Campest-4-en-3-one (BioDeep_00000010913)

Main id: BioDeep_00000636739

 

human metabolite Endogenous natural product


代谢物信息卡片


(1S,2R,10S,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

化学式: C28H46O (398.3548466)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(C)C(C)CCC(C)C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C
InChI: InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h17-20,23-26H,7-16H2,1-6H3/t19-,20-,23+,24-,25+,26+,27+,28-/m1/s1

描述信息

Campest-4-en-3-one is an intermediate in Brassinolide Biosynthesis pathway.The conversion of the membrane Sterol Campesterol to BL occurs via a series of reductions, hydroxylations, epimerizations and oxidations that have been extensively studied in several species. The conversion of Campesterol to Campestanol is not a single step, but composed of the biosynthetic sequence of Campesterol 4-en-3Beta-ol ---> 4-en-3-one ---> 3-one ---> Campestanol in Arabidopsis. In the first step, Campesterol is converted to Campest-4-en-3Beta-ol in presence of enzyme Delta-5-3-Ketosteroid Isomerase. Enzymes that catalyze the conversion from 3-Beta-Hydroxy-Delta,5-6-Steroid to 3-oxo-Delta-4-5 Isomerase have been reported in Bacteria and Mammals. Campest-4-en-3 Beta-ol is converted to Campest-4-en-3-one in presence of enzyme 3-Beta-Hydroxysteroid Dehydrogenase. In the next step, Campest-4-en-3-one is converted to Campestanol via 5-Alpha-Campestan-3-one. 3-Oxo-5Alpha-Steroid 4-Dehydrogenase family members (encoded by Det2 in Arabidopsis) catalyze the formation of 5-Alpha-Campestan-3-one.
Isoo. from Phoenix dactylifera (date). (24R)-Ergost-4-en-3-one is found in many foods, some of which are rowanberry, chicory leaves, common hazelnut, and common thyme.

同义名列表

8 个代谢物同义名

(1S,2R,10S,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one; (24R)-24-Methyl-cholest-4-en-3-one; 3-Dehydro-delta4-5-campesterol; 3-Dehydro-Δ4-5-campesterol; (24R)-Ergost-4-en-3-one; Methylcholestenone; campest-4-en-3-one; ST 28:2;O



数据库引用编号

16 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(3)

PlantCyc(5)

代谢反应

556 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(7)

WikiPathways(1)

Plant Reactome(201)

INOH(0)

PlantCyc(347)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

45 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

  • Azis Saifudin, Ken Tanaka, Shigetoshi Kadota, Yasuhiro Tezuka. Protein tyrosine phosphatase 1B (PTP1B)-inhibiting constituents from the leaves of Syzygium polyanthum. Planta medica. 2012 Aug; 78(12):1378-81. doi: 10.1055/s-0032-1315000. [PMID: 22763740]
  • Se-Hwan Joo, Tae-Wuk Kim, Seung-Hyun Son, Woo Sung Lee, Takao Yokota, Seong-Ki Kim. Biosynthesis of a cholesterol-derived brassinosteroid, 28-norcastasterone, in Arabidopsis thaliana. Journal of experimental botany. 2012 Mar; 63(5):1823-33. doi: 10.1093/jxb/err354. [PMID: 22170941]
  • Thomas Hartwig, Claudia Corvalan, Norman B Best, Joshua S Budka, Jia-Ying Zhu, Sunghwa Choe, Burkhard Schulz. Propiconazole is a specific and accessible brassinosteroid (BR) biosynthesis inhibitor for Arabidopsis and maize. PloS one. 2012; 7(5):e36625. doi: 10.1371/journal.pone.0036625. [PMID: 22590578]
  • Jogchum Plat, Ronald P Mensink. Plant stanol esters lower serum triacylglycerol concentrations via a reduced hepatic VLDL-1 production. Lipids. 2009 Dec; 44(12):1149-53. doi: 10.1007/s11745-009-3361-z. [PMID: 19856194]
  • Kunio Suzuki, Rie Konno, Takeshi Shimzu, Tadashi Nagashima, Akihiko Kimura. A fermentation product of phytosterol including campestenone reduces body fat storage and body weight gain in mice. Journal of nutritional science and vitaminology. 2007 Feb; 53(1):63-7. doi: 10.3177/jnsv.53.63. [PMID: 17484382]
  • Toshiyuki Ohnishi, Bunta Watanabe, Kanzo Sakata, Masaharu Mizutani. CYP724B2 and CYP90B3 function in the early C-22 hydroxylation steps of brassinosteroid biosynthetic pathway in tomato. Bioscience, biotechnology, and biochemistry. 2006 Sep; 70(9):2071-80. doi: 10.1271/bbb.60034. [PMID: 16960392]
  • D J Murphy. The extracellular pollen coat in members of the Brassicaceae: composition, biosynthesis, and functions in pollination. Protoplasma. 2006 Aug; 228(1-3):31-9. doi: 10.1007/s00709-006-0163-5. [PMID: 16937052]
  • Ikuo Ikeda, Rie Konno, Takeshi Shimizu, Takashi Ide, Nobuyuki Takahashi, Teruo Kawada, Koji Nagao, Nao Inoue, Teruyoshi Yanagita, Tadateru Hamada, Yae Morinaga, Hiroko Tomoyori, Katsumi Imaizumi, Kunio Suzuki. Campest-5-en-3-one, an oxidized derivative of campesterol, activates PPARalpha, promotes energy consumption and reduces visceral fat deposition in rats. Biochimica et biophysica acta. 2006 May; 1760(5):800-7. doi: 10.1016/j.bbagen.2006.02.017. [PMID: 16616424]
  • Shizuka Tamaru, Yo Suzuki, Masanobu Sakono, Nobuhiro Fukuda, Ikuo Ikeda, Rie Konno, Takeshi Shimizu, Kunio Suzuki. Dietary 5-campestenone (campest-5-en-3-one) enhances fatty acid oxidation in perfused rat liver. Journal of nutritional science and vitaminology. 2006 Apr; 52(2):127-33. doi: 10.3177/jnsv.52.127. [PMID: 16802693]
  • R Konno, Y Kaneko, K Suzuki, Y Matsui. Effect of 5-Campestenone (24-methylcholest-5-en-3-one) on Zucker diabetic fatty rats as a type 2 diabetes mellitus model. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme. 2005 Feb; 37(2):79-83. doi: 10.1055/s-2005-861171. [PMID: 15778923]
  • Takahito Nomura, Corinne E Jager, Yukiko Kitasaka, Keiichi Takeuchi, Motohiro Fukami, Koichi Yoneyama, Yasuhiko Matsushita, Hiroshi Nyunoya, Suguru Takatsuto, Shozo Fujioka, Jennifer J Smith, L Huub J Kerckhoffs, James B Reid, Takao Yokota. Brassinosteroid deficiency due to truncated steroid 5alpha-reductase causes dwarfism in the lk mutant of pea. Plant physiology. 2004 Aug; 135(4):2220-9. doi: 10.1104/pp.104.043786. [PMID: 15286289]
  • Yoshihito Suzuki, Kazuyuki Saso, Shozo Fujioka, Shigeo Yoshida, Eiji Nitasaka, Shinji Nagata, Hiromichi Nagasawa, Suguru Takatsuto, Isomaro Yamaguchi. A dwarf mutant strain of Pharbitis nil, Uzukobito (kobito), has defective brassinosteroid biosynthesis. The Plant journal : for cell and molecular biology. 2003 Nov; 36(3):401-10. doi: 10.1046/j.1365-313x.2003.01887.x. [PMID: 14617096]
  • K Suzuki, M Tanaka, R Konno, Y Kaneko. Effects of 5-campestenone (24-methylcholest-5-en-3-one) on the type 2 diabetes mellitus model animal C57BL/KsJ-db/db mice. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme. 2002 Mar; 34(3):121-6. doi: 10.1055/s-2002-23194. [PMID: 11972300]