5alpha-Campestan-3-one | 27212-88-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 5alpha-Campestan-3-one
• 英文别名: (5S,8R,9S,10S,13R,14S,17R)-17-[(2R,5R)-5,6-dimethylheptan-2-yl]-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• CAS: 27212-88-0
• 化学式: C₂₈H₄₈O
• 分子量: 400.7
• InChiKey: DDJMOMHMVFXEQF-JBQSTXLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5alpha-Campestan-3-one 、 NADP⁺ 生成 campest-4-en-3-one 、 氢(+1)阳离子 、 NADPH(4-)
  参考文献：
  名称：

  5α-Reductase activity in Lycopersicon esculentum: Cloning and functional characterization of LeDET2 and evidence of the presence of two isoenzymes

  摘要：

  The full-length cDNA (LeDET2) encoding a 257 amino acid protein homolog of Arabidopsis DET2 (AtDET2) was isolated in tomato (Lycopersicon esculentum). LeDET2 has 76% similarity with AtDET2 and structural characteristics conserved among plant and mammalian steroid 5 alpha-reductases (5 alpha Rs). LeDET2 is ubiquitously expressed in tomato tissues with higher levels in leaf than in stem, root, seed and callus. When expressed in mammalian cells (COS-7), recombinant LeDET2 was active on substrates typical of mammalian 5 alpha LRs (progesterone, testosterone, androstenedione), but reduced at very low levels campestenone, the substrate described for AtDET2. Similar results were obtained with the expression in COS-7 of recombinant AtDET2 that showed 5 alpha R activity for progesterone and not for campestenone. Recombinant LeDET2 was inhibited by several inhibitors of the human 5 alpha Rs and the application of an active inhibitor to tomato seedlings induced dwarfism and morphological changes similar to BR-deficient mutants. In tomato tissues, campestenone was 5 alpha-reduced in leaf, stem and root homogenates, like progesterone and testosterone, while androstenedione was converted to testosterone, evidencing for the first time a 17 beta-hydroxysteroid dehydrogenase activity in plants. Moreover, two separate 5 alpha R activities with different kinetic characteristic and response to inhibitors were characterized in tomato tissues. The presence of two 5 alpha R isoenzymes was demonstrated also in Arabidopsis using the det2-1 mutant, in which a residual 5 alpha R activity for campestenone and progesterone was evidenced and characterized. Therefore, the existence of two isoenzymes of 5 alpha R is probably characteristic of the whole plant kingdom highlighting the similarities between the animal and plant steroid biosynthetic pathways. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.jsbmb.2005.04.035

文献信息

• Methods for the identification of inhibitors of 3-oxo-5-alpha-steroid 4-dehydrogenase expression or activity in plants
  申请人：——

  公开号：US20040265789A1

  公开（公告）日：2004-12-30

  The present inventors have discovered that 3-oxo-5-alpha-steroid 4-dehydrogenase (DET2) is essential for plant growth. Specifically, the inhibition of DET2 gene expression in plant seedlings resulted in seedlings that are shorter than controls and chlorotic. Thus, DET2 can be used as a target for the identification of herbicides. Accordingly, the present invention provides methods for the identification of compounds that inhibit DET2 expression or activity, comprising: contacting a compound with a DET2 and detecting the presence and/or absence of binding between said compound and said DET2, or detecting a decrease in DET2 expression or activity. The methods of the invention are useful for the identification of herbicides.

  本发明者发现，3-氧代-5-α-类固醇 4-脱氢酶（DET2）对植物生长至关重要。具体来说，抑制 DET2 基因在植物幼苗中的表达会导致幼苗比对照组矮小，并出现萎蔫现象。因此，DET2 可用作除草剂的鉴定靶标。因此，本发明提供了鉴定抑制 DET2 表达或活性的化合物的方法，包括：将化合物与 DET2 接触，检测所述化合物与所述 DET2 之间是否存在和/或不存在结合，或检测 DET2 表达或活性的降低。本发明的方法可用于除草剂的鉴定。
• METHODS FOR THE IDENTIFICATION OF INHIBITORS OF 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE EXPRESSION OR ACTIVITY IN PLANTS
  申请人：Paradigm Genetics Inc.

  公开号：EP1407270A2

  公开（公告）日：2004-04-14
• EP1407270A4
  申请人：——

  公开号：EP1407270A4

  公开（公告）日：2005-05-25
• ACIDE NUCLEIQUE REGULATEUR PERMETTANT L'EXPRESSION D'UN POLYNUCLEOTIDE D'INTERET SPECIFIQUEMENT DANS L'ENDOTHELIUM D'UNE GRAINE DE PLANTE, ET SES APPLICATIONS.
  申请人：Institut National de la Recherche Agronomique (INRA)

  公开号：EP1414966A2

  公开（公告）日：2004-05-06
• [EN] METHODS FOR THE IDENTIFICATION OF INHIBITORS OF 3-OXO-5-ALPHA-STEROID 4-DEHYDROGENASE EXPRESSION OR ACTIVITY IN PLANTS<br/>[FR] PROCEDES POUR IDENTIFIER DES INHIBITEURS DE L'EXPRESSION OU DE L'ACTIVITE DE LA 3-OXO-5-ALPHA-STEROIDE 4-DESHYDROGENASE DANS DES PLANTES
  申请人：PARADIGM GENETICS INC

  公开号：WO2002096198A2

  公开（公告）日：2002-12-05

  The present inventors have discovered that 3-oxo-5-alpha-steroid 4-dehydrogenase (DET2) is essential for plant growth. Specifically, the inhibition of DET2 gene expression in plant seedlings resulted in seedlings that are shorter than controls and chlorotic. Thus, DET2 can be used as a target for the identification of herbicides. Accordingly, the present invention provides methods for the identification of compounds that inhibit DET2 expression or activity, comprising: contacting a compound with a DET2 and detecting the presence and/or absence of binding between said compound and said DET2, or detecting a decrease in DET2 expression or activity. The methods of the invention are useful for the identification of herbicides.