11beta-OHA4 (BioDeep_00000004018)
Secondary id: BioDeep_00000019030, BioDeep_00000873190, BioDeep_00001868492
PANOMIX_OTCML-2023
代谢物信息卡片
11β-hydroxyandrost-4-ene-3,17-dione
化学式: C19H26O3 (302.1881846)
中文名称: 4-雄烯-11β-醇-3,17-二酮
谱图信息:
最多检出来源 Homo sapiens(blood) 10.19%
分子结构信息
SMILES: CC12CC(O)C3C(CCC4=CC(=O)CCC43C)C1CCC2=O
InChI: InChI=1S/C19H26O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-15,17,21H,3-8,10H2,1-2H3/t13-,14-,15-,17+,18-,19-/m0/s1
描述信息
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
CONFIDENCE standard compound; INTERNAL_ID 2829
11-Beta-hydroxyandrostenedione (4-Androsten-11β-ol-3,17-dione) is a steroid mainly found in the the adrenal origin (11β-hydroxylase is present in adrenal tissue, but absent in ovarian tissue). 11-Beta-hydroxyandrostenedione is a 11β-hydroxysteroid dehydrogenase (11βHSD) isozymes inhibitor. As 4-androstenedione increases, measuring plasma 11-Beta-hydroxyandrostenedione can distinguish the adrenal or ovarian origin of hyperandrogenism[1][2].
同义名列表
数据库引用编号
19 个数据库交叉引用编号
- ChEBI: CHEBI:27967
- KEGG: C05284
- PubChem: 94141
- Metlin: METLIN41861
- ChEMBL: CHEMBL2311170
- LipidMAPS: LMST02020066
- CAS: 382-44-5
- MoNA: AU282905
- MoNA: AU282903
- MoNA: AU282902
- MoNA: AU282906
- MoNA: AU282904
- MoNA: AU282901
- PMhub: MS000014677
- ChEBI: CHEBI:190716
- PubChem: 7671
- 3DMET: B01832
- NIKKAJI: J104.102I
- medchemexpress: HY-114464
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
6 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(6)
- Androstenedione Metabolism:
Androstanedione + Hydrogen Ion + NADH ⟶ Androsterone + NAD - Androstenedione Metabolism:
Androstanedione + Hydrogen Ion + NADH ⟶ Androsterone + NAD - Androstenedione Metabolism:
Androstanedione + Hydrogen Ion + NADH ⟶ Androsterone + NAD - Androstenedione Metabolism:
Androstanedione + Hydrogen Ion + NADH ⟶ Androsterone + NAD - Androstenedione Metabolism:
Androstanedione + Hydrogen Ion + NADH ⟶ Androsterone + NAD - Androstenedione Metabolism:
Androstanedione + Hydrogen Ion + NADH ⟶ Androsterone + NAD
PharmGKB(0)
2 个相关的物种来源信息
- 9606 Homo sapiens: 10.1007/S11306-016-1051-4
- 9606 Homo sapiens: 10.1007/S11306-016-1051-4
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
- Patrick Caron, Véronique Turcotte, Chantal Guillemette. A quantitative analysis of total and free 11-oxygenated androgens and its application to human serum and plasma specimens using liquid-chromatography tandem mass spectrometry.
Journal of chromatography. A.
2021 Aug; 1650(?):462228. doi:
10.1016/j.chroma.2021.462228. [PMID: 34090133] - James M Hawley, Joanne E Adaway, Laura J Owen, Brian G Keevil. Development of a total serum testosterone, androstenedione, 17-hydroxyprogesterone, 11β-hydroxyandrostenedione and 11-ketotestosterone LC-MS/MS assay and its application to evaluate pre-analytical sample stability.
Clinical chemistry and laboratory medicine.
2020 04; 58(5):741-752. doi:
10.1515/cclm-2019-0959. [PMID: 31926069] - Therina du Toit, Amanda C Swart. Inefficient UGT-conjugation of adrenal 11β-hydroxyandrostenedione metabolites highlights C11-oxy C19 steroids as the predominant androgens in prostate cancer.
Molecular and cellular endocrinology.
2018 02; 461(?):265-276. doi:
10.1016/j.mce.2017.09.026. [PMID: 28939401] - Michael W O'Reilly, Punith Kempegowda, Carl Jenkinson, Angela E Taylor, Jonathan L Quanson, Karl-Heinz Storbeck, Wiebke Arlt. 11-Oxygenated C19 Steroids Are the Predominant Androgens in Polycystic Ovary Syndrome.
The Journal of clinical endocrinology and metabolism.
2017 03; 102(3):840-848. doi:
10.1210/jc.2016-3285. [PMID: 27901631] - Therina du Toit, Liezl M Bloem, Jonathan L Quanson, Riaan Ehlers, Antonio M Serafin, Amanda C Swart. Profiling adrenal 11β-hydroxyandrostenedione metabolites in prostate cancer cells, tissue and plasma: UPC2-MS/MS quantification of 11β-hydroxytestosterone, 11keto-testosterone and 11keto-dihydrotestosterone.
The Journal of steroid biochemistry and molecular biology.
2017 02; 166(?):54-67. doi:
10.1016/j.jsbmb.2016.06.009. [PMID: 27345701] - 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] - Martín Blasco, Pedro Carriquiriborde, Damián Marino, Alicia E Ronco, Gustavo M Somoza. A quantitative HPLC-MS method for the simultaneous determination of testosterone, 11-ketotestosterone and 11-beta hydroxyandrostenedione in fish serum.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2009 May; 877(14-15):1509-15. doi:
10.1016/j.jchromb.2009.03.028. [PMID: 19369122] - Fidaa Ibrahim, Frank Giton, Philippe Boudou, Jean Marie Villette, René Julien, Hervé Galons, Jean Fiet. Plasma 11beta-hydroxy-4-androstene-3,17-dione: comparison of a time-resolved fluoroimmunoassay using a biotinylated tracer with a radioimmunoassay using a tritiated tracer.
The Journal of steroid biochemistry and molecular biology.
2003 Apr; 84(5):563-8. doi:
10.1016/s0960-0760(03)00077-3. [PMID: 12767281] - J F Dorgan, P Boudou, F Z Stanczyk, C Longcope, A A Tejpar, R T Falk, N Schussler, H E Stephenson. Sources of elevated serum androgens in postmenopausal women who develop breast cancer.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2001 Apr; 10(4):407-10. doi:
NULL. [PMID: 11319184] - R Huerta, D Dewailly, C Decanter, E S Knochenhauer, L R Boots, R Azziz. 11beta-hydroxyandrostenedione and delta5-androstenediol as markers of adrenal androgen production in patients with 21-hydroxylase-deficient nonclassic adrenal hyperplasia.
Fertility and sterility.
1999 Dec; 72(6):996-1000. doi:
10.1016/s0015-0282(99)00402-1. [PMID: 10593370] - M Bicíková, M Hill, R Hampl, L Stárka. Inhibition of rat renal and testicular 11 beta-hydroxysteroid dehydrogenase by some antihypertensive drugs, diuretics, and epitestosterone.
Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme.
1997 Sep; 29(9):465-8. doi:
10.1055/s-2007-979079. [PMID: 9370118] - E Carmina, F Gonzalez, L Chang, R A Lobo. Reassessment of adrenal androgen secretion in women with polycystic ovary syndrome.
Obstetrics and gynecology.
1995 Jun; 85(6):971-6. doi:
10.1016/0029-7844(95)00065-y. [PMID: 7770269] - M Mikulecky, A Kreze, Z Putz, M Moravcik. Daily variation of serum cortisol, 17-hydroxyprogesterone and five androgens in healthy women.
Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas.
1995 Apr; 28(4):485-90. doi:
NULL. [PMID: 8520547] - J Fiet, J P Gosling, H Soliman, H Galons, P Boudou, P Aubin, A Belanger, J M Villette, R Julien, J L Brérault. Hirsutism and acne in women: coordinated radioimmunoassays for eight relevant plasma steroids.
Clinical chemistry.
1994 Dec; 40(12):2296-305. doi:
. [PMID: 7988017] - R W Schulz, M C van der Sanden, P T Bosma, H J Goos. Effects of gonadotrophin-releasing hormone during the pubertal development of the male African catfish (Clarias gariepinus): gonadotrophin and androgen levels in plasma.
The Journal of endocrinology.
1994 Feb; 140(2):265-73. doi:
10.1677/joe.0.1400265. [PMID: 8169559] - B Bélanger, J Fiet, A Bélanger. Effects of adrenocorticotropin on adrenal and plasma 11 beta-hydroxyandrostenedione in the guinea pig and determination of its relative androgen potency.
Steroids.
1993 Jan; 58(1):29-34. doi:
10.1016/0039-128x(93)90014-e. [PMID: 8381568] - P H Provencher, Y Tremblay, B Bélanger, A Bélanger. Steroidogenesis in guinea pig adrenal cortex: effects of ACTH on steroid secretion and steroidogenic enzyme activities and expression.
The Journal of steroid biochemistry and molecular biology.
1992 Dec; 43(8):855-62. doi:
10.1016/0960-0760(92)90312-7. [PMID: 22217829] - E J Owen, P Holownia, G S Conway, H S Jacobs, J W Honour. 11 beta-hydroxyandrostenedione in plasma, follicular fluid, and granulosa cells of women with normal and polycystic ovaries.
Fertility and sterility.
1992 Oct; 58(4):713-8. doi:
. [PMID: 1426315] - E Carmina, F Z Stanczyk, L Chang, R A Miles, R A Lobo. The ratio of androstenedione:11 beta-hydroxyandrostenedione is an important marker of adrenal androgen excess in women.
Fertility and sterility.
1992 Jul; 58(1):148-52. doi:
10.1016/s0015-0282(16)55152-8. [PMID: 1623996] - P Holownia, E J Owen, G S Conway, J Round, J W Honour. Studies to confirm the source of 11 beta-hydroxyandrostenedione.
The Journal of steroid biochemistry and molecular biology.
1992 Mar; 41(3-8):875-80. doi:
10.1016/0960-0760(92)90441-k. [PMID: 1532906] - R Hampl, M Lachman, Z Novák, J Sulcová, L Stárka. Serum levels of steroid hormones in men with varicocele and oligospermia as compared to normozoospermic men.
Experimental and clinical endocrinology.
1992; 100(3):117-9. doi:
10.1055/s-0029-1211189. [PMID: 1305061] - F Z Stanczyk, L Chang, E Carmina, Z Putz, R A Lobo. Is 11 beta-hydroxyandrostenedione a better marker of adrenal androgen excess than dehydroepiandrosterone sulfate?.
American journal of obstetrics and gynecology.
1991 Dec; 165(6 Pt 1):1837-42. doi:
10.1016/0002-9378(91)90042-p. [PMID: 1836306] - P Holownia, E J Owen, R Hampl, H S Jacobs, J W Honour. The determination of 11 beta-hydroxyandrostenedione in human follicular fluid and plasma.
The Journal of steroid biochemistry and molecular biology.
1991 Mar; 38(3):389-98. doi:
10.1016/0960-0760(91)90112-i. [PMID: 2009230] - T L Gehris, R Kathol, W H Meller, J F Lopez, R S Jaeckle. Multiple steroid hormone levels in depressed patients and normal controls before and after exogenous ACTH.
Psychoneuroendocrinology.
1991; 16(6):481-97. doi:
10.1016/0306-4530(91)90032-o. [PMID: 1667335] - R Schlaghecke, D Beuscher, H K Kley, E Juli. Age-related changes in 11 beta-hydroxyandrostenedione concentration in normal and osteoporotic women.
The Journal of steroid biochemistry and molecular biology.
1991; 40(4-6):731-3. doi:
10.1016/0960-0760(91)90298-j. [PMID: 1958571] - B Bélanger, J Couture, S Caron, P Bodou, J Fiet, A Bélanger. Production and secretion of C-19 steroids by rat and guinea pig adrenals.
Steroids.
1990 Aug; 55(8):360-5. doi:
10.1016/0039-128x(90)90060-o. [PMID: 2173170] - I Mayer, B Borg, R Schulz. Seasonal changes in and effect of castration/androgen replacement on the plasma levels of five androgens in the male three-spined stickleback, Gasterosteus aculeatus L.
General and comparative endocrinology.
1990 Jul; 79(1):23-30. doi:
10.1016/0016-6480(90)90084-y. [PMID: 2354778] - J Sulcová, L Lisá, P Dvorák, R Hampl, L Stárka. [Use of steroid indicators in monitoring the treatment of congenital adrenal hyperplasia].
Ceskoslovenska pediatrie.
1990 Jun; 45(6):353-6. doi:
. [PMID: 2289256] - J Imperato-McGinley, C Shackleton, S Orlic, E Stoner. C19 and C21 5 beta/5 alpha metabolite ratios in subjects treated with the 5 alpha-reductase inhibitor finasteride: comparison of male pseudohermaphrodites with inherited 5 alpha-reductase deficiency.
The Journal of clinical endocrinology and metabolism.
1990 Mar; 70(3):777-82. doi:
10.1210/jcem-70-3-777. [PMID: 1689740] - D W Polson, M J Reed, S Franks, M J Scanlon, V H James. Serum 11 beta-hydroxyandrostenedione as an indicator of the source of excess androgen production in women with polycystic ovaries.
The Journal of clinical endocrinology and metabolism.
1988 May; 66(5):946-50. doi:
10.1210/jcem-66-5-946. [PMID: 3129451] - Z Putz, R Hampl, J Velemínský, A Kreze, J Sulcová, L Stárka. Radioimmunoassay of 11 beta-hydroxyandrostenedione in laboratory diagnostics of selected endocrine disorders.
Journal of clinical chemistry and clinical biochemistry. Zeitschrift fur klinische Chemie und klinische Biochemie.
1987 Oct; 25(10):723-7. doi:
10.1515/cclm.1987.25.10.723. [PMID: 3694130] - R Hampl, M Bicíková, K Motlík, L Stárka. Effect of etomidate on adrenal function in rats.
Endocrinologia experimentalis.
1987 Sep; 21(3):229-35. doi:
. [PMID: 3499308] - C Lejeune-Lenain, E Van Cauter, D Désir, M Beyloos, J R Franckson. Control of circadian and episodic variations of adrenal androgens secretion in man.
Journal of endocrinological investigation.
1987 Jun; 10(3):267-76. doi:
10.1007/bf03348129. [PMID: 2957420] - W G Schoonen, J C Granneman, J G Lambert, W J Viveen, P G van Oordt. Quantitative studies of steroid bioconversions in the seminal vesicles of spawning male African catfish, Clarias gariepinus (Burchell), under natural conditions, and of non-spawning catfish under natural and fish farm conditions.
Comparative biochemistry and physiology. B, Comparative biochemistry.
1987; 87(4):687-95. doi:
10.1016/0305-0491(87)90375-0. [PMID: 3665422] - J I Mason, W E Rainey. Steroidogenesis in the human fetal adrenal: a role for cholesterol synthesized de novo.
The Journal of clinical endocrinology and metabolism.
1987 Jan; 64(1):140-7. doi:
10.1210/jcem-64-1-140. [PMID: 3023427] - R Schulz. In vitro metabolism of steroid hormones in the liver and in blood cells of male rainbow trout (Salmo gairdneri Richardson).
General and comparative endocrinology.
1986 Nov; 64(2):312-9. doi:
10.1016/0016-6480(86)90019-5. [PMID: 3557096] - R E Peterson, J Imperato-McGinley, T Gautier, C Shackleton. Male pseudohermaphroditism due to multiple defects in steroid-biosynthetic microsomal mixed-function oxidases. A new variant of congenital adrenal hyperplasia.
The New England journal of medicine.
1985 Nov; 313(19):1182-91. doi:
10.1056/nejm198511073131903. [PMID: 2932643] - C W Burke. Adrenocortical insufficiency.
Clinics in endocrinology and metabolism.
1985 Nov; 14(4):947-76. doi:
10.1016/s0300-595x(85)80084-0. [PMID: 3002680] - R E Peterson, J Imperato-McGinley, T Gautier, C Shackleton. Urinary steroid metabolites in subjects with male pseudohermaphroditism due to 5 alpha-reductase deficiency.
Clinical endocrinology.
1985 Jul; 23(1):43-53. doi:
10.1111/j.1365-2265.1985.tb00181.x. [PMID: 4028464] - J Imperato-McGinley, R E Peterson, T Gautier, A Arthur, C Shackleton. Decreased urinary C19 and C21 steroid 5 alpha-metabolites in parents of male pseudohermaphrodites with 5 alpha-reductase deficiency: detection of carriers.
The Journal of clinical endocrinology and metabolism.
1985 Mar; 60(3):553-8. doi:
10.1210/jcem-60-3-553. [PMID: 3972966] - C Lejeune-Lenain, D Bosson, R Wolter, G Copinschi, J R Franckson. Evolution of the delta 4-adrenal androgens responsiveness in childhood during insulin test.
Helvetica paediatrica acta.
1984 Oct; 39(4):331-40. doi:
. [PMID: 6399716] - V D Bokkenheuser, G N Morris, A E Ritchie, L V Holdeman, J Winter. Biosynthesis of androgen from cortisol by a species of Clostridium recovered from human fecal flora.
The Journal of infectious diseases.
1984 Apr; 149(4):489-94. doi:
10.1093/infdis/149.4.489. [PMID: 6725987] - H Sekihara. 19-hydroxyandrostenedione as a new hypertensinogenic agent.
Journal of steroid biochemistry.
1982 Feb; 16(2):329-31. doi:
10.1016/0022-4731(82)90185-6. [PMID: 7043093] - J Fiet, B Gourmel, J M Villette, J L Brerault, R Julien, G Cathelineau, C Dreux. Simultaneous radioimmunoassay of androstenedione, dehydroepiandrosterone and 11-beta-hydroxyandrostenedione in plasma.
Hormone research.
1980; 13(3):133-49. doi:
10.1159/000179280. [PMID: 6259044]