Olivetolic acid (BioDeep_00000013432)
代谢物信息卡片
化学式: C12H16O4 (224.1049)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(otcml) 29.89%
分子结构信息
SMILES: C1(O)C=C(CCCCC)C(C(O)=O)=C(O)C=1
InChI: InChI=1S/C12H16O4/c1-2-3-4-5-8-6-9(13)7-10(14)11(8)12(15)16/h6-7,13-14H,2-5H2,1H3,(H,15,16)
描述信息
A member of the class of benzoic acids that is salicylic acid in which the hydrogens ortho- and para- to the carboxy group are replaced by a pentyl and a hydroxy group, respectively.
D000893 - Anti-Inflammatory Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D012459 - Salicylates
同义名列表
数据库引用编号
12 个数据库交叉引用编号
- ChEBI: CHEBI:66955
- KEGG: C20417
- PubChem: 2826719
- ChEMBL: CHEMBL3134414
- LipidMAPS: LMPK15040016
- MetaCyc: CPD-7165
- KNApSAcK: C00053608
- CAS: 491-72-5
- PMhub: MS000027888
- MetaboLights: MTBLC66955
- PubChem: 163312154
- PDB-CCD: 4MX
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)
0 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 |
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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] - 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] - Jingbo Ma, Yang Gu, Peng Xu. Biosynthesis of cannabinoid precursor olivetolic acid in genetically engineered Yarrowia lipolytica.
Communications biology.
2022 11; 5(1):1239. doi:
10.1038/s42003-022-04202-1. [PMID: 36371560] - Johann E Kufs, Christin Reimer, Emily Steyer, Vito Valiante, Falk Hillmann, Lars Regestein. Scale-up of an amoeba-based process for the production of the cannabinoid precursor olivetolic acid.
Microbial cell factories.
2022 Oct; 21(1):217. doi:
10.1186/s12934-022-01943-w. [PMID: 36266656] - Ikechukwu C Okorafor, Mengbin Chen, Yi Tang. High-Titer Production of Olivetolic Acid and Analogs in Engineered Fungal Host Using a Nonplant Biosynthetic Pathway.
ACS synthetic biology.
2021 09; 10(9):2159-2166. doi:
10.1021/acssynbio.1c00309. [PMID: 34415146] - Thies Gülck, J K Booth, Â Carvalho, B Khakimov, C Crocoll, M S Motawia, B L Møller, J Bohlmann, N J Gallage. Synthetic Biology of Cannabinoids and Cannabinoid Glucosides in Nicotiana benthamiana and Saccharomyces cerevisiae.
Journal of natural products.
2020 10; 83(10):2877-2893. doi:
10.1021/acs.jnatprod.0c00241. [PMID: 33000946] - 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] - Zaigao Tan, James M Clomburg, Ramon Gonzalez. Synthetic Pathway for the Production of Olivetolic Acid in Escherichia coli.
ACS synthetic biology.
2018 08; 7(8):1886-1896. doi:
10.1021/acssynbio.8b00075. [PMID: 29976061] - Xinmei Yang, Takashi Matsui, Takeshi Kodama, Takahiro Mori, Xiaoxi Zhou, Futoshi Taura, Hiroshi Noguchi, Ikuro Abe, Hiroyuki Morita. Structural basis for olivetolic acid formation by a polyketide cyclase from Cannabis sativa.
The FEBS journal.
2016 Mar; 283(6):1088-106. doi:
10.1111/febs.13654. [PMID: 26783002] - Xinmei Yang, Takashi Matsui, Takahiro Mori, Futoshi Taura, Hiroshi Noguchi, Ikuro Abe, Hiroyuki Morita. Expression, purification and crystallization of a plant polyketide cyclase from Cannabis sativa.
Acta crystallographica. Section F, Structural biology communications.
2015 Dec; 71(Pt 12):1470-4. doi:
10.1107/s2053230x15020385. [PMID: 26625288] - Steve J Gagne, Jake M Stout, Enwu Liu, Zakia Boubakir, Shawn M Clark, Jonathan E Page. Identification of olivetolic acid cyclase from Cannabis sativa reveals a unique catalytic route to plant polyketides.
Proceedings of the National Academy of Sciences of the United States of America.
2012 Jul; 109(31):12811-6. doi:
10.1073/pnas.1200330109. [PMID: 22802619] - Tomohisa Kuzuyama, Joseph P Noel, Stéphane B Richard. Structural basis for the promiscuous biosynthetic prenylation of aromatic natural products.
Nature.
2005 Jun; 435(7044):983-7. doi:
10.1038/nature03668. [PMID: 15959519] - 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]
