Cannabichromene (BioDeep_00000002600)

 

Secondary id: BioDeep_00001868564

human metabolite PANOMIX_OTCML-2023 blood metabolite Volatile Flavor Compounds natural product


代谢物信息卡片


2-methyl-2-(4-methylpent-3-en-1-yl)-7-pentyl-2H-chromen-5-ol

化学式: C21H30O2 (314.224568)
中文名称: (±)-Cannabichromene, 大麻色原烯, 大麻素
谱图信息: 最多检出来源 Homo sapiens(blood) 0.39%

分子结构信息

SMILES: c1(cc(c2c(c1)O[C@@](C=C2)(C)CCC=C(C)C)O)CCCCC
InChI: InChI=1S/C21H30O2/c1-5-6-7-10-17-14-19(22)18-11-13-21(4,23-20(18)15-17)12-8-9-16(2)3/h9,11,13-15,22H,5-8,10,12H2,1-4H3

描述信息

同义名列表

5 个代谢物同义名

2-methyl-2-(4-methylpent-3-en-1-yl)-7-pentyl-2H-chromen-5-ol; CANNABICHROMENE; CBC; Cannabichromene; Cannabichromene



数据库引用编号

18 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

4 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(3)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

19 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

  • Jenny L Wiley, Julie A Marusich, Bruce E Blough, Ojas Namjoshi, Marcus Brackeen, Luli R Akinfiresoye, Teneille D Walker, Cassandra Prioleau, Daniel G Barrus, Thomas F Gamage. Evaluation of cannabimimetic effects of selected minor cannabinoids and Terpenoids in mice. Progress in neuro-psychopharmacology & biological psychiatry. 2024 Jun; 132(?):110984. doi: 10.1016/j.pnpbp.2024.110984. [PMID: 38417478]
  • Evangelos Dadiotis, Meng Cui, Maria Gerasi, Vangelis Mitsis, Eleni Melliou, Alexandros Makriyannis, Diomedes E Logothetis, Prokopios Magiatis. A Simple Chiral 1H NMR Method for the Discrimination of (R)- and (S)-Cannabichromene in Complex Natural Mixtures and Their Effects on TRPA1 Activity. Journal of natural products. 2024 Jan; 87(1):77-84. doi: 10.1021/acs.jnatprod.3c00796. [PMID: 38158562]
  • Dylan T Marsh, Ayato Sugiyama, Yuta Imai, Ryuji Kato, Scott D Smid. The structurally diverse phytocannabinoids cannabichromene, cannabigerol and cannabinol significantly inhibit amyloid β-evoked neurotoxicity and changes in cell morphology in PC12 cells. Basic & clinical pharmacology & toxicology. 2023 Sep; ?(?):. doi: 10.1111/bcpt.13943. [PMID: 37697481]
  • Andrea Calcaterra, Gabriele Cianfoni, Carola Tortora, Simone Manetto, Giulio Grassi, Bruno Botta, Francesco Gasparrini, Giulia Mazzoccanti, Giovanni Appendino. Natural Cannabichromene (CBC) Shows Distinct Scalemicity Grades and Enantiomeric Dominance in Cannabis sativa Strains. Journal of natural products. 2023 Apr; ?(?):. doi: 10.1021/acs.jnatprod.2c01139. [PMID: 37023389]
  • Yang Zhao, Estatira Sepehr, Cory Vaught, Jeffrey Yourick, Robert L Sprando. Development and validation of a fit-for-purpose UHPLC-ESI-MS/MS method for the quantitation of cannabinoids in different matrices. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2023 Mar; 1218(?):123629. doi: 10.1016/j.jchromb.2023.123629. [PMID: 36854205]
  • Fabian Thomas, Oliver Kayser. Improving CBCA synthase activity through rational protein design. Journal of biotechnology. 2023 Feb; 363(?):40-49. doi: 10.1016/j.jbiotec.2023.01.004. [PMID: 36681096]
  • Yuting Wen, Zefeng Wang, Rui Zhang, Yuying Zhu, Guoqiang Lin, Ruixiang Li, Jiange Zhang. The antinociceptive activity and mechanism of action of cannabigerol. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Feb; 158(?):114163. doi: 10.1016/j.biopha.2022.114163. [PMID: 36916438]
  • Rie Tanaka, Sakumi Mizutani, Maiko Kawamura, Hiroyuki Fuchino, Nobuo Kawahara, Ruri Kikura-Hanajiri. [Determination of 11 Cannabinoids in Cannabis sativa L. by Liquid Chromatography Quadrupole Time-of-Flight Mass Spectrometry (LC-Q-TOF-MS)]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2023; 143(4):411-418. doi: 10.1248/yakushi.22-00198. [PMID: 37005243]
  • Maia G Etchart, Lyndsey L Anderson, Adam Ametovski, Peter M Jones, Anthony M George, Samuel D Banister, Jonathon C Arnold. In vitro evaluation of the interaction of the cannabis constituents cannabichromene and cannabichromenic acid with ABCG2 and ABCB1 transporters. European journal of pharmacology. 2022 May; 922(?):174836. doi: 10.1016/j.ejphar.2022.174836. [PMID: 35306000]
  • Erica N Peters, Laura MacNair, Irina Mosesova, Uwe Christians, Cristina Sempio, Jost Klawitter, M Hunter Land, Mark A Ware, Cynthia Turcotte, Marcel O Bonn-Miller. Pharmacokinetics of cannabichromene in a medical cannabis product also containing cannabidiol and Δ9-tetrahydrocannabinol: a pilot study. European journal of clinical pharmacology. 2022 Feb; 78(2):259-265. doi: 10.1007/s00228-021-03232-8. [PMID: 34664109]
  • Peter B Sampson. Phytocannabinoid Pharmacology: Medicinal Properties of Cannabis sativa Constituents Aside from the 'Big Two'. Journal of natural products. 2021 01; 84(1):142-160. doi: 10.1021/acs.jnatprod.0c00965. [PMID: 33356248]
  • Lyndsey L Anderson, Adam Ametovski, Jia Lin Luo, Declan Everett-Morgan, Iain S McGregor, Samuel D Banister, Jonathon C Arnold. Cannabichromene, Related Phytocannabinoids, and 5-Fluoro-cannabichromene Have Anticonvulsant Properties in a Mouse Model of Dravet Syndrome. ACS chemical neuroscience. 2021 01; 12(2):330-339. doi: 10.1021/acschemneuro.0c00677. [PMID: 33395525]
  • Omer Anis, Ajjampura C Vinayaka, Nurit Shalev, Dvora Namdar, Stalin Nadarajan, Seegehalli M Anil, Ofer Cohen, Eduard Belausov, Jacob Ramon, Einav Mayzlish Gati, Hinanit Koltai. Cannabis-Derived Compounds Cannabichromene and Δ9-Tetrahydrocannabinol Interact and Exhibit Cytotoxic Activity against Urothelial Cell Carcinoma Correlated with Inhibition of Cell Migration and Cytoskeleton Organization. Molecules (Basel, Switzerland). 2021 Jan; 26(2):. doi: 10.3390/molecules26020465. [PMID: 33477303]
  • Ayat Zagzoog, Kawthar A Mohamed, Hye Ji J Kim, Eunhyun D Kim, Connor S Frank, Tallan Black, Pramodkumar D Jadhav, Larry A Holbrook, Robert B Laprairie. In vitro and in vivo pharmacological activity of minor cannabinoids isolated from Cannabis sativa. Scientific reports. 2020 11; 10(1):20405. doi: 10.1038/s41598-020-77175-y. [PMID: 33230154]
  • Yannick Nuapia, Hlanganani Tutu, Luke Chimuka, Ewa Cukrowska. Selective Extraction of Cannabinoid Compounds from Cannabis Seed Using Pressurized Hot Water Extraction. Molecules (Basel, Switzerland). 2020 Mar; 25(6):. doi: 10.3390/molecules25061335. [PMID: 32183432]
  • Abdullateef Isiaka Alagbonsi, Luqman Aribidesi Olayaki, Halimat Amin Abdulrahim, Thomson Sijuade Adetona, Gbemileke Tobiloba Akinyemi. Cannabinoid-deficient Benin republic hemp (Cannabis sativa L.) improves semen parameters by reducing prolactin and enhancing anti-oxidant status. BMC complementary and alternative medicine. 2019 Jun; 19(1):132. doi: 10.1186/s12906-019-2541-5. [PMID: 31208410]
  • Yedukondalu Nalli, Mohd Saleem Dar, Nasima Bano, Javeed Ur Rasool, Aminur R Sarkar, Junaid Banday, Aadil Qadir Bhat, Basit Rafia, Ram A Vishwakarma, Mohd Jamal Dar, Asif Ali. Analyzing the role of cannabinoids as modulators of Wnt/β-catenin signaling pathway for their use in the management of neuropathic pain. Bioorganic & medicinal chemistry letters. 2019 05; 29(9):1043-1046. doi: 10.1016/j.bmcl.2019.03.013. [PMID: 30871771]
  • Christopher W Cunningham. Plant-Based Modulators of Endocannabinoid Signaling. Journal of natural products. 2019 03; 82(3):636-646. doi: 10.1021/acs.jnatprod.8b00874. [PMID: 30816712]
  • Sarah E Turner, Claire M Williams, Leslie Iversen, Benjamin J Whalley. Molecular Pharmacology of Phytocannabinoids. Progress in the chemistry of organic natural products. 2017 ; 103(?):61-101. doi: 10.1007/978-3-319-45541-9_3. [PMID: 28120231]
  • Wendy Swift, Alex Wong, Kong M Li, Jonathon C Arnold, Iain S McGregor. Analysis of cannabis seizures in NSW, Australia: cannabis potency and cannabinoid profile. PloS one. 2013; 8(7):e70052. doi: 10.1371/journal.pone.0070052. [PMID: 23894589]
  • L De Petrocellis, P Orlando, A Schiano Moriello, G Aviello, C Stott, A A Izzo, V Di Marzo. Cannabinoid actions at TRPV channels: effects on TRPV3 and TRPV4 and their potential relevance to gastrointestinal inflammation. Acta physiologica (Oxford, England). 2012 Feb; 204(2):255-66. doi: 10.1111/j.1748-1716.2011.02338.x. [PMID: 21726418]
  • Hemant Lata, Suman Chandra, Natascha Techen, Ikhlas A Khan, Mahmoud A ElSohly. Molecular analysis of genetic fidelity in Cannabis sativa L. plants grown from synthetic (encapsulated) seeds following in vitro storage. Biotechnology letters. 2011 Dec; 33(12):2503-8. doi: 10.1007/s10529-011-0712-7. [PMID: 21805186]
  • Harm van Bakel, Jake M Stout, Atina G Cote, Carling M Tallon, Andrew G Sharpe, Timothy R Hughes, Jonathan E Page. The draft genome and transcriptome of Cannabis sativa. Genome biology. 2011 Oct; 12(10):R102. doi: 10.1186/gb-2011-12-10-r102. [PMID: 22014239]
  • Ethan B Russo. Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects. British journal of pharmacology. 2011 Aug; 163(7):1344-64. doi: 10.1111/j.1476-5381.2011.01238.x. [PMID: 21749363]
  • Luciano De Petrocellis, Alessia Ligresti, Aniello Schiano Moriello, Marco Allarà, Tiziana Bisogno, Stefania Petrosino, Colin G Stott, Vincenzo Di Marzo. Effects of cannabinoids and cannabinoid-enriched Cannabis extracts on TRP channels and endocannabinoid metabolic enzymes. British journal of pharmacology. 2011 Aug; 163(7):1479-94. doi: 10.1111/j.1476-5381.2010.01166.x. [PMID: 21175579]
  • Naoki Iwata, Susumu Kitanaka. New cannabinoid-like chromane and chromene derivatives from Rhododendron anthopogonoides. Chemical & pharmaceutical bulletin. 2011; 59(11):1409-12. doi: 10.1248/cpb.59.1409. [PMID: 22041081]
  • Justin L Poklis, Candace C Thompson, Kelly A Long, Aron H Lichtman, Alphonse Poklis. Disposition of cannabichromene, cannabidiol, and Δ⁹-tetrahydrocannabinol and its metabolites in mouse brain following marijuana inhalation determined by high-performance liquid chromatography-tandem mass spectrometry. Journal of analytical toxicology. 2010 Oct; 34(8):516-20. doi: 10.1093/jat/34.8.516. [PMID: 21258613]
  • Angie Garcia, Dan Borchardt, Chia-En A Chang, Michael J Marsella. Thermal isomerization of cannabinoid analogues. Journal of the American Chemical Society. 2009 Nov; 131(46):16640-1. doi: 10.1021/ja907062v. [PMID: 19919138]
  • Lamont Booker, Pattipati S Naidu, Raj K Razdan, Anu Mahadevan, Aron H Lichtman. Evaluation of prevalent phytocannabinoids in the acetic acid model of visceral nociception. Drug and alcohol dependence. 2009 Nov; 105(1-2):42-7. doi: 10.1016/j.drugalcdep.2009.06.009. [PMID: 19679411]
  • Giovanni Appendino, Simon Gibbons, Anna Giana, Alberto Pagani, Gianpaolo Grassi, Michael Stavri, Eileen Smith, M Mukhlesur Rahman. Antibacterial cannabinoids from Cannabis sativa: a structure-activity study. Journal of natural products. 2008 Aug; 71(8):1427-30. doi: 10.1021/np8002673. [PMID: 18681481]
  • Luciano De Petrocellis, Vittorio Vellani, Aniello Schiano-Moriello, Pietro Marini, Pier Cosimo Magherini, Pierangelo Orlando, Vincenzo Di Marzo. Plant-derived cannabinoids modulate the activity of transient receptor potential channels of ankyrin type-1 and melastatin type-8. The Journal of pharmacology and experimental therapeutics. 2008 Jun; 325(3):1007-15. doi: 10.1124/jpet.107.134809. [PMID: 18354058]
  • Ethan B Russo, Hong-En Jiang, Xiao Li, Alan Sutton, Andrea Carboni, Francesca del Bianco, Giuseppe Mandolino, David J Potter, You-Xing Zhao, Subir Bera, Yong-Bing Zhang, En-Guo Lü, David K Ferguson, Francis Hueber, Liang-Cheng Zhao, Chang-Jiang Liu, Yu-Fei Wang, Cheng-Sen Li. Phytochemical and genetic analyses of ancient cannabis from Central Asia. Journal of experimental botany. 2008; 59(15):4171-82. doi: 10.1093/jxb/ern260. [PMID: 19036842]
  • Supaart Sirikantaramas, Futoshi Taura, Satoshi Morimoto, Yukihiro Shoyama. Recent advances in Cannabis sativa research: biosynthetic studies and its potential in biotechnology. Current pharmaceutical biotechnology. 2007 Aug; 8(4):237-43. doi: 10.2174/138920107781387456. [PMID: 17691992]
  • Alessia Ligresti, Aniello Schiano Moriello, Katarzyna Starowicz, Isabel Matias, Simona Pisanti, Luciano De Petrocellis, Chiara Laezza, Giuseppe Portella, Maurizio Bifulco, Vincenzo Di Marzo. Antitumor activity of plant cannabinoids with emphasis on the effect of cannabidiol on human breast carcinoma. The Journal of pharmacology and experimental therapeutics. 2006 Sep; 318(3):1375-87. doi: 10.1124/jpet.106.105247. [PMID: 16728591]