4-ene-Valproic acid (BioDeep_00000011326)

Main id: BioDeep_00000628725

 

human metabolite Endogenous blood metabolite


代谢物信息卡片


2-Propyl-4-pentenoic acid, (+-)-isomer

化学式: C8H14O2 (142.0994)
中文名称: (±)-2-propyl-4-Pentenoic Acid
谱图信息: 最多检出来源 Homo sapiens(blood) 40.9%

分子结构信息

SMILES: C=CCC(CCC)C(=O)O
InChI: InChI=1S/C8H14O2/c1-3-5-7(6-4-2)8(9)10/h3,7H,1,4-6H2,2H3,(H,9,10)

描述信息

4-ene-Valproic acid is only found in individuals that have used or taken Valproic Acid. 4-ene-Valproic acid is a metabolite of Valproic Acid. 4-ene-valproic acid belongs to the family of Branched Fatty Acids. These are fatty acids containing a branched chain.
D009676 - Noxae > D013723 - Teratogens

同义名列表

18 个代谢物同义名

2-Propyl-4-pentenoic acid, (+-)-isomer; 2-Propyl-4-pentenoic acid, (R)-isomer; 2-Propyl-4-pentenoic acid, (S)-isomer; (±)-2-Propyl-4-pentenoic acid; 2-n-Propyl-4-pentenoic acid; 4-Pentenoic acid, 2-propyl-; 2-Propyl-4-pentenoic acid; 2-propylpent-4-enoic acid; 4-ene-Valproic acid; 4-Ene valproic acid; 4-En-valproic acid; 4-Ene-valproate; 4-En-valproate; delta(4)-VPA; 4-Ene vpa; 4-Ene-vpa; 4-En-vpa; 2-n-Propyl-4-pentenoic acid



数据库引用编号

14 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

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(1)

PharmGKB(0)

1 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 12 CDR2, CYP1A1, CYP2A6, CYP2B6, CYP2C19, CYP2C8, CYP2C9, CYP2E1, CYP3A4, CYP4F2, HDAC9, PANK1
Peripheral membrane protein 4 CYP1A1, CYP2B6, CYP2E1, CYP4F2
Endoplasmic reticulum membrane 13 CYP19A1, CYP1A1, CYP1A2, CYP2A6, CYP2B6, CYP2C19, CYP2C8, CYP2C9, CYP2E1, CYP3A4, CYP4F2, UGT1A6, UGT2B7
Nucleus 2 HDAC9, PANK1
cytosol 2 GPT, PANK1
nucleoplasm 1 HDAC9
Multi-pass membrane protein 2 CPT1A, CYP19A1
glutamatergic synapse 1 ICAM5
mitochondrial inner membrane 2 CYP1A1, CYP2E1
postsynapse 1 ICAM5
plasma membrane 4 CYP2C19, CYP2C8, CYP2C9, ICAM5
Membrane 8 CPT1A, CYP19A1, CYP2A6, CYP3A4, CYP4F2, ICAM5, UGT1A6, UGT2B7
apical plasma membrane 1 CYP4F2
extracellular exosome 1 GPT
endoplasmic reticulum 2 CYP19A1, UGT1A6
mitochondrion 3 ACSM2A, CPT1A, CYP1A1
intracellular membrane-bounded organelle 11 CYP1A1, CYP1A2, CYP2A6, CYP2B6, CYP2C19, CYP2C8, CYP2C9, CYP2E1, CYP3A4, CYP4F2, UGT1A6
Microsome membrane 8 CYP19A1, CYP1A1, CYP1A2, CYP2B6, CYP2C9, CYP2E1, CYP3A4, CYP4F2
Single-pass type I membrane protein 1 ICAM5
Mitochondrion outer membrane 1 CPT1A
Single-pass membrane protein 2 UGT1A6, UGT2B7
mitochondrial outer membrane 1 CPT1A
mitochondrial matrix 1 ACSM2A
transcription regulator complex 1 HDAC9
nucleolus 1 PANK1
recycling endosome 1 PANK1
Mitochondrion inner membrane 2 CYP1A1, CYP2E1
cell periphery 1 PANK1
Nucleus, nucleolus 1 PANK1
[Isoform 2]: Cytoplasm, cytosol 1 PANK1
clathrin-coated vesicle 1 PANK1
histone methyltransferase complex 1 HDAC9
histone deacetylase complex 1 HDAC9
Cytoplasmic vesicle, clathrin-coated vesicle 1 PANK1
[Isoform 1]: Nucleus 1 PANK1
cytoplasmic microtubule 1 CYP2A6


文献列表

  • Hongying Ma, Wu Zhu, Can Wang, Jing Pan, Xue Yang, Jian Luo, Ping Wang. Association of valproic acid and 2-propyl-4-pentenoic acid concentrations with adverse reaction in 254 Chinese patients with epilepsy. Zhong nan da xue xue bao. Yi xue ban = Journal of Central South University. Medical sciences. 2019 Jul; 44(7):775-783. doi: 10.11817/j.issn.1672-7347.2019.180548. [PMID: 31413215]
  • Mingming Zhao, Ti Zhang, Guofei Li, Feng Qiu, Yaxin Sun, Limei Zhao. Associations of CYP2C9 and CYP2A6 Polymorphisms with the Concentrations of Valproate and its Hepatotoxin Metabolites and Valproate-Induced Hepatotoxicity. Basic & clinical pharmacology & toxicology. 2017 Aug; 121(2):138-143. doi: 10.1111/bcpt.12776. [PMID: 28273397]
  • Zhuo-Jia Chen, Xue-Ding Wang, Lie-Min Zhou, Zi-Yan Fang, Hong-Sheng Wang, Jia-Li Li, Jue-Qian Zhou, Hong-Bing Huang, Min Huang. [Effects of carbamazepine on plasma concentrations of valproic acid and its toxic metabolite in epileptic patients]. Yao xue xue bao = Acta pharmaceutica Sinica. 2014 Apr; 49(4):530-4. doi: . [PMID: 24974473]
  • Zhuo-Jia Chen, Xue-Ding Wang, Hong-Sheng Wang, Shu-da Chen, Lie-Min Zhou, Jia-Li Li, Wen-Ying Shu, Jue-Qian Zhou, Zi-Yan Fang, Yu Zhang, Min Huang. Simultaneous determination of valproic acid and 2-propyl-4-pentenoic acid for the prediction of clinical adverse effects in Chinese patients with epilepsy. Seizure. 2012 Mar; 21(2):110-7. doi: 10.1016/j.seizure.2011.10.002. [PMID: 22055352]
  • Byung Hwa Jung, Bo Jun Kim, Min Sun Lee, Joo Hyun Lee, Ju-Hee Oh, Young-Joo Lee. Dose-dependent pharmacokinetics of toxic metabolites is not related to increased toxicity following high-dose valproic acid in rats. Journal of applied toxicology : JAT. 2010 Nov; 30(8):775-8. doi: 10.1002/jat.1608. [PMID: 21157986]
  • Min Sun Lee, Young-Joo Lee, Bo Joon Kim, Kye Jung Shin, Bong Chul Chung, Du-Jong Baek, Byung Hwa Jung. The relationship between glucuronide conjugate levels and hepatotoxicity after oral administration of valproic acid. Archives of pharmacal research. 2009 Jul; 32(7):1029-35. doi: 10.1007/s12272-009-1708-x. [PMID: 19641884]
  • Hao Cheng, Zhongfa Liu, William Blum, John C Byrd, Rebecca Klisovic, Michael R Grever, Guido Marcucci, Kenneth K Chan. Quantification of valproic acid and its metabolite 2-propyl-4-pentenoic acid in human plasma using HPLC-MS/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2007 May; 850(1-2):206-12. doi: 10.1016/j.jchromb.2006.11.027. [PMID: 17147984]
  • I B Ostretsova, A A Nikiforov. Weak organic acid uptake in rat renal tubules in vitro: stimulation by pent-4-enoic acid. Comparative biochemistry and physiology. Part C, Pharmacology, toxicology & endocrinology. 1997 May; 117(1):1-6. doi: 10.1016/s0742-8413(96)00200-9. [PMID: 9185322]
  • W Tang, F S Abbott. A comparative investigation of 2-propyl-4-pentenoic acid (4-ene VPA) and its alpha-fluorinated analogue: phase II metabolism and pharmacokinetics. Drug metabolism and disposition: the biological fate of chemicals. 1997 Feb; 25(2):219-27. doi: . [PMID: 9029053]
  • W Tang, F S Abbott. Characterization of thiol-conjugated metabolites of 2-propylpent-4-enoic acid (4-ene VPA), a toxic metabolite of valproic acid, by electrospray tandem mass spectrometry. Journal of mass spectrometry : JMS. 1996 Aug; 31(8):926-36. doi: 10.1002/(sici)1096-9888(199608)31:8<926::aid-jms383>3.0.co;2-p. [PMID: 8799319]
  • K Kassahun, P Hu, M P Grillo, M R Davis, L Jin, T A Baillie. Metabolic activation of unsaturated derivatives of valproic acid. Identification of novel glutathione adducts formed through coenzyme A-dependent and -independent processes. Chemico-biological interactions. 1994 Mar; 90(3):253-75. doi: 10.1016/0009-2797(94)90014-0. [PMID: 8168173]
  • M Elhamri, B Ferrier, M Martin, G Baverel. Effect of valproate and of two of its metabolites on renal substrate uptake and ammoniagenesis in the rat in vivo. Contributions to nephrology. 1994; 110(?):41-5. doi: 10.1159/000423396. [PMID: 7956255]
  • M Elhamri, B Ferrier, M Martin, G Baverel. Effect of valproate, sodium 2-propyl-4-pentenoate and sodium 2-propyl-2-pentenoate on renal substrate uptake and ammoniagenesis in the rat. The Journal of pharmacology and experimental therapeutics. 1993 Jul; 266(1):89-96. doi: . [PMID: 8331578]
  • J H Thurston, R E Hauhart. Reversal of the adverse chronic effects of the unsaturated derivative of valproic acid--2-n-propyl-4-pentenoic acid--on ketogenesis and liver coenzyme A metabolism by a single injection of pantothenate, carnitine, and acetylcysteine in developing mice. Pediatric research. 1993 Jan; 33(1):72-6. doi: 10.1203/00006450-199301000-00015. [PMID: 8433865]
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  • H Y Yu, Y Z Shen, J S Chen, S C Yang. Effects of sodium valproate and 4en-valproic acid on isolated hepatocytes of guinea pigs. Journal of the Formosan Medical Association = Taiwan yi zhi. 1991 Feb; 90(2):181-8. doi: NULL. [PMID: 1678414]
  • R H Levy, A W Rettenmeier, G D Anderson, A J Wilensky, P N Friel, T A Baillie, A Acheampong, J Tor, M Guyot, P Loiseau. Effects of polytherapy with phenytoin, carbamazepine, and stiripentol on formation of 4-ene-valproate, a hepatotoxic metabolite of valproic acid. Clinical pharmacology and therapeutics. 1990 Sep; 48(3):225-35. doi: 10.1038/clpt.1990.144. [PMID: 2119269]
  • D J Porubek, M P Grillo, T A Baillie. The covalent binding to protein of valproic acid and its hepatotoxic metabolite, 2-n-propyl-4-pentenoic acid, in rats and in isolated rat hepatocytes. Drug metabolism and disposition: the biological fate of chemicals. 1989 Mar; 17(2):123-30. doi: . [PMID: 2565201]
  • K Singh, J M Orr, F S Abbott. Pharmacokinetics and enterohepatic circulation of 2-n-propyl-4-pentenoic acid in the rat. Drug metabolism and disposition: the biological fate of chemicals. 1988 Nov; 16(6):848-52. doi: NULL. [PMID: 2907464]
  • K Singh, F S Abbott, J M Orr. Capillary GCMS assay of 2-n-propyl-4-pentenoic acid (4-ene VPA) in rat plasma and urine. Research communications in chemical pathology and pharmacology. 1987 May; 56(2):211-23. doi: NULL. [PMID: 3602586]
  • M Paganini, G Zaccara, F Moroni, R Campostrini, L Bendoni, G Arnetoli, R Zappoli. Lack of relationship between sodium valproate-induced adverse effects and the plasma concentration of its metabolite 2-propylpenten-4-oic acid. European journal of clinical pharmacology. 1987; 32(2):219-22. doi: 10.1007/bf00542201. [PMID: 3108013]
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  • A W Rettenmeier, K S Prickett, W P Gordon, S M Bjorge, S L Chang, R H Levy, T A Baillie. Studies on the biotransformation in the perfused rat liver of 2-n-propyl-4-pentenoic acid, a metabolite of the antiepileptic drug valproic acid. Evidence for the formation of chemically reactive intermediates. Drug metabolism and disposition: the biological fate of chemicals. 1985 Jan; 13(1):81-96. doi: . [PMID: 2858383]
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