5-Alpha-妊娠-3-alpha-17-二醇-20-酮 | 6890-65-9

• 物质功能分类: 有机原料 - 酮类化合物
• 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
• 中文名称: 5-Alpha-妊娠-3-alpha-17-二醇-20-酮
• 英文名称: 3α,17α-dihydroxy-5α-pregnan-20-one
• 英文别名: 5α-pregnane-3α,17α-diol-20-one；3α,17-dihydroxy-5α-pregnan-20-one；3α,17-Dihydroxy-5α-pregnan-20-on；3alpha,17-Dihydroxy-5alpha-pregnan-20-one；1-[(3R,5S,8R,9S,10S,13S,14S,17R)-3,17-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 6890-65-9
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: LKQDFQLSEHWIRK-JRRMKBMNSA-N

物化性质

• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.952
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Alpha-妊娠-3-alpha-17-二醇-20-酮 在 甲醇 、 sodium tetrahydroborate 作用下， 生成 5α-孕烷-3α,17α,20β-三醇
  参考文献：
  名称：

  Synthesis of 17α,20α-Dihydroxysteroids¹

  摘要：

  DOI：

  10.1021/jo01096a006
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 生成 5-Alpha-妊娠-3-alpha-17-二醇-20-酮
  参考文献：
  名称：

  Fukushima et al., Journal of Biological Chemistry, 1954, vol. 210, p. 129,132

  摘要：

  DOI：

文献信息

• Steroids excreted in urine by neonates with 21-hydroxylase deficiency: Characterization, using GC–MS and GC–MS/MS, of the D-ring and side chain structure of pregnanes and pregnenes
  作者：Sofia Christakoudi、David A. Cowan、Norman F. Taylor

  DOI：10.1016/j.steroids.2009.09.011

  日期：2010.1

  conditions, were used together to determine the structure of the D-ring and the side chain of 20-oxo and 20-hydroxy pregnane(ene)s without oxo groups on the A-, B-, and C-ring. All possible combinations of D-ring and side chain configuration were considered. Most fragmentations could be interpreted as partial or complete D-ring cleavages with loss of the side chain, aided by comparison with spectra of deuterated

  缺乏21-羟化酶的新生儿尿液中的类固醇代谢物主要是多羟基化的17-羟孕酮和雄激素代谢物，大多数结构不完全明确。这项研究是表征和鉴定这些特征的综合项目的一部分，以增强诊断并进一步阐明新生儿类固醇代谢的类型。在萃取和酶促共轭水解后，类固醇以甲基肟-三甲基甲硅烷基醚衍生物的形式在与四极杆和离子阱质谱仪联用的气相色谱仪上进行分析。在恒定激发条件下获得的GC-MS和GC-MS / MS光谱一起用于确定D-环和20-羟基和20-羟基孕烯（烯）的侧链的结构，这些烯基上没有氧基。 A环，B环和C环。考虑了D形环和侧链构型的所有可能组合。通过与氘代衍生物和硼氢化物还原的代谢物的光谱比较，可以将大多数片段解释为部分或完全的D环裂解，并丢失了侧链。还讨论了可能的重排离子。鉴定了140多种内源性代谢物。GC-MS / MS对于表征具有16,17-二羟基-20-氧代结构的化合物特别有用，该结构被解释为子宫内酶诱导的
• Romo; Lisci, Boletin del Instituto de Quimica de la Universidad Nacional Autonoma de Mexico, 1955, vol. 7, p. 63,66
  作者：Romo、Lisci

  DOI：——

  日期：——
• Study of the direct effect of LHRH agonist on testicular 17-hydroxylase and 5 α-reductase activities in non-hypophysectomized adult rats treated with an anti-luteinizing hormone serum
  作者：Réjean Carmichael、Alain Belanger

  DOI：10.1016/0039-128x(84)90054-0

  日期：1984.1

  In order to study both direct and pituitary-mediated mechanisms of action of the LHRH analogue [D-Ser(TBU)6, des-Gly-NH2(10)]LHRH ethylamide upon testicular steroidogenesis in adult rat, we compared the effects of the agonist when administered alone or concomitantly with an anti-LH serum to non-hypophysectomized rats. Testicular steroid contents and in vitro progesterone and testosterone metabolism were determined. Anti-LH serum administration was able to prevent 5 alpha-reductase stimulation by the agonistic peptide, but not the inhibition of 17-hydroxylase activity. These data suggest that modulation of 17-hydroxylase involves both direct and pituitary-mediated processes, while 5 alpha-reductase stimulation is mainly if not only due to a pituitary-mediated mechanism.
• Romo; Lisci, Boletin del Instituto de Quimica de la Universidad Nacional Autonoma de Mexico, 1955, vol. 7, p. 63,65
  作者：Romo、Lisci

  DOI：——

  日期：——
• Use of hydroxypregnenolone derivatives for enhancing health and physical performance
  申请人：Marchewitz Eric D.

  公开号：US20130281418A1

  公开（公告）日：2013-10-24

  A method for the use of derivatives of hydroxypregnenolone (3-beta,17-alpha-dihydroxypregn-5-en-3-one) to enhance health and physical performance in humans and more particularly to the use of hydroxypregnenolone derivatives for restoring renal hormonal balance, decreasing body weight, reducing adipose tissue, increasing endurance, promoting skeletal muscle growth, boosting androgen levels, inhibiting aromatase, and increasing cognitive function.