Cannabigerolic acid (BioDeep_00000265057)

Main id: BioDeep_00000002656

 

natural product


代谢物信息卡片


Cannabigerolic acid

化学式: C22H32O4 (360.23)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: c1(c(c(c(c(c1)CCCCC)C(=O)O)O)C/C=C(/CCC=C(C)C)\C)O
InChI: InChI=1S/C22H32O4/c1-5-6-7-11-17-14-19(23)18(21(24)20(17)22(25)26)13-12-16(4)10-8-9-15(2)3/h9,12,14,23-24H,5-8,10-11,13H2,1-4H3,(H,25,26)/b16-12+

描述信息

A dihydroxybenzoic acid that is olivetolic acid in which the hydrogen at position 3 is substituted by a geranyl group. A biosynthetic precursor to Delta(9)-tetrahydrocannabinol, the principal psychoactive constituent of the cannabis plant.

同义名列表

1 个代谢物同义名

Cannabigerolic acid



数据库引用编号

9 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)

21 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 8 CASP3, CNR1, CNR2, DLK1, FDPS, GFAP, PTGS1, PTGS2
Peripheral membrane protein 3 MGLL, PTGS1, PTGS2
Endosome membrane 1 CD68
Endoplasmic reticulum membrane 5 FAAH, MGLL, PTGS1, PTGS2, TRPM8
Nucleus 2 CASP3, PPARA
cytosol 4 CASP3, FDPS, GFAP, MGLL
dendrite 1 CNR2
nuclear body 1 SCN1A
nucleoplasm 4 CASP3, FDPS, PPARA, SCN1A
Cell membrane 8 CNR1, GPR55, GPRC5A, SCN1A, TNF, TRPM7, TRPM8, TRPV1
Cell projection, axon 1 CNR1
Multi-pass membrane protein 8 CNR1, FAAH, GPR55, GPRC5A, SCN1A, TRPM7, TRPM8, TRPV1
cell surface 1 TNF
glutamatergic synapse 3 CASP3, CNR1, FAAH
Golgi apparatus 1 PTGS1
growth cone 1 CNR1
lysosomal membrane 1 CD68
neuronal cell body 4 CASP3, SCN1A, TNF, TRPV1
postsynapse 1 FAAH
presynaptic membrane 1 CNR1
Cytoplasm, cytosol 1 MGLL
Lysosome 1 CD68
Presynapse 2 CNR1, FAAH
plasma membrane 11 CD68, CNR1, CNR2, GPR55, GPRC5A, MGLL, SCN1A, TNF, TRPM7, TRPM8, TRPV1
Membrane 10 CD68, DLK1, FAAH, FDPS, GPR55, MGLL, SCN1A, TRPM7, TRPM8, TRPV1
axon 1 CNR1
caveola 1 PTGS2
extracellular exosome 2 GPRC5A, PTGS1
Lysosome membrane 1 CD68
endoplasmic reticulum 3 CNR2, FAAH, PTGS2
extracellular space 3 CXCL8, DLK1, TNF
intercalated disc 1 SCN1A
protein-containing complex 1 PTGS2
intracellular membrane-bounded organelle 2 GPRC5A, PTGS1
Microsome membrane 3 FAAH, PTGS1, PTGS2
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 CD68
Secreted 1 CXCL8
extracellular region 2 CXCL8, TNF
Mitochondrion outer membrane 1 CNR1
Single-pass membrane protein 2 DLK1, FAAH
mitochondrial outer membrane 1 CNR1
astrocyte end-foot 1 GFAP
mitochondrial matrix 1 FDPS
photoreceptor outer segment 1 PTGS1
external side of plasma membrane 3 TNF, TRPM8, TRPV1
actin cytoskeleton 1 CNR1
T-tubule 1 SCN1A
perikaryon 1 CNR2
Z disc 1 SCN1A
cytoplasmic vesicle 1 TRPM7
nucleolus 1 GPRC5A
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
vesicle 1 GPRC5A
postsynaptic membrane 2 CNR2, TRPV1
Membrane raft 3 CNR1, TNF, TRPM8
Cytoplasm, cytoskeleton 1 FAAH
GABA-ergic synapse 2 CNR1, TRPV1
Peroxisome 1 FDPS
intermediate filament 1 GFAP
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Postsynaptic cell membrane 1 TRPV1
ruffle 1 TRPM7
receptor complex 1 GPRC5A
Cell projection, neuron projection 1 TRPV1
neuron projection 2 PTGS1, PTGS2
chromatin 1 PPARA
Late endosome membrane 1 CD68
cell projection 1 GFAP
phagocytic cup 1 TNF
cytoskeleton 1 FAAH
organelle membrane 1 FAAH
Endomembrane system 2 FAAH, PTGS1
Cytoplasmic vesicle membrane 2 GPRC5A, TRPM7
axon initial segment 1 SCN1A
Cell projection, dendrite 1 CNR2
cell body 1 GFAP
intermediate filament cytoskeleton 1 GFAP
plasma membrane raft 1 TRPM8
endoplasmic reticulum lumen 1 PTGS2
azurophil granule membrane 1 CD68
node of Ranvier 1 SCN1A
extrinsic component of cytoplasmic side of plasma membrane 1 CNR2
death-inducing signaling complex 1 CASP3
voltage-gated sodium channel complex 1 SCN1A
Cell projection, dendritic spine membrane 1 TRPV1
dendritic spine membrane 1 TRPV1
cytoplasmic side of lysosomal membrane 1 GFAP
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
[TRPM7 kinase, cleaved form]: Nucleus 1 TRPM7


文献列表

  • Christina Schmidt, Marco Aras, Oliver Kayser. Engineering cannabinoid production in Saccharomyces cerevisiae. Biotechnology journal. 2024 Feb; 19(2):e2300507. doi: 10.1002/biot.202300507. [PMID: 38403455]
  • Sayuri Suzuki, Clay Wakano, Mahealani K Monteilh-Zoller, Aaron J Cullen, Andrea Fleig, Reinhold Penner. Cannabigerolic Acid (CBGA) Inhibits the TRPM7 Ion Channel Through its Kinase Domain. Function (Oxford, England). 2024; 5(1):zqad069. doi: 10.1093/function/zqad069. [PMID: 38162115]
  • Saskia Spitzer, Jasmin Wloka, Joerg Pietruszka, Oliver Kayser. Generation of cannabigerolic acid derivatives and their precursors using the promiscuity of the aromatic prenyltransferase NphB. Chembiochem : a European journal of chemical biology. 2023 Sep; ?(?):e202300441. doi: 10.1002/cbic.202300441. [PMID: 37690998]
  • Kara Amstutz, Wayne S Schwark, Alexander Zakharov, Beatriz Gomez, Alex Lyubimov, Karolynn Ellis, Kurt P Venator, Joseph J Wakshlag. Single dose and chronic oral administration of cannabigerol and cannabigerolic acid-rich hemp extract in fed and fasted dogs: Physiological effect and pharmacokinetic evaluation. Journal of veterinary pharmacology and therapeutics. 2022 May; 45(3):245-254. doi: 10.1111/jvp.13048. [PMID: 35246858]
  • Richard B van Breemen, Ruth N Muchiri, Timothy A Bates, Jules B Weinstein, Hans C Leier, Scotland Farley, Fikadu G Tafesse. Cannabinoids Block Cellular Entry of SARS-CoV-2 and the Emerging Variants. Journal of natural products. 2022 01; 85(1):176-184. doi: 10.1021/acs.jnatprod.1c00946. [PMID: 35007072]
  • Lyndsey L Anderson, Marika Heblinski, Nathan L Absalom, Nicole A Hawkins, Michael T Bowen, Melissa J Benson, Fan Zhang, Dilara Bahceci, Peter T Doohan, Mary Chebib, Iain S McGregor, Jennifer A Kearney, Jonathon C Arnold. Cannabigerolic acid, a major biosynthetic precursor molecule in cannabis, exhibits divergent effects on seizures in mouse models of epilepsy. British journal of pharmacology. 2021 12; 178(24):4826-4841. doi: 10.1111/bph.15661. [PMID: 34384142]
  • Andrea R Garfinkel, Matthew Otten, Seth Crawford. SNP in Potentially Defunct Tetrahydrocannabinolic Acid Synthase Is a Marker for Cannabigerolic Acid Dominance in Cannabis sativa L. Genes. 2021 02; 12(2):. doi: 10.3390/genes12020228. [PMID: 33557333]
  • Meaghan A Valliere, Tyler P Korman, Mark A Arbing, James U Bowie. A bio-inspired cell-free system for cannabinoid production from inexpensive inputs. Nature chemical biology. 2020 12; 16(12):1427-1433. doi: 10.1038/s41589-020-0631-9. [PMID: 32839605]
  • Lyndsey L Anderson, Ivan K Low, Samuel D Banister, Iain S McGregor, Jonathon C Arnold. Pharmacokinetics of Phytocannabinoid Acids and Anticonvulsant Effect of Cannabidiolic Acid in a Mouse Model of Dravet Syndrome. Journal of natural products. 2019 11; 82(11):3047-3055. doi: 10.1021/acs.jnatprod.9b00600. [PMID: 31686510]
  • 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]
  • Enrico D'Aniello, Tariq Fellous, Fabio Arturo Iannotti, Alessandra Gentile, Marco Allarà, Francesca Balestrieri, Roy Gray, Pietro Amodeo, Rosa Maria Vitale, Vincenzo Di Marzo. Identification and characterization of phytocannabinoids as novel dual PPARα/γ agonists by a computational and in vitro experimental approach. Biochimica et biophysica acta. General subjects. 2019 03; 1863(3):586-597. doi: 10.1016/j.bbagen.2019.01.002. [PMID: 30611848]
  • Xiaozhou Luo, Michael A Reiter, Leo d'Espaux, Jeff Wong, Charles M Denby, Anna Lechner, Yunfeng Zhang, Adrian T Grzybowski, Simon Harth, Weiyin Lin, Hyunsu Lee, Changhua Yu, John Shin, Kai Deng, Veronica T Benites, George Wang, Edward E K Baidoo, Yan Chen, Ishaan Dev, Christopher J Petzold, Jay D Keasling. Complete biosynthesis of cannabinoids and their unnatural analogues in yeast. Nature. 2019 03; 567(7746):123-126. doi: 10.1038/s41586-019-0978-9. [PMID: 30814733]
  • Bastian Zirpel, Oliver Kayser, Felix Stehle. Elucidation of structure-function relationship of THCA and CBDA synthase from Cannabis sativaL. Journal of biotechnology. 2018 Oct; 284(?):17-26. doi: 10.1016/j.jbiotec.2018.07.031. [PMID: 30053500]
  • Bastian Zirpel, Friederike Degenhardt, Chantale Zammarelli, Daniel Wibberg, Jörn Kalinowski, Felix Stehle, Oliver Kayser. Optimization of Δ9-tetrahydrocannabinolic acid synthase production in Komagataella phaffii via post-translational bottleneck identification. Journal of biotechnology. 2018 Apr; 272-273(?):40-47. doi: 10.1016/j.jbiotec.2018.03.008. [PMID: 29549004]
  • Xavier Nadal, Carmen Del Río, Salvatore Casano, Belén Palomares, Carlos Ferreiro-Vera, Carmen Navarrete, Carolina Sánchez-Carnerero, Irene Cantarero, Maria Luz Bellido, Stefan Meyer, Gaetano Morello, Giovanni Appendino, Eduardo Muñoz. Tetrahydrocannabinolic acid is a potent PPARγ agonist with neuroprotective activity. British journal of pharmacology. 2017 Dec; 174(23):4263-4276. doi: 10.1111/bph.14019. [PMID: 28853159]
  • Kerstin Lange, Andreas Schmid, Mattijs K Julsing. Δ(9)-Tetrahydrocannabinolic acid synthase production in Pichia pastoris enables chemical synthesis of cannabinoids. Journal of biotechnology. 2015 Oct; 211(?):68-76. doi: 10.1016/j.jbiotec.2015.06.425. [PMID: 26197418]
  • Bastian Zirpel, Felix Stehle, Oliver Kayser. Production of Δ9-tetrahydrocannabinolic acid from cannabigerolic acid by whole cells of Pichia (Komagataella) pastoris expressing Δ9-tetrahydrocannabinolic acid synthase from Cannabis sativa L. Biotechnology letters. 2015 Sep; 37(9):1869-75. doi: 10.1007/s10529-015-1853-x. [PMID: 25994576]
  • 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]
  • 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]
  • M Fellermeier, M H Zenk. Prenylation of olivetolate by a hemp transferase yields cannabigerolic acid, the precursor of tetrahydrocannabinol. FEBS letters. 1998 May; 427(2):283-5. doi: 10.1016/s0014-5793(98)00450-5. [PMID: 9607329]
  • F Taura, S Morimoto, Y Shoyama. Purification and characterization of cannabidiolic-acid synthase from Cannabis sativa L.. Biochemical analysis of a novel enzyme that catalyzes the oxidocyclization of cannabigerolic acid to cannabidiolic acid. The Journal of biological chemistry. 1996 Jul; 271(29):17411-6. doi: 10.1074/jbc.271.29.17411. [PMID: 8663284]