Cannabidiolate (BioDeep_00000002561)
代谢物信息卡片
Cannabidiolic acid
化学式: C22H30O4 (358.2144)
中文名称: 大麻二酚酸
谱图信息:
最多检出来源 Homo sapiens(plant) 12.28%
分子结构信息
SMILES: c1(c(cc(c(c1O)C(=O)O)CCCCC)O)[C@H]1C=C(CC[C@H]1C(=C)C)C
InChI: InChI=1S/C22H30O4/c1-5-6-7-8-15-12-18(23)20(21(24)19(15)22(25)26)17-11-14(4)9-10-16(17)13(2)3/h11-12,16-17,23-24H,2,5-10H2,1,3-4H3,(H,25,26)/t16-,17+/m0/s1
描述信息
A dihydroxybenzoic acid that is olivetolic acid in which the hydrogen at position 3 is substituted by a 3-p-mentha-1,8-dien-3-yl (limonene) group.
同义名列表
5 个代谢物同义名
Cannabidiolic acid; Cannabidiolate; CBDA; SCHEMBL16769848; Cannabidiolic acid
数据库引用编号
16 个数据库交叉引用编号
- ChEBI: CHEBI:3359
- KEGG: C10784
- PubChem: 160570
- PubChem: 4486399
- Metlin: METLIN41052
- ChEMBL: CHEMBL498672
- LipidMAPS: LMPK13120003
- MetaCyc: CPD-7170
- KNApSAcK: C00002642
- CAS: 1244-58-2
- PMhub: MS000003951
- MetaboLights: MTBLC3359
- PubChem: 12967
- 3DMET: B04121
- NIKKAJI: J14.354E
- KNApSAcK: 3359
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
1 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(1)
- CBD synthetic pathway:
delta(9)-Tetrahydrocannabinolic acid (D9-THCA) ⟶ Delta(9)-tetrahydrocannabinol (D9-THC)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 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
- Matej Maly, Frantisek Benes, Zuzana Binova, Marie Zlechovcova, Petr Kastanek, Jana Hajslova. Effective isolation of cannabidiol and cannabidiolic acid free of psychotropic phytocannabinoids from hemp extract by fast centrifugal partition chromatography.
Analytical and bioanalytical chemistry.
2023 Jun; ?(?):. doi:
10.1007/s00216-023-04782-9. [PMID: 37382652] - 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] - Wayne S Schwark, Joseph J Wakshlag. A One Health perspective on comparative cannabidiol and cannabidiolic acid pharmacokinetics and biotransformation in humans and domestic animals.
American journal of veterinary research.
2023 Mar; ?(?):1-9. doi:
10.2460/ajvr.23.02.0031. [PMID: 36972696] - Masayasu Ukai, Stephanie McGrath, Joseph Wakshlag. The clinical use of cannabidiol and cannabidiolic acid-rich hemp in veterinary medicine and lessons from human medicine.
Journal of the American Veterinary Medical Association.
2023 Mar; ?(?):1-9. doi:
10.2460/javma.23.02.0064. [PMID: 36965472] - Fabiana Russo, Francesco Tolomeo, Maria Angela Vandelli, Giuseppe Biagini, Aldo Laganà, Anna Laura Capriotti, Andrea Cerrato, Luigi Carbone, Elisabetta Perrone, Alberto Cavazzini, Vincenzo Maiorano, Giuseppe Gigli, Giuseppe Cannazza, Cinzia Citti. Enantioseparation of chiral phytocannabinoids in medicinal cannabis.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2023 Mar; 1221(?):123682. doi:
10.1016/j.jchromb.2023.123682. [PMID: 36965450] - Mariana Sosa-Higareda, David Sanchez-Migallon Guzman, Heather Knych, Alex Lyubimov, Alexander Zakharov, Beatriz Gomez, Hugues Beaufrère. Twice-daily oral administration of a cannabidiol and cannabidiolic acid-rich hemp extract was well tolerated in orange-winged Amazon parrots (Amazona amazonica) and has a favorable pharmacokinetic profile.
American journal of veterinary research.
2023 Feb; ?(?):1-11. doi:
10.2460/ajvr.22.11.0197. [PMID: 36795552] - 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] - Tess A Rooney, James W Carpenter, Butch KuKanich, Sara M Gardhouse, Géraldine C Magnin, Thomas N Tully. Feeding decreases the oral bioavailability of cannabidiol and cannabidiolic acid in hemp oil in New Zealand White rabbits (Oryctolagus cuniculus).
American journal of veterinary research.
2022 Aug; 83(10):. doi:
10.2460/ajvr.22.01.0006. [PMID: 35947680] - Melissa Loewinger, Joseph J Wakshlag, Daniel Bowden, Jeanine Peters-Kennedy, Andrew Rosenberg. The effect of a mixed cannabidiol and cannabidiolic acid based oil on client-owned dogs with atopic dermatitis.
Veterinary dermatology.
2022 Aug; 33(4):329-e77. doi:
10.1111/vde.13077. [PMID: 35644533] - Kenneth J Olejar, Min Hong, Sun-Yeop Lee, Tae-Hyung Kwon, Soo-Ung Lee, Chad A Kinney, Joon-Hee Han, Sang-Hyuck Park. Ultrasonic-Assisted Extraction of Cannabidiolic Acid from Cannabis Biomass.
Journal of visualized experiments : JoVE.
2022 05; ?(183):. doi:
10.3791/63076. [PMID: 35695545] - Elad Ben-Cnaan, Anna Permyakova, Shahar Azar, Shira Hirsch, Saja Baraghithy, Liad Hinden, Joseph Tam. The Metabolic Efficacy of a Cannabidiolic Acid (CBDA) Derivative in Treating Diet- and Genetic-Induced Obesity.
International journal of molecular sciences.
2022 May; 23(10):. doi:
10.3390/ijms23105610. [PMID: 35628417] - Laísa S Umpierrez, Priscila A Costa, Eden A Michelutti, Sarah J Baracz, Melanie Sauer, Anita J Turner, Nicholas A Everett, Jonathon C Arnold, Iain S McGregor, Jennifer L Cornish. Cannabidiol but not cannabidiolic acid reduces behavioural sensitisation to methamphetamine in rats, at pharmacologically effective doses.
Psychopharmacology.
2022 May; 239(5):1593-1603. doi:
10.1007/s00213-022-06119-3. [PMID: 35435462] - Ersilia Nigro, Maria Tommasina Pecoraro, Marialuisa Formato, Simona Piccolella, Sara Ragucci, Marta Mallardo, Rosita Russo, Antimo Di Maro, Aurora Daniele, Severina Pacifico. Cannabidiolic acid in Hemp Seed Oil Table Spoon and Beyond.
Molecules (Basel, Switzerland).
2022 Apr; 27(8):. doi:
10.3390/molecules27082566. [PMID: 35458762] - Michael D Kleinhenz, Mikaela Weeder, Shawnee Montgomery, Miriam Martin, Andrew Curtis, Geraldine Magnin, Zhoumeng Lin, Jason Griffin, Johann F Coetzee. Short term feeding of industrial hemp with a high cannabidiolic acid (CBDA) content increases lying behavior and reduces biomarkers of stress and inflammation in Holstein steers.
Scientific reports.
2022 03; 12(1):3683. doi:
10.1038/s41598-022-07795-z. [PMID: 35256692] - 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, Maia G Etchart, Dilara Bahceci, Taliesin A Golembiewski, Jonathon C Arnold. Cannabis constituents interact at the drug efflux pump BCRP to markedly increase plasma cannabidiolic acid concentrations.
Scientific reports.
2021 07; 11(1):14948. doi:
10.1038/s41598-021-94212-6. [PMID: 34294753] - 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] - Brett Goerl, Sarah Watkins, Cameron Metcalf, Misty Smith, Mark Beenhakker. Cannabidiolic acid exhibits entourage-like improvements of anticonvulsant activity in an acute rat model of seizures.
Epilepsy research.
2021 01; 169(?):106525. doi:
10.1016/j.eplepsyres.2020.106525. [PMID: 33310415] - 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] - Laia Alegre-Zurano, Ana Martín-Sánchez, Olga Valverde. Behavioural and molecular effects of cannabidiolic acid in mice.
Life sciences.
2020 Oct; 259(?):118271. doi:
10.1016/j.lfs.2020.118271. [PMID: 32798553] - Giulia Corni, Virginia Brighenti, Federica Pellati, Gertrud E Morlock. Effect-directed analysis of bioactive compounds in Cannabis sativa L. by high-performance thin-layer chromatography.
Journal of chromatography. A.
2020 Oct; 1629(?):461511. doi:
10.1016/j.chroma.2020.461511. [PMID: 32896687] - Luana Izzo, Severina Pacifico, Simona Piccolella, Luigi Castaldo, Alfonso Narváez, Michela Grosso, Alberto Ritieni. Chemical Analysis of Minor Bioactive Components and Cannabidiolic Acid in Commercial Hemp Seed Oil.
Molecules (Basel, Switzerland).
2020 Aug; 25(16):. doi:
10.3390/molecules25163710. [PMID: 32823936] - Michael D Kleinhenz, Geraldine Magnin, Zhoumeng Lin, Jason Griffin, Katie E Kleinhenz, Shawnee Montgomery, Andrew Curtis, Miriam Martin, Johann F Coetzee. Plasma concentrations of eleven cannabinoids in cattle following oral administration of industrial hemp (Cannabis sativa).
Scientific reports.
2020 07; 10(1):12753. doi:
10.1038/s41598-020-69768-4. [PMID: 32728233] - 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] - Masayo Hirao-Suzuki, Shuso Takeda, Takayuki Koga, Masufumi Takiguchi, Akihisa Toda. Cannabidiolic acid dampens the expression of cyclooxygenase-2 in MDA-MB-231 breast cancer cells: Possible implication of the peroxisome proliferator-activated receptor β/δ abrogation.
The Journal of toxicological sciences.
2020; 45(4):227-236. doi:
10.2131/jts.45.227. [PMID: 32238697] - 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] - Dvora Namdar, Hillary Voet, Vinayaka Ajjampura, Stalin Nadarajan, Einav Mayzlish-Gati, Moran Mazuz, Nurit Shalev, Hinanit Koltai. Terpenoids and Phytocannabinoids Co-Produced in Cannabis Sativa Strains Show Specific Interaction for Cell Cytotoxic Activity.
Molecules (Basel, Switzerland).
2019 Aug; 24(17):. doi:
10.3390/molecules24173031. [PMID: 31438532] - Johannes R Popp, Eleftherios A Petrakis, Apostolis Angelis, Maria Halabalaki, Günther K Bonn, Hermann Stuppner, Leandros A Skaltsounis. Rapid isolation of acidic cannabinoids from Cannabis sativa L. using pH-zone-refining centrifugal partition chromatography.
Journal of chromatography. A.
2019 Aug; 1599(?):196-202. doi:
10.1016/j.chroma.2019.04.048. [PMID: 31027757] - Matthew T Welling, Lei Liu, Carolyn A Raymond, Tobias Kretzschmar, Omid Ansari, Graham J King. Complex Patterns of Cannabinoid Alkyl Side-Chain Inheritance in Cannabis.
Scientific reports.
2019 08; 9(1):11421. doi:
10.1038/s41598-019-47812-2. [PMID: 31388099] - 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] - 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] - Vaida Kitrytė, Dovyda Bagdonaitė, Petras Rimantas Venskutonis. Biorefining of industrial hemp (Cannabis sativa L.) threshing residues into cannabinoid and antioxidant fractions by supercritical carbon dioxide, pressurized liquid and enzyme-assisted extractions.
Food chemistry.
2018 Nov; 267(?):420-429. doi:
10.1016/j.foodchem.2017.09.080. [PMID: 29934186] - Paul Ebersbach, Felix Stehle, Oliver Kayser, Erik Freier. Chemical fingerprinting of single glandular trichomes of Cannabis sativa by Coherent anti-Stokes Raman scattering (CARS) microscopy.
BMC plant biology.
2018 Nov; 18(1):275. doi:
10.1186/s12870-018-1481-4. [PMID: 30419820] - 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] - Federica Pellati, Virginia Brighenti, Johanna Sperlea, Lucia Marchetti, Davide Bertelli, Stefania Benvenuti. New Methods for the Comprehensive Analysis of Bioactive Compounds in Cannabis sativa L. (hemp).
Molecules (Basel, Switzerland).
2018 Oct; 23(10):. doi:
10.3390/molecules23102639. [PMID: 30322208] - Antonella Smeriglio, Salvatore V Giofrè, Enza M Galati, Maria T Monforte, Nicola Cicero, Valeria D'Angelo, Gianpaolo Grassi, Clara Circosta. Inhibition of aldose reductase activity by Cannabis sativa chemotypes extracts with high content of cannabidiol or cannabigerol.
Fitoterapia.
2018 Jun; 127(?):101-108. doi:
10.1016/j.fitote.2018.02.002. [PMID: 29427593] - Cinzia Citti, Barbara Pacchetti, Maria Angela Vandelli, Flavio Forni, Giuseppe Cannazza. Analysis of cannabinoids in commercial hemp seed oil and decarboxylation kinetics studies of cannabidiolic acid (CBDA).
Journal of pharmaceutical and biomedical analysis.
2018 Feb; 149(?):532-540. doi:
10.1016/j.jpba.2017.11.044. [PMID: 29182999] - Qingfang Meng, Beth Buchanan, Jonathan Zuccolo, Mathieu-Marc Poulin, Joseph Gabriele, David Charles Baranowski. A reliable and validated LC-MS/MS method for the simultaneous quantification of 4 cannabinoids in 40 consumer products.
PloS one.
2018; 13(5):e0196396. doi:
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British journal of pharmacology.
2017 Dec; 174(23):4263-4276. doi:
10.1111/bph.14019. [PMID: 28853159] - Masayo Suzuki, Shuso Takeda, Hiroyuki Okazaki, Kazuhito Watanabe, Masufumi Takiguchi, Hironori Aramaki. Cannabidiolic Acid-Mediated Interference with AP-1 Transcriptional Activity in MDA-MB-231 Breast Cancer Cells.
Natural product communications.
2017 May; 12(5):759-761. doi:
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Journal of natural medicines.
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Journal of natural products.
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The Journal of toxicological sciences.
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Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.
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Toxicology letters.
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The Plant journal : for cell and molecular biology.
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Genome biology.
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Biological & pharmaceutical bulletin.
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Plant signaling & behavior.
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Toxicology.
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