Cannabinol (BioDeep_00000001922)

 

Secondary id: BioDeep_00000408305

human metabolite PANOMIX_OTCML-2023 blood metabolite natural product


代谢物信息卡片


3-Amyl-1-hydroxy-6,6,9-trimethyl-6H-dibenzo[b,d]pyran

化学式: C21H26O2 (310.1933)
中文名称: 大麻酚
谱图信息: 最多检出来源 Homo sapiens(blood) 29.56%

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

6 个代谢物同义名

3-Amyl-1-hydroxy-6,6,9-trimethyl-6H-dibenzo[b,d]pyran; 6,6,9-Trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol; 6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromen-1-ol; cannabinol; CBN; Cannabinol



数据库引用编号

19 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)

20 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。

亚细胞结构定位 关联基因列表
Cytoplasm 11 ABCB1, ALB, CNR1, CNR2, CYP1A1, CYP2C19, CYP2C9, CYP3A4, DLK1, NFKB1, TRPV2
Peripheral membrane protein 3 CYP1A1, CYP1B1, GBA1
Endoplasmic reticulum membrane 8 CYP1A1, CYP1A2, CYP1B1, CYP2C19, CYP2C9, CYP3A4, UGT1A9, UGT2B7
Nucleus 3 ALB, JUND, NFKB1
cytosol 2 ALB, NFKB1
dendrite 1 CNR2
trans-Golgi network 1 GBA1
centrosome 1 ALB
nucleoplasm 2 JUND, NFKB1
RNA polymerase II transcription regulator complex 1 JUND
Cell membrane 5 ABCB1, CNR1, TNF, TRPV1, TRPV2
Cell projection, axon 1 CNR1
Multi-pass membrane protein 4 ABCB1, CNR1, TRPV1, TRPV2
cell surface 3 ABCB1, TNF, TRPV2
glutamatergic synapse 1 CNR1
Golgi apparatus 2 ALB, GBA1
growth cone 1 CNR1
lysosomal membrane 1 GBA1
mitochondrial inner membrane 1 CYP1A1
neuronal cell body 2 TNF, TRPV1
presynaptic membrane 1 CNR1
Lysosome 1 GBA1
Presynapse 1 CNR1
plasma membrane 8 ABCB1, CNR1, CNR2, CYP2C19, CYP2C9, TNF, TRPV1, TRPV2
Membrane 8 ABCB1, CYP1B1, CYP3A4, DLK1, TRPV1, TRPV2, UGT1A9, UGT2B7
apical plasma membrane 1 ABCB1
axon 1 CNR1
extracellular exosome 3 ABCB1, ALB, GBA1
Lysosome membrane 1 GBA1
Lumenal side 1 GBA1
endoplasmic reticulum 4 ALB, CNR2, GBA1, UGT1A9
extracellular space 4 ALB, DLK1, IL2, TNF
lysosomal lumen 1 GBA1
mitochondrion 3 CYP1A1, CYP1B1, NFKB1
protein-containing complex 1 ALB
intracellular membrane-bounded organelle 6 CYP1A1, CYP1A2, CYP1B1, CYP2C19, CYP2C9, CYP3A4
Microsome membrane 5 CYP1A1, CYP1A2, CYP1B1, CYP2C9, CYP3A4
Secreted 2 ALB, IL2
extracellular region 4 ALB, IL2, NFKB1, TNF
Mitochondrion outer membrane 1 CNR1
Single-pass membrane protein 3 DLK1, UGT1A9, UGT2B7
mitochondrial outer membrane 1 CNR1
anchoring junction 1 ALB
transcription regulator complex 2 JUND, NFKB1
external side of plasma membrane 2 TNF, TRPV1
actin cytoskeleton 1 CNR1
perikaryon 1 CNR2
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 2 CNR2, TRPV1
Apical cell membrane 1 ABCB1
Mitochondrion inner membrane 1 CYP1A1
Membrane raft 2 CNR1, TNF
GABA-ergic synapse 2 CNR1, TRPV1
Postsynaptic cell membrane 1 TRPV1
Cell projection, neuron projection 1 TRPV1
ciliary basal body 1 ALB
chromatin 2 JUND, NFKB1
axonal growth cone 1 TRPV2
phagocytic cup 1 TNF
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 1 ALB
Cell projection, dendrite 1 CNR2
Melanosome 1 TRPV2
cell body 1 TRPV2
secretory granule lumen 1 NFKB1
endoplasmic reticulum lumen 1 ALB
transcription repressor complex 1 JUND
platelet alpha granule lumen 1 ALB
specific granule lumen 1 NFKB1
extrinsic component of cytoplasmic side of plasma membrane 1 CNR2
external side of apical plasma membrane 1 ABCB1
Cell projection, dendritic spine membrane 1 TRPV1
dendritic spine membrane 1 TRPV1
transcription factor AP-1 complex 1 JUND
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
growth cone membrane 1 TRPV2
[Nuclear factor NF-kappa-B p105 subunit]: Cytoplasm 1 NFKB1
[Nuclear factor NF-kappa-B p50 subunit]: Nucleus 1 NFKB1
I-kappaB/NF-kappaB complex 1 NFKB1
NF-kappaB p50/p65 complex 1 NFKB1
ciliary transition fiber 1 ALB
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


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]
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  • 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]
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  • 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]
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  • 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]
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  • 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]
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  • 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]
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  • 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]
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  • Karl B Scheidweiler, David M Schwope, Erin L Karschner, Nathalie A Desrosiers, David A Gorelick, Marilyn A Huestis. In vitro stability of free and glucuronidated cannabinoids in blood and plasma following controlled smoked cannabis. Clinical chemistry. 2013 Jul; 59(7):1108-17. doi: 10.1373/clinchem.2012.201467. [PMID: 23519966]
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