Piperitone (BioDeep_00000017665)

 

Secondary id: BioDeep_00000007661, BioDeep_00000619421, BioDeep_00000638370, BioDeep_00000869747, BioDeep_00001892215

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


2-Cyclohexen-1-one, 3-methyl-6-(1-methylethyl)-, (S)-

化学式: C10H16O (152.12010859999998)
中文名称: 胡椒酮(对映异构体的混合物, 以(R)-(-)-型为主), 胡椒酮
谱图信息: 最多检出来源 Homo sapiens(urine) 13.68%

分子结构信息

SMILES: CC(C)C1CCC(C)=CC1=O
InChI: InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3

描述信息

Piperitone is found in ceylan cinnamon. Piperitone is a flavouring ingredient.Piperitone is a natural monoterpene ketone which is a component of some essential oils. Both stereoisomers, the D-form and the L-form, are known. The D-form has a peppermint-like aroma and has been isolated from the oils of plants from the genera Cymbopogon, Andropogon, and Mentha. The L-form has been isolated from Sitka spruce. (Wikipedia
Piperitone is a p-menthane monoterpenoid that is cyclohex-2-en-1-one substituted by a methyl group at position 3 and an isopropyl group at position 6. It has a role as a volatile oil component and a plant metabolite. It is a p-menthane monoterpenoid and a cyclic terpene ketone.
Piperitone is a natural product found in Clinopodium dalmaticum, Eucalyptus fasciculosa, and other organisms with data available.
A p-menthane monoterpenoid that is cyclohex-2-en-1-one substituted by a methyl group at position 3 and an isopropyl group at position 6.
Flavouring ingredient
Piperitone is as a powerful repellent and antiappetent agent. Piperitone is very toxic to Cymbopogon schoenanthus (C. schoenanthus) adults, newly laid eggs and to neonate larvae. Insecticidal activity[1].
Piperitone is as a powerful repellent and antiappetent agent. Piperitone is very toxic to Cymbopogon schoenanthus (C. schoenanthus) adults, newly laid eggs and to neonate larvae. Insecticidal activity[1].

同义名列表

26 个代谢物同义名

2-Cyclohexen-1-one, 3-methyl-6-(1-methylethyl)-, (S)-; 6-Isopropyl-3-methyl-2-cyclohexen-1-one predominantly; 2-Cyclohexen-1-one, 3-methyl-6-(1-methylethyl)-; 3-methyl-6-(1-methylethyl)-2-cyclohexen-1-one; 2-07-00-00075 (Beilstein Handbook Reference); 3-methyl-6-(propan-2-yl)cyclohex-2-en-1-one; 6-Isopropyl-3-methyl-2-cyclohexen-1-one #; 3-methyl-6-propan-2-ylcyclohex-2-en-1-one; 6-Isopropyl-3-methyl-2-cyclohexen-1-one; 1-Methyl-4-isopropyl-1-cyclohexen-3-one; 6-Isopropyl-3-methylcyclohex-2-enone; 6-Isopropyl-3-methyl-2-cyclohexenone; Piperitone, analytical standard; 2-Cyclohexen-1-one, dimer; p-Menth-1-en-3-one; 3-Carvomenthenone; PIPERITONE [MI]; UNII-1VZ8RG269R; (+-)-Piperitone; PIPERITONE, DL-; DL-Piperitone; Piperitone; 1VZ8RG269R; FEMA 2910; AI3-16053; D-piperitone



数据库引用编号

23 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)

117 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

  • Eveleny Tirsa Vaca Meza, Jorge Vasquez-Kool, Noé Ildefonso Costilla Sánchez, Amandio Vieira, Rodney Alexandre Ferreira Rodrigues, Adilson Sartoratto, Angela Del Pilar Flores Granados, Carmen Luisa Marin Tello, Ana Lucia Tasca Gois Ruiz. Chemical composition and anti-proliferative activity of essential oils from some medicinal plants from Cachicadán, Región La Libertad, Perú. Natural product research. 2023 Jul; ?(?):1-6. doi: 10.1080/14786419.2023.2238114. [PMID: 37470420]
  • Lucia Barrientos Ramírez, José Antonio Silva Guzmán, Edison Antonio Osorio Muñoz, Carlos Alvarez Moya, Mónica Reynoso Silva, Abraham Francisco Cetina Corona, Josefina Casas Solis, J Jesús Vargas Radillo. Chemical Composition, Antioxidant Properties, and Antibacterial Activity of Essential Oils of Satureja macrostema (Moc. and Sessé ex Benth.) Briq. Molecules (Basel, Switzerland). 2023 Jun; 28(12):. doi: 10.3390/molecules28124719. [PMID: 37375274]
  • Aoken Aimila, Xueping Ma, Numonov Sodik, Xamxikamar Mamat, H A Aisa, Maitinuer Maiwulanjiang. Separation and Qualitative Study of Mentha asiatica Boriss. Essential Oil Components by prep-GC, GC-QTOF-MS, NMR and Prediction of Bioactive Compounds. Chemistry & biodiversity. 2023 Feb; ?(?):e202200566. doi: 10.1002/cbdv.202200566. [PMID: 36795002]
  • Mohammed Messaoudi, Abdelkrim Rebiai, Barbara Sawicka, Maria Atanassova, Hamza Ouakouak, Imane Larkem, Chukwuebuka Egbuna, Chinaza Godswill Awuchi, Sihem Boubekeur, Mohamed Amine Ferhat, Samir Begaa, Naima Benchikha. Effect of Extraction Methods on Polyphenols, Flavonoids, Mineral Elements, and Biological Activities of Essential Oil and Extracts of Mentha pulegium L. Molecules (Basel, Switzerland). 2021 Dec; 27(1):. doi: 10.3390/molecules27010011. [PMID: 35011242]
  • Tai-Ying Chiou, Shiori Nomura, Masaaki Konishi, Chien-Sen Liao, Yasutaka Shimotori, Miki Murata, Naofumi Ohtsu, Yoshihito Kohari, Wei-Ju Lee, Tsung-Yu Tsai, Yuichi Nagata, Tohru Saitoh. Conversion and Hydrothermal Decomposition of Major Components of Mint Essential Oil by Small-Scale Subcritical Water Treatment. Molecules (Basel, Switzerland). 2020 Apr; 25(8):. doi: 10.3390/molecules25081953. [PMID: 32331471]
  • Anna Carolina F Valadares, Cassia Cristina F Alves, José Milton Alves, Isabella P B DE Deus, Josemar G DE Oliveira Filho, Tainá Caroline L Dos Santos, Herbert Júnior Dias, Antônio Eduardo M Crotti, Mayker L D Miranda. Essential oils from Piper aduncum inflorescences and leaves: chemical composition and antifungal activity against Sclerotinia sclerotiorum. Anais da Academia Brasileira de Ciencias. 2018 Sep; 90(3):2691-2699. doi: 10.1590/0001-3765201820180033. [PMID: 30304214]
  • John A Byers, Yonatan Maoz, David Wakarchuk, Daniela Fefer, Anat Levi Zada. Inhibitory Effects of Semiochemicals on the Attraction of an Ambrosia Beetle Euwallacea nr. fornicatus to Quercivorol. Journal of chemical ecology. 2018 Jun; 44(6):565-575. doi: 10.1007/s10886-018-0959-8. [PMID: 29663165]
  • Mehdi Teymouri, Ardalan Alizadeh. Chemical composition and antimicrobial activity of the essential oil of Mentha mozaffarianii Jamzad growing wild and cultivated in Iran. Natural product research. 2018 Jun; 32(11):1320-1323. doi: 10.1080/14786419.2017.1342082. [PMID: 28658991]
  • Raju Sripathi, Dharani Jayagopal, Subban Ravi. A study on the seasonal variation of the essential oil composition from Plectranthus hadiensis and its antibacterial activity. Natural product research. 2018 Apr; 32(7):871-874. doi: 10.1080/14786419.2017.1363748. [PMID: 28783957]
  • Jiehui Huang, Chao Qian, Hongjie Xu, Yanjie Huang. Antibacterial activity of Artemisia asiatica essential oil against some common respiratory infection causing bacterial strains and its mechanism of action in Haemophilus influenzae. Microbial pathogenesis. 2018 Jan; 114(?):470-475. doi: 10.1016/j.micpath.2017.12.032. [PMID: 29241769]
  • Juan Antonio Llorens-Molina, Cynthia Fiorella Rivera Seclén, Sandra Vacas Gonzalez, Herminio Boira Tortajada. Mentha suaveolens Ehrh. Chemotypes in Eastern Iberian Peninsula: Essential Oil Variation and Relation with Ecological Factors. Chemistry & biodiversity. 2017 Dec; 14(12):. doi: 10.1002/cbdv.201700320. [PMID: 28886241]
  • Athanasios C Kimbaris, Azucena González-Coloma, Maria Fe Andrés, Veroniki P Vidali, Moschos G Polissiou, Omar Santana-Méridas. Biocidal Compounds from Mentha sp. Essential Oils and Their Structure-Activity Relationships. Chemistry & biodiversity. 2017 Mar; 14(3):. doi: 10.1002/cbdv.201600270. [PMID: 27770481]
  • Heng Yu Li, Xin Chao Liu, Xu Bo Chen, Qi Zhi Liu, Zhi Long Liu. Chemical Composition and Insecticidal Activities of the Essential Oil of Clinopodium chinense (Benth.) Kuntze Aerial Parts against Liposcelis bostrychophila Badonnel. Journal of food protection. 2015 Oct; 78(10):1870-4. doi: 10.4315/0362-028x.jfp-15-089. [PMID: 26408136]
  • K B Rameshkumar, D B Alan Sheeja, Mangalam S Nair, V George. Curcuma ecalcarata - new natural source of pinocembrin and piperitenone. Natural product research. 2015; 29(13):1276-9. doi: 10.1080/14786419.2014.994210. [PMID: 25553726]
  • M Schäffer, T Gröger, M Pütz, R Zimmermann. Forensic profiling of sassafras oils based on comprehensive two-dimensional gas chromatography. Forensic science international. 2013 Jun; 229(1-3):108-15. doi: 10.1016/j.forsciint.2013.03.046. [PMID: 23683915]
  • Sanja Ćavar, Danijela Vidic, Milka Maksimović. Volatile constituents, phenolic compounds, and antioxidant activity of Calamintha glandulosa (Req.) Bentham. Journal of the science of food and agriculture. 2013 May; 93(7):1758-64. doi: 10.1002/jsfa.5967. [PMID: 23184904]
  • Mitscheli S Da Rocha, Puttappa R Dodmane, Lora L Arnold, Karen L Pennington, Muhammad M Anwar, Bret R Adams, Sean V Taylor, Clint Wermes, Timothy B Adams, Samuel M Cohen. Mode of action of pulegone on the urinary bladder of F344 rats. Toxicological sciences : an official journal of the Society of Toxicology. 2012 Jul; 128(1):1-8. doi: 10.1093/toxsci/kfs135. [PMID: 22499580]
  • Charalabos D Kanakis, Eleftherios A Petrakis, Athanasios C Kimbaris, Christos Pappas, Petros A Tarantilis, Moschos G Polissiou. Classification of Greek Mentha pulegium L. (Pennyroyal) samples, according to geographical location by Fourier transform infrared spectroscopy. Phytochemical analysis : PCA. 2012 Jan; 23(1):34-43. doi: 10.1002/pca.1322. [PMID: 21618307]
  • Morten Hyldgaard, Tina Mygind, Rikke Louise Meyer. Essential oils in food preservation: mode of action, synergies, and interactions with food matrix components. Frontiers in microbiology. 2012; 3(?):12. doi: 10.3389/fmicb.2012.00012. [PMID: 22291693]
  • Rajendra C Padalia, Ram S Verma. Comparative study of volatile oil compositions of two Plectranthus species from northern India. Natural product research. 2011 Oct; 25(18):1727-32. doi: 10.1080/14786419.2010.513975. [PMID: 21707228]
  • Márcia M M Marques, Selene M Morais, Icaro G P Vieira, Mariano G S Vieira, Ana Raquel, A Silva, Raimundo Rafael De Almeida, Maria Izabel F Guedes. Larvicidal activity of Tagetes erecta against Aedes aegypti. Journal of the American Mosquito Control Association. 2011 Jun; 27(2):156-8. doi: 10.2987/10-6056.1. [PMID: 21805850]
  • Sobhy Mohamed Abdallah Sallam, Samir Abdelazim Mohamed Abdelgaleil, Ives Claudio da Silva Bueno, Mohamed Emad Abdelwahab Nasser, Rafael Canonenco Araujo, Adibe Luiz Abdalla. Effect of some essential oils on in vitro methane emission. Archives of animal nutrition. 2011 Jun; 65(3):203-14. doi: 10.1080/1745039x.2011.568275. [PMID: 21776837]
  • Nurhayat Tabanca, Betül Demirci, Ilhan Gürbüz, Fatih Demirci, James J Becnel, David E Wedge, Kemal Hüsnü Can Başer. Essential oil composition of five collections of Achillea biebersteinii from central Turkey and their antifungal and insecticidal activity. Natural product communications. 2011 May; 6(5):701-6. doi: . [PMID: 21615036]
  • Donatella Pietrella, Letizia Angiolella, Elisabetta Vavala, Anna Rachini, Francesca Mondello, Rino Ragno, Francesco Bistoni, Anna Vecchiarelli. Beneficial effect of Mentha suaveolens essential oil in the treatment of vaginal candidiasis assessed by real-time monitoring of infection. BMC complementary and alternative medicine. 2011 Feb; 11(?):18. doi: 10.1186/1472-6882-11-18. [PMID: 21356078]
  • Alessandra Bertoli, Michele Leonardi, Justine Krzyzanowska, Wieslaw Oleszek, Luisa Pistelli. Mentha longifolia in vitro cultures as safe source of flavouring ingredients. Acta biochimica Polonica. 2011; 58(4):581-7. doi: . [PMID: 22175048]
  • Esra Küpeli Akkol, Ufuk Koca, Ipek Pesin, Demet Yilmazer. Evaluation of the Wound Healing Potential of Achillea biebersteinii Afan. (Asteraceae) by In Vivo Excision and Incision Models. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):474026. doi: 10.1093/ecam/nep039. [PMID: 19546149]
  • Yasuo Morimoto, Yujiro Shibata. Effects of various fragrant ingredients on desmopressin-induced fluid retention in mice. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2010 Jul; 130(7):983-7. doi: 10.1248/yakushi.130.983. [PMID: 20606379]
  • Ameur Elaissi, Hanène Marzouki, Hanène Medini, Mohamed Larbi Khouja, Farhat Farhat, Fréderic Lynene, Fethia Harzallah-Skhiri, Rachid Chemli. Variation in volatile leaf oils of 13 Eucalyptus species harvested from Souinet arboreta (Tunisia). Chemistry & biodiversity. 2010 Apr; 7(4):909-21. doi: 10.1002/cbdv.200900229. [PMID: 20397231]
  • Ariel C Toloza, Julio Zygadlo, Fernando Biurrun, Alicia Rotman, María I Picollo. Bioactivity of Argentinean essential oils against permethrin-resistant head lice, Pediculus humanus capitis. Journal of insect science (Online). 2010; 10(?):185. doi: 10.1673/031.010.14145. [PMID: 21062140]
  • T Q Effowe, K Amevoin, Y Nuto, D Mondedji, I A Glitho. Reproductive capacities and development of a seed Bruchid beetle, Acanthoscelides macrophthalmus, a potential host for the mass rearing of the parasitoid, Dinarmus basalis. Journal of insect science (Online). 2010; 10(?):129. doi: 10.1673/031.010.12901. [PMID: 20879923]
  • Mohaddese Mahboubi, Ghasem Haghi. Antimicrobial activity and chemical composition of Mentha pulegium L. essential oil. Journal of ethnopharmacology. 2008 Sep; 119(2):325-7. doi: 10.1016/j.jep.2008.07.023. [PMID: 18703127]
  • Héctor Ponce-Monter, María G Campos, Salud Pérez, Cuauhtémoc Pérez, Miguel Zavala, Arturo Macías, Martha Oropeza, Norma Cárdenas. Chemical composition and antispasmodic effect of Casimiroa pringlei essential oil on rat uterus. Fitoterapia. 2008 Sep; 79(6):446-50. doi: 10.1016/j.fitote.2008.04.005. [PMID: 18538506]
  • Samir A M Abdelgaleil, Moustafa A Abbassy, Abdel-Salam H Belal, Mona A A Abdel Rasoul. Bioactivity of two major constituents isolated from the essential oil of Artemisia judaica L. Bioresource technology. 2008 Sep; 99(13):5947-50. doi: 10.1016/j.biortech.2007.10.043. [PMID: 18054484]
  • Carolina Marangon Jardim, Gulab Newandram Jham, Onkar Dev Dhingra, Marcelo Moreira Freire. Composition and antifungal activity of the essential oil of the Brazilian Chenopodium ambrosioides L. Journal of chemical ecology. 2008 Sep; 34(9):1213-8. doi: 10.1007/s10886-008-9526-z. [PMID: 18679750]
  • Andrea L Medina-Holguín, F Omar Holguín, Sandra Micheletto, Sondra Goehle, Julian A Simon, Mary A O'Connell. Chemotypic variation of essential oils in the medicinal plant, Anemopsis californica. Phytochemistry. 2008 Feb; 69(4):919-27. doi: 10.1016/j.phytochem.2007.11.006. [PMID: 18177907]
  • Bharti Sapra, Subheet Jain, A K Tiwary. Percutaneous permeation enhancement by terpenes: mechanistic view. The AAPS journal. 2008; 10(1):120-32. doi: 10.1208/s12248-008-9012-0. [PMID: 18446512]
  • S A Nirmal, A S Girme, R D Bhalke. Major constituents and anthelmintic activity of volatile oils from leaves and flowers of Cymbopogon martini Roxb. Natural product research. 2007 Nov; 21(13):1217-20. doi: 10.1080/14786410701552152. [PMID: 17987504]
  • Ling-Jen Chen Ferguson, Edward H Lebetkin, Fred B Lih, Kenneth B Tomer, Horace D Parkinson, Susan J Borghoff, Leo T Burka. 14C-labeled pulegone and metabolites binding to alpha2u-globulin in kidneys of male F-344 rats. Journal of toxicology and environmental health. Part A. 2007 Sep; 70(17):1416-23. doi: 10.1080/15287390701382720. [PMID: 17687727]
  • Cheryl Lans. Comparison of plants used for skin and stomach problems in Trinidad and Tobago with Asian ethnomedicine. Journal of ethnobiology and ethnomedicine. 2007 Jan; 3(?):3. doi: 10.1186/1746-4269-3-3. [PMID: 17207273]
  • Fatemeh Rafii, Ahmad R Shahverdi. Comparison of essential oils from three plants for enhancement of antimicrobial activity of nitrofurantoin against enterobacteria. Chemotherapy. 2007; 53(1):21-5. doi: 10.1159/000098246. [PMID: 17192709]
  • Guillaume K Ketoh, Honore K Koumaglo, Isabelle A Glitho, Jacques Huignard. Comparative effects of Cymbopogon schoenanthus essential oil and piperitone on Callosobruchus maculatus development. Fitoterapia. 2006 Dec; 77(7-8):506-10. doi: 10.1016/j.fitote.2006.05.031. [PMID: 16938411]
  • Mahmoud A Saleh, Mohamed H Belal, Gamal el-Baroty. Fungicidal activity of Artemisia herba alba Asso (Asteraceae). Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2006; 41(3):237-44. doi: 10.1080/03601230500354774. [PMID: 16484084]
  • Andrea L Medina, Mary E Lucero, F Omar Holguin, Rick E Estell, Jeff J Posakony, Julian Simon, Mary A O'Connell. Composition and Antimicrobial Activity of Anemopsis californica leaf oil. Journal of agricultural and food chemistry. 2005 Nov; 53(22):8694-8. doi: 10.1021/jf0511244. [PMID: 16248573]
  • Norma C Cárdenas-Ortega, Miguel A Zavala-Sánchez, J Rogelio Aguirre-Rivera, Cuauhtémoc Pérez-González, Salud Pérez-Gutiérrez. Chemical composition and antifungal activity of essential oil of Chrysactinia mexicana gray. Journal of agricultural and food chemistry. 2005 Jun; 53(11):4347-9. doi: 10.1021/jf040372h. [PMID: 15913293]
  • C Romagnoli, R Bruni, E Andreotti, M K Rai, C B Vicentini, D Mares. Chemical characterization and antifungal activity of essential oil of capitula from wild Indian Tagetes patula L. Protoplasma. 2005 Apr; 225(1-2):57-65. doi: 10.1007/s00709-005-0084-8. [PMID: 15868213]
  • A R Shahverdi, F Rafii, F Tavassoli, M Bagheri, F Attar, A Ghahraman. Piperitone from Mentha longifolia var. chorodictya Rech F. reduces the nitrofurantoin resistance of strains of enterobacteriaceae. Phytotherapy research : PTR. 2004 Nov; 18(11):911-4. doi: 10.1002/ptr.1566. [PMID: 15597306]
  • Atalay Sökmen, Münevver Sökmen, Dimitra Daferera, Moschos Polissiou, Ferda Candan, Mehmet Unlü, H Aşkin Akpulat. The in vitro antioxidant and antimicrobial activities of the essential oil and methanol extracts of Achillea biebersteini Afan. (Asteraceae). Phytotherapy research : PTR. 2004 Jun; 18(6):451-6. doi: 10.1002/ptr.1438. [PMID: 15287068]
  • Elena E Stashenko, Beatriz E Jaramillo, Jairo René Martínez. Comparison of different extraction methods for the analysis of volatile secondary metabolites of Lippia alba (Mill.) N.E. Brown, grown in Colombia, and evaluation of its in vitro antioxidant activity. Journal of chromatography. A. 2004 Jan; 1025(1):93-103. doi: 10.1016/j.chroma.2003.10.058. [PMID: 14753676]
  • Atalay Sökmen, Gülhan Vardar-Unlü, Moschos Polissiou, Dimitra Daferera, Münevver Sökmen, Erol Dönmez. Antimicrobial activity of essential oil and methanol extracts of Achillea sintenisii Hub. Mor. (Asteraceae). Phytotherapy research : PTR. 2003 Nov; 17(9):1005-10. doi: 10.1002/ptr.1274. [PMID: 14595577]
  • Wolfgang Engel. In vivo studies on the metabolism of the monoterpene pulegone in humans using the metabolism of ingestion-correlated amounts (MICA) approach: explanation for the toxicity differences between (S)-(-)- and (R)-(+)-pulegone. Journal of agricultural and food chemistry. 2003 Oct; 51(22):6589-97. doi: 10.1021/jf034702u. [PMID: 14558782]
  • S Fuchs, V Montag, A Mosandl. Menthone and isomenthone biosynthesis in Pelargonium tomentosum Jacq. Enantiomer. 2001; 6(6):319-27. doi: . [PMID: 11958337]