Rapanone (BioDeep_00000008072)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


2,5-Cyclohexadiene-1,4-dione, 2,5-dihydroxy-3-tridecyl-

化学式: C19H30O4 (322.214398)
中文名称: 2,5-二羟基-3-十三基-[1,4]苯醌, 拉帕酮, 酸藤子醌
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 13.33%

分子结构信息

SMILES: C1(O)C(=O)C(CCCCCCCCCCCCC)=C(O)C(=O)C=1
InChI: InChI=1S/C19H30O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18(22)16(20)14-17(21)19(15)23/h14,20,23H,2-13H2,1H3

描述信息

Rapanone is a member of dihydroxy-1,4-benzoquinones.
Rapanone is a natural product found in Badula barthesia, Ardisia crenata, and other organisms with data available.
Rapanone is a natural benzoquinone. Rapanone exhibits a broad spectrum of biological actions, including anti-tumor, antioxidant, anti-inflammatory, antibacterial and antiparasitic. Rapanone also is a potent and selective human synovial PLA2 inhibitor, with an IC50 of 2.6 μM[1][2][3][4].
Rapanone is a natural benzoquinone. Rapanone exhibits a broad spectrum of biological actions, including anti-tumor, antioxidant, anti-inflammatory, antibacterial and antiparasitic. Rapanone also is a potent and selective human synovial PLA2 inhibitor, with an IC50 of 2.6 μM[1][2][3][4].
Rapanone is a natural benzoquinone. Rapanone exhibits a broad spectrum of biological actions, including anti-tumor, antioxidant, anti-inflammatory, antibacterial and antiparasitic. Rapanone also is a potent and selective human synovial PLA2 inhibitor, with an IC50 of 2.6 μM[1][2][3][4].

同义名列表

22 个代谢物同义名

2,5-Cyclohexadiene-1,4-dione, 2,5-dihydroxy-3-tridecyl-; 2,5-Cyclohexadiene-1,4-dione,2,5-dihydroxy-3-tridecyl-; 2,5-Dihydroxy-3-tridecylcyclohexa-2,5-diene-1,4-dione; 2,5-DIHYDROXY-3-TRIDECYL-2,5-CYCLOHEXADIENE-1,4-DIONE; 2,5-Dihydroxy-3-tridecyl-[1,4]benzoquinone; P-BENZOQUINONE, 2,5-DIHYDROXY-3-TRIDECYL-; 2,5-dihydroxy-3-tridecyl-1,4-benzoquinone; UNII-SH52PPU72X; MEGxp0_002021; ACon1_001259; SH52PPU72X; Rapanone; ROPANONE; AC1L2P79; 2,5-dihydroxy-3-tridecyl-cyclohexa-2,5-diene-1,4-dione; 2,5-dihydroxy-3-tridecyl-p-benzoquinone; AIDS-104286; NSC 340285; AIDS104286; NSC340285; 573-40-0; C10399



数据库引用编号

17 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)

36 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

  • Dagmara Wróbel-Biedrawa, Agnieszka Galanty, Paweł Zagrodzki, Irma Podolak. Optimization of Extraction Conditions and Cytotoxic Activity of Rapanone in Comparison to Its Homologue, Embelin. Molecules (Basel, Switzerland). 2022 Nov; 27(22):. doi: 10.3390/molecules27227912. [PMID: 36432013]
  • Irma Podolak, Adam Mynarski, Dagmara Wróbel, Karolina Grabowska, Agnieszka Galanty. Bioactive benzoquinones content variability in red-berry and white-berry varieties of Ardisia crenata Sims. and assessment of cytotoxic activity. Natural product research. 2021 Jan; 35(1):157-161. doi: 10.1080/14786419.2019.1614575. [PMID: 31135229]
  • Dagmara Wróbel-Biedrawa, Karolina Grabowska, Agnieszka Galanty, Danuta Sobolewska, Paweł Żmudzki, Irma Podolak. Anti-melanoma potential of two benzoquinone homologues embelin and rapanone - a comparative in vitro study. Toxicology in vitro : an international journal published in association with BIBRA. 2020 Jun; 65(?):104826. doi: 10.1016/j.tiv.2020.104826. [PMID: 32169436]
  • Karen de la Vega-Hernández, Manuel Antuch, Osmany Cuesta-Rubio, Yanier Núñez-Figueredo, Gilberto L Pardo-Andreu. Discerning the antioxidant mechanism of rapanone: A naturally occurring benzoquinone with iron complexing and radical scavenging activities. Journal of inorganic biochemistry. 2017 05; 170(?):134-147. doi: 10.1016/j.jinorgbio.2017.02.019. [PMID: 28237732]
  • Victor Kuete, Leonidah K Omosa, Viviane R Sipowo Tala, Jacob O Midiwo, Armelle T Mbaveng, Sauda Swaleh, Oğuzhan Karaosmanoğlu, Hülya Sivas. Cytotoxicity of Plumbagin, Rapanone and 12 other naturally occurring Quinones from Kenyan Flora towards human carcinoma cells. BMC pharmacology & toxicology. 2016 12; 17(1):60. doi: 10.1186/s40360-016-0104-7. [PMID: 27998305]
  • Raphaella Correia da Costa, Dandara Braga Santana, Renata Mendonça Araújo, José Elias de Paula, Patrícia Coelho do Nascimento, Norberto Peporine Lopes, Raimundo Braz-Filho, Laila Salmen Espindola. Discovery of the rapanone and suberonone mixture as a motif for leishmanicidal and antifungal applications. Bioorganic & medicinal chemistry. 2014 Jan; 22(1):135-40. doi: 10.1016/j.bmc.2013.11.044. [PMID: 24331757]
  • Pengcheng Lin, Shuai Li, Sujuan Wang, Yongchun Yang, Jiangong Shi. A nitrogen-containing 3-alkyl-1,4-benzoquinone and a gomphilactone derivative from Embelia ribes. Journal of natural products. 2006 Nov; 69(11):1629-32. doi: 10.1021/np060284m. [PMID: 17125236]
  • C P Cordero, S Gómez-González, C J León-Acosta, S J Morantes-Medina, F A Aristizabal. Cytotoxic activity of five compounds isolated from Colombian plants. Fitoterapia. 2004 Mar; 75(2):225-7. doi: 10.1016/j.fitote.2003.12.017. [PMID: 15030931]
  • L F Ospina, J Calle, L Arteaga, R Pinzón, M J Alcaraz, M Payá. Inhibition of acute and chronic inflammatory responses by the hydroxybenzoquinonic derivative rapanone. Planta medica. 2001 Dec; 67(9):791-5. doi: 10.1055/s-2001-18839. [PMID: 11745012]
  • G Hussein, H Miyashiro, N Nakamura, M Hattori, N Kakiuchi, K Shimotohno. Inhibitory effects of sudanese medicinal plant extracts on hepatitis C virus (HCV) protease. Phytotherapy research : PTR. 2000 Nov; 14(7):510-6. doi: 10.1002/1099-1573(200011)14:7<510::aid-ptr646>3.0.co;2-b. [PMID: 11054840]
  • V Shah, R Sunder, N J de Souza. Chonemorphine and rapanone--antiparasitic agents from plant sources. Journal of natural products. 1987 Jul; 50(4):730-1. doi: 10.1021/np50052a026. [PMID: 3430168]