ST 27:4;O3 (BioDeep_00000637361)
Secondary id: BioDeep_00000001995
代谢物信息卡片
(25R)-5alpha,8alpha-epidioxy-24R,26-cyclo-cholest-6,22E-dien-3beta-ol
化学式: C27H40O3 (412.297729)
中文名称: 环戊丙酸睾酮
谱图信息:
最多检出来源 Viridiplantae(plant) 66.67%
分子结构信息
SMILES: C1C[C@]2([H])[C@@]3(C)CC[C@H](O)C[C@]43OO[C@@]2(C=C4)[C@]2([H])CC[C@]([H])([C@@](C)([H])/C=C/[C@]3([H])C[C@H]3C)[C@@]12C
InChI: InChI=1S/C27H40O3/c1-26-15-13-20(28)17-19(26)8-9-21-22-10-11-24(27(22,2)16-14-23(21)26)30-25(29)12-7-18-5-3-4-6-18/h17-18,21-24H,3-16H2,1-2H3/t21-,22-,23-,24-,26-,27-/m0/s1
描述信息
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D045930 - Anabolic Agents
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D000728 - Androgens
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C2360 - Anabolic Steroid
同义名列表
数据库引用编号
16 个数据库交叉引用编号
- ChEBI: CHEBI:9463
- ChEBI: CHEBI:187563
- KEGG: C08156
- PubChem: 441404
- PubChem: 52931503
- PubChem: 52931491
- DrugBank: DB13943
- ChEMBL: CHEMBL1201101
- LipidMAPS: LMST02020074
- LipidMAPS: LMST01160007
- LipidMAPS: LMST01110018
- CAS: 58-20-8
- PubChem: 10356
- 3DMET: B02147
- NIKKAJI: J22.726I
- RefMet: ST 27:4;O3
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
- Kadden H Kothmann, Victoria Jacobsen, Emily Laffitte, Corinne Bromfield, Matthew Grizzaffi, Monica Jarboe, Andrea G Braundmeier-Fleming, Janice M Bahr, Romana A Nowak, Annie E Newell-Fugate. Virilizing doses of testosterone decrease circulating insulin levels and differentially regulate insulin signaling in liver and adipose tissue of females.
American journal of physiology. Endocrinology and metabolism.
2021 06; 320(6):E1107-E1118. doi:
10.1152/ajpendo.00281.2020. [PMID: 33900852] - Samuel R Denmeade, Hao Wang, Neeraj Agarwal, David C Smith, Michael T Schweizer, Mark N Stein, Vasileios Assikis, Przemyslaw W Twardowski, Thomas W Flaig, Russell Z Szmulewitz, Jeffrey M Holzbeierlein, Ralph J Hauke, Guru Sonpavde, Jorge A Garcia, Arif Hussain, Oliver Sartor, Shifeng Mao, Harry Cao, Wei Fu, Ting Wang, Rehab Abdallah, Su Jin Lim, Vanessa Bolejack, Channing J Paller, Michael A Carducci, Mark C Markowski, Mario A Eisenberger, Emmanuel S Antonarakis. TRANSFORMER: A Randomized Phase II Study Comparing Bipolar Androgen Therapy Versus Enzalutamide in Asymptomatic Men With Castration-Resistant Metastatic Prostate Cancer.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology.
2021 04; 39(12):1371-1382. doi:
10.1200/jco.20.02759. [PMID: 33617303] - Alexander Justin Lin, Thomas Baranski, Deyali Chaterjee, Will Chapman, Gretchen Foltz, Hyun Kim. Androgen-receptor-positive hepatocellular carcinoma in a transgender teenager taking exogenous testosterone.
Lancet (London, England).
2020 07; 396(10245):198. doi:
10.1016/s0140-6736(20)31538-5. [PMID: 32682485] - Teri N Hreha, Christina A Collins, Allyssa L Daugherty, Joy Twentyman, Nitin Paluri, David A Hunstad. TGFβ1 orchestrates renal fibrosis following Escherichia coli pyelonephritis.
Physiological reports.
2020 03; 8(6):e14401. doi:
10.14814/phy2.14401. [PMID: 32227630] - Teri N Hreha, Christina A Collins, Allyssa L Daugherty, Jessie M Griffith, Keith A Hruska, David A Hunstad. Androgen-Influenced Polarization of Activin A-Producing Macrophages Accompanies Post-pyelonephritic Renal Scarring.
Frontiers in immunology.
2020; 11(?):1641. doi:
10.3389/fimmu.2020.01641. [PMID: 32849562] - Mônica S Campos, João P A Silva, Danilo S Lima, Luis O Regasini, Mara Rúbia Marques, Manoel F Biancardi, Sebastião R Taboga, Fernanda C A Santos. Short-term exposure to chrysin promotes proliferative responses in the ventral male prostate and female prostate of adult gerbils.
International journal of experimental pathology.
2019 06; 100(3):192-201. doi:
10.1111/iep.12317. [PMID: 31131507] - Pilar Martín-Escudero, Jesús A Muñoz-Guerra, Soledad Vargas García-Tenorio, Ester Serrano Garde, Ana B Soldevilla-Navarro, Mercedes Galindo-Canales, Nayade Prado, Manuel E Fuentes-Ferrer, Cristina Fernández-Pérez. Impact of the UGT2B17 polymorphism on the steroid profile. Results of a crossover clinical trial in athletes submitted to testosterone administration.
Steroids.
2019 01; 141(?):104-113. doi:
10.1016/j.steroids.2018.11.009. [PMID: 30503386] - Leonardo O Mendes, Anthony C S Castilho, Cristiane F Pinho, Bianca F Gonçalvez, Eduardo M Razza, Luiz Gustavo A Chuffa, Janete A Anselmo-Franci, Wellerson R Scarano, Francisco E Martinez. Modulation of inflammatory and hormonal parameters in response to testosterone therapy: Effects on the ventral prostate of adult rats.
Cell biology international.
2018 Sep; 42(9):1200-1211. doi:
10.1002/cbin.10990. [PMID: 29771451] - Jamili D B Santos, Andréa A S Mendonça, Rafaela C Sousa, Thaiany G S Silva, Solange M Bigonha, Eliziária C Santos, Reggiani V Gonçalves, Rômulo D Novaes. Food-drug interaction: Anabolic steroids aggravate hepatic lipotoxicity and nonalcoholic fatty liver disease induced by trans fatty acids.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2018 Jun; 116(Pt B):360-368. doi:
10.1016/j.fct.2018.04.056. [PMID: 29704577] - Nasimeh Yazdani, Stacy Matthews Branch. Daily subcutaneous testosterone for management of testosterone deficiency.
Frontiers in bioscience (Elite edition).
2018 03; 10(2):334-343. doi:
10.2741/e825. [PMID: 29293461] - Naiara C S Ribeiro, Mônica S Campos, Mariana B Santos, Gabriela M Ayusso, Patrícia S L Vilamaior, Luis O Regasini, Sebastião R Taboga, Manoel F Biancardi, Ana P S Perez, Fernanda C A Santos. Prepubertal chrysin exposure upregulates either AR in male ventral prostate or AR and ERα in Skene's paraurethral gland of pubertal and adult gerbils.
Fitoterapia.
2018 Jan; 124(?):137-144. doi:
10.1016/j.fitote.2017.11.003. [PMID: 29132837] - Benjamin A Teply, Hao Wang, Brandon Luber, Rana Sullivan, Irina Rifkind, Ashley Bruns, Avery Spitz, Morgan DeCarli, Victoria Sinibaldi, Caroline F Pratz, Changxue Lu, John L Silberstein, Jun Luo, Michael T Schweizer, Charles G Drake, Michael A Carducci, Channing J Paller, Emmanuel S Antonarakis, Mario A Eisenberger, Samuel R Denmeade. Bipolar androgen therapy in men with metastatic castration-resistant prostate cancer after progression on enzalutamide: an open-label, phase 2, multicohort study.
The Lancet. Oncology.
2018 01; 19(1):76-86. doi:
10.1016/s1470-2045(17)30906-3. [PMID: 29248236] - Hua-Ling Zhai, Hui Wu, Hui Xu, Pan Weng, Fang-Zhen Xia, Yi Chen, Ying-Li Lu. Trace glucose and lipid metabolism in high androgen and high-fat diet induced polycystic ovary syndrome rats.
Reproductive biology and endocrinology : RB&E.
2012 Jan; 10(?):5. doi:
10.1186/1477-7827-10-5. [PMID: 22276997] - M H Blokland, E F Van Tricht, H J Van Rossum, S S Sterk, M W F Nielen. Endogenous steroid profiling by gas chromatography-tandem mass spectrometry and multivariate statistics for the detection of natural hormone abuse in cattle.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment.
2012; 29(7):1030-45. doi:
10.1080/19440049.2012.675593. [PMID: 22651818] - Prasanth N Surampudi, Christina Wang, Ronald Swerdloff. Hypogonadism in the aging male diagnosis, potential benefits, and risks of testosterone replacement therapy.
International journal of endocrinology.
2012; 2012(?):625434. doi:
10.1155/2012/625434. [PMID: 22505891] - Wagner J Fávaro, Valéria H A Cagnon. Effect of combined hormonal and insulin therapy on the steroid hormone receptors and growth factors signalling in diabetic mice prostate.
International journal of experimental pathology.
2010 Dec; 91(6):537-45. doi:
10.1111/j.1365-2613.2010.00739.x. [PMID: 21039986] - P Dandona, M T Rosenberg. A practical guide to male hypogonadism in the primary care setting.
International journal of clinical practice.
2010 May; 64(6):682-96. doi:
10.1111/j.1742-1241.2010.02355.x. [PMID: 20518947] - A A M Stolker, M J Groot, J J P Lasaroms, A W J M Nijrolder, M H Blokland, I Riedmaier, C Becker, H H D Meyer, M W F Nielen. Detectability of testosterone esters and estradiol benzoate in bovine hair and plasma following pour-on treatment.
Analytical and bioanalytical chemistry.
2009 Oct; 395(4):1075-87. doi:
10.1007/s00216-009-3037-9. [PMID: 19705109] - Carolyn M Webb, Andrew G Elkington, Mustafa M Kraidly, Niall Keenan, Dudley J Pennell, Peter Collins. Effects of oral testosterone treatment on myocardial perfusion and vascular function in men with low plasma testosterone and coronary heart disease.
The American journal of cardiology.
2008 Mar; 101(5):618-24. doi:
10.1016/j.amjcard.2007.09.114. [PMID: 18308009] - Kalamegam Gauthaman, Adaikan P Ganesan. The hormonal effects of Tribulus terrestris and its role in the management of male erectile dysfunction--an evaluation using primates, rabbit and rat.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2008 Jan; 15(1-2):44-54. doi:
10.1016/j.phymed.2007.11.011. [PMID: 18068966] - S Kahl, T H Elsasser. Exogenous testosterone modulates tumor necrosis factor-alpha and acute phase protein responses to repeated endotoxin challenge in steers.
Domestic animal endocrinology.
2006 Nov; 31(4):301-11. doi:
10.1016/j.domaniend.2005.11.005. [PMID: 16386401] - Emily Darby, Bradley D Anawalt. Male hypogonadism : an update on diagnosis and treatment.
Treatments in endocrinology.
2005; 4(5):293-309. doi:
10.2165/00024677-200504050-00003. [PMID: 16185098] - Tadahiko Tokumoto, Kazunari Tanabe, Hiroshi Toma, Takashi Akiba. [Treatment of bone disease in chronic kidney disease and in renal transplant recipients under K/DOQI clinical practice guidelines].
Clinical calcium.
2004 May; 14(5):710-8. doi:
clica0405710718. [PMID: 15577031] - Ratna Chatterjee, Susan Wood, Hugh H McGarrigle, William R Lees, David J Ralph, Guy H Neild. A novel therapy with testosterone and sildenafil for erectile dysfunction in patients on renal dialysis or after renal transplantation.
The journal of family planning and reproductive health care.
2004 Apr; 30(2):88-90. doi:
10.1783/147118904322995438. [PMID: 15086991] - John L Ubels, Eric Veenstra, Jonathon Ditlev, Kyle Ingersoll. Interactions of testosterone and all-trans retinoic acid in regulation of androgen receptor expression in rat lacrimal gland.
Experimental eye research.
2003 Dec; 77(6):741-8. doi:
10.1016/j.exer.2003.07.006. [PMID: 14609562] - T C Phillips, R E Larsen, J Hernandez, L Strachan, D Samuelson, V M Shille, L F Archbald. Selective control of the estrous cycle of the dog through suppression of estrus and reduction of the length of anestrus.
Theriogenology.
2003 Mar; 59(5-6):1441-8. doi:
10.1016/s0093-691x(02)01183-4. [PMID: 12527090] - Paul J Perry, William R Yates, Richard D Williams, Arnold E Andersen, John H MacIndoe, Brian C Lund, Timothy L Holman. Testosterone therapy in late-life major depression in males.
The Journal of clinical psychiatry.
2002 Dec; 63(12):1096-101. doi:
10.4088/jcp.v63n1202. [PMID: 12523867] - R Chatterjee, P D Kottaridis, H H McGarrigle, D C Linch. Management of erectile dysfunction by combination therapy with testosterone and sildenafil in recipients of high-dose therapy for haematological malignancies.
Bone marrow transplantation.
2002 Apr; 29(7):607-10. doi:
10.1038/sj.bmt.1703421. [PMID: 11979311] - V Dumestre-Toulet, V Cirimele, B Ludes, S Gromb, P Kintz. Hair analysis of seven bodybuilders for anabolic steroids, ephedrine, and clenbuterol.
Journal of forensic sciences.
2002 Jan; 47(1):211-4. doi:
. [PMID: 12064656] - J S Kao, A Garg, M Mao-Qiang, D Crumrine, R Ghadially, K R Feingold, P M Elias. Testosterone perturbs epidermal permeability barrier homeostasis.
The Journal of investigative dermatology.
2001 Mar; 116(3):443-51. doi:
10.1046/j.1523-1747.2001.01281.x. [PMID: 11231319] - D R Goldstein, T Dobbs, B Krull, V J Plumb. Clenbuterol and anabolic steroids: a previously unreported cause of myocardial infarction with normal coronary arteriograms.
Southern medical journal.
1998 Aug; 91(8):780-4. doi:
". [PMID: 9715231] - G J Wagner, J G Rabkin. Testosterone therapy for clinical symptoms of hypogonadism in eugonadal men with AIDS.
International journal of STD & AIDS.
1998 Jan; 9(1):41-4. doi:
10.1258/0956462981921639. [PMID: 9518014] - R R Hajjar, F E Kaiser, J E Morley. Outcomes of long-term testosterone replacement in older hypogonadal males: a retrospective analysis.
The Journal of clinical endocrinology and metabolism.
1997 Nov; 82(11):3793-6. doi:
10.1210/jcem.82.11.4387. [PMID: 9360543] - F H Bronson, C M Matherne. Exposure to anabolic-androgenic steroids shortens life span of male mice.
Medicine and science in sports and exercise.
1997 May; 29(5):615-9. doi:
10.1097/00005768-199705000-00005. [PMID: 9140897] - E M Kouri, H G Pope, P S Oliva. Changes in lipoprotein-lipid levels in normal men following administration of increasing doses of testosterone cypionate.
Clinical journal of sport medicine : official journal of the Canadian Academy of Sport Medicine.
1996 Jul; 6(3):152-7. doi:
10.1097/00042752-199607000-00003. [PMID: 8792045] - M Labib, A Haddon. The adverse effects of anabolic steroids on serum lipids.
Annals of clinical biochemistry.
1996 May; 33 ( Pt 3)(?):263-4. doi:
10.1177/000456329603300316. [PMID: 8791993] - E T Koh, J K Yeh, J E Bourdeau, M M Chen, A S Om. Bone histomorphometry of ovariectomized or orchiectomized rats fed a moderately magnesium-deficient fructose diet and treated with exogenous oestrogen or testosterone.
Magnesium research.
1996 Mar; 9(1):13-21. doi:
. [PMID: 8819090] - E T Koh, W L Owen, A S Om. Exogenous oestrogen affects calcium metabolism differently from exogenous testosterone in ovariectomized or orchiectomized rats fed a high fructose diet severely deficient in magnesium.
Magnesium research.
1996 Mar; 9(1):23-31. doi:
. [PMID: 8819091] - E M Kouri, H G Pope, D L Katz, P Oliva. Fat-free mass index in users and nonusers of anabolic-androgenic steroids.
Clinical journal of sport medicine : official journal of the Canadian Academy of Sport Medicine.
1995 Oct; 5(4):223-8. doi:
10.1097/00042752-199510000-00003. [PMID: 7496846] - A A Welder, J W Robertson, R B Melchert. Toxic effects of anabolic-androgenic steroids in primary rat hepatic cell cultures.
Journal of pharmacological and toxicological methods.
1995 Aug; 33(4):187-95. doi:
10.1016/1056-8719(94)00073-d. [PMID: 8527826] - A A Ajayi, R Mathur, P V Halushka. Testosterone increases human platelet thromboxane A2 receptor density and aggregation responses.
Circulation.
1995 Jun; 91(11):2742-7. doi:
10.1161/01.cir.91.11.2742. [PMID: 7758179] - A S Clark, M C Mitre, T Brinck-Johnsen. Anabolic-androgenic steroid and adrenal steroid effects on hippocampal plasticity.
Brain research.
1995 May; 679(1):64-71. doi:
10.1016/0006-8993(95)00202-2. [PMID: 7648266] - E T Koh, W C Tae, J E Bourdeau, K W Chung. Oestrogen but not testosterone increases bone density in orchiectomized rats more when fed moderately magnesium-deficient fructose than moderately magnesium-deficient cornstarch.
Magnesium research.
1994 Dec; 7(3-4):223-32. doi:
. [PMID: 7786685] - U K Walle, T C Fagan, M J Topmiller, E C Conradi, T Walle. The influence of gender and sex steroid hormones on the plasma binding of propranolol enantiomers.
British journal of clinical pharmacology.
1994 Jan; 37(1):21-5. doi:
10.1111/j.1365-2125.1994.tb04233.x. [PMID: 8148214] - E T Koh, J E Bourdeau, W C Tae. A magnesium-deficient high fructose diet augments bone-sparing action of exogenous oestrogen in ovariectomized rats.
Magnesium research.
1993 Dec; 6(4):333-42. doi:
. [PMID: 8155484] - R I Wood, F J Ebling, H I'Anson, D C Bucholtz, S M Yellon, D L Foster. Prenatal androgens time neuroendocrine sexual maturation.
Endocrinology.
1991 May; 128(5):2457-68. doi:
10.1210/endo-128-5-2457. [PMID: 2019261] - G F Weinbauer, B Jackwerth, Y D Yoon, H M Behre, C H Yeung, E Nieschlag. Pharmacokinetics and pharmacodynamics of testosterone enanthate and dihydrotestosterone enanthate in non-human primates.
Acta endocrinologica.
1990 Apr; 122(4):432-42. doi:
10.1530/acta.0.1220432. [PMID: 2333732] - W C Chang. Effects of estradiol on prostaglandin E2 biosynthesis and prostaglandin metabolic enzyme activity in rat kidneys.
Advances in prostaglandin, thromboxane, and leukotriene research.
1989; 19(?):225-8. doi:
NULL. [PMID: 2526473] - D M Sackett, P J Wright, F M Darvill. Plasma testosterone concentrations in wethers treated with commercial preparations of testosterone.
Australian veterinary journal.
1987 Dec; 64(12):386-7. doi:
10.1111/j.1751-0813.1987.tb09613.x. [PMID: 3452309] - H R Nankin. Hormone kinetics after intramuscular testosterone cypionate.
Fertility and sterility.
1987 Jun; 47(6):1004-9. doi:
. [PMID: 3595893] - H Tamura, G S Greenwald. Angiogenesis and its hormonal control in the corpus luteum of the pregnant rat.
Biology of reproduction.
1987 Jun; 36(5):1149-54. doi:
10.1095/biolreprod36.5.1149. [PMID: 2441768] - L R Solomon, E D Hendler. Androgen therapy in haemodialysis patients. II. Effects on red cell metabolism.
British journal of haematology.
1987 Feb; 65(2):223-30. doi:
10.1111/j.1365-2141.1987.tb02269.x. [PMID: 3828230] - H R Nankin, T Lin, J Osterman. Chronic testosterone cypionate therapy in men with secondary impotence.
Fertility and sterility.
1986 Aug; 46(2):300-7. doi:
10.1016/s0015-0282(16)49529-4. [PMID: 3525237] - R L Rosenfield, R Furlanetto. Physiologic testosterone or estradiol induction of puberty increases plasma somatomedin-C.
The Journal of pediatrics.
1985 Sep; 107(3):415-7. doi:
10.1016/s0022-3476(85)80522-9. [PMID: 4040964] - K E Friedl, S R Plymate, C A Paulsen. Transient reduction in serum HDL-cholesterol following medroxyprogesterone acetate and testosterone cypionate administration to healthy men.
Contraception.
1985 Apr; 31(4):409-20. doi:
10.1016/0010-7824(85)90007-1. [PMID: 3159547] - F R Kaufman, G Costin, U Goebelsmann, F Z Stanczyk, M Zachmann. Male pseudohermaphroditism due to 17,20-desmolase deficiency.
The Journal of clinical endocrinology and metabolism.
1983 Jul; 57(1):32-6. doi:
10.1210/jcem-57-1-32. [PMID: 6853680] - L K Malendowicz, W Młynarczyk. Sex differences in adrenocortical structure and function. X. Lipid and corticosterone in the rat adrenal as affected by gonadectomy and testosterone or estradiol replacement.
Endokrinologie.
1982 Jun; 79(2):292-300. doi:
". [PMID: 7128546] - S Hatanaka, S Sawada, O Midorikawa. Effect of hormonal milieu on the growth of transplantable granulosa cell tumors in mice.
Gan.
1981 Feb; 72(1):151-5. doi:
NULL. [PMID: 7274640] - M Schulte-Beerbühl, E Nieschlag. Comparison of testosterone, dihydrotestosterone, luteinizing hormone, and follicle-stimulating hormone in serum after injection of testosterone enanthate of testosterone cypionate.
Fertility and sterility.
1980 Feb; 33(2):201-3. doi:
10.1016/s0015-0282(16)44543-7. [PMID: 7353699] - Z N Zhang. [The treatment of chronic aplastic anemia with testosterone-3, 17-cyclopentylpropionate in combination with Chinese traditional medicine (author's transl)].
Zhonghua nei ke za zhi.
1979; 18(3):184-6. doi:
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