fenchone (BioDeep_00000007642)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(1R,4S)-(+)-fenchone;(1R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one

化学式: C10H16O (152.12010859999998)
中文名称: 葑酮
谱图信息: 最多检出来源 Viridiplantae(plant) 23.85%

分子结构信息

SMILES: C12(C(=O)C(C)(C)C(CC1)C2)C
InChI: InChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3

描述信息

A carbobicyclic compound that is fenchane in which the hydrogens at position 2 are replaced by an oxo group. It is a component of essential oil from fennel (Foeniculum vulgare).
Fenchone is a natural organic compound classified as a monoterpene and a ketone. It is a colorless oily liquid. It has a structure and an odor similar to camphor. Fenchone is a constituent of absinthe and the essential oil of fennel. Fenchone is used as a flavor in foods and in perfumery. Only 2 stereoisomers are possible: D-fenchone (enantiomer 1S,4R is dextrogyre (+)) and L-fenchone (enantiomer 1R,4S is levogyre (-)). Due to the small size of the cycle, the 2 other diastereoisomers (1S4S and 1R4R) are not possible. [Wikipedia]. Fenchone is found in many foods, some of which are ceylon cinnamon, sweet basil, saffron, and dill.
(-)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. (-)-Fenchone is oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives by CYP2A6 and CYP2B6 in human liver microsomes with CYP2A6 playing a more important role than CYP2B6[1].
(-)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. (-)-Fenchone is oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives by CYP2A6 and CYP2B6 in human liver microsomes with CYP2A6 playing a more important role than CYP2B6[1].
(-)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. (-)-Fenchone is oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives by CYP2A6 and CYP2B6 in human liver microsomes with CYP2A6 playing a more important role than CYP2B6[1].
(-)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. (-)-Fenchone is oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives by CYP2A6 and CYP2B6 in human liver microsomes with CYP2A6 playing a more important role than CYP2B6[1].

同义名列表

6 个代谢物同义名

fenchone; (1R,4S)-(+)-fenchone;(1R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one; (1R,4S)-fenchan-2-one; (1R,4S)-fenchone; (.+/-.)-Fenchone; (-)-Fenchone



数据库引用编号

22 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)

231 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

  • Li Cui, Yongzhi Hua, Shuting Zou, Chao Gu, Hui Li. Combination of fenchone and sodium hyaluronate ameliorated constipation-predominant irritable bowel syndrome and underlying mechanisms. Chemical biology & drug design. 2024 Jan; 103(1):e14397. doi: 10.1111/cbdd.14397. [PMID: 38030381]
  • Li Cui, Bin Zhang, Shuting Zou, Jing Liu, Pingrong Wang, Hui Li, Zhenhai Zhang. Fenchone Ameliorates ConstipationPredominant Irritable Bowel Syndrome via Modulation of SCF/c-Kit Pathway and Gut Microbiota. Journal of microbiology and biotechnology. 2023 Oct; 34(2):1-12. doi: 10.4014/jmb.2308.08011. [PMID: 38073315]
  • Shoaib Nawaz, Hafiz Muhammad Irfan, Alamgeer, Laiba Arshad, Shah Jahan. Attenuation of CFA-induced chronic inflammation by a bicyclic monoterpene fenchone targeting inducible nitric oxide, prostaglandins, C-reactive protein and urea. Inflammopharmacology. 2023 Sep; ?(?):. doi: 10.1007/s10787-023-01333-7. [PMID: 37689616]
  • Farzad Rasouli, Yousef Nasiri, Mohammad Bagher Hassanpouraghdam, Mohammad Asadi, Taher Qaderi, Amini Trifa, Maciej Strzemski, Sławomir Dresler, Małgorzata Szczepanek. Seaweed extract and arbuscular mycorrhiza co-application affect the growth responses and essential oil composition of Foeniculum vulgare L. Scientific reports. 2023 07; 13(1):11902. doi: 10.1038/s41598-023-39194-3. [PMID: 37488427]
  • Elaheh Sadat Hosseini, Mohammad Mahdi Majidi, Mohammad Hossein Ehtemam, N Hughes. Characterization of fennel germplasm for physiological persistence and drought recovery: Association with biochemical properties. Plant physiology and biochemistry : PPB. 2023 Jan; 194(?):499-512. doi: 10.1016/j.plaphy.2022.11.037. [PMID: 36516537]
  • Olga I Yarovaya, Kseniya S Kovaleva, Anna A Zaykovskaya, Liudmila N Yashina, Nadezda S Scherbakova, Dmitry N Scherbakov, Sophia S Borisevich, Fedor I Zubkov, Alexandra S Antonova, Roman Yu Peshkov, Ilia V Eltsov, Oleg V Pyankov, Rinat A Maksyutov, Nariman F Salakhutdinov. New class of hantaan virus inhibitors based on conjugation of the isoindole fragment to (+)-camphor or (-)-fenchone hydrazonesv. Bioorganic & medicinal chemistry letters. 2021 05; 40(?):127926. doi: 10.1016/j.bmcl.2021.127926. [PMID: 33705902]
  • Michelle Liz de Souza Pessoa, Leiliane Macena Oliveira Silva, Maria Elaine Cristina Araruna, Catarina Alves de Lima Serafim, Edvaldo Balbino Alves Júnior, Alessa Oliveira Silva, Matheus Marley Bezerra Pessoa, Hermes Diniz Neto, Edeltrudes de Oliveira Lima, Leônia Maria Batista. Antifungal activity and antidiarrheal activity via antimotility mechanisms of (-)-fenchone in experimental models. World journal of gastroenterology. 2020 Nov; 26(43):6795-6809. doi: 10.3748/wjg.v26.i43.6795. [PMID: 33268962]
  • J S Rosa, L Oliveira, R M O F Sousa, C B Escobar, M Fernandes-Ferreira. Bioactivity of some Apiaceae essential oils and their constituents against Sitophilus zeamais (Coleoptera: Curculionidae). Bulletin of entomological research. 2020 Jun; 110(3):406-416. doi: 10.1017/s0007485319000774. [PMID: 31813390]
  • Sukhchain Singh, Pawan Gupta, Jeena Gupta. Virtual Structural Similarity Elucidates Bioactivity of Fenchone: A Phytochemical Enriched in Fennel Essential Oil. Current drug discovery technologies. 2020; 17(5):619-630. doi: 10.2174/1570163816666190321142826. [PMID: 30907324]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Shinsuke Marumoto, Yoshiharu Okuno, Mitsuo Miyazawa. Inhibition of β-Secretase Activity by Monoterpenes, Sesquiterpenes, and C13 Norisoprenoids. Journal of oleo science. 2017 Aug; 66(8):851-855. doi: 10.5650/jos.ess16188. [PMID: 28381772]
  • Thaísa Leite Rolim, Déborah Ribeiro Pessoa Meireles, Tatianne Mota Batista, Tatyanna Kelvia Gomes de Sousa, Vivianne Mendes Mangueira, Renata Albuquerque de Abrantes, João Carlos Lima Rodrigues Pita, Aline Lira Xavier, Vicente Carlos Oliveira Costa, Leônia Maria Batista, Marcelo Sobral da Silva, Marianna Vieira Sobral. Toxicity and antitumor potential of Mesosphaerum sidifolium (Lamiaceae) oil and fenchone, its major component. BMC complementary and alternative medicine. 2017 Jul; 17(1):347. doi: 10.1186/s12906-017-1779-z. [PMID: 28673306]
  • I Keskin, Y Gunal, S Ayla, B Kolbasi, A Sakul, U Kilic, O Gok, K Koroglu, H Ozbek. Effects of Foeniculum vulgare essential oil compounds, fenchone and limonene, on experimental wound healing. Biotechnic & histochemistry : official publication of the Biological Stain Commission. 2017; 92(4):274-282. doi: 10.1080/10520295.2017.1306882. [PMID: 28426256]
  • Valtcho D Zheljazkov, Thomas Horgan, Tess Astatkie, Vicki Schlegel. Distillation time modifies essential oil yield, composition, and antioxidant capacity of fennel (Foeniculum vulgare Mill). Journal of oleo science. 2013; 62(9):665-72. doi: 10.5650/jos.62.665. [PMID: 24005011]
  • M Zuzarte, M J Gonçalves, M T Cruz, C Cavaleiro, J Canhoto, S Vaz, E Pinto, L Salgueiro. Lavandula luisieri essential oil as a source of antifungal drugs. Food chemistry. 2012 Dec; 135(3):1505-10. doi: 10.1016/j.foodchem.2012.05.090. [PMID: 22953886]
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  • Hugo J de Boer, Vichith Lamxay, Lars Björk. Steam sauna and mother roasting in Lao PDR: practices and chemical constituents of essential oils of plant species used in postpartum recovery. BMC complementary and alternative medicine. 2011 Dec; 11(?):128. doi: 10.1186/1472-6882-11-128. [PMID: 22171719]
  • Maria Graça Miguel, Maria Dulce Antunes. Is propolis safe as an alternative medicine?. Journal of pharmacy & bioallied sciences. 2011 Oct; 3(4):479-95. doi: 10.4103/0975-7406.90101. [PMID: 22219581]
  • Ill-Min Chung, Hee-Myong Ro, Huyng-In Moon. Major essential oils composition and immunotoxicity activity from leaves of Foeniculum vulgare against Aedes aegypti L. Immunopharmacology and immunotoxicology. 2011 Sep; 33(3):450-3. doi: 10.3109/08923973.2010.532805. [PMID: 21077804]
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  • Dimitroula Tsiri, Konstantia Graikou, Loretta Pobłocka-Olech, Miroslawa Krauze-Baranowska, Caroline Spyropoulos, Ioanna Chinou. Chemosystematic value of the essential oil composition of Thuja species cultivated in Poland-antimicrobial activity. Molecules (Basel, Switzerland). 2009 Nov; 14(11):4707-15. doi: 10.3390/molecules14114707. [PMID: 19935470]
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