Pregnanetriol (BioDeep_00000710846)

Main id: BioDeep_00000002627

 

Volatile Flavor Compounds


代谢物信息卡片


3-alpha,17-alpha,20-beta-trihydroxy-5-alpha-pregnane

化学式: C21H36O3 (336.26643060000004)
中文名称: 5β-孕烷-3α,17α,20α-三醇, 别孕烷-3Α,17Α,20Β-三醇
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC(C1(CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C)O)O
InChI: InChI=1S/C21H36O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h13-18,22-24H,4-12H2,1-3H3

描述信息

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

同义名列表

5 个代谢物同义名

3-alpha,17-alpha,20-beta-trihydroxy-5-alpha-pregnane; 5beta-Pregnane-3alpha,17alpha,20alpha-triol; Pregnane-3,17,20-triol,(3a,5b,20S)-; Pregnanetriol; 5beta-Pregnane-3alpha,17alpha,20alpha-triol



数据库引用编号

12 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

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)

PathBank(0)

PharmGKB(0)

0 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

  • Loredana Iannella, Cristiana Colamonici, Davide Curcio, Francesco Botrè, Xavier de la Torre. Detecting the abuse of 19-norsteroids in doping controls: A new gas chromatography coupled to isotope ratio mass spectrometry method for the analysis of 19-norandrosterone and 19-noretiocholanolone. Drug testing and analysis. 2021 Apr; 13(4):770-784. doi: 10.1002/dta.2985. [PMID: 33242373]
  • Tomoyo Itonaga, Masako Izawa, Takashi Hamajima, Yukihiro Hasegawa. First Morning Pregnanetriol and 17-Hydroxyprogesterone Correlated Significantly in 21-Hydroxylase Deficiency. Frontiers in endocrinology. 2021; 12(?):808254. doi: 10.3389/fendo.2021.808254. [PMID: 35140686]
  • Xavier de la Torre, Daniel Jardines, Davide Curcio, Cristiana Colamonici, Francesco Botrè. Isotope ratio mass spectrometry in antidoping analysis: The use of endogenous reference compounds. Rapid communications in mass spectrometry : RCM. 2019 Mar; 33(6):579-586. doi: 10.1002/rcm.8377. [PMID: 30589473]
  • Christopher M Jones, Ashwini Mallappa, Nicole Reisch, Nikolaos Nikolaou, Nils Krone, Beverly A Hughes, Donna M O'Neil, Martin J Whitaker, Jeremy W Tomlinson, Karl-Heinz Storbeck, Deborah P Merke, Richard J Ross, Wiebke Arlt. Modified-Release and Conventional Glucocorticoids and Diurnal Androgen Excretion in Congenital Adrenal Hyperplasia. The Journal of clinical endocrinology and metabolism. 2017 06; 102(6):1797-1806. doi: 10.1210/jc.2016-2855. [PMID: 27845856]
  • Clemens Kamrath, Michaela F Hartmann, Claudia Boettcher, Klaus-Peter Zimmer, Stefan A Wudy. Diagnosis of 21-hydroxylase deficiency by urinary metabolite ratios using gas chromatography-mass spectrometry analysis: Reference values for neonates and infants. The Journal of steroid biochemistry and molecular biology. 2016 Feb; 156(?):10-6. doi: 10.1016/j.jsbmb.2015.10.013. [PMID: 26493852]
  • Tina Keller-Costa, Peter C Hubbard, Christian Paetz, Yoko Nakamura, José P da Silva, Ana Rato, Eduardo N Barata, Bernd Schneider, Adelino V M Canario. Identity of a tilapia pheromone released by dominant males that primes females for reproduction. Current biology : CB. 2014 Sep; 24(18):2130-2135. doi: 10.1016/j.cub.2014.07.049. [PMID: 25155507]
  • Weiming Li, Tyler Buchinger. Pheromone signaling: a pissing contest in tilapia. Current biology : CB. 2014 Sep; 24(18):R843-R845. doi: 10.1016/j.cub.2014.08.001. [PMID: 25247358]
  • Clemens Kamrath, Michaela F Hartmann, Claudia Boettcher, Stefan A Wudy. Reduced activity of 11β-hydroxylase accounts for elevated 17α-hydroxyprogesterone in preterms. The Journal of pediatrics. 2014 Aug; 165(2):280-4. doi: 10.1016/j.jpeds.2014.04.011. [PMID: 24862381]
  • Nicole Reisch, Marietta Rottenkolber, Anais Greifenstein, Nils Krone, Heinrich Schmidt, Martin Reincke, Hans-Peter Schwarz, Felix Beuschlein. Testicular adrenal rest tumors develop independently of long-term disease control: a longitudinal analysis of 50 adult men with congenital adrenal hyperplasia due to classic 21-hydroxylase deficiency. The Journal of clinical endocrinology and metabolism. 2013 Nov; 98(11):E1820-6. doi: 10.1210/jc.2012-3181. [PMID: 23969190]
  • Masayuki Hayashi, Yuko Kataoka, Yoshihisa Sugimura, Fumiko Kato, Maki Fukami, Tsutomu Ogata, Keiko Homma, Tomonobu Hasegawa, Yutaka Oiso, Hironobu Sasano, Hiroshi Tanaka. A 68-year-old phenotypically male patient with 21-hydroxylase deficiency and concomitant adrenocortical neoplasm producing testosterone and cortisol. The Tohoku journal of experimental medicine. 2013 10; 231(2):75-84. doi: 10.1620/tjem.231.75. [PMID: 24077358]
  • D Martínez-Brito, M T Correa Vidal, X de la Torre, V García-Mir, O Ledea Lozano, M Granda Fraga. Reference ranges for the urinary steroid profile in a Latin-American population. Drug testing and analysis. 2013 Aug; 5(8):619-26. doi: 10.1002/dta.1448. [PMID: 23339119]
  • Tatsuya Higashi, Katsumi Kawasaki, Nagisa Matsumoto, Shoujiro Ogawa, Kuniko Mitamura, Shigeo Ikegawa. LC/MS/MS of steroids having vicinal diol as electrospray-active boronates. Chemical & pharmaceutical bulletin. 2013; 61(3):326-32. doi: 10.1248/cpb.c12-00979. [PMID: 23449202]
  • Norman F Taylor, Angel O K Chan. New strategies for detecting steroid metabolic disorders--paneling vs profiling. Clinical chemistry. 2012 Aug; 58(8):1262-3. doi: 10.1373/clinchem.2012.189613. [PMID: 22626831]
  • Yuhei Koyama, Keiko Homma, Maki Fukami, Masayuki Miwa, Kazushige Ikeda, Tsutomu Ogata, Tomonobu Hasegawa, Mitsuru Murata. Two-step biochemical differential diagnosis of classic 21-hydroxylase deficiency and cytochrome P450 oxidoreductase deficiency in Japanese infants by GC-MS measurement of urinary pregnanetriolone/ tetrahydroxycortisone ratio and 11β-hydroxyandrosterone. Clinical chemistry. 2012 Apr; 58(4):741-7. doi: 10.1373/clinchem.2011.173286. [PMID: 22273564]
  • Cedric H L Shackleton. Role of a disordered steroid metabolome in the elucidation of sterol and steroid biosynthesis. Lipids. 2012 Jan; 47(1):1-12. doi: 10.1007/s11745-011-3605-6. [PMID: 21874273]
  • María Concepción Robles Gil, R Timón, A F Toribio, D Muñoz, J I Maynar, M J Caballero, M Maynar. Effects of aerobic exercise on urinary estrogens and progestagens in pre and postmenopausal women. European journal of applied physiology. 2012 Jan; 112(1):357-64. doi: 10.1007/s00421-011-1982-4. [PMID: 21559948]
  • Andrew Dauber, Mark Kellogg, Joseph A Majzoub. Monitoring of therapy in congenital adrenal hyperplasia. Clinical chemistry. 2010 Aug; 56(8):1245-51. doi: 10.1373/clinchem.2010.146035. [PMID: 20558634]
  • Yoshiro Toma, Takumi Yanaihara. [Pregnanediol (P2), pregnanetriol (P3)]. Nihon rinsho. Japanese journal of clinical medicine. 2010 Jul; 68 Suppl 7(?):466-70. doi: NULL. [PMID: 20960813]
  • Nicole Reisch, Michael Scherr, Linda Flade, Martin Bidlingmaier, Hans-Peter Schwarz, Ullrich Müller-Lisse, Martin Reincke, Marcus Quinkler, Felix Beuschlein. Total adrenal volume but not testicular adrenal rest tumor volume is associated with hormonal control in patients with 21-hydroxylase deficiency. The Journal of clinical endocrinology and metabolism. 2010 May; 95(5):2065-72. doi: 10.1210/jc.2009-1929. [PMID: 20190160]
  • Anita Bufa, Ildikó Bíró, Viktória Poór, Gábor Molnár, Kálmán A Kovács, Attila Felinger, Sára Jeges, Ferenc Kilár, Péter Miklós Gocze. Altered urinary profiles of endogenous steroids in postmenopausal women with adenocarcinoma endometrii. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology. 2010 Jan; 26(1):10-5. doi: 10.3109/09513590903159581. [PMID: 19670000]
  • Thomas M K Völkl, Diemud Simm, Antje Körner, Wieland Kiess, Jürgen Kratzsch, Helmuth G Dörr. Adiponectin levels are high in children with classic congenital adrenal hyperplasia (CAH) due to 21-hydroxylase deficiency. Acta paediatrica (Oslo, Norway : 1992). 2009 May; 98(5):885-91. doi: 10.1111/j.1651-2227.2009.01231.x. [PMID: 19236311]
  • Manfred Rauh. Steroid measurement with LC-MS/MS in pediatric endocrinology. Molecular and cellular endocrinology. 2009 Mar; 301(1-2):272-81. doi: 10.1016/j.mce.2008.10.007. [PMID: 19007847]
  • Thomas M K Völkl, Diemud Simm, Antje Körner, Wolfgang Rascher, Wieland Kiess, Jürgen Kratzsch, Helmuth G Dörr. Does an altered leptin axis play a role in obesity among children and adolescents with classical congenital adrenal hyperplasia due to 21-hydroxylase deficiency?. European journal of endocrinology. 2009 Feb; 160(2):239-47. doi: 10.1530/eje-08-0770. [PMID: 19004982]
  • M Nováková, R Palme, H Kutalová, L Janský, D Frynta. The effects of sex, age and commensal way of life on levels of fecal glucocorticoid metabolites in spiny mice (Acomys cahirinus). Physiology & behavior. 2008 Sep; 95(1-2):187-93. doi: 10.1016/j.physbeh.2008.05.017. [PMID: 18586285]
  • Cedric H L Shackleton, Josep Marcos, Glenn E Palomaki, Wendy Y Craig, Richard I Kelley, Lisa E Kratz, James E Haddow. Dehydrosteroid measurements in maternal urine or serum for the prenatal diagnosis of Smith-Lemli-Opitz syndrome (SLOS). American journal of medical genetics. Part A. 2007 Sep; 143A(18):2129-36. doi: 10.1002/ajmg.a.31901. [PMID: 17702049]
  • Keiko Homma, Tomonobu Hasegawa, Toshiro Nagai, Masanori Adachi, Reiko Horikawa, Ikuma Fujiwara, Toshihiro Tajima, Ryoujun Takeda, Maki Fukami, Tsutomu Ogata. Urine steroid hormone profile analysis in cytochrome P450 oxidoreductase deficiency: implication for the backdoor pathway to dihydrotestosterone. The Journal of clinical endocrinology and metabolism. 2006 Jul; 91(7):2643-9. doi: 10.1210/jc.2005-2460. [PMID: 16608896]
  • A Jezela-Stanek, E M Małunowicz, E Ciara, E Popowska, B Goryluk-Kozakiewicz, K Spodar, M Czerwiecka, J Jezuita, M J M Nowaczyk, M Krajewska-Walasek. Maternal urinary steroid profiles in prenatal diagnosis of Smith-Lemli-Opitz syndrome: first patient series comparing biochemical and molecular studies. Clinical genetics. 2006 Jan; 69(1):77-85. doi: 10.1111/j.1399-0004.2006.00551.x. [PMID: 16451140]
  • Yoshiro Toma, Takumi Yanaihara. [Pregnanediol (P2), pregnanetriol (P3)]. Nihon rinsho. Japanese journal of clinical medicine. 2005 Aug; 63 Suppl 8(?):443-7. doi: NULL. [PMID: 16149547]
  • Jing-zhu Wang, Mou-tian Wu, Yi-nong Zhang, Xin Liu, Zhi-yong Yang. [Detection of the metabolites of dehydroepiandrosterone in urine with gas chromatography-combustion-isotope ratio mass spectrometry]. Yao xue xue bao = Acta pharmaceutica Sinica. 2005 Feb; 40(2):159-63. doi: NULL. [PMID: 15875674]
  • Keiko Homma, Tomonobu Hasegawa, Eiko Takeshita, Kiyoaki Watanabe, Makoto Anzo, Takio Toyoura, Kazuhiko Jinno, Toya Ohashi, Takashi Hamajima, Yukihiro Takahashi, Takao Takahashi, Nobutake Matsuo. Elevated urine pregnanetriolone definitively establishes the diagnosis of classical 21-hydroxylase deficiency in term and preterm neonates. The Journal of clinical endocrinology and metabolism. 2004 Dec; 89(12):6087-91. doi: 10.1210/jc.2004-0473. [PMID: 15579762]
  • Haruo Mizuno, Yoichiro Ohro, Yukari Sugiyama, Tetsuya Ito, Tomonobu Hasegawa, Keiko Homma, Hajime Ueshiba, Makoto Ono, Hajime Togari. Transient hyper-17-OHPnemia unrelated to cross-reactions with residual fetal adrenal cortex products. Hormone research. 2004; 61(5):242-5. doi: 10.1159/000076961. [PMID: 14988602]
  • S W Bai, B H Jung, B C Chung, S U Kim, J Y Kim, K H Rha, J S Cho, Y W Park, K H Park. Relationship between urinary profile of the endogenous steroids and postmenopausal women with stress urinary incontinence. Neurourology and urodynamics. 2003; 22(3):198-205. doi: 10.1002/nau.10063. [PMID: 12707870]
  • Cedric Shackleton, Esther Roitman, Li Wei Guo, William K Wilson, Forbes D Porter. Identification of 7(8) and 8(9) unsaturated adrenal steroid metabolites produced by patients with 7-dehydrosterol-delta7-reductase deficiency (Smith-Lemli-Opitz syndrome). The Journal of steroid biochemistry and molecular biology. 2002 Oct; 82(2-3):225-32. doi: 10.1016/s0960-0760(02)00155-3. [PMID: 12477489]
  • C H Shackleton, E Roitman, L Kratz, R Kelley. Dehydro-oestriol and dehydropregnanetriol are candidate analytes for prenatal diagnosis of Smith-Lemli-Opitz syndrome. Prenatal diagnosis. 2001 Mar; 21(3):207-12. doi: 10.1002/1097-0223(200103)21:3<207::aid-pd27>3.0.co;2-i. [PMID: 11260610]
  • M Dehnhard, M Heistermann, F Göritz, R Hermes, T Hildebrandt, H Haber. Demonstration of 2-unsaturated C19-steroids in the urine of female Asian elephants, Elephas maximus, and their dependence on ovarian activity. Reproduction (Cambridge, England). 2001 Mar; 121(3):475-84. doi: 10.1530/rep.0.1210475. [PMID: 11226074]
  • H Vierhapper, P Nowotny. The stress of being a doctor: steroid excretion rates in internal medicine residents on and off duty. The American journal of medicine. 2000 Oct; 109(6):492-4. doi: 10.1016/s0002-9343(00)00578-7. [PMID: 11042240]
  • S Fürst-Recktenwald, H G Dörr, F Rosanowski. Androglottia in a young female adolescent with congenital adrenal hyperplasia and 21-hydroxylase deficiency. Journal of pediatric endocrinology & metabolism : JPEM. 2000 Jul; 13(7):959-62. doi: 10.1515/jpem.2000.13.7.959. [PMID: 10968487]
  • H Tveiten, A P Scott, H K Johnsen. Plasma-sulfated C21-steroids increase during the periovulatory period in female common wolffish and are influenced by temperature during vitellogenesis. General and comparative endocrinology. 2000 Mar; 117(3):464-73. doi: 10.1006/gcen.1999.7433. [PMID: 10764557]
  • Y Toma, T Yanaihara. [Pregnanediol (P2), pregnanetriol (P3)]. Nihon rinsho. Japanese journal of clinical medicine. 1999 Dec; 57 Suppl(?):274-8. doi: NULL. [PMID: 10778116]
  • M Takeyasu, T Kato. [Urinary excretion of steroid hormone and 3 beta-hydroxysteroid dehydrogenase activity in normal young adult women]. Rinsho byori. The Japanese journal of clinical pathology. 1999 Jan; 47(1):70-5. doi: NULL. [PMID: 10067368]
  • S Frenzel, H G Dörr. [Problems of delayed diagnosis of an uncomplicated adrenogenital syndrome (AGS) with 21-hydroxylase defect in a 7-year-old boy]. Deutsche medizinische Wochenschrift (1946). 1998 Jul; 123(27):827-31. doi: 10.1055/s-2007-1024074. [PMID: 9685841]
  • G Phillipov. Effect of hypercortisolism and ACTH on the metabolism of cortisol. Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association. 1998; 106(1):57-60. doi: 10.1055/s-0029-1211951. [PMID: 9516061]
  • A P Scott, R M Inbaraj, E L Vermeirssen. Use of a radioimmunoassay which detects C21 steroids with a 17, 20beta-dihydroxyl configuration to identify and measure steroids involved in final oocyte maturation in female plaice (Pleuronectes platessa). General and comparative endocrinology. 1997 Jan; 105(1):62-70. doi: 10.1006/gcen.1996.6798. [PMID: 9000468]
  • R M Inbaraj, A P Scott, E L Vermeirssen. Use of a radioimmunoassay which detects C21 steroids with a 5beta-reduced, 3alpha-hydroxylated configuration to identify and measure steroids involved in final oocyte maturation in female plaice (Pleuronectes platessa). General and comparative endocrinology. 1997 Jan; 105(1):50-61. doi: 10.1006/gcen.1996.6797. [PMID: 9000467]
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  • Y Yang, S Saisho, T Toyoura, K Shimozawa, J Yata. Urinary pregnanetriol-3-glucuronide in children: age-related change and application to the management of 21-hydroxylase deficiency. Acta paediatrica Japonica : Overseas edition. 1996 Apr; 38(2):107-13. doi: 10.1111/j.1442-200x.1996.tb03449.x. [PMID: 8677783]
  • A Y Reeder, G E Joannou. 15 beta-hydroxysteroids (Part IV). Steroids of the human perinatal period: the synthesis of 3 alpha,15 beta,17 alpha-trihydroxy-5 alpha-pregnan-20-one and its A/B-ring configurational isomers. Steroids. 1995 Dec; 60(12):796-801. doi: 10.1016/0039-128x(95)00142-d. [PMID: 8650701]
  • A Kambegawa. [Pregnanetriol (P3)]. Nihon rinsho. Japanese journal of clinical medicine. 1995 Mar; 53 Su Pt 2(?):580-3. doi: NULL. [PMID: 8753309]
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  • D E Kime, A P Scott, A V Canario. In vitro biosynthesis of steroids, including 11-deoxycortisol and 5 alpha-pregnane-3 beta,7 alpha,17,20 beta-tetrol, by ovaries of the goldfish Carassius auratus during the stage of oocyte final maturation. General and comparative endocrinology. 1992 Sep; 87(3):375-84. doi: 10.1016/0016-6480(92)90044-k. [PMID: 1426940]
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  • A V Canario, A P Scott. Levels of 17 alpha,20 alpha-dihydroxy-4-pregnen-3-one, 3 beta,17 alpha,20 alpha-trihydroxy-5 beta-pregnane, and other sex steroids, in blood plasma of male dab, Limanda limanda (marine flatfish) injected with human chorionic gonadotrophin. General and comparative endocrinology. 1991 Aug; 83(2):258-64. doi: 10.1016/0016-6480(91)90029-6. [PMID: 1916213]
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  • J C Job, A Munck, J L Chaussain, P Canlorbe. [Treatment of virilizing adrenal hyperplasia in adolescents. Use and side-effects of dexamethasone]. Archives francaises de pediatrie. 1985 Nov; 42(9):765-9. doi: NULL. [PMID: 4083978]
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