Adrenosterone (BioDeep_00000405684)

Main id: BioDeep_00000003080

 

natural product PANOMIX_OTCML-2023


代谢物信息卡片


4-Androstenl-3,11,17-trione

化学式: C19H24O3 (300.1725)
中文名称: 肾上腺甾酮
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 12.12%

分子结构信息

SMILES: C1CC(=O)C=C2CC[C@@]3([H])[C@@]4(CCC(=O)[C@@]4(C)CC(=O)[C@]3([H])[C@@]12C)[H]
InChI: InChI=1S/C19H24O3/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/h9,13-14,17H,3-8,10H2,1-2H3/t13-,14-,17+,18-,19-/m0/s1

描述信息

A 3-oxo Delta(4)-steroid that is androst-4-ene carrying three oxo-substituents at positions 3, 11 and 17.
Adrenosterone ((+)-Adrenosterone) is a competitive hydroxysteroid (11-beta) dehydrogenase 1 (HSD11β1) inhibitor. Adrenosterone is a steroid hormone with weak androgenic effect. Adrenosterone is a dietary supplement that can decrease fat and increase muscle mass. Adrenosterone acts as a suppressor of metastatic progression of human cancer cells[1][2][3].

同义名列表

7 个代谢物同义名

Adrenosterone; 4-Androstenl-3,11,17-trione; Reichsteins substance G; 11-keto-androstenedione; ST 19:4;O3; (+)-Adrenosterone; Adrenosterone



数据库引用编号

35 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)

8 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
Cytoplasm 8 AR, CDH1, EGFR, ERC1, MAPK3, NR3C1, NR3C2, PTGS2
Peripheral membrane protein 4 CYP1B1, ERC1, HSD17B6, PTGS2
Endosome membrane 1 EGFR
Endoplasmic reticulum membrane 9 CYP17A1, CYP19A1, CYP1B1, EGFR, GUCY2C, HSD11B1, HSD17B3, NR3C2, PTGS2
Nucleus 6 AR, CDH1, EGFR, MAPK3, NR3C1, NR3C2
cytosol 5 AR, CDH1, MAPK3, NR3C1, NR3C2
trans-Golgi network 1 CDH1
centrosome 2 ERC1, NR3C1
nucleoplasm 5 AR, CDH1, MAPK3, NR3C1, NR3C2
Cell membrane 3 CDH1, EGFR, GUCY2C
lamellipodium 1 CDH1
ruffle membrane 1 EGFR
Early endosome membrane 2 EGFR, HSD17B6
Multi-pass membrane protein 1 CYP19A1
Golgi apparatus membrane 1 ERC1
Synapse 2 ERC1, NR3C1
cell junction 2 CDH1, EGFR
cell surface 1 EGFR
glutamatergic synapse 3 CDH1, EGFR, MAPK3
Golgi apparatus 2 CDH1, MAPK3
Golgi membrane 3 EGFR, ERC1, INS
neuronal cell body 1 CYP17A1
postsynapse 1 CDH1
presynaptic membrane 1 ERC1
Presynapse 1 ERC1
endosome 2 CDH1, EGFR
plasma membrane 6 AR, CDH1, EGFR, GUCY2C, MAPK3, REN
Membrane 9 AR, CDH1, CYP19A1, CYP1B1, EGFR, ERC1, HSD11B1, NR3C1, REN
apical plasma membrane 1 EGFR
axon 1 CYP17A1
basolateral plasma membrane 1 EGFR
caveola 2 MAPK3, PTGS2
extracellular exosome 2 CDH1, SHBG
Lumenal side 1 HSD17B6
endoplasmic reticulum 5 CYP17A1, CYP19A1, HSD17B3, HSD17B6, PTGS2
extracellular space 5 AMH, CGA, EGFR, INS, REN
perinuclear region of cytoplasm 2 CDH1, EGFR
adherens junction 1 CDH1
mitochondrion 3 CYP1B1, MAPK3, NR3C1
protein-containing complex 4 AR, EGFR, NR3C1, PTGS2
intracellular membrane-bounded organelle 4 CYP1B1, HSD11B1, HSD17B3, HSD17B6
Microsome membrane 5 CYP17A1, CYP19A1, CYP1B1, HSD17B6, PTGS2
Single-pass type I membrane protein 3 CDH1, EGFR, GUCY2C
Secreted 5 AMH, CGA, INS, REN, SHBG
extracellular region 6 AMH, CDH1, CGA, INS, REN, SHBG
cytoplasmic side of plasma membrane 1 CDH1
mitochondrial matrix 1 NR3C1
anchoring junction 1 ERC1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 2 ERC1, NR3C1
nuclear membrane 2 CDH1, EGFR
actin cytoskeleton 1 CDH1
Early endosome 1 MAPK3
apical part of cell 1 REN
Single-pass type II membrane protein 1 HSD11B1
Membrane raft 1 EGFR
Cell junction, focal adhesion 1 MAPK3
Cytoplasm, cytoskeleton 1 ERC1
Cytoplasm, cytoskeleton, spindle 1 NR3C1
focal adhesion 2 EGFR, MAPK3
spindle 1 NR3C1
Cell junction, adherens junction 1 CDH1
flotillin complex 1 CDH1
intracellular vesicle 1 EGFR
lateral plasma membrane 1 CDH1
nuclear speck 2 AR, NR3C1
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Late endosome 1 MAPK3
receptor complex 2 EGFR, NR3C2
neuron projection 1 PTGS2
ciliary basal body 1 ERC1
chromatin 3 AR, NR3C1, NR3C2
Chromosome 1 NR3C1
cytoskeleton 2 ERC1, MAPK3
Cell projection, podosome 1 ERC1
podosome 1 ERC1
Golgi apparatus, trans-Golgi network 1 CDH1
nuclear envelope 1 MAPK3
Endomembrane system 1 ERC1
endosome lumen 1 INS
Membrane, caveola 1 MAPK3
Nucleus, nucleoplasm 1 NR3C1
Presynaptic cell membrane 1 ERC1
pseudopodium 1 MAPK3
basal plasma membrane 1 EGFR
synaptic membrane 1 EGFR
secretory granule lumen 1 INS
Golgi lumen 2 CGA, INS
endoplasmic reticulum lumen 3 INS, MAPK3, PTGS2
transport vesicle 1 INS
anaphase-promoting complex 1 CDH1
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
IkappaB kinase complex 1 ERC1
clathrin-coated endocytic vesicle membrane 1 EGFR
[Isoform 2]: Nucleus 1 CDH1
cytoskeleton of presynaptic active zone 1 ERC1
apical junction complex 1 CDH1
Cell junction, desmosome 1 CDH1
desmosome 1 CDH1
catenin complex 1 CDH1
[Isoform Alpha]: Cytoplasm 1 NR3C1
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
follicle-stimulating hormone complex 1 CGA
pituitary gonadotropin complex 1 CGA
[Isoform Beta]: Nucleus 1 NR3C1
[Isoform Alpha-B]: Nucleus 1 NR3C1


文献列表

  • Marina A Skiba, Robin J Bell, Rakibul M Islam, David J Handelsman, Reena Desai, Susan R Davis. Androgens During the Reproductive Years: What Is Normal for Women?. The Journal of clinical endocrinology and metabolism. 2019 11; 104(11):5382-5392. doi: 10.1210/jc.2019-01357. [PMID: 31390028]
  • 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]
  • Lance Brooker, Adam Cawley, Ray Kazlauskas, Catrin Goebel, Adrian George. Carbon isotope ratio analysis of endogenous glucocorticoid urinary metabolites after cortisone acetate and adrenosterone administration for doping control. Drug testing and analysis. 2012 Dec; 4(12):951-61. doi: 10.1002/dta.1403. [PMID: 22987608]
  • Ying-Yong Zhao, Jing Liu, Xian-Long Cheng, Xu Bai, Rui-Chao Lin. Urinary metabonomics study on biochemical changes in an experimental model of chronic renal failure by adenine based on UPLC Q-TOF/MS. Clinica chimica acta; international journal of clinical chemistry. 2012 Mar; 413(5-6):642-9. doi: 10.1016/j.cca.2011.12.014. [PMID: 22227165]
  • Yasuto Kido, Pär Matsson, Kathleen M Giacomini. Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. Journal of medicinal chemistry. 2011 Jul; 54(13):4548-58. doi: 10.1021/jm2001629. [PMID: 21599003]
  • Peter T Vedell, Karen L Svenson, Gary A Churchill. Stochastic variation of transcript abundance in C57BL/6J mice. BMC genomics. 2011 Mar; 12(?):167. doi: 10.1186/1471-2164-12-167. [PMID: 21450099]
  • Lance Brooker, Maria Kristina Parr, Adam Cawley, Ulrich Flenker, Christopher Howe, Rymantas Kazlauskas, Wilhelm Schänzer, Adrian George. Development of criteria for the detection of adrenosterone administration by gas chromatography-mass spectrometry and gas chromatography-combustion-isotope ratio mass spectrometry for doping control. Drug testing and analysis. 2009 Nov; 1(11-12):587-95. doi: 10.1002/dta.108. [PMID: 20355175]
  • Ignasi Forné, María J Agulleiro, Esther Asensio, Joaquín Abián, Joan Cerdà. 2-D DIGE analysis of Senegalese sole (Solea senegalensis) testis proteome in wild-caught and hormone-treated F1 fish. Proteomics. 2009 Apr; 9(8):2171-81. doi: 10.1002/pmic.200800696. [PMID: 19322785]
  • Anna Hellqvist, Monika Schmitz, Bertil Borg. Effects of castration and androgen-treatment on the expression of FSH-beta and LH-beta in the three-spine stickleback, gasterosteus aculeatus--feedback differences mediating the photoperiodic maturation response?. General and comparative endocrinology. 2008 Sep; 158(2):178-82. doi: 10.1016/j.ygcen.2008.07.004. [PMID: 18664367]
  • Maria J Agulleiro, Alexander P Scott, Neil Duncan, Constantinos C Mylonas, Joan Cerdà. Treatment of GnRHa-implanted Senegalese sole (Solea senegalensis) with 11-ketoandrostenedione stimulates spermatogenesis and increases sperm motility. Comparative biochemistry and physiology. Part A, Molecular & integrative physiology. 2007 Aug; 147(4):885-92. doi: 10.1016/j.cbpa.2007.02.008. [PMID: 17360211]
  • H J Th Goos, D Consten. Stress adaptation, cortisol and pubertal development in the male common carp, Cyprinus carpio. Molecular and cellular endocrinology. 2002 Nov; 197(1-2):105-16. doi: 10.1016/s0303-7207(02)00284-8. [PMID: 12431803]
  • C A Manire, L E Rasmussen, T S Gross. Serum steroid hormones including 11-ketotestosterone, 11-ketoandrostenedione, and dihydroprogesterone in juvenile and adult bonnethead sharks, Sphyrna tiburo. The Journal of experimental zoology. 1999 Oct; 284(5):595-603. doi: 10.1002/(sici)1097-010x(19991001)284:5<595::aid-jez15>3.0.co;2-6. [PMID: 10469997]
  • B Borg, E Antonopoulou, I Mayer, E Andersson, I Berglund, P Swanson. Effects of gonadectomy and androgen treatments on pituitary and plasma levels of gonadotropins in mature male Atlantic salmon, Salmo salar, parr--positive feedback control of both gonadotropins. Biology of reproduction. 1998 Mar; 58(3):814-20. doi: 10.1095/biolreprod58.3.814. [PMID: 9510971]
  • I Mayer, M Rand-Weaver, B Borg. Effects of gonadectomy and steroids on plasma and pituitary levels of somatolactin in Atlantic salmon, Salmo salar. General and comparative endocrinology. 1998 Feb; 109(2):223-31. doi: 10.1006/gcen.1997.7015. [PMID: 9473366]
  • I Mayer, N R Liley, B Borg. Stimulation of spawning behavior in castrated rainbow trout (Oncorhynchus mykiss) by 17 alpha,20 beta-dihydroxy-4-pregnen-3-one, but not by 11-ketoandrostenedione. Hormones and behavior. 1994 Jun; 28(2):181-90. doi: 10.1006/hbeh.1994.1015. [PMID: 7927284]
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  • 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]
  • I Mayer, B Borg, R Schulz. Conversion of 11-ketoandrostenedione to 11-ketotestosterone by blood cells of six fish species. General and comparative endocrinology. 1990 Jan; 77(1):70-4. doi: 10.1016/0016-6480(90)90207-3. [PMID: 2295425]
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