9-hydroxyoctadecanoic acid (BioDeep_00000017524)

   

human metabolite PANOMIX_OTCML-2023 Endogenous Antitumor activity


代谢物信息卡片


9-hydroxystearic acid, (S)-isomer

化学式: C18H36O3 (300.2664)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(otcml) 13.08%

分子结构信息

SMILES: C(CCCCCC(O)CCCCCCCCC)CC(=O)O
InChI: InChI=1S/C18H36O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h17,19H,2-16H2,1H3,(H,20,21)

描述信息

9-hydroxyoctadecanoic acid is a hydroxyoctadecanoic acid that is octadecanoic acid (stearic acid) which has been substituted by a hydroxy group at position 9. It is a conjugate acid of a 9-hydroxyoctadecanoate.
9-Hydroxyoctadecanoic acid is a long-chain hydroxy fatty acid. In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation.
9-Hydroxyoctadecanoic acid (9-HSA) is an HDAC1 inhibitor that inhibits ～66.4\% HDAC1 enzymatic activity at 5 μM. 9-Hydroxyoctadecanoic acid shows anticancer activity[1].

同义名列表

18 个代谢物同义名

9-hydroxystearic acid, (S)-isomer; 9(or 10)-Hydroxyoctadecanoic acid; 9-hydroxystearic acid, (R)-isomer; Octadecanoic acid, 9-hydroxy-; 9-hydroxy-octadecanoic acid; 9-Hydroxyoctadecanoic acid; 10(9)-Hydroxystearic acid; DL-9-hydroxy stearic acid; 9-DL-Hydroxystearic acid; 9-​hydroxystearic acid; 9-hydroxy Stearic Acid; 9-Hydroxyoctadecanoate; DL-9-Hydroxy stearate; 9-hydroxystearic acid; 9-Hydroxystearate; 18:0(9-OH); FA 18:0;O; 9-HSA



数据库引用编号

12 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)

2 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

  • Meric Erikci Ertunc, Bernard P Kok, William H Parsons, Justin G Wang, Dan Tan, Cynthia J Donaldson, Antonio F M Pinto, Joan M Vaughan, Nhi Ngo, Kenneth M Lum, Cassandra L Henry, Aundrea R Coppola, Micah J Niphakis, Benjamin F Cravatt, Enrique Saez, Alan Saghatelian. AIG1 and ADTRP are endogenous hydrolases of fatty acid esters of hydroxy fatty acids (FAHFAs) in mice. The Journal of biological chemistry. 2020 05; 295(18):5891-5905. doi: 10.1074/jbc.ra119.012145. [PMID: 32152231]
  • Natalia Calonghi, Carla Boga, Dario Telese, Silvia Bordoni, Giorgio Sartor, Chiara Torsello, Gabriele Micheletti. Synthesis of 9-Hydroxystearic Acid Derivatives and Their Antiproliferative Activity on HT 29 Cancer Cells. Molecules (Basel, Switzerland). 2019 Oct; 24(20):. doi: 10.3390/molecules24203714. [PMID: 31619025]
  • Ondrej Kuda, Marie Brezinova, Jan Silhavy, Vladimir Landa, Vaclav Zidek, Chandra Dodia, Franziska Kreuchwig, Marek Vrbacky, Laurence Balas, Thierry Durand, Norbert Hübner, Aron B Fisher, Jan Kopecky, Michal Pravenec. Nrf2-Mediated Antioxidant Defense and Peroxiredoxin 6 Are Linked to Biosynthesis of Palmitic Acid Ester of 9-Hydroxystearic Acid. Diabetes. 2018 06; 67(6):1190-1199. doi: 10.2337/db17-1087. [PMID: 29549163]
  • Carola Parolin, Natalia Calonghi, Enrica Presta, Carla Boga, Paolo Caruana, Marina Naldi, Vincenza Andrisano, Lanfranco Masotti, Giorgio Sartor. Mechanism and stereoselectivity of HDAC I inhibition by (R)-9-hydroxystearic acid in colon cancer. Biochimica et biophysica acta. 2012 Oct; 1821(10):1334-40. doi: 10.1016/j.bbalip.2012.07.007. [PMID: 22814230]
  • Satoru Tamura, Masafumi Kaneko, Atsushi Shiomi, Guang-Ming Yang, Toshiaki Yamaura, Nobutoshi Murakami. Unprecedented NES non-antagonistic inhibitor for nuclear export of Rev from Sida cordifolia. Bioorganic & medicinal chemistry letters. 2010 Mar; 20(6):1837-9. doi: 10.1016/j.bmcl.2010.01.165. [PMID: 20176483]
  • N Calonghi, E Pagnotta, C Parolin, C Molinari, C Boga, F Dal Piaz, G L Brusa, M A Santucci, L Masotti. Modulation of apoptotic signalling by 9-hydroxystearic acid in osteosarcoma cells. Biochimica et biophysica acta. 2007 Feb; 1771(2):139-46. doi: 10.1016/j.bbalip.2006.11.012. [PMID: 17234448]
  • Eleonora Pagnotta, Natalia Calonghi, Carla Boga, Lanfranco Masotti. N-methylformamide and 9-hydroxystearic acid: two anti-proliferative and differentiating agents with different modes of action in colon cancer cells. Anti-cancer drugs. 2006 Jun; 17(5):521-6. doi: 10.1097/00001813-200606000-00005. [PMID: 16702808]
  • Natalia Calonghi, Concettina Cappadone, Eleonora Pagnotta, Carla Boga, Carlo Bertucci, Jessica Fiori, Gianluca Tasco, Rita Casadio, Lanfranco Masotti. Histone deacetylase 1: a target of 9-hydroxystearic acid in the inhibition of cell growth in human colon cancer. Journal of lipid research. 2005 Aug; 46(8):1596-603. doi: 10.1194/jlr.m400424-jlr200. [PMID: 15716589]
  • N Calonghi, C Cappadone, E Pagnotta, G Farruggia, F Buontempo, C Boga, G L Brusa, M A Santucci, L Masotti. 9-Hydroxystearic acid upregulates p21(WAF1) in HT29 cancer cells. Biochemical and biophysical research communications. 2004 Jan; 314(1):138-42. doi: 10.1016/j.bbrc.2003.12.066. [PMID: 14715257]
  • C Bertucci, M Hudaib, C Boga, N Calonghi, C Cappadone, L Masotti. Gas chromatography/mass spectrometric assay of endogenous cellular lipid peroxidation products: quantitative analysis of 9- and 10-hydroxystearic acids. Rapid communications in mass spectrometry : RCM. 2002; 16(9):859-64. doi: 10.1002/rcm.656. [PMID: 11948817]
  • G Cavalli, E Casali, A Spisni, L Masotti. Identification of the peroxidation product hydroxystearic acid in Lewis lung carcinoma cells. Biochemical and biophysical research communications. 1991 Aug; 178(3):1260-5. doi: 10.1016/0006-291x(91)91029-c. [PMID: 1872846]