Helvolic acid (BioDeep_00000405020)

   

natural product


代谢物信息卡片


NCGC00169132-02_C33H44O8_(4alpha,5alpha,6beta,8alpha,9beta,13alpha,14beta,16beta,17Z)-6,16-Diacetoxy-4,8,14-trimethyl-3,7-dioxo-18-norcholesta-1,17,24-trien-21-oic acid

化学式: C33H44O8 (568.3036)
中文名称: 烟曲霉酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC(=O)[C@@H](C)[C@]2([H])[C@H](OC(C)=O)C(=O)[C@@]3(C)[C@]([H])([C@]21C)CC[C@@]1([H])/C(=C(/C(O)=O)\CC/C=C(\C)/C)/[C@@H](OC(C)=O)C[C@@]13C
InChI: InChI=1S/C33H44O8/c1-17(2)10-9-11-21(30(38)39)26-22-12-13-25-31(6)15-14-23(36)18(3)27(31)28(41-20(5)35)29(37)33(25,8)32(22,7)16-24(26)40-19(4)34/h10,14-15,18,22,24-25,27-28H,9,11-13,16H2,1-8H3,(H,38,39)/b26-21-/t18-,22+,24+,25+,27-,28+,31-,32+,33-/m1/s1

描述信息

A steroid C-21 acid having a 29-nordammarane skeleton substituted with an acetoxy group at C-16 and oxo groups at C-3 and -7, with double bonds at C-1, -17(20) and -24.

同义名列表

3 个代谢物同义名

Helvolic acid; (4alpha,6beta,8alpha,9beta,13alpha,14beta,16beta,17beta)-6,16- bis(acetyloxy)-3,7-dioxo-29-nordammara-1,17(20),24-trien-21-oic acid; NCGC00169132-02_C33H44O8_(4alpha,5alpha,6beta,8alpha,9beta,13alpha,14beta,16beta,17Z)-6,16-Diacetoxy-4,8,14-trimethyl-3,7-dioxo-18-norcholesta-1,17,24-trien-21-oic acid



数据库引用编号

9 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)

15 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

  • Yanlei Sun, Song Hong, Haimin Chen, Ying Yin, Chengshu Wang. Production of Helvolic Acid in Metarhizium Contributes to Fungal Infection of Insects by Bacteriostatic Inhibition of the Host Cuticular Microbiomes. Microbiology spectrum. 2022 10; 10(5):e0262022. doi: 10.1128/spectrum.02620-22. [PMID: 36047778]
  • Zhi-Bin Zhang, Si-Yao Du, Bo Ji, Chang-Jiu Ji, Yi-Wen Xiao, Ri-Ming Yan, Du Zhu. New Helvolic Acid Derivatives with Antibacterial Activities from Sarocladium oryzae DX-THL3, an Endophytic Fungus from Dongxiang Wild Rice (Oryza rufipogon Griff.). Molecules (Basel, Switzerland). 2021 Mar; 26(7):. doi: 10.3390/molecules26071828. [PMID: 33805102]
  • Kaat José Peeters, Ashley Haeck, Lies Harinck, Oluwatoyin Oluwakemi Afolabi, Kristof Demeestere, Kris Audenaert, Monica Höfte. Morphological, Pathogenic and Toxigenic Variability in the Rice Sheath Rot Pathogen Sarocladium Oryzae. Toxins. 2020 02; 12(2):. doi: 10.3390/toxins12020109. [PMID: 32046323]
  • Zhi-Qin Cao, Jian-Ming Lv, Qiu Liu, Sheng-Ying Qin, Guo-Dong Chen, Ping Dai, Yue Zhong, Hao Gao, Xin-Sheng Yao, Dan Hu. Biosynthetic Study of Cephalosporin P1 Reveals a Multifunctional P450 Enzyme and a Site-Selective Acetyltransferase. ACS chemical biology. 2020 01; 15(1):44-51. doi: 10.1021/acschembio.9b00863. [PMID: 31860257]
  • Jian-Ming Lv, Dan Hu, Hao Gao, Tetsuo Kushiro, Takayoshi Awakawa, Guo-Dong Chen, Chuan-Xi Wang, Ikuro Abe, Xin-Sheng Yao. Biosynthesis of helvolic acid and identification of an unusual C-4-demethylation process distinct from sterol biosynthesis. Nature communications. 2017 11; 8(1):1644. doi: 10.1038/s41467-017-01813-9. [PMID: 29158519]
  • Xiaowei Luo, Xuefeng Zhou, Xiuping Lin, Xiaochu Qin, Tianyu Zhang, Junfeng Wang, Zhengchao Tu, Bin Yang, Shengrong Liao, Yongqi Tian, Xiaoyan Pang, Kumaravel Kaliyaperumal, Jian Lin Li, Huaming Tao, Yonghong Liu. Antituberculosis compounds from a deep-sea-derived fungus Aspergillus sp. SCSIO Ind09F01. Natural product research. 2017 Aug; 31(16):1958-1962. doi: 10.1080/14786419.2016.1266353. [PMID: 28068839]
  • War War May Zin, Suradet Buttachon, Tida Dethoup, Carla Fernandes, Sara Cravo, Madalena M M Pinto, Luís Gales, José A Pereira, Artur M S Silva, Nazim Sekeroglu, Anake Kijjoa. New Cyclotetrapeptides and a New Diketopiperzine Derivative from the Marine Sponge-Associated Fungus Neosartorya glabra KUFA 0702. Marine drugs. 2016 Jul; 14(7):. doi: 10.3390/md14070136. [PMID: 27447650]
  • Shailaja Hittalmani, H B Mahesh, Channappa Mahadevaiah, Mothukapalli Krishnareddy Prasannakumar. De novo genome assembly and annotation of rice sheath rot fungus Sarocladium oryzae reveals genes involved in Helvolic acid and Cerulenin biosynthesis pathways. BMC genomics. 2016 Mar; 17(?):271. doi: 10.1186/s12864-016-2599-0. [PMID: 27036298]
  • Xiao-Jun Li, Qiang Zhang, An-Ling Zhang, Jin-Ming Gao. Metabolites from Aspergillus fumigatus, an endophytic fungus associated with Melia azedarach, and their antifungal, antifeedant, and toxic activities. Journal of agricultural and food chemistry. 2012 Apr; 60(13):3424-31. doi: 10.1021/jf300146n. [PMID: 22409377]
  • Jianglin Zhao, Yan Mou, Tijiang Shan, Yan Li, Shiqiong Lu, Ligang Zhou. Preparative separation of helvolic acid from the endophytic fungus Pichia guilliermondii Ppf9 by high-speed counter-current chromatography. World journal of microbiology & biotechnology. 2012 Mar; 28(3):835-40. doi: 10.1007/s11274-011-0878-0. [PMID: 22805802]
  • Jianglin Zhao, Yan Mou, Tijiang Shan, Yan Li, Ligang Zhou, Mingan Wang, Jingguo Wang. Antimicrobial metabolites from the endophytic fungus Pichia guilliermondii isolated from Paris polyphylla var. yunnanensis. Molecules (Basel, Switzerland). 2010 Nov; 15(11):7961-70. doi: 10.3390/molecules15117961. [PMID: 21060302]
  • Ming-Shi Shiao, Jing-Jing Chiu, Bao-Wen Chang, Jane Wang, Wei-Ping Jen, Ye-Jer Wu, Yuh-Lien Chen. In search of antioxidants and anti-atherosclerotic agents from herbal medicines. BioFactors (Oxford, England). 2008; 34(2):147-57. doi: 10.1002/biof.5520340206. [PMID: 19706980]
  • Niraikulam Ayyadurai, Sundar Isaac Kirubakaran, Sirobhooshanam Srisha, Natarajan Sakthivel. Biological and molecular variability of Sarocladium oryzae, the sheath rot pathogen of rice (Oryza sativa L.). Current microbiology. 2005 Jun; 50(6):319-23. doi: 10.1007/s00284-005-4509-6. [PMID: 15968500]
  • J Y Liu, Y C Song, Z Zhang, L Wang, Z J Guo, W X Zou, R X Tan. Aspergillus fumigatus CY018, an endophytic fungus in Cynodon dactylon as a versatile producer of new and bioactive metabolites. Journal of biotechnology. 2004 Nov; 114(3):279-87. doi: 10.1016/j.jbiotec.2004.07.008. [PMID: 15522437]
  • M Fox, G Gray, K Kavanagh, C Lewis, S Doyle. Detection of Aspergillus fumigatus mycotoxins: immunogen synthesis and immunoassay development. Journal of microbiological methods. 2004 Feb; 56(2):221-30. doi: 10.1016/j.mimet.2003.10.009. [PMID: 14744451]
  • M K Ghosh, R Amudha, S Jayachandran, N Sakthivel. Detection and quantification of phytotoxic metabolites of Sarocladium oryzae in sheath rot-infected grains of rice. Letters in applied microbiology. 2002; 34(6):398-401. doi: 10.1046/j.1472-765x.2002.01111.x. [PMID: 12028418]