Cannabinol (BioDeep_00000001922)
Secondary id: BioDeep_00000408305
human metabolite PANOMIX_OTCML-2023 blood metabolite
代谢物信息卡片
3-Amyl-1-hydroxy-6,6,9-trimethyl-6H-dibenzo[b,d]pyran
化学式: C21H26O2 (310.1932696)
中文名称: 大麻酚
谱图信息:
最多检出来源 Chinese Herbal Medicine(otcml) 2.29%
分子结构信息
SMILES: CCCCCC1=CC(=C2C(=C1)OC(C3=C2C=C(C=C3)C)(C)C)O
InChI: InChI=1S/C21H26O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h9-13,22H,5-8H2,1-4H3
描述信息
C308 - Immunotherapeutic Agent > C574 - Immunosuppressant
同义名列表
数据库引用编号
17 个数据库交叉引用编号
- ChEBI: CHEBI:3360
- KEGG: C07580
- PubChem: 2543
- HMDB: HMDB0249590
- Metlin: METLIN41033
- DrugBank: DB14737
- ChEMBL: CHEMBL74415
- Wikipedia: Cannabinol
- MeSH: Cannabinol
- KNApSAcK: C00002675
- chemspider: 2447
- CAS: 521-35-7
- PMhub: MS000001452
- PubChem: 9782
- LipidMAPS: LMPK13120002
- 3DMET: B02128
- NIKKAJI: J6.613C
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)
3 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
- Ning Wang, Boyu Liu, Donghua Wang, Kaiwen Xing, Wen Wang, Tong Wang, Dianyu Yu. Oil-in-water and oleogel-in-water emulsion encapsulate with hemp seed oil containing Δ9-tetrahydrocannabinol and cannabinol: Stability, degradation and in vitro simulation characteristics.
Food chemistry.
2024 Jun; 444(?):138633. doi:
10.1016/j.foodchem.2024.138633. [PMID: 38330607] - 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] - Oleh Durydivka, Petr Palivec, Matej Gazdarica, Ken Mackie, Jaroslav Blahos, Martin Kuchar. Hexahydrocannabinol (HHC) and Δ9-tetrahydrocannabinol (Δ9-THC) driven activation of cannabinoid receptor 1 results in biased intracellular signaling.
Scientific reports.
2024 04; 14(1):9181. doi:
10.1038/s41598-024-58845-7. [PMID: 38649680] - 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] - Beatriz Correia, Samir Marcos Ahmad, Alexandre Quintas. Determination of phytocannabinoids in cannabis samples by ultrasound-assisted solid-liquid extraction and high-performance liquid chromatography with diode array detector analysis.
Journal of chromatography. A.
2023 Aug; 1705(?):464191. doi:
10.1016/j.chroma.2023.464191. [PMID: 37454455] - Fresia Melina Silva Sofrás, Rosario Alonso, Daiana Sabrina Retta, Paola Di Leo Lira, Martin Federico Desimone, Catalina María van Baren. Development and Validation of a Simple, Fast, and Accessible HPLC-UV Method for Cannabinoids Determination in Cannabis sativa L. Extracts and Medicinal Oils.
Current pharmaceutical design.
2023 Aug; ?(?):. doi:
10.2174/1381612829666230809094304. [PMID: 37559239] - Man Shao, Xiao-Qin Yu, Li-Juan Huang, Huan Yao, Shu-Cai Li. [Determination of eight cannabinoids in foods with enhanced matrix removal-lipid adsorbent by ultra performance liquid chromatography-tandem mass spectrometry].
Se pu = Chinese journal of chromatography.
2023 May; 41(5):426-433. doi:
10.3724/sp.j.1123.2022.08010. [PMID: 37087608] - 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] - Zsófia Pénzes, Shahrzad Alimohammadi, Dorottya Horváth, Attila Oláh, Balázs István Tóth, Attila Bácsi, Attila Gábor Szöllősi. The dual role of cannabidiol on monocyte-derived dendritic cell differentiation and maturation.
Frontiers in immunology.
2023; 14(?):1240800. doi:
10.3389/fimmu.2023.1240800. [PMID: 37680639] - Farzaneh Darigh, Alireza Iranbakhsh, Zahra Oraghi Ardebili, Mostafa Ebadi. Non-thermal plasma improved callogenesis performance and elicited the production of cannabinoids by modifying DNA methylome, expression of WRKY1 and ERF1B transcription factors, and expression of genes that contributed to the biosynthesis of cannabinoids.
Protoplasma.
2023 Jan; 260(1):159-170. doi:
10.1007/s00709-022-01769-8. [PMID: 35503387] - 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] - Si Huang, Ruiying Qiu, Zhengfa Fang, Ke Min, Teris A van Beek, Ming Ma, Bo Chen, Han Zuilhof, Gert Ij Salentijn. Semiquantitative Screening of THC Analogues by Silica Gel TLC with an Ag(I) Retention Zone and Chromogenic Smartphone Detection.
Analytical chemistry.
2022 Oct; 94(40):13710-13718. doi:
10.1021/acs.analchem.2c01627. [PMID: 36178203] - Shubhashis Chakrabarty, Eric M Serum, Thomas M Winders, Bryan Neville, Michael D Kleinhenz, Geraldine Magnin, Johann F Coetzee, Carl R Dahlen, Kendall C Swanson, David J Smith. Rapid quantification of cannabinoids in beef tissues and bodily fluids using direct-delivery electrospray ionization mass spectrometry.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment.
2022 Oct; 39(10):1705-1717. doi:
10.1080/19440049.2022.2107711. [PMID: 35939416] - Maíra Ribeiro de Souza, Mariana Koetz, Renata Pereira Limberger, Amélia Teresinha Henriques. DoE-assisted development and validation of a stability-indicating HPLC-DAD method for simultaneous determination of five cannabinoids in Cannabis sativa L. based on analytical quality by design (AQbD) concept.
Phytochemical analysis : PCA.
2022 Oct; 33(7):999-1017. doi:
10.1002/pca.3154. [PMID: 35733081] - Wuttichai Jaidee, Ittipon Siridechakorn, Siwames Nessopa, Vanuchawan Wisuitiprot, Nathareen Chaiwangrach, Kornkanok Ingkaninan, Neti Waranuch. Kinetics of CBD, Δ9-THC Degradation and Cannabinol Formation in Cannabis Resin at Various Temperature and pH Conditions.
Cannabis and cannabinoid research.
2022 08; 7(4):537-547. doi:
10.1089/can.2021.0004. [PMID: 34096805] - Priska Frei, Stephanie Frauchiger, Eva Scheurer, Katja Mercer-Chalmers-Bender. Quantitative determination of five cannabinoids in blood and urine by gas chromatography tandem mass spectrometry applying automated on-line solid phase extraction.
Drug testing and analysis.
2022 Jul; 14(7):1223-1233. doi:
10.1002/dta.3241. [PMID: 35187817] - Virgínia Martins Carvalho, Fernando Gomes de Almeida, Ana Cláudia de Macêdo Vieira, Ernesto Díaz Rocha, Lucio Mendes Cabral, Robert M Strongin. Chemical profiling of Cannabis varieties cultivated for medical purposes in southeastern Brazil.
Forensic science international.
2022 Jun; 335(?):111309. doi:
10.1016/j.forsciint.2022.111309. [PMID: 35462181] - Piotr Holowinski, Rafal Typek, Andrzej L Dawidowicz, Michal Rombel, Michal P Dybowski. Formation of trifluoroacetic artefacts in gas chromatograph injector during Cannabidiol analysis.
Journal of chromatography. A.
2022 May; 1671(?):463020. doi:
10.1016/j.chroma.2022.463020. [PMID: 35405405] - Evangelos Dadiotis, Vangelis Mitsis, Eleni Melliou, Prokopios Magiatis. Direct Quantitation of Phytocannabinoids by One-Dimensional 1H qNMR and Two-Dimensional 1H-1H COSY qNMR in Complex Natural Mixtures.
Molecules (Basel, Switzerland).
2022 May; 27(9):. doi:
10.3390/molecules27092965. [PMID: 35566314] - Ahmed E Altyar, Fadia S Youssef, Maram M Kurdi, Renad J Bifari, Mohamed L Ashour. The Role of Cannabis sativa L. as a Source of Cannabinoids against Coronavirus 2 (SARS-CoV-2): An In Silico Study to Evaluate Their Activities and ADMET Properties.
Molecules (Basel, Switzerland).
2022 Apr; 27(9):. doi:
10.3390/molecules27092797. [PMID: 35566148] - Shamema Nasrin, Christy J W Watson, Yadira X Perez-Paramo, Philip Lazarus. Cannabinoid Metabolites as Inhibitors of Major Hepatic CYP450 Enzymes, with Implications for Cannabis-Drug Interactions.
Drug metabolism and disposition: the biological fate of chemicals.
2021 12; 49(12):1070-1080. doi:
10.1124/dmd.121.000442. [PMID: 34493602] - Shamema Nasrin, Christy J W Watson, Keti Bardhi, Gabriela Fort, Gang Chen, Philip Lazarus. Inhibition of UDP-Glucuronosyltransferase Enzymes by Major Cannabinoids and Their Metabolites.
Drug metabolism and disposition: the biological fate of chemicals.
2021 12; 49(12):1081-1089. doi:
10.1124/dmd.121.000530. [PMID: 34493601] - Cynthia Coulter, Jarrad R Wagner. Cannabinoids in Oral Fluid: Limiting Potential Sources of Cannabidiol Conversion to Δ9- and Δ8-Tetrahydrocannabinol.
Journal of analytical toxicology.
2021 Sep; 45(8):807-812. doi:
10.1093/jat/bkab074. [PMID: 34137890] - 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] - Marilyn A Huestis, Cristina Sempio, Matthew N Newmeyer, Maria Andersson, Allan J Barnes, Osama A Abulseoud, Benjamin C Blount, Jennifer Schroeder, Michael L Smith. Free and Glucuronide Urine Cannabinoids after Controlled Smoked, Vaporized and Oral Cannabis Administration in Frequent and Occasional Cannabis Users.
Journal of analytical toxicology.
2020 Oct; 44(7):651-660. doi:
10.1093/jat/bkaa046. [PMID: 32369162] - Ieremias Chousidis, Theodoros Chatzimitakos, Dimitrios Leonardos, Michaela D Filiou, Constantine D Stalikas, Ioannis D Leonardos. Cannabinol in the spotlight: Toxicometabolomic study and behavioral analysis of zebrafish embryos exposed to the unknown cannabinoid.
Chemosphere.
2020 Aug; 252(?):126417. doi:
10.1016/j.chemosphere.2020.126417. [PMID: 32200177] - Anubhav Pratap Singh, Farahnaz Fathordoobady, Yigong Guo, Anika Singh, David D Kitts. Antioxidants help favorably regulate the kinetics of lipid peroxidation, polyunsaturated fatty acids degradation and acidic cannabinoids decarboxylation in hempseed oil.
Scientific reports.
2020 06; 10(1):10567. doi:
10.1038/s41598-020-67267-0. [PMID: 32601363] - Stevie C Britch, Alan G Goodman, Jenny L Wiley, Abby M Pondelick, Rebecca M Craft. Antinociceptive and Immune Effects of Delta-9-Tetrahydrocannabinol or Cannabidiol in Male Versus Female Rats with Persistent Inflammatory Pain.
The Journal of pharmacology and experimental therapeutics.
2020 06; 373(3):416-428. doi:
10.1124/jpet.119.263319. [PMID: 32179573] - Grace M Kroner, Kamisha L Johnson-Davis, Kelly Doyle, Gwendolyn A McMillin. Cannabinol (CBN) Cross-Reacts with Two Urine Immunoassays Designed to Detect Tetrahydrocannabinol (THC) Metabolite.
The journal of applied laboratory medicine.
2020 05; 5(3):569-574. doi:
10.1093/jalm/jfaa020. [PMID: 32445358] - Theresa Schmidt, Annemarie Elisabeth Kramell, Florian Oehler, Ralph Kluge, Dieter Demske, Pavel E Tarasov, René Csuk. Identification and quantification of cannabinol as a biomarker for local hemp retting in an ancient sedimentary record by HPTLC-ESI-MS.
Analytical and bioanalytical chemistry.
2020 Apr; 412(11):2633-2644. doi:
10.1007/s00216-020-02492-0. [PMID: 32060580] - 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] - 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] - Rhea S Ramnarine, Justin L Poklis, Carl E Wolf. Determination of Cannabinoids in Breast Milk Using QuEChERS and Ultra-Performance Liquid Chromatography and Tandem Mass Spectrometry.
Journal of analytical toxicology.
2019 Oct; 43(9):746-752. doi:
10.1093/jat/bkz072. [PMID: 31436289] - Marianne Hädener, Stefan König, Wolfgang Weinmann. Quantitative determination of CBD and THC and their acid precursors in confiscated cannabis samples by HPLC-DAD.
Forensic science international.
2019 Jun; 299(?):142-150. doi:
10.1016/j.forsciint.2019.03.046. [PMID: 31005710] - Yuli Qian, Xinwen Wang, John S Markowitz. In Vitro Inhibition of Carboxylesterase 1 by Major Cannabinoids and Selected Metabolites.
Drug metabolism and disposition: the biological fate of chemicals.
2019 05; 47(5):465-472. doi:
10.1124/dmd.118.086074. [PMID: 30833288] - 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] - Ricardo Plancarte-Sánchez, Armando Mansilla-Olivares, Víctor Alfonso De Los Reyes-Pacheco, Fernando Meneses-González. Aplicaciones terapéuticas por acción de los cannabinoides.
Gaceta medica de Mexico.
2019; 155(3):307-318. doi:
10.24875/gmm.18004928. [PMID: 31219471] - Madhur P Motwani, Frances Bennett, Paul C Norris, Alexander A Maini, Marc J George, Justine Newson, Alice Henderson, Adrian J Hobbs, Mark Tepper, Barbara White, Charles N Serhan, Raymond MacAllister, Derek W Gilroy. Potent Anti-Inflammatory and Pro-Resolving Effects of Anabasum in a Human Model of Self-Resolving Acute Inflammation.
Clinical pharmacology and therapeutics.
2018 10; 104(4):675-686. doi:
10.1002/cpt.980. [PMID: 29238967] - Neus Jornet-Martínez, Adrián Ortega-Sierra, Jorge Verdú-Andrés, Rosa Herráez-Hernández, Pilar Campíns-Falcó. Analysis of Contact Traces of Cannabis by In-Tube Solid-Phase Microextraction Coupled to Nanoliquid Chromatography.
Molecules (Basel, Switzerland).
2018 Sep; 23(9):. doi:
10.3390/molecules23092359. [PMID: 30223565] - Cristiana Gambelunghe, Nadia Fucci, Kyriaki Aroni, Mauro Bacci, Antonio Marcelli, Riccardo Rossi. Cannabis Use Surveillance by Sweat Analysis.
Therapeutic drug monitoring.
2016 10; 38(5):634-9. doi:
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The Journal of pharmacology and experimental therapeutics.
2016 08; 358(2):334-41. doi:
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Nature.
2015 Sep; 525(7570):S10-1. doi:
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The Journal of investigative dermatology.
2015 Jun; 135(6):1629-1637. doi:
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Forensic science international.
2014 Oct; 243(?):107-11. doi:
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Forensic science international.
2014 May; 238(?):113-9. doi:
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Clinical chemistry.
2013 Jul; 59(7):1108-17. doi:
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Drug metabolism and disposition: the biological fate of chemicals.
2013 Mar; 41(3):568-74. doi:
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The Journal of pharmacology and experimental therapeutics.
2013 Jan; 344(1):8-14. doi:
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Forensic science international.
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Drug metabolism and pharmacokinetics.
2012; 27(3):294-300. doi:
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Clinical chemistry.
2011 Oct; 57(10):1406-14. doi:
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Se pu = Chinese journal of chromatography.
2010 Nov; 28(11):1015-9. doi:
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Drug and alcohol dependence.
2009 Nov; 105(1-2):42-7. doi:
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Analytica chimica acta.
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European journal of pharmacology.
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Journal of natural products.
2008 Aug; 71(8):1427-30. doi:
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Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
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Planta medica.
2007 Mar; 73(3):273-5. doi:
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BMC clinical pharmacology.
2007 Jan; 7(?):1. doi:
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Journal of analytical toxicology.
2005 Nov; 29(8):782-9. doi:
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Toxicology.
2005 Jan; 206(3):471-8. doi:
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Handbook of experimental pharmacology.
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