narimatsu, Akihiko Kameyama. Enrichment method of sulfated glycopeptides by a sulfate emerging and ion exchange chromatography. Analytical chemistry. 2009 Aug; 81(15):6140-7. doi: 10.1021/ac900592t. [PMID: 19572564]
  • Mary E Bollard, Hector C Keun, Olaf Beckonert, Tim M D Ebbels, Henrik Antti, Andrew W Nicholls, John P Shockcor, Glenn H Cantor, Greg Stevens, John C Lindon, Elaine Holmes, Jeremy K Nicholson. Comparative metabonomics of differential hydrazine toxicity in the rat and mouse. Toxicology and applied pharmacology. 2005 Apr; 204(2):135-51. doi: 10.1016/j.taap.2004.06.031. [PMID: 15808519]
  • Victoria E Richards, Binh Chau, M Randy White, Charlene A McQueen. Hepatic gene expression and lipid homeostasis in C57BL/6 mice exposed to hydrazine or acetylhydrazine. Toxicological sciences : an official journal of the Society of Toxicology. 2004 Nov; 82(1):318-32. doi: 10.1093/toxsci/kfh232. [PMID: 15282401]
  • Abbas Afkhami, Ali Reza Zarei. Simultaneous kinetic-spectrophotometric determination of hydrazine and acetylhydrazine in micellar media using the H-point standard addition method. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry. 2004 Aug; 20(8):1199-203. doi: 10.2116/analsci.20.1199. [PMID: 15352511]
  • Micaela Zonta, Annalisa Sebelin, Sara Gobbo, Tommaso Fellin, Tullio Pozzan, Giorgio Carmignoto. Glutamate-mediated cytosolic calcium oscillations regulate a pulsatile prostaglandin release from cultured rat astrocytes. The Journal of physiology. 2003 Dec; 553(Pt 2):407-14. doi: 10.1113/jphysiol.2003.046706. [PMID: 14500777]
  • Grazia Tamma, Burkhard Wiesner, Jens Furkert, Daniel Hahm, Alexander Oksche, Michael Schaefer, Giovanna Valenti, Walter Rosenthal, Enno Klussmann. The prostaglandin E2 analogue sulprostone antagonizes vasopressin-induced antidiuresis through activation of Rho. Journal of cell science. 2003 Aug; 116(Pt 16):3285-94. doi: 10.1242/jcs.00640. [PMID: 12829746]
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  • T C Sarich, M Youssefi, T Zhou, S P Adams, R A Wall, J M Wright. Role of hydrazine in the mechanism of isoniazid hepatotoxicity in rabbits. Archives of toxicology. 1996; 70(12):835-40. doi: 10.1007/s002040050347. [PMID: 8911642]
  • R L Zhang, Z Y Wang, D Li, W B Cheng. Effects of rifampicin on pharmacokinetics of isoniazid and its metabolite acetylhydrazine in rats. Zhongguo yao li xue bao = Acta pharmacologica Sinica. 1992 Nov; 13(6):494-6. doi: . [PMID: 1302435]
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  • G Karlaganis, E Peretti, B H Lauterburg. Analysis of isoniazid, acetylhydrazine and [15N2]acetylhydrazine in serum by capillary gas chromatography-ammonia chemical ionization mass spectrometry. Journal of chromatography. 1987 Sep; 420(1):171-7. doi: 10.1016/0378-4347(87)80169-x. [PMID: 3667818]
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