epsilon-Caprolactone (BioDeep_00000004784)

 

Secondary id: BioDeep_00000868727, BioDeep_00001868255

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


epsilon-Captolactamium hydrogen sulfate

化学式: C6H10O2 (114.068076)
中文名称: ε-己内酯, 6-己内酯
谱图信息: 最多检出来源 Viridiplantae(plant) 0.34%

分子结构信息

SMILES: C1CCC(=O)OCC1
InChI: InChI=1S/C6H10O2/c7-6-4-2-1-3-5-8-6/h1-5H2

描述信息

ε-Caprolactone, also known simply as caprolactone, is a compound belonging to the family of compounds known as lactones. Lactones are cyclic esters of hydroxyl carboxylic acids, wherein the functional group has become part of a ring structure with carbon atoms. Caprolactone consists of a seven membered ring derived from the cyclization of caproic acid. As a monomer it used in the production of highly specialized plastics and polymers. Caprolactone is produced by the Baeyer-Villiger oxidation of cyclohexanone with peracetic acid, and was used previously (until economically inviable) as a precursor in the production of caprolactam. Several other caprolactone isomers are known. These isomers include α-, β-, γ-, and δ-caprolactones. All are chiral. (R)-γ-caprolactone is a component of floral scents and of the aromas of some fruits and vegetables (Journal of Agricultural and Food Chemistry. 37: 413–418), while δ-caprolactone is found in heated milk fat (Journal of Dairy Science. 48 (5): 615–616).

同义名列表

21 个代谢物同义名

epsilon-Captolactamium hydrogen sulfate; 6-Hydroxyhexanoic acid, epsilon-lactone; 6-Hydroxyhexanoate, epsilon-lactone; 6-Hydroxyhexanoic acid lactone; Hexanoic acid, epsilon-lactone; epsilon-Caprolactone monomer; 6-Hydroxyhexanoate lactone; Hexanoate, epsilon-lactone; 2-Oxohexamethylene oxide; ε-Captrolactone; 1-Oxa-2-oxocycloheptane; Epsilon-Caprolactone; 2-Oxacycloheptanone; Hexano-6-lactone; 6-Hexanolactone; 1,6-Hexanolide; Hexan-6-olide; oxepan-2-one; Caprolactone; 6-Hexanolide; 2-Oxepanone



数据库引用编号

17 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

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

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。



文献列表

  • Chengzhang Xu, Jun Young Cheong, Xiumei Mo, Valérie Jérôme, Ruth Freitag, Seema Agarwal, Reza Gharibi, Andreas Greiner. Thoroughly Hydrophilized Electrospun Poly(L-Lactide)/ Poly(ε-Caprolactone) Sponges for Tissue Engineering Application. Macromolecular bioscience. 2023 11; 23(11):e2300143. doi: 10.1002/mabi.202300143. [PMID: 37357761]
  • Erveton Pinheiro Pinto, Sarah Olivia Alves Mendes da Costa, Cecile D'Haese, Bernard Nysten, Francisco Paiva Machado, Leandro Machado Rocha, Tiago Marcolino de Souza, Ana Beloqui, Renes Resende Machado, Raquel Silva Araújo. Poly-ɛ-caprolactone nanocapsules loaded with copaiba essential oil reduce inflammation and pain in mice. International journal of pharmaceutics. 2023 Jul; 642(?):123147. doi: 10.1016/j.ijpharm.2023.123147. [PMID: 37336298]
  • Mohammad Shahrousvand, Nadereh Golshan Ebrahimi. Designing nanofibrous poly(ε-caprolactone)/hydroxypropyl cellulose/zinc oxide/Melilotus Officinalis wound dressings using response surface methodology. International journal of pharmaceutics. 2022 Dec; 629(?):122338. doi: 10.1016/j.ijpharm.2022.122338. [PMID: 36309291]
  • Tugba Celiker, Faezeh Ghorbanizamani, Hichem Moulahoum, Emine Guler Celik, Kerem Tok, Figen Zihnioglu, Candan Cicek, Ruchan Sertoz, Bilgin Arda, Tuncay Goksel, Kutsal Turhan, Suna Timur, Yusuf Yagci. Fluorescent bioassay for SARS-CoV-2 detection using polypyrene-g-poly(ε-caprolactone) prepared by simultaneous photoinduced step-growth and ring-opening polymerizations. Mikrochimica acta. 2022 04; 189(5):202. doi: 10.1007/s00604-022-05244-2. [PMID: 35474492]
  • Wangcheng Zhao, Yan Du, Shameen Ashfaq, Shafaqat Ali, Amer M Alanazi, Moreno Santi. Evaluation of the Efficacy, Biocompatibility, and Permeation of Bupivacaine-Loaded Poly(epsilon-caprolactone) Nano-Capsules as an Anesthetic. Journal of biomedical nanotechnology. 2022 Jan; 18(1):268-276. doi: 10.1166/jbn.2022.3223. [PMID: 35180921]
  • David S Ruppert, Mahmoud M Mohammed, Mohamed M Ibrahim, Emilio O Bachtiar, Kevin Erning, Kayvan Ansari, Jeffrey I Everitt, David Brown, Bruce Klitzman, William Koshut, Ken Gall, Howard Levinson. Poly(lactide-co-ε-caprolactone) scaffold promotes equivalent tissue integration and supports skin grafts compared to a predicate collagen scaffold. Wound repair and regeneration : official publication of the Wound Healing Society [and] the European Tissue Repair Society. 2021 11; 29(6):1035-1050. doi: 10.1111/wrr.12951. [PMID: 34129714]
  • Raghav D Ravani, Saumya Yadav, Brijesh Takkar, Seema Sen, Seema Kashyap, Deepika Gupta, Manjeet Jassal, Ashwini Agrawal, Sujata Mohanty, Radhika Tandon. Experimental evaluation of safety and efficacy of plasma-treated poly-ε-caprolactone membrane as a substitute for human amniotic membrane in treating corneal epithelial defects in rabbit eyes. Indian journal of ophthalmology. 2021 Sep; 69(9):2412-2416. doi: 10.4103/ijo.ijo_2986_20. [PMID: 34427233]
  • Xiangke Zhang, Wenbin Liu, Jiawei Liu, Yihe Hu, Honglian Dai. Poly-ε-caprolactone/Whitlockite Electrospun Bionic Membrane with an Osteogenic-Angiogenic Coupling Effect for Periosteal Regeneration. ACS biomaterials science & engineering. 2021 07; 7(7):3321-3331. doi: 10.1021/acsbiomaterials.1c00426. [PMID: 34148343]
  • Xiao-Shuai Wang, Jia-Ming Yang, Ren-Jie Ding, Xi-Zhe Liu, Xiao-Bing Jiang, Zhi-Jian Yang, Ze-Min Ling, Tian-Xue Hu, Fu-Xin Wei. Fabrication of a Polylactide-Glycolide/Poly-ε-Caprolactone/Dextran/Plastrum Testudinis Extract Composite Anti-Inflammation Nanofiber Membrane via Electrospinning for Annulus Fibrosus Regeneration. Journal of biomedical nanotechnology. 2021 05; 17(5):873-888. doi: 10.1166/jbn.2021.3070. [PMID: 34082873]
  • Yanna Liu, Marcel H A M Fens, Robin Bruno Capomaccio, Dora Mehn, Luca Scrivano, Robbert J Kok, Sabrina Oliveira, Wim E Hennink, Cornelus F van Nostrum. Correlation between in vitro stability and pharmacokinetics of poly(ε-caprolactone)-based micelles loaded with a photosensitizer. Journal of controlled release : official journal of the Controlled Release Society. 2020 12; 328(?):942-951. doi: 10.1016/j.jconrel.2020.10.040. [PMID: 33098910]
  • Andreanne G Vasconcelos, Martina O Valim, Adriany G N Amorim, Constança Pais do Amaral, Miguel Peixoto de Almeida, Tatiana K S Borges, Renato Socodato, Camila C Portugal, Guilherme D Brand, Jacó Saraiva C Mattos, João Relvas, Alexandra Plácido, Peter Eaton, Doralina A R Ramos, Selma A S Kückelhaus, José Roberto S A Leite. Cytotoxic activity of poly-ɛ-caprolactone lipid-core nanocapsules loaded with lycopene-rich extract from red guava (Psidium guajava L.) on breast cancer cells. Food research international (Ottawa, Ont.). 2020 10; 136(?):109548. doi: 10.1016/j.foodres.2020.109548. [PMID: 32846600]
  • Dong-Hwan Yang, Gwang-Min Heo, Hong-Ju Park, Hee-Kyun Oh, Min-Suk Kook. Comparative Effectiveness of Surface Functionalized Poly-ε-Caprolactone Scaffold and β-TCP Mixed PCL Scaffold for Bone Regeneration. Journal of nanoscience and nanotechnology. 2020 09; 20(9):5349-5355. doi: 10.1166/jnn.2020.17672. [PMID: 32331102]
  • J Jann, O Drevelle, M-A Lauzon, N Faucheux. Adhesion, intracellular signalling and osteogenic differentiation of mesenchymal progenitor cells and preosteoblasts on poly(epsilon)caprolactone films functionalized by peptides derived from fibronectin and/or BMP-9. Materials science & engineering. C, Materials for biological applications. 2020 Sep; 114(?):111088. doi: 10.1016/j.msec.2020.111088. [PMID: 32994028]
  • Hanan Al-Lawati, Mohammad Reza Vakili, Afsaneh Lavasanifar, Surur Ahmed, Fakhreddin Jamali. Reduced Heart Exposure of Diclofenac by Its Polymeric Micellar Formulation Normalizes CYP-Mediated Metabolism of Arachidonic Acid Imbalance in An Adjuvant Arthritis Rat Model: Implications in Reduced Cardiovascular Side Effects of Diclofenac by Nanodrug Delivery. Molecular pharmaceutics. 2020 04; 17(4):1377-1386. doi: 10.1021/acs.molpharmaceut.0c00069. [PMID: 32023064]
  • Xiaolong Liu, Bing Yang, Zhaosheng Hou, Na Zhang, Yuanyuan Gao. A mild method for surface-grafting MPC onto poly(ester-urethane) based on aliphatic diurethane diisocyanate with high grafting efficiency. Materials science & engineering. C, Materials for biological applications. 2019 Nov; 104(?):109952. doi: 10.1016/j.msec.2019.109952. [PMID: 31499985]
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  • Siriwan Srisang, Norased Nasongkla. Spray coating of foley urinary catheter by chlorhexidine-loadedpoly(ε-caprolactone) nanospheres: effect of lyoprotectants, characteristics, and antibacterial activity evaluation. Pharmaceutical development and technology. 2019 Apr; 24(4):402-409. doi: 10.1080/10837450.2018.1502317. [PMID: 30265590]
  • Katja Jansen, Miguel Castilho, Sanne Aarts, Michael M Kaminski, Soeren S Lienkamp, Roman Pichler, Jos Malda, Tina Vermonden, Jitske Jansen, Rosalinde Masereeuw. Fabrication of Kidney Proximal Tubule Grafts Using Biofunctionalized Electrospun Polymer Scaffolds. Macromolecular bioscience. 2019 02; 19(2):e1800412. doi: 10.1002/mabi.201800412. [PMID: 30548802]
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  • Linlin Miao, Jia Su, Xuezhi Zhuo, Lifeng Luo, Yihan Kong, Jingxin Gou, Tian Yin, Yu Zhang, Haibing He, Xing Tang. mPEG5k- b-PLGA2k/PCL3.4k/MCT Mixed Micelles as Carriers of Disulfiram for Improving Plasma Stability and Antitumor Effect in Vivo. Molecular pharmaceutics. 2018 04; 15(4):1556-1564. doi: 10.1021/acs.molpharmaceut.7b01094. [PMID: 29505711]
  • Hussein O Ammar, Mahmoud M Ghorab, Azza A Mahmoud, Iman M Higazy. Lamotrigine loaded poly-ɛ-(d,l-lactide-co-caprolactone) nanoparticles as brain delivery system. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2018 Mar; 115(?):77-87. doi: 10.1016/j.ejps.2018.01.028. [PMID: 29341900]
  • Silvia Laura Guzmán-Gutiérrez, Antonio Nieto-Camacho, Jorge Ivan Castillo-Arellano, Elizabeth Huerta-Salazar, Griselda Hernández-Pasteur, Mayra Silva-Miranda, Omar Argüello-Nájera, Omar Sepúlveda-Robles, Clara Inés Espitia, Ricardo Reyes-Chilpa. Mexican Propolis: A Source of Antioxidants and Anti-Inflammatory Compounds, and Isolation of a Novel Chalcone and ε-Caprolactone Derivative. Molecules (Basel, Switzerland). 2018 Feb; 23(2):. doi: 10.3390/molecules23020334. [PMID: 29415430]
  • Graziela Scheuer Gomes, Tamara Ramos Maciel, Eduarda Martini Piegas, Luana Roberta Michels, Letícia Marques Colomé, Rodrigo José Freddo, Daiana Silva de Ávila, Andre Gundel, Sandra Elisa Haas. Optimization of Curcuma Oil/Quinine-Loaded Nanocapsules for Malaria Treatment. AAPS PharmSciTech. 2018 Feb; 19(2):551-564. doi: 10.1208/s12249-017-0854-6. [PMID: 28875471]
  • Behzad Sharif Makhmalzadeh, Ommoleila Molavi, Mohammad Reza Vakili, Hai-Feng Zhang, Amir Solimani, Hoda Soleymani Abyaneh, Raimar Loebenberg, Raymond Lai, Afsaneh Lavasanifar. Functionalized Caprolactone-Polyethylene Glycol Based Thermo-Responsive Hydrogels of Silibinin for the Treatment of Malignant Melanoma. Journal of pharmacy & pharmaceutical sciences : a publication of the Canadian Society for Pharmaceutical Sciences, Societe canadienne des sciences pharmaceutiques. 2018; 21(1):143-159. doi: 10.18433/jpps29726. [PMID: 29789104]
  • Dinghu Zhang, Zhengyun Zou, Wei Ren, Hanqing Qian, Qianfeng Cheng, Liulian Ji, Baorui Liu, Qin Liu. Gambogic acid-loaded PEG-PCL nanoparticles act as an effective antitumor agent against gastric cancer. Pharmaceutical development and technology. 2018 Jan; 23(1):33-40. doi: 10.1080/10837450.2017.1295068. [PMID: 29069711]
  • Yu-Fang Hsieh, Khoren Sahagian, Fang Huang, Kang Xu, Shyam Patel, Song Li. Comparison of plasma and chemical modifications of poly-L-lactide-co-caprolactone scaffolds for heparin conjugation. Biomedical materials (Bristol, England). 2017 Oct; 12(6):065004. doi: 10.1088/1748-605x/aa81aa. [PMID: 28980527]
  • Hala Mahmoud Helal, Sana Mohamed Mortada, Marwa Ahmed Sallam. Paliperidone-Loaded Nanolipomer System for Sustained Delivery and Enhanced Intestinal Permeation: Superiority to Polymeric and Solid Lipid Nanoparticles. AAPS PharmSciTech. 2017 Aug; 18(6):1946-1959. doi: 10.1208/s12249-016-0657-1. [PMID: 27914041]
  • Ping Huang, Jing Zhao, Chiju Wei, Xiaohu Hou, Pingzhang Chen, Yan Tan, Cheng-Yi He, Zhiyong Wang, Zhi-Ying Chen. Erythrocyte membrane based cationic polymer-mcDNA complexes as an efficient gene delivery system. Biomaterials science. 2016 Dec; 5(1):120-127. doi: 10.1039/c6bm00638h. [PMID: 27892545]
  • Lisi Xie, Yan Tan, Zhiyong Wang, Hong Liu, Na Zhang, Chao Zou, Xin Liu, Gang Liu, Jian Lu, Hairong Zheng. ε-Caprolactone-Modified Polyethylenimine as Efficient Nanocarriers for siRNA Delivery in Vivo. ACS applied materials & interfaces. 2016 Nov; 8(43):29261-29269. doi: 10.1021/acsami.6b08542. [PMID: 27574860]
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  • Ozan Ozkan, Hilal Turkoglu Sasmazel. Effects of nozzle type atmospheric dry air plasma on L929 fibroblast cells hybrid poly (ε-caprolactone)/chitosan/poly (ε-caprolactone) scaffolds interactions. Journal of bioscience and bioengineering. 2016 Aug; 122(2):232-9. doi: 10.1016/j.jbiosc.2016.01.004. [PMID: 26906227]
  • Rui Li, Xiao-ning Song, Hua Zhang, Wen-bing Dai, Bing He, Ying Zheng, Qiang Zhang, Xue-qing Wang. [The integrity study on PEG-PCL micelles transcellular transported across MDCK epithelial cell monolayer using FRET technology]. Yao xue xue bao = Acta pharmaceutica Sinica. 2016 08; 51(8):1316-24. doi: NULL. [PMID: 29906041]
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