开环苯酚 | 2394-69-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 开环苯酚
• 英文名称: 3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione
• 英文别名: 3-Hydroxy-9,10-seco-1,3,5(10)-androstatrien-9,17-dione；3-hydroxy-9,10-secoandrost-1,3,5(10)-triene-9,17-dione；3-HSA；3-hydroxy-9,10-seco-androsta-1,3,5(10)-triene-9,17-dione；3-Hydroxy-9,10-seco-androsta-1,3,5(10)-trien-9,17-dion；9,10-seco-Δ^1,3,5(10)-Androstatrien-3-ol-9,17-dion；(3aS,4S,7aS)-4-[2-(5-hydroxy-2-methylphenyl)ethyl]-7a-methyl-2,3,3a,4,6,7-hexahydroindene-1,5-dione
• CAS: 2394-69-6
• 化学式: C₁₉H₂₄O₃
• 分子量: 300.398
• InChiKey: ZWXONJFCJAGEBA-BXWFABGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  开环苯酚 在 recombinant Mycobacterium tuberculosis 3-hydroxy-9,10-seconandrost-1,3,5⁽¹⁰⁾-triene-9,17-dione 4-hydroxylase 、 氧气 、 2,6-蒽二酚 、 还原型辅酶Ⅰ 作用下， 以 水 为溶剂， 生成 6'-羟基七苯酚
  参考文献：
  名称：

  A Flavin-dependent Monooxygenase from Mycobacterium tuberculosis Involved in Cholesterol Catabolism

  摘要：

  Mycobacterium tuberculosis (Mtb) and Rhodococcus jostii RHA1 have similar cholesterol catabolic pathways. This pathway contributes to the pathogenicity of Mtb. The hsaAB cholesterol catabolic genes have been predicted to encode the oxygenase and reductase, respectively, of a flavin-dependent mono-oxygenase that hydroxylates 3-hydroxy-9,10-seconandrost-1,3,5(10)-triene-9,17- dione (3-HSA) to a catechol. An hsaA deletion mutant of RHA1 did not grow on cholesterol but transformed the latter to 3-HSA and related metabolites in which each of the two keto groups was reduced: 3,9-dihydroxy-9,10-seconandrost-1,3,5(10)-triene- 17-one (3,9-DHSA) and 3,17-dihydroxy-9,10-seconandrost-1,3,5( 10)-triene-9-one (3,17-DHSA). Purified 3-hydroxy-9,10- seconandrost-1,3,5(10)-triene-9,17-dione 4-hydroxylase (HsaAB) from Mtb had higher specificity for 3-HSA than for 3,17-DHSA (apparent k(cat)/K-m =1000 +/- 100 M-1 s(-1) versus 700 +/- 100 M-1 s(-1)). However, 3,9-DHSA was a poorer substrate than 3-hydroxybiphenyl (apparent k(cat)/K-m = 80 +/- 40 M-1 s(-1)). In the presence of 3-HSA the K-mapp for O-2 was 100 +/- 10 mu M. The crystal structure of HsaA to 2.5-angstrom resolution revealed that the enzyme has the same fold, flavin-binding site, and catalytic residues as p-hydroxyphenyl acetate hydroxylase. However, HsaA has a much larger phenol-binding site, consistent with the enzyme's substrate specificity. In addition, a second crystal form of HsaA revealed that a C-terminal flap (Val(367)-Val(394)) could adopt two conformations differing by a rigid body rotation of 25 degrees around Arg(366). This rotation appears to gate the likely flavin entrance to the active site. In docking studies with 3-HSA and flavin, the closed conformation provided a rationale for the enzyme's substrate specificity. Overall, the structural and functional data establish the physiological role of HsaAB and provide a basis to further investigate an important class of monooxygenases as well as the bacterial catabolism of steroids.

  DOI：

  10.1074/jbc.m109.099028
• 作为产物：
  描述：

  黄体酮 生成 开环苯酚
  参考文献：
  名称：

  Microbiological Transformations. VII. The Hydroxylation of Steroids at C-9

  摘要：

  DOI：

  10.1021/ja01483a030

文献信息

• PHARMACEUTICAL COMPOSITIONS AND METHODS FOR TREATING TUBERCULOSIS
  申请人：Van Der Geize Robert

  公开号：US20120058977A1

  公开（公告）日：2012-03-08

  A pharmaceutical composition for the treatment of a disease caused by a bacterium that belongs to the group of nocardioform actinomycetes, said composition comprising an effective amount of a compound selected from compound I, (+)-compound II, (−)-compound II, compound III, or mixtures thereof.

  一种用于治疗由属于诺卡菌类放线菌菌群的细菌引起的疾病的药物组合物，该组合物包括从化合物I、(+)-化合物II、(-)-化合物II、化合物III或它们的混合物中选择的有效量化合物。
• The anaerobic degradation of deoxycholic acid by PSEUDOMONAS SP. NCIB 10590
  作者：R.W. Owen、A.N. Mason、R.F. Bilton

  DOI：10.1016/s0040-4020(01)91191-3

  日期：1984.1

  The anaerobic metabolism of deoxycholic acid by Pseudomonas sp. NCIB 10590 was studied. The metabolic pathway was similar to that operating under aerobic conditions with 12β-hydroxyandrosta-1,4-dien-3,17-dione as the major neutral product an metabolites which are not produced during aerobic metabolism were isolated and evidence is presented for the following structures: 9α-hydroxyandrost-1-en-3,17-dione

  假单胞菌（Pseudomonas sp。）对脱氧胆酸的厌氧代谢。对NCIB 10590进行了研究。代谢途径类似于在有氧条件下运行的途径，其中主要的中性产物为12β-羟基雄烷-1,4-二烯-3,17-二酮，分离出有氧代谢过程中未产生的代谢物，并提供了以下证据结构：9α-羟基雄烷-1-烯-3,17-二酮，12α，17）β-二羟基雄甾烯-1,4-二烯-3-酮；3β，12β-dihydroxy-5β-androstan-17-一种酚类固醇的形成及其意义进行了讨论。
• JPS05615692A
  申请人：——

  公开号：JPS05615692A

  公开（公告）日：1981-02-14
• JPS5615692A
  申请人：——

  公开号：JPS5615692A

  公开（公告）日：1981-02-14
• Method for the Production of Modified Steroid Degrading Microorganisms and their Use
  申请人：van der Geize Robert

  公开号：US20090186390A1

  公开（公告）日：2009-07-23

  A method is described to construct genetically modified strains of steroid degrading micro-organisms wherein the method comprises inactivation of at least one gene involved in methylhexahydroindanedione propionate degradation. Strains with (multiple) inactivated steroid degrading enzyme genes according to the invention can be used in the accumulation of steroid intermediates. Accumulation products are for example 3aα-H-4α(3′-propionic acid)-7aβ-methylhexahydro-1,5-indanedione (HIP), 3-hydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione (3-HSA), 1,4-androstadiene-3,17-dione (ADD) and 3aα-H-4α(3′-propionic acid)-5α-hydroxy-7aβ-methylhexahydro-1-indanone-δ-lactone (HIL).