18-Hydroxycortisol (BioDeep_00000027568)

   

human metabolite Endogenous blood metabolite


代谢物信息卡片


(1S,2R,10S,11S,14S,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

化学式: C21H30O6 (378.204228)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(feces) 63.99%

分子结构信息

SMILES: CC12CCC(=O)C=C1CCC3C2C(CC4(C3CCC4(C(=O)CO)O)CO)O
InChI: InChI=1S/C21H30O6/c1-19-6-4-13(24)8-12(19)2-3-14-15-5-7-21(27,17(26)10-22)20(15,11-23)9-16(25)18(14)19/h8,14-16,18,22-23,25,27H,2-7,9-11H2,1H3/t14-,15-,16-,18+,19-,20+,21+/m0/s1

描述信息

18-Hydroxycortisol is a derivative of cortIsolated It may be synthesized by zona fasciculata 11-beta hydroxylase in normal human adrenal cortex. (PMID 15356073; 1751390) Overproduction of 18-hydroxycortisol is an aid in the detection of Glucocorticoid-remediable aldosteronism which is an inherited form of mineralocorticoid excess associated with moderate overproduction of aldosterone, in which biochemical and clinical remission is dramatically induced by small amounts of glucocorticoids.(PMID: 1879399) [HMDB]
18-Hydroxycortisol is a derivative of cortIsolated It may be synthesized by zona fasciculata 11-beta hydroxylase in normal human adrenal cortex. (PMID 15356073; 1751390) Overproduction of 18-hydroxycortisol is an aid in the detection of Glucocorticoid-remediable aldosteronism which is an inherited form of mineralocorticoid excess associated with moderate overproduction of aldosterone, in which biochemical and clinical remission is dramatically induced by small amounts of glucocorticoids.(PMID: 1879399).
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

同义名列表

3 个代谢物同义名

(1S,2R,10S,11S,14S,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-15-(hydroxymethyl)-2-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one; 11,17,18,21-Tetrahydroxy-pregn-4-ene-3,20-dione; 18-Hydroxycortisol



数据库引用编号

8 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。

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1 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

  • Yuta Tezuka, Kae Ishii, Lili Zhao, Yuto Yamazaki, Ryo Morimoto, Hironobu Sasano, Aaron M Udager, Fumitoshi Satoh, Adina F Turcu. ACTH Stimulation Maximizes the Accuracy of Peripheral Steroid Profiling in Primary Aldosteronism Subtyping. The Journal of clinical endocrinology and metabolism. 2021 09; 106(10):e3969-e3978. doi: 10.1210/clinem/dgab420. [PMID: 34117870]
  • Jacques W M Lenders, Tracy Ann Williams, Martin Reincke, Celso E Gomez-Sanchez. DIAGNOSIS OF ENDOCRINE DISEASE: 18-Oxocortisol and 18-hydroxycortisol: is there clinical utility of these steroids?. European journal of endocrinology. 2018 Jan; 178(1):R1-R9. doi: 10.1530/eje-17-0563. [PMID: 28904009]
  • Fumitoshi Satoh, Ryo Morimoto, Yoshikiyo Ono, Yoshitsugu Iwakura, Kei Omata, Masataka Kudo, Kei Takase, Kazumasa Seiji, Hidehiko Sasamoto, Seijiro Honma, Mitsunobu Okuyama, Kouwa Yamashita, Celso E Gomez-Sanchez, William E Rainey, Yoichi Arai, Hironobu Sasano, Yasuhiro Nakamura, Sadayoshi Ito. Measurement of peripheral plasma 18-oxocortisol can discriminate unilateral adenoma from bilateral diseases in patients with primary aldosteronism. Hypertension (Dallas, Tex. : 1979). 2015 May; 65(5):1096-102. doi: 10.1161/hypertensionaha.114.04453. [PMID: 25776074]
  • Shigeki Jin, Norio Wada, Yuji Takahashi, Shu-Ping Hui, Toshihiro Sakurai, Hirotoshi Fuda, Seiji Takeda, Masato Fujikawa, Katsuyuki Yanagisawa, Shigeo Ikegawa, Takao Kurosawa, Hitoshi Chiba. Quantification of urinary 18-hydroxycortisol using LC-MS/MS. Annals of clinical biochemistry. 2013 Sep; 50(Pt 5):450-6. doi: 10.1177/0004563213476272. [PMID: 23847032]
  • Paolo Mulatero, Stefania Morra di Cella, Silvia Monticone, Domenica Schiavone, Maria Manzo, Giulio Mengozzi, Franco Rabbia, Massimo Terzolo, Elise P Gomez-Sanchez, Celso E Gomez-Sanchez, Franco Veglio. 18-hydroxycorticosterone, 18-hydroxycortisol, and 18-oxocortisol in the diagnosis of primary aldosteronism and its subtypes. The Journal of clinical endocrinology and metabolism. 2012 Mar; 97(3):881-9. doi: 10.1210/jc.2011-2384. [PMID: 22238407]
  • Cristian A Carvajal, Carmen Campino, Alejandro Martinez-Aguayo, Juan E Tichauer, Rodrigo Bancalari, Carolina Valdivia, Pamela Trejo, Marlene Aglony, René Baudrand, Carlos F Lagos, Cecilia Mellado, Hernán Garcia, Carlos E Fardella. A new presentation of the chimeric CYP11B1/CYP11B2 gene with low prevalence of primary aldosteronism and atypical gene segregation pattern. Hypertension (Dallas, Tex. : 1979). 2012 Jan; 59(1):85-91. doi: 10.1161/hypertensionaha.111.180513. [PMID: 22083159]
  • Clemens Kamrath, Christiane Maser-Gluth, Christine Haag, Egbert Schulze. Diagnosis of glucocorticoid-remediable aldosteronism in hypertensive children. Hormone research in paediatrics. 2011; 76(2):93-8. doi: 10.1159/000326524. [PMID: 21625068]
  • Riccardo Maria Fagugli, Chiara Taglioni. Changes in the perceived epidemiology of primary hyperaldosteronism. International journal of hypertension. 2011; 2011(?):162804. doi: 10.4061/2011/162804. [PMID: 21837271]
  • Ihn Suk Lee, Seul Young Kim, Hye Won Jang, Min Kyeong Kim, Ju Hee Lee, Yun Hyeong Lee, Young Suk Jo. Genetic analyses of the chimeric CYP11B1/CYP11B2 gene in a Korean family with glucocorticoid-remediable aldosteronism. Journal of Korean medical science. 2010 Sep; 25(9):1379-83. doi: 10.3346/jkms.2010.25.9.1379. [PMID: 20808686]
  • V Matti Vehaskari. Heritable forms of hypertension. Pediatric nephrology (Berlin, Germany). 2009 Oct; 24(10):1929-37. doi: 10.1007/s00467-007-0537-8. [PMID: 17647025]
  • E M Freel, R Bernhardt, M Bernhardt, M Ingram, R Ingram, A M Wallace, R Fraser, E Davies, J M C Connell. Endogenous corticosteroid biosynthesis in subjects after bilateral adrenalectomy. Clinical endocrinology. 2007 May; 66(5):659-65. doi: 10.1111/j.1365-2265.2007.02791.x. [PMID: 17381495]
  • Oliver Vonend, Christian Altenhenne, Nicolaus J Büchner, Gabriele Dekomien, Christiane Maser-Gluth, Stefan M Weiner, Lorenz Sellin, Stefan Hofebauer, Jörg T Epplen, Lars C Rump. A German family with glucocorticoid-remediable aldosteronism. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2007 Apr; 22(4):1123-30. doi: 10.1093/ndt/gfl706. [PMID: 17277347]
  • Hitoshi Chiba. [18-Hydroxycortisol, 18-oxocortisol, and 6beta-hydroxycortisol]. Nihon rinsho. Japanese journal of clinical medicine. 2005 Aug; 63 Suppl 8(?):311-5. doi: NULL. [PMID: 16149517]
  • R M Reynolds, L A Shakerdi, K Sandhu, A M Wallace, P J Wood, B R Walker. The utility of three different methods for measuring urinary 18-hydroxycortisol in the differential diagnosis of suspected primary hyperaldosteronism. European journal of endocrinology. 2005 Jun; 152(6):903-7. doi: 10.1530/eje.1.01922. [PMID: 15941931]
  • K Müssig, M Wehrmann, M Horger, R Teichmann, C Maser-Gluth, H-U Häring, D Overkamp. Steroid profile in an adrenocortical carcinoma producing aldosterone. Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association. 2005 Apr; 113(4):236-40. doi: 10.1055/s-2005-837663. [PMID: 15891961]
  • E Marie Freel, Loai A Shakerdi, Elaine C Friel, A Michael Wallace, Eleanor Davies, Robert Fraser, John M C Connell. Studies on the origin of circulating 18-hydroxycortisol and 18-oxocortisol in normal human subjects. The Journal of clinical endocrinology and metabolism. 2004 Sep; 89(9):4628-33. doi: 10.1210/jc.2004-0379. [PMID: 15356073]
  • Jérôme Nicod, Bernhard Dick, Felix J Frey, Paolo Ferrari. Mutation analysis of CYP11B1 and CYP11B2 in patients with increased 18-hydroxycortisol production. Molecular and cellular endocrinology. 2004 Feb; 214(1-2):167-74. doi: 10.1016/j.mce.2003.10.056. [PMID: 15062555]
  • F Fallo, C Pilon, T A Williams, N Sonino, S Morra Di Cella, F Veglio, R De Iasio, P Montanari, P Mulatero. Coexistence of different phenotypes in a family with glucocorticoid-remediable aldosteronism. Journal of human hypertension. 2004 Jan; 18(1):47-51. doi: 10.1038/sj.jhh.1001636. [PMID: 14688810]
  • Keiko Homma, Tomonobu Hasegawa, Masami Masumoto, Eiko Takeshita, Kiyoaki Watanabe, Hitoshi Chiba, Takao Kurosawa, Takao Takahashi, Nobutake Matsuo. Reference values for urinary steroids in Japanese newborn infants: gas chromatography/mass spectrometry in selected ion monitoring. Endocrine journal. 2003 Dec; 50(6):783-92. doi: 10.1507/endocrj.50.783. [PMID: 14709852]
  • Stefania Morra di Cella, Franco Veglio, Paolo Mulatero, Valerie Christensen, Keli Aycock, Zheng Zhu, Elise P Gomez-Sanchez, Celso E Gomez-Sanchez. A time-resolved fluoroimmunoassay for 18-oxocortisol and 18-hydroxycortisol. Development of a monoclonal antibody to 18-oxocortisol. The Journal of steroid biochemistry and molecular biology. 2002 Sep; 82(1):83-8. doi: 10.1016/s0960-0760(02)00142-5. [PMID: 12429142]
  • Paolo Mulatero, Stefania Morra di Cella, Tracy A Williams, Alberto Milan, Giulio Mengozzi, Livio Chiandussi, Celso E Gomez-Sanchez, Franco Veglio. Glucocorticoid remediable aldosteronism: low morbidity and mortality in a four-generation italian pedigree. The Journal of clinical endocrinology and metabolism. 2002 Jul; 87(7):3187-91. doi: 10.1210/jcem.87.7.8647. [PMID: 12107222]
  • L Mosso, C E Gómez-Sánchez, M F Foecking, C Fardella. Serum 18-hydroxycortisol in primary aldosteronism, hypertension, and normotensives. Hypertension (Dallas, Tex. : 1979). 2001 Sep; 38(3 Pt 2):688-91. doi: 10.1161/01.hyp.38.3.688. [PMID: 11566957]
  • H Chiba. [18-hydroxycortisol, 18-oxocortisol, and 6 beta-hydroxycortisol]. Nihon rinsho. Japanese journal of clinical medicine. 1999 Dec; 57 Suppl(?):134-8. doi: NULL. [PMID: 10778083]
  • J H Pratt, J F Rebhun, L Zhou, W T Ambrosius, S A Newman, C E Gomez-Sanchez, D F Mayes. Levels of mineralocorticoids in whites and blacks. Hypertension (Dallas, Tex. : 1979). 1999 Aug; 34(2):315-9. doi: 10.1161/01.hyp.34.2.315. [PMID: 10454460]
  • H Ueshiba, M Shimojo, Y Miyachi. 18-Hydroxycortisol and 18-oxocortisol in Cushing's syndrome. Scandinavian journal of clinical and laboratory investigation. 1997 Aug; 57(5):395-400. doi: 10.3109/00365519709084586. [PMID: 9279964]
  • R De Matteo, C N May, J P Coghlan, T Kurosawa, T Yoshimura, H Chiba, J G McDougall. Investigation of the mineralocorticoid and hypertensinogenic activity of 18-hydroxycortisol in conscious sheep. Steroids. 1997 Apr; 62(4):351-7. doi: 10.1016/s0039-128x(96)00245-0. [PMID: 9090795]
  • M Palermo, C Gomez-Sanchez, E Roitman, C H Shackleton. Quantitation of cortisol and related 3-oxo-4-ene steroids in urine using gas chromatography/mass spectrometry with stable isotope-labeled internal standards. Steroids. 1996 Oct; 61(10):583-9. doi: 10.1016/s0039-128x(96)00118-9. [PMID: 8910971]
  • Y Takeda, I Miyamori, T Yoneda, K Iki, H Hatakeyama, R Takeda. Effect of aging on urinary excretion of 18-hydroxycortisol. The Journal of steroid biochemistry and molecular biology. 1994 Aug; 50(3-4):167-8. doi: 10.1016/0960-0760(94)90024-8. [PMID: 8049145]
  • H Kohno, S Sato, H Chiba, K Kobayashi, S Ikegawa, T Kurosawa, M Tohma. Monoclonal antibodies specific for 18-hydroxycortisol and their use in an enzyme immunoassay for human urinary 18-hydroxycortisol for diagnosis of primary aldosteronism. Clinical biochemistry. 1994 Aug; 27(4):277-82. doi: 10.1016/0009-9120(94)90030-2. [PMID: 8001289]
  • N Yamakita, C E Gomez-Sanchez, T Mune, H Morita, H Yoshida, S Miyazaki, K Yasuda. Simultaneous measurement of plasma 18-oxocortisol and 18-hydroxycortisol levels in normal man. European journal of endocrinology. 1994 Jul; 131(1):74-9. doi: 10.1530/eje.0.1310074. [PMID: 8038908]
  • M C Zennaro, P Borensztein, X Jeunemaitre, D Armanini, F Soubrier. No alteration in the primary structure of the mineralocorticoid receptor in a family with pseudohypoaldosteronism. The Journal of clinical endocrinology and metabolism. 1994 Jul; 79(1):32-8. doi: 10.1210/jcem.79.1.8027248. [PMID: 8027248]
  • N Yamakita, C E Gomez-Sanchez, T Mune, H Yoshida, S Miyazaki, K Yasuda, T Nakai. Regulation of 18-oxocortisol and 18-hydroxycortisol by the renin-angiotensin system and ACTH in man. The Journal of steroid biochemistry and molecular biology. 1993 Sep; 46(3):395-9. doi: 10.1016/0960-0760(93)90230-t. [PMID: 9831489]
  • H Chiba, S Ikegawa, T Kurosawa, T Yoshimura, Y Ito, K Matsuno, K Kobayashi, M Tohma. A direct enzyme immunoassay for 18-hydroxycortisol in urine: a new tool for screening primary aldosteronism. The Journal of steroid biochemistry and molecular biology. 1993 Jul; 46(1):85-9. doi: 10.1016/0960-0760(93)90212-f. [PMID: 8338794]
  • H Chiba, Y Ito, K Matsuno, K Kobayashi, T Kurosawa, S Ikegawa, R Mahara, M Tohma. Determination of urinary 18-hydroxycortisol by isocratic normal-phase high-performance liquid chromatography. Journal of chromatography. 1993 Mar; 613(1):132-6. doi: 10.1016/0378-4347(93)80206-j. [PMID: 8458890]
  • I Miyamori, Y Takeda, H Takasaki, Y Itoh, K Iki, R Takeda. Determination of urinary 18-hydroxycortisol in the diagnosis of primary aldosteronism. Journal of endocrinological investigation. 1992 Jan; 15(1):19-24. doi: 10.1007/bf03348648. [PMID: 1560187]
  • C E Gomez-Sanchez, P G Zager, M F Foecking, O B Holland, A Ganguly. 18-oxocortisol: effect of dexamethasone, ACTH and sodium restriction. Journal of steroid biochemistry. 1989 Mar; 32(3):409-12. doi: 10.1016/0022-4731(89)90214-8. [PMID: 2539538]
  • J R Davis, D Burt, J E Corrie, C R Edwards, M C Sheppard. Dexamethasone-suppressible hyperaldosteronism: studies on overproduction of 18-hydroxycortisol in three affected family members. Clinical endocrinology. 1988 Sep; 29(3):297-308. doi: 10.1111/j.1365-2265.1988.tb01228.x. [PMID: 3251669]
  • C E Gomez-Sanchez, J R Gill, A Ganguly, R D Gordon. Glucocorticoid-suppressible aldosteronism: a disorder of the adrenal transitional zone. The Journal of clinical endocrinology and metabolism. 1988 Sep; 67(3):444-8. doi: 10.1210/jcem-67-3-444. [PMID: 2842358]
  • C E Gomez-Sanchez, J N Clore, H L Estep, C O Watlington. Effect of chronic adrenocorticotropin stimulation on the excretion of 18-hydroxycortisol and 18-oxocortisol. The Journal of clinical endocrinology and metabolism. 1988 Aug; 67(2):322-6. doi: 10.1210/jcem-67-2-322. [PMID: 2839536]
  • C E Gomez-Sanchez, R J Upcavage, P G Zager, M F Foecking, O B Holland, A Ganguly. Urinary 18-hydroxycortisol and its relationship to the excretion of other adrenal steroids. The Journal of clinical endocrinology and metabolism. 1987 Aug; 65(2):310-4. doi: 10.1210/jcem-65-2-310. [PMID: 3036905]
  • C E Gomez-Sanchez, L Uribe, M W Ferris, M F Foecking, E P Gomez-Sanchez. The production of a monoclonal antibody to 18-hydroxycortisol and other 18-hydroxylated steroids. Steroids. 1987 Apr; 49(4-5):335-40. doi: 10.1016/0039-128x(87)90008-0. [PMID: 3455046]
  • C E Gomez-Sanchez, E P Gomez-Sanchez, O B Holland. Role of 18-hydroxylated cortisols in hypertension. Journal of steroid biochemistry. 1987; 27(4-6):971-5. doi: 10.1016/0022-4731(87)90176-2. [PMID: 3320570]
  • J M Connell, C J Kenyon, J E Corrie, R Fraser, R Watt, A F Lever. Dexamethasone-suppressible hyperaldosteronism. Adrenal transition cell hyperplasia?. Hypertension (Dallas, Tex. : 1979). 1986 Aug; 8(8):669-76. doi: 10.1161/01.hyp.8.8.669. [PMID: 3015796]
  • J E Corrie, C R Edwards, D B Jones, P L Padfield, P S Budd. Factors affecting the secretion of 18-hydroxycortisol, a novel steroid of relevance to Conn's syndrome. Clinical endocrinology. 1985 Nov; 23(5):579-86. doi: 10.1111/j.1365-2265.1985.tb01118.x. [PMID: 3002670]
  • J E Corrie, C R Edwards, P S Budd. A radioimmunoassay for 18-hydroxycortisol in plasma and urine. Clinical chemistry. 1985 Jun; 31(6):849-52. doi: 10.1093/clinchem/31.6.849. [PMID: 3995762]
  • C E Gomez-Sanchez, D N Kirk, R D Farrant, L Milewich. 18-Substituted steroids: synthesis of 18-hydroxycortisol (11 beta,17 alpha,18,21-tetrahydroxy-4-pregnene-3,20-dione) and 18-hydroxycortisone (17 alpha,18,21-trihydroxy-4-pregnene-3,11,20-trione). Journal of steroid biochemistry. 1985 Jan; 22(1):141-6. doi: 10.1016/0022-4731(85)90154-2. [PMID: 3974224]
  • E P Gomez-Sanchez, C E Gomez-Sanchez, J S Smith, M W Ferris, M Foecking. Receptor binding and biological activity of 18-hydroxycortisol. Endocrinology. 1984 Aug; 115(2):462-6. doi: 10.1210/endo-115-2-462. [PMID: 6086271]
  • B H Arison, M D Chu, S Ulick. A proton magnetic resonance study of the 18-hydroxy derivatives of cortisol and corticosterone. Journal of steroid biochemistry. 1982 Nov; 17(5):467-9. doi: 10.1016/0022-4731(82)90003-6. [PMID: 6294412]
  • M D Chu, S Ulick. Isolation and identification of 18-hydroxycortisol from the urine of patients with primary aldosteronism. The Journal of biological chemistry. 1982 Mar; 257(5):2218-24. doi: 10.1016/s0021-9258(18)34909-3. [PMID: 7061419]