Boldione (BioDeep_00000002683)

 

Secondary id: BioDeep_00001868302

human metabolite natural product


代谢物信息卡片


(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-5,14-dione

化学式: C19H24O2 (284.1776)
中文名称: 1,4-雄烯二酮, 雄甾-1,4-二烯-3,17-二酮
谱图信息: 最多检出来源 Homo sapiens(plant) 4.28%

分子结构信息

SMILES: C1[C@H]2[C@H]([C@H]3[C@](C1)(C(=O)CC3)C)CCC1=CC(=O)C=C[C@@]21C
InChI: InChI=1S/C19H24O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h7,9,11,14-16H,3-6,8,10H2,1-2H3/t14-,15-,16-,18+,19-/m0/s1

描述信息

Boldione is a direct precursor (prohormone) to the anabolic steroid boldenone (1,4-androstadiene-17beta-ol-3-one). It is advertised as a highly anabolic/androgenic compound promoting muscularity, enhancing strength and overall physical performance, and is available on the Internet and in health stores. Conflicting findings regarding the boldenone content of bovine faeces suggest it may be synthesized de novo in emitted faeces. Boldione is the oxidized form of boldenone, an this anabolic steroid is forbidden in EU countries in calves and bulls bred for meat production, and is illegally used as growth promoters, as they improve the growth and feed conversion in food producing animals. (PMID: 16449054, 16308875, 16244993) [HMDB]
Boldione is a direct precursor (prohormone) to the anabolic steroid boldenone (1,4-androstadiene-17beta-ol-3-one). It is advertised as a highly anabolic/androgenic compound promoting muscularity, enhancing strength and overall physical performance, and is available on the Internet and in health stores. Conflicting findings regarding the boldenone content of bovine faeces suggest it may be synthesized de novo in emitted faeces. Boldione is the oxidized form of boldenone, an this anabolic steroid is forbidden in EU countries in calves and bulls bred for meat production, and is illegally used as growth promoters, as they improve the growth and feed conversion in food producing animals. (PMID: 16449054, 16308875, 16244993).

同义名列表

15 个代谢物同义名

(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-diene-5,14-dione; (+)-Androsta-1,4-diene-3,17-dione; Androstane-1,4-diene-3, 17-dione; Androsta-1,4-diene-3, 17-dione; Androstra-1,4-diene-3,17-dione; Androsta-1,4-diene-3,17-dione; Androst-1,4-diene-3,17-dione; 1,4-Androstadiene-3,17-dione; 1-Dehydroandrostenedione; Androstane-1,17-dione; Androstadienedione; Boldione; ADT; ADD; Androsta-1,4-diene-3,17-dione



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(4)

PlantCyc(0)

代谢反应

9 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(9)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

10 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, CYP2E1, CYP4A11, ESR1, FH, HADH, METTL3, PHB1
Peripheral membrane protein 4 CYP1B1, CYP2E1, CYP4A11, ESR1
Endoplasmic reticulum membrane 6 CYP17A1, CYP19A1, CYP1B1, CYP2E1, CYP4A11, UGT2B17
Nucleus 6 AR, ESR1, FH, METTL3, PCNA, PHB1
cytosol 6 APOA1, AR, ESR1, FH, METTL3, UNC119
nuclear body 2 METTL3, PCNA
centrosome 2 PCNA, UNC119
nucleoplasm 6 AR, ESR1, HADH, METTL3, PCNA, PHB1
Cell membrane 3 ESR1, GPM6B, PHB1
Cytoplasmic side 1 ESR1
Multi-pass membrane protein 2 CYP19A1, GPM6B
Synapse 1 UNC119
cell surface 1 PHB1
Golgi apparatus 2 ESR1, METTL3
mitochondrial inner membrane 3 CYP2E1, HADH, PHB1
neuronal cell body 1 CYP17A1
plasma membrane 6 APOA1, AR, ESR1, GPM6B, PHB1, TNFRSF12A
Membrane 8 AR, CYP19A1, CYP1B1, CYP4A11, ESR1, GPM6B, PHB1, UGT2B17
apical plasma membrane 1 CYP4A11
axon 1 CYP17A1
extracellular exosome 4 APOA1, FH, PCNA, PHB1
endoplasmic reticulum 2 CYP17A1, CYP19A1
extracellular space 1 APOA1
mitochondrion 6 CYP1B1, ETFA, ETFB, FH, HADH, PHB1
protein-containing complex 2 AR, ESR1
intracellular membrane-bounded organelle 3 CYP1B1, CYP2E1, CYP4A11
Microsome membrane 5 CYP17A1, CYP19A1, CYP1B1, CYP2E1, CYP4A11
Secreted 1 APOA1
extracellular region 1 APOA1
Single-pass membrane protein 1 UGT2B17
Mitochondrion matrix 3 ETFA, ETFB, HADH
mitochondrial matrix 4 ETFA, ETFB, FH, HADH
transcription regulator complex 1 ESR1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 UNC119
Extracellular vesicle 1 APOA1
chylomicron 1 APOA1
high-density lipoprotein particle 1 APOA1
low-density lipoprotein particle 1 APOA1
very-low-density lipoprotein particle 1 APOA1
cytoplasmic vesicle 1 APOA1
Early endosome 2 APOA1, PHB1
spindle midzone 1 UNC119
Mitochondrion inner membrane 3 CYP2E1, HADH, PHB1
Membrane raft 1 GPM6B
Cytoplasm, cytoskeleton, spindle 1 UNC119
mitochondrial nucleoid 1 HADH
collagen-containing extracellular matrix 1 APOA1
nuclear speck 2 AR, METTL3
chromatin 3 AR, ESR1, PCNA
Chromosome 1 FH
spindle pole 1 UNC119
nuclear replication fork 1 PCNA
chromosome, telomeric region 1 PCNA
blood microparticle 1 APOA1
site of double-strand break 1 FH
Cytoplasm, cytoskeleton, spindle pole 1 UNC119
intercellular bridge 1 UNC119
Nucleus speckle 1 METTL3
euchromatin 1 ESR1
replication fork 1 PCNA
myelin sheath 1 GPM6B
secretory granule lumen 1 APOA1
endoplasmic reticulum lumen 1 APOA1
male germ cell nucleus 1 PCNA
endocytic vesicle 1 APOA1
mitochondrial fatty acid beta-oxidation multienzyme complex 1 HADH
nuclear lamina 1 PCNA
[Isoform 1]: Nucleus 1 ESR1
cyclin-dependent protein kinase holoenzyme complex 1 PCNA
spherical high-density lipoprotein particle 1 APOA1
oxidoreductase complex 1 METTL3
endocytic vesicle lumen 1 APOA1
[Isoform Mitochondrial]: Mitochondrion 1 FH
[Isoform Cytoplasmic]: Cytoplasm, cytosol 1 FH
PCNA complex 1 PCNA
PCNA-p21 complex 1 PCNA
replisome 1 PCNA
electron transfer flavoprotein complex 2 ETFA, ETFB
mitochondrial prohibitin complex 1 PHB1
RNA N6-methyladenosine methyltransferase complex 1 METTL3


文献列表

  • Anneleen Decloedt, Sander Damen, Lynn Vanhaecke. Revealing the influence of glucocorticoid treatment on the excretion of anabolic-androgenic steroids in horses through in vitro digestive simulations and an in vivo case study. Research in veterinary science. 2017 Dec; 115(?):132-137. doi: 10.1016/j.rvsc.2017.02.024. [PMID: 28342428]
  • Surya Prakash, Abhay Bajaj. Process for Biotransformation of Androsta-4-ene-3, 17-Dione (4-AD) to Androsta-1,4-Diene-3,17-Dione (ADD). Methods in molecular biology (Clifton, N.J.). 2017; 1645(?):227-238. doi: 10.1007/978-1-4939-7183-1_16. [PMID: 28710632]
  • Aurasorn Saraphanchotiwitthaya, Pattana Sripalakit. Production of 4-androstene-3,17-dione and 1,4-androstadiene-3,17-dione from rice germ and wheat germ extracts by Mycobacterium sp. Biotechnology letters. 2016 Sep; 38(9):1595-602. doi: 10.1007/s10529-016-2140-1. [PMID: 27262293]
  • Min Liu, Zhan-Tao Zhu, Xin-Yi Tao, Feng-Qing Wang, Dong-Zhi Wei. RNA-Seq analysis uncovers non-coding small RNA system of Mycobacterium neoaurum in the metabolism of sterols to accumulate steroid intermediates. Microbial cell factories. 2016 Apr; 15(?):64. doi: 10.1186/s12934-016-0462-2. [PMID: 27112590]
  • Luca Chiesa, Maria Nobile, Sara Panseri, Daniele Vigo, Radmila Pavlovic, Francesco Arioli. Suitability of bovine bile compared to urine for detection of free, sulfate and glucuronate boldenone, androstadienedione, cortisol, cortisone, prednisolone, prednisone and dexamethasone by LC-MS/MS. Food chemistry. 2015 Dec; 188(?):473-80. doi: 10.1016/j.foodchem.2015.04.131. [PMID: 26041220]
  • A I Decloedt, L Bailly-Chouriberry, J Vanden Bussche, P Garcia, M-A Popot, Y Bonnaire, L Vanhaecke. In vitro simulation of the equine hindgut as a tool to study the influence of phytosterol consumption on the excretion of anabolic-androgenic steroids in horses. The Journal of steroid biochemistry and molecular biology. 2015 Aug; 152(?):180-92. doi: 10.1016/j.jsbmb.2015.06.001. [PMID: 26094581]
  • Luca Chiesa, Radmila Pavlovic, Guglielmo Dusi, Elisa Pasquale, Alessio Casati, Sara Panseri, Francesco Arioli. Determination of α- and β-boldenone sulfate, glucuronide and free forms, and androstadienedione in bovine urine using immunoaffinity columns clean-up and liquid chromatography tandem mass spectrometry analysis. Talanta. 2015 Jan; 131(?):163-9. doi: 10.1016/j.talanta.2014.07.035. [PMID: 25281088]
  • L Chiesa, M Nobile, S Panseri, C A Sgoifo Rossi, R Pavlovic, F Arioli. Detection of boldenone, its conjugates and androstadienedione, as well as five corticosteroids in bovine bile through a unique immunoaffinity column clean-up and two validated liquid chromatography-tandem mass spectrometry analyses. Analytica chimica acta. 2014 Dec; 852(?):137-45. doi: 10.1016/j.aca.2014.09.002. [PMID: 25441890]
  • Andreu Fabregat, Josep Marcos, Lorena Garrostas, Jordi Segura, Oscar J Pozo, Rosa Ventura. Evaluation of urinary excretion of androgens conjugated to cysteine in human pregnancy by mass spectrometry. The Journal of steroid biochemistry and molecular biology. 2014 Jan; 139(?):192-200. doi: 10.1016/j.jsbmb.2013.01.014. [PMID: 23410595]
  • C Gómez, O J Pozo, A Fabregat, J Marcos, K Deventer, P Van Eenoo, J Segura, R Ventura. Detection and characterization of urinary metabolites of boldione by LC-MS/MS. Part I: Phase I metabolites excreted free, as glucuronide and sulfate conjugates, and released after alkaline treatment of the urine. Drug testing and analysis. 2012 Oct; 4(10):775-85. doi: 10.1002/dta.1433. [PMID: 23090723]
  • Oscar J Pozo, Cristina Gómez, Josep Marcos, Jordi Segura, Rosa Ventura. Detection and characterization of urinary metabolites of boldione by LC-MS/MS. Part II: Conjugates with cysteine and N-acetylcysteine. Drug testing and analysis. 2012 Oct; 4(10):786-97. doi: 10.1002/dta.1431. [PMID: 23097153]
  • Colton H F Wong, David K K Leung, Francis P W Tang, Jenny K Y Wong, Nola H Yu, Terence S M Wan. Rapid screening of anabolic steroids in horse urine with ultra-high-performance liquid chromatography/tandem mass spectrometry after chemical derivatisation. Journal of chromatography. A. 2012 Apr; 1232(?):257-65. doi: 10.1016/j.chroma.2011.12.095. [PMID: 22265177]
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  • Natasha M Nesbitt, Xinxin Yang, Patricia Fontán, Irina Kolesnikova, Issar Smith, Nicole S Sampson, Eugenie Dubnau. A thiolase of Mycobacterium tuberculosis is required for virulence and production of androstenedione and androstadienedione from cholesterol. Infection and immunity. 2010 Jan; 78(1):275-82. doi: 10.1128/iai.00893-09. [PMID: 19822655]
  • Blandine Destrez, Emmanuelle Bichon, Lauriane Rambaud, Frédérique Courant, Fabrice Monteau, Gaud Pinel, Jean-Philippe Antignac, Bruno Le Bizec. Criteria to distinguish between natural situations and illegal use of boldenone, boldenone esters and boldione in cattle 2. Direct measurement of 17beta-boldenone sulpho-conjugate in calf urine by liquid chromatography--high resolution and tandem mass spectrometry. Steroids. 2009 Oct; 74(10-11):803-8. doi: 10.1016/j.steroids.2009.04.010. [PMID: 19409402]
  • Karolien Verheyden, Herlinde Noppe, Lynn Vanhaecke, Klaas Wille, Julie Vanden Bussche, Karen Bekaert, Olivier Thas, Colin R Janssen, Hubert F De Brabander. Excretion of endogenous boldione in human urine: influence of phytosterol consumption. The Journal of steroid biochemistry and molecular biology. 2009 Oct; 117(1-3):8-14. doi: 10.1016/j.jsbmb.2009.06.001. [PMID: 19520162]
  • Jenna K Capyk, Igor D'Angelo, Natalie C Strynadka, Lindsay D Eltis. Characterization of 3-ketosteroid 9{alpha}-hydroxylase, a Rieske oxygenase in the cholesterol degradation pathway of Mycobacterium tuberculosis. The Journal of biological chemistry. 2009 Apr; 284(15):9937-46. doi: 10.1074/jbc.m900719200. [PMID: 19234303]
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