Androstenol (BioDeep_00000021046)

   

human metabolite Endogenous


代谢物信息卡片


(1S,2S,5R,7S,10R,11S,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-13-en-5-ol

化学式: C19H30O (274.2297)
中文名称: (3α,5α)-16-烯-3-甾醇
谱图信息: 最多检出来源 Homo sapiens(endogenous) 9.89%

分子结构信息

SMILES: CC12C=CCC1C1CCC3CC(O)CCC3(C)C1CC2
InChI: InChI=1S/C19H30O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13-17,20H,4-8,10-12H2,1-2H3

描述信息

Androstenol is a steroidal compound belonging to the group of odorous 16-androstenes, first isolated from boar testes and also found in humans. Androstenol has pheromone-like properties in both animals and humans, but the molecular targets of its pheromonal activity are unknown. Androstenol as a pheromone is well suited because of high volatility and lipophilicity. (PMID: 1419890, 8142319, 16415088). 3a-Hydroxyandrost-16-ene is a steroidal compound belonging to the group of odorous 16-androstenes, first isolated from boar testes and also found in humans. 3a-Hydroxyandrost-16-ene has pheromone-like properties in both animals and humans, but the molecular targets of its pheromonal activity are unknown. 3a-Hydroxyandrost-16-ene is structurally similar to endogenous A-ring reduced neurosteroids that act as positive modulators of GABAA receptors. 3a-Hydroxyandrost-16-ene has neurosteroid-like activity as a GABAA receptor modulator. The various actions of 3a-Hydroxyandrost-16-ene in the whole-animal models are consistent with its activity as a GABAA receptor modulator. GABAA receptors could represent a target for 3a-Hydroxyandrost-16-ene as a pheromone, for which it is well suited because of high volatility and lipophilicity, or as a conventional hormonal neurosteroid. (PMID: 1419890, 8142319, 16415088).

同义名列表

22 个代谢物同义名

(1S,2S,5R,7S,10R,11S,15R)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-13-en-5-ol; 10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; (3alpha,5alpha)-Androst-16-en-3-ol; 5 alpha-Androst-16-en-3 alpha-ol; 5alpha-Androst-16-en-3alpha-ol; 3alpha-Hydroxyandrost-16-ene; 3a-Hydroxy-5a-androst-16-ene; (3a,5a)-Androst-16-en-3-ol; (3Α,5α)-androst-16-en-3-ol; 3Α-hydroxyandrost-16-ene; 3a-Hydroxyandrost-16-ene; Androst-16-en-3 alpha-ol; androst-16-en-3alpha-ol; 5a-Androst-16-en-3a-ol; 16,17-Androstene-3-ol; 3a-Hydroxyandrostene; Androst-16-en-3a-ol; Androst-16-en-3α-ol; Androst-16-en-3-ol; Α-androstenol; a-Androstenol; Androstenol



数据库引用编号

11 个数据库交叉引用编号

分类词条

相关代谢途径

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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)

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PharmGKB(0)

2 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

  • Tzu Pin Shentu, Igor Titushkin, Dev K Singh, Keith J Gooch, Papasani V Subbaiah, Michael Cho, Irena Levitan. oxLDL-induced decrease in lipid order of membrane domains is inversely correlated with endothelial stiffness and network formation. American journal of physiology. Cell physiology. 2010 Aug; 299(2):C218-29. doi: 10.1152/ajpcell.00383.2009. [PMID: 20410437]
  • Thomas Piper, Mario Thevis, Ulrich Flenker, Wilhelm Schänzer. Determination of the deuterium/hydrogen ratio of endogenous urinary steroids for doping control purposes. Rapid communications in mass spectrometry : RCM. 2009 Jul; 23(13):1917-26. doi: 10.1002/rcm.4098. [PMID: 19462405]
  • Rafal M Kaminski, Herbert Marini, Pavel I Ortinski, Stefano Vicini, Michael A Rogawski. The pheromone androstenol (5 alpha-androst-16-en-3 alpha-ol) is a neurosteroid positive modulator of GABAA receptors. The Journal of pharmacology and experimental therapeutics. 2006 May; 317(2):694-703. doi: 10.1124/jpet.105.098319. [PMID: 16415088]
  • Christophe Saudan, Aurélien Desmarchelier, Pierre-Edouard Sottas, Patrice Mangin, Martial Saugy. Urinary marker of oral pregnenolone administration. Steroids. 2005 Mar; 70(3):179-83. doi: 10.1016/j.steroids.2004.12.007. [PMID: 15763596]
  • Penny Soucy, Lucille Lacoste, Van Luu-The. Assessment of porcine and human 16-ene-synthase, a third activity of P450c17, in the formation of an androstenol precursor. Role of recombinant cytochrome b5 and P450 reductase. European journal of biochemistry. 2003 Mar; 270(6):1349-55. doi: 10.1046/j.1432-1033.2003.03508.x. [PMID: 12631293]
  • Jean D Wilson, Michael W Leihy, Geoffrey Shaw, Marilyn B Renfree. Androgen physiology: unsolved problems at the millennium. Molecular and cellular endocrinology. 2002 Dec; 198(1-2):1-5. doi: 10.1016/s0303-7207(02)00362-3. [PMID: 12573808]
  • Gyesik Min, Hwajin Kim, Yangjin Bae, Larry Petz, Jongsook Kim Kemper. Inhibitory cross-talk between estrogen receptor (ER) and constitutively activated androstane receptor (CAR). CAR inhibits ER-mediated signaling pathway by squelching p160 coactivators. The Journal of biological chemistry. 2002 Sep; 277(37):34626-33. doi: 10.1074/jbc.m205239200. [PMID: 12114525]
  • I Dufort, P Soucy, L Lacoste, V Luu-The. Comparative biosynthetic pathway of androstenol and androgens. The Journal of steroid biochemistry and molecular biology. 2001 Jun; 77(4-5):223-7. doi: 10.1016/s0960-0760(01)00057-7. [PMID: 11457660]
  • J D Wilson. The role of 5alpha-reduction in steroid hormone physiology. Reproduction, fertility, and development. 2001; 13(7-8):673-8. doi: 10.1071/rd01074. [PMID: 11999320]
  • S Stefańczyk-Krzymowska, T Krzymowski, W Grzegorzewski, B W sowska, J Skipor. Humoral pathway for local transfer of the priming pheromone androstenol from the nasal cavity to the brain and hypophysis in anaesthetized gilts. Experimental physiology. 2000 Nov; 85(6):801-9. doi: 10.1111/j.1469-445x.2000.02056.x. [PMID: 11187974]
  • E L Hurden, D B Gower, F A Harrison. Comparative rates of formation, in vivo, of 16-androstenes, testosterone and androstenedione in boar testis. The Journal of endocrinology. 1984 Nov; 103(2):179-86. doi: 10.1677/joe.0.1030179. [PMID: 6491575]
  • W W CLEVELAND, K SAVARD. STUDIES OF EXCRETION OF ANDROST-16-EN-3-ALPHA-OL. The Journal of clinical endocrinology and metabolism. 1964 Oct; 24(?):983-7. doi: 10.1210/jcem-24-10-983. [PMID: 14231758]
  • B W L BROOKSBANK, G A D HASLEWOOD. The isolation of androst-16-en-3 alpha-ol from women's urine. The Biochemical journal. 1952 May; 51(2):286-8. doi: 10.1042/bj0510286. [PMID: 14944590]