Olivetol (BioDeep_00000279339)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


5-n-Pentylresorcinol;5-Pentyl-1,3-benzenediol

化学式: C11H16O2 (180.115)
中文名称: 橄榄醇, 3,5-二羟基戊苯, 橄榄醇;
谱图信息: 最多检出来源 Viridiplantae(plant) 71.52%

Reviewed

Last reviewed on 2024-07-12.

Cite this Page

Olivetol. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/olivetol (retrieved 2024-12-23) (BioDeep RN: BioDeep_00000279339). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1(O)C=C(CCCCC)C=C(O)C=1
InChI: InChI=1S/C11H16O2/c1-2-3-4-5-9-6-10(12)8-11(13)7-9/h6-8,12-13H,2-5H2,1H3

描述信息

Olivetol appears as off-white crystals or olive to light purple waxy solid. Forms monohydrate (melting point: 102-106 °F). (NTP, 1992)
Olivetol is a member of the class of resorcinols that is resorcinol in which the hydrogen at position 5 is replaced by a pentyl group. It has a role as a lichen metabolite.
Olivetol is a natural product found in Ardisia virens, Primula obconica, and Cannabis sativa with data available.
A member of the class of resorcinols that is resorcinol in which the hydrogen at position 5 is replaced by a pentyl group.

Olivetol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=500-66-3 (retrieved 2024-07-12) (CAS RN: 500-66-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Olivetol is a naturally phenol found in lichens and produced by certain insects, acting as a competitive inhibitor of the cannabinoid receptors CB1 and CB2[3]. Olivetol also inhibits CYP2C19 and CYP2D6 activity, with IC50s of 15.3 μM, 7.21 μM and Kis of 2.71 μM, 2.87 μM, respectively[1][2].
Olivetol is a naturally phenol found in lichens and produced by certain insects, acting as a competitive inhibitor of the cannabinoid receptors CB1 and CB2[3]. Olivetol also inhibits CYP2C19 and CYP2D6 activity, with IC50s of 15.3 μM, 7.21 μM and Kis of 2.71 μM, 2.87 μM, respectively[1][2].

同义名列表

28 个代谢物同义名

5-n-Pentylresorcinol;5-Pentyl-1,3-benzenediol; 3-06-00-04695 (Beilstein Handbook Reference); 1,3-Benzenediol, 5-pentyl- (9CI); 1,3-Dihydroxy-5-pentylbenzene; 5-pentyl-1,3-dihydroxybenzene; Resorcinol, 5-pentyl- (8CI); 1,3-Benzenediol, 5-pentyl-; 5-Pentyl-1,3-benzenediol #; 5-pentyl-benzene-1,3-diol; 5-pentylbenzene-1,3-diol; 3,5-Dihydroxyamylbenzene; 5-Pentyl-1,3-benzenediol; 5-(1-pentyl)resorcinol; Resorcinol, 5-pentyl-; 5-n-pentyl resorcinol; 5-n-Pentylresorcinol; 5-n-Amylresorcinol; 5-Pentylresorcinol; UNII-65OP0NEZ1P; Olivetol, 95\\%; While Olivetol; Olivetol (6CI); Tox21_303332; Tox21_202349; SMP1_000226; 65OP0NEZ1P; Olivetol; Olivetol



数据库引用编号

18 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

123 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(121)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

22 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


文献列表

  • Andukuri Reshma, T Tamilanban, V Chitra, Vetriselvan Subramaniyan, Gaurav Gupta, Neeraj Kumar Fuloria, Mahendran Sekar, Shivkanya Fuloria, Rakesh Sahu, J Narayanan, Srikumar Chakravarthy, Siddharthan Selvaraj. Anti-obesity effects of olivetol in adult zebrafish model induced by short-term high-fat diet. Scientific reports. 2023 10; 13(1):18449. doi: 10.1038/s41598-023-44462-3. [PMID: 37891223]
  • Gyeong Han Jeong, Seungil Park, Seong Bong Kim, Cheorun Jo, Tae Hoon Kim. Molecular hybridization based on (-)-epigallocatechin gallate as a new class of antiglycation agents. Bioscience, biotechnology, and biochemistry. 2021 Apr; 85(5):1069-1076. doi: 10.1093/bbb/zbab020. [PMID: 33704410]
  • Miroslav Sisa, Marcela Dvorakova, Veronika Temml, Veronika Jarosova, Tomas Vanek, Premysl Landa. Synthesis, inhibitory activity and in silico docking of dual COX/5-LOX inhibitors with quinone and resorcinol core. European journal of medicinal chemistry. 2020 Oct; 204(?):112620. doi: 10.1016/j.ejmech.2020.112620. [PMID: 32738413]
  • Tatjana Mitrović, Slaviša Stamenković, Vladimir Cvetković, Svetlana Tošić, Milan Stanković, Ivana Radojević, Olgica Stefanović, Ljiljana Comić, Dragana Dačić, Milena Curčić, Snežana Marković. Antioxidant, antimicrobial and antiproliferative activities of five lichen species. International journal of molecular sciences. 2011; 12(8):5428-48. doi: 10.3390/ijms12085428. [PMID: 21954369]
  • Isvett J Flores-Sanchez, Huub J M Linthorst, Robert Verpoorte. In silicio expression analysis of PKS genes isolated from Cannabis sativa L. Genetics and molecular biology. 2010 Oct; 33(4):703-13. doi: 10.1590/s1415-47572010005000088. [PMID: 21637580]
  • Daniel Cook, Agnes M Rimando, Thomas E Clemente, Joachim Schröder, Franck E Dayan, N P Dhammika Nanayakkara, Zhiqiang Pan, Brice P Noonan, Mark Fishbein, Ikuro Abe, Stephen O Duke, Scott R Baerson. Alkylresorcinol synthases expressed in Sorghum bicolor root hairs play an essential role in the biosynthesis of the allelopathic benzoquinone sorgoleone. The Plant cell. 2010 Mar; 22(3):867-87. doi: 10.1105/tpc.109.072397. [PMID: 20348430]
  • Futoshi Taura, Shinji Tanaka, Chiho Taguchi, Tomohide Fukamizu, Hiroyuki Tanaka, Yukihiro Shoyama, Satoshi Morimoto. Characterization of olivetol synthase, a polyketide synthase putatively involved in cannabinoid biosynthetic pathway. FEBS letters. 2009 Jun; 583(12):2061-6. doi: 10.1016/j.febslet.2009.05.024. [PMID: 19454282]
  • M David Marks, Li Tian, Jonathan P Wenger, Stephanie N Omburo, Wilfredo Soto-Fuentes, Ji He, David R Gang, George D Weiblen, Richard A Dixon. Identification of candidate genes affecting Delta9-tetrahydrocannabinol biosynthesis in Cannabis sativa. Journal of experimental botany. 2009; 60(13):3715-26. doi: 10.1093/jxb/erp210. [PMID: 19581347]
  • 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]
  • Franck E Dayan, Susan B Watson, N P Dhammika Nanayakkara. Biosynthesis of lipid resorcinols and benzoquinones in isolated secretory plant root hairs. Journal of experimental botany. 2007; 58(12):3263-72. doi: 10.1093/jxb/erm173. [PMID: 17928374]
  • 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]
  • Tri J Raharjo, Wen-Te Chang, Marianne C Verberne, Anja M G Peltenburg-Looman, Huub J M Linthorst, Robert Verpoorte. Cloning and over-expression of a cDNA encoding a polyketide synthase from Cannabis sativa. Plant physiology and biochemistry : PPB. 2004 Apr; 42(4):291-7. doi: 10.1016/j.plaphy.2004.02.011. [PMID: 15120113]
  • 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]
  • J Hładyszowski, L Zubik, A Kozubek. Quantum mechanical and experimental oxidation studies of pentadecylresorcinol, olivetol, orcinol and resorcinol. Free radical research. 1998 Apr; 28(4):359-68. doi: 10.3109/10715769809070804. [PMID: 9684980]
  • D Rauls, L L Penney. Analysis of olivetol in rabbit serum by high-performance liquid chromatography. Journal of chromatography. 1982 Jan; 234(2):500-2. doi: 10.1016/s0021-9673(00)81896-8. [PMID: 7056834]