Androstanedione (BioDeep_00000003827)

 

Secondary id: BioDeep_00000405396, BioDeep_00001892819

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite natural product


代谢物信息卡片


(5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-dione

化学式: C19H28O2 (288.2089)
中文名称: 5a-雄甾烷二酮
谱图信息: 最多检出来源 Homo sapiens(blood) 16.74%

分子结构信息

SMILES: CC12CCC(=O)CC1CCC3C2CCC4(C3CCC4=O)C
InChI: InChI=1S/C19H28O2/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/h12,14-16H,3-11H2,1-2H3/t12-,14-,15-,16-,18-,19-/m0/s1

描述信息

Androstanedione belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, androstanedione is considered to be a steroid lipid molecule. Androstanedione is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Androstanedione is a steroid metabolite and a procursor of both testosterone and estrone. It is a product of enzyme 3alpha-hydroxysteroid dehydrogenase [EC 1.1.1.50] in pathway Androgen and estrogen metabolism (KEGG). [HMDB]
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

同义名列表

29 个代谢物同义名

(5S,8R,9S,10S,13S,14S)-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-3,17-dione; (1S,2S,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14-dione; Androstane-3,17-dione, (4-(3)H-labeled, (4alpha,5beta))-isomer; Androstane-3,17-dione, (2-3(H)-labeled, (2alpha,5beta))-isomer; Androstane-3,17-dione, (4-(3)H-labeled, (4beta,5beta))-isomer; Androstane-3,17-dione, (2-3(H)-labeled, (2beta,5beta))-isomer; Androstane-3,17-dione, (5alpha)-isomer; Androstane-3,17-dione, (5beta)-isomer; 17beta-hydroxyandrosta-4,6-dien-3-one; 5α-androstane-3,17-dione; 5 alpha-Androstane-3,17-dione; 3,17-Dioxy-5 alpha-androstane; 5-alpha-Androstane-3,17-dione; 5 beta-Androstane-3,17-dione; 5alpha-androstane-3,17-dione; 5alpha-Androstan-3,17-dione; (5a)-Androstane-3,17-dione; 5a-Androstane-3, 17-dione; 5a-Androstane-3,17-dione; 5a-Androstan-3,17-dione; 5 alpha-Androstanedione; 5Α-androstan-3,17-dione; 5alpha-Androstanedione; 5a-Androsta-3,17-dione; Androstane-3,17-dione; Androstane-3,7-dione; 5a-Androstanedione; Androstanedione; 5alpha-Androstane-3,17-dione



数据库引用编号

23 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(2)

PlantCyc(0)

代谢反应

11 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(4)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(6)

PharmGKB(0)

14 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 6 AKR1C3, AKR1C4, AR, PKD1, PKD2, PTGS2
Peripheral membrane protein 2 HSD17B6, PTGS2
Endoplasmic reticulum membrane 8 CYP17A1, CYP19A1, DHRS9, PKD2, PTGS2, RDH16, SRD5A1, SRD5A2
Nucleus 5 AKR1C3, AR, PKD1, PKD2, TGFBR1
cytosol 7 AKR1C1, AKR1C2, AKR1C3, AKR1C4, AR, PKD1, PKD2
trans-Golgi network 1 PKD1
nucleoplasm 3 AR, PKD2, TMPRSS2
Cell membrane 5 GLRA2, PKD1, PKD2, TGFBR1, TMPRSS2
lamellipodium 1 PKD2
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 6 CYP19A1, GLRA2, PKD1, PKD2, SRD5A1, SRD5A2
Synapse 1 GLRA2
cell cortex 1 PKD1
cell surface 2 PKD1, TGFBR1
Golgi apparatus 2 PKD1, PKD2
Golgi membrane 2 INS, PKD1
neuronal cell body 3 CYP17A1, SRD5A1, SRD5A2
Cytoplasm, cytosol 3 AKR1C1, AKR1C2, AKR1C4
endosome 1 TGFBR1
plasma membrane 6 AR, GLRA2, PKD1, PKD2, TGFBR1, TMPRSS2
Membrane 8 AR, CYP19A1, GLRA2, PKD1, PKD2, SRD5A1, TGFBR1, TMPRSS2
axon 1 CYP17A1
basolateral plasma membrane 2 PKD1, PKD2
caveola 1 PTGS2
extracellular exosome 6 AKR1C1, AKR1C3, AKR1C4, PKD1, PKD2, TMPRSS2
Lumenal side 1 HSD17B6
endoplasmic reticulum 6 CYP17A1, CYP19A1, HSD17B6, PKD1, PKD2, PTGS2
extracellular space 1 INS
perinuclear region of cytoplasm 2 PKD1, SRD5A1
Cell junction, tight junction 1 TGFBR1
bicellular tight junction 1 TGFBR1
protein-containing complex 2 AR, PTGS2
intracellular membrane-bounded organelle 4 DHRS9, GLRA2, HSD17B6, RDH16
Microsome membrane 6 CYP17A1, CYP19A1, DHRS9, HSD17B6, PTGS2, RDH16
Single-pass type I membrane protein 1 TGFBR1
Secreted 1 INS
extracellular region 2 INS, TMPRSS2
Single-pass membrane protein 1 RDH16
Cell projection, cilium 2 PKD1, PKD2
ciliary membrane 2 PKD1, PKD2
motile cilium 2 PKD1, PKD2
Z disc 1 PKD1
cell-cell junction 2 PKD1, PKD2
Single-pass type II membrane protein 1 TMPRSS2
vesicle 2 PKD1, PKD2
Membrane raft 1 TGFBR1
GABA-ergic synapse 1 GLRA2
lateral plasma membrane 1 PKD1
nuclear speck 1 AR
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Postsynaptic cell membrane 1 GLRA2
receptor complex 1 TGFBR1
neuron projection 2 GLRA2, PTGS2
ciliary basal body 1 PKD2
cilium 2 PKD1, PKD2
chromatin 1 AR
autophagosome membrane 1 PKD1
cell projection 2 GLRA2, PKD2
mitotic spindle 1 PKD2
Golgi apparatus, trans-Golgi network 2 PKD1, PKD2
non-motile cilium 1 PKD2
transmembrane transporter complex 1 GLRA2
Basolateral cell membrane 1 PKD2
Endomembrane system 2 PKD1, PKD2
endosome lumen 1 INS
chloride channel complex 1 GLRA2
monoatomic ion channel complex 1 PKD2
Cytoplasmic vesicle membrane 1 PKD2
cell body fiber 2 SRD5A1, SRD5A2
Golgi-associated vesicle membrane 1 PKD1
basal plasma membrane 1 PKD2
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 INS, PTGS2
transport vesicle 1 INS
Secreted, extracellular exosome 2 PKD1, PKD2
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
calcium channel complex 1 PKD1
[Transmembrane protease serine 2 catalytic chain]: Secreted 1 TMPRSS2
lumenal side of endoplasmic reticulum membrane 1 PKD2
postsynaptic specialization membrane 1 GLRA2
Cell projection, cilium membrane 1 PKD2
basal cortex 1 PKD2
glycinergic synapse 1 GLRA2
migrasome 2 PKD1, PKD2
cytoplasmic side of endoplasmic reticulum membrane 1 PKD2
activin receptor complex 1 TGFBR1
transforming growth factor beta ligand-receptor complex 1 TGFBR1
cation channel complex 2 PKD1, PKD2
polycystin complex 2 PKD1, PKD2


文献列表

  • Monica Mazzarino, Maria Gabriella Abate, Roberto Alocci, Francesca Rossi, Raffaella Stinchelli, Francesco Molaioni, Xavier de la Torre, Francesco Botrè. Urine stability and steroid profile: towards a screening index of urine sample degradation for anti-doping purpose. Analytica chimica acta. 2011 Jan; 683(2):221-6. doi: 10.1016/j.aca.2010.10.003. [PMID: 21167974]
  • Véronique Bellemare, Frédérick Faucher, Rock Breton, Van Luu-The. Characterization of 17alpha-hydroxysteroid dehydrogenase activity (17alpha-HSD) and its involvement in the biosynthesis of epitestosterone. BMC biochemistry. 2005 Jul; 6(?):12. doi: 10.1186/1471-2091-6-12. [PMID: 16018803]
  • Baerbel U Panter, Joachim Jose, Rolf W Hartmann. 5alpha-reductase in human embryonic kidney cell line HEK293: evidence for type II enzyme expression and activity. Molecular and cellular biochemistry. 2005 Feb; 270(1-2):201-8. doi: 10.1007/s11010-005-4508-8. [PMID: 15792368]
  • Xue-Ying He, Ying-Zi Yang, Donna M Peehl, Alexander Lauderdale, Horst Schulz, Song-Yu Yang. Oxidative 3alpha-hydroxysteroid dehydrogenase activity of human type 10 17beta-hydroxysteroid dehydrogenase. The Journal of steroid biochemistry and molecular biology. 2003 Nov; 87(2-3):191-8. doi: 10.1016/j.jsbmb.2003.07.007. [PMID: 14672739]
  • X F Huang, V Luu-The. Characterization of the oxidative 3alpha-hydroxysteroid dehydrogenase activity of human recombinant 11-cis-retinol dehydrogenase. Biochimica et biophysica acta. 2001 Jun; 1547(2):351-8. doi: 10.1016/s0167-4838(01)00200-x. [PMID: 11410291]
  • R de la Torre, X de la Torre, C Alía, J Segura, T Baró, J M Torres-Rodríguez. Changes in androgenic steroid profile due to urine contamination by microorganisms: a prospective study in the context of doping control. Analytical biochemistry. 2001 Feb; 289(2):116-23. doi: 10.1006/abio.2000.4918. [PMID: 11161304]
  • M L Barbaccia, S Lello, T Sidiropoulou, T Cocco, R P Sorge, A Cocchiarale, V Piermarini, A F Sabato, M Trabucchi, C Romanini. Plasma 5alpha-androstane-3alpha,17betadiol, an endogenous steroid that positively modulates GABA(A) receptor function, and anxiety: a study in menopausal women. Psychoneuroendocrinology. 2000 Oct; 25(7):659-75. doi: 10.1016/s0306-4530(00)00017-2. [PMID: 10938447]
  • S K Agarwal, H L Judd, D A Magoffin. A mechanism for the suppression of estrogen production in polycystic ovary syndrome. The Journal of clinical endocrinology and metabolism. 1996 Oct; 81(10):3686-91. doi: 10.1210/jcem.81.10.8855823. [PMID: 8855823]
  • M Callender, H Benghuzzi, M Tucci, A Mohamed, Z Cason, L Lemos, A Tsao. Immunochemical and histopathological evaluation associated with sustained delivery of 5-alpha androstanedione using adult rats as a model. Biomedical sciences instrumentation. 1996; 32(?):55-62. doi: . [PMID: 8672690]
  • H Dai, F W Edens, R M Roe. Glutathione S-transferases in the Japanese quail: tissue distribution and purification of the liver isozymes. Journal of biochemical toxicology. 1996; 11(2):85-96. doi: 10.1002/(sici)1522-7146(1996)11:2<85::aid-jbt6>3.0.co;2-q. [PMID: 8884469]
  • L Milewich, J D Madden, C E Gomez-Sanchez. 5 alpha-androstane-3,17-dione in peripheral plasma of men and women. The Journal of steroid biochemistry and molecular biology. 1992 Feb; 41(2):185-90. doi: 10.1016/0960-0760(92)90047-m. [PMID: 1543687]
  • M Canonaco, S Andò, A Valenti, R Tavolaro, M L Panno, M Maggiolini, F Dessì-Fulgheri. The in-vitro transformation of [3H]dehydroepiandrosterone into its principal metabolites in the adrenal cortex of adult castrated male rats and following steroid treatment. The Journal of endocrinology. 1989 Jun; 121(3):419-24. doi: 10.1677/joe.0.1210419. [PMID: 2526845]
  • B A Schlinger, G V Callard. Aromatase activity in quail brain: correlation with aggressiveness. Endocrinology. 1989 Jan; 124(1):437-43. doi: 10.1210/endo-124-1-437. [PMID: 2909376]
  • E Perel, D Daniilescu, S Kindler, L Kharlip, D W Killinger. The formation of 5 alpha-reduced androgens in stromal cells from human breast adipose tissue. The Journal of clinical endocrinology and metabolism. 1986 Feb; 62(2):314-8. doi: 10.1210/jcem-62-2-314. [PMID: 3941160]
  • L A Loseva, V G Degtiar', V A Isachenkov. [Changes in the concentration of luteinizing hormone in the blood serum and of luliberin in the hypothalamus of castrated rats after the administration of testosterone and its 5 alpha-reduced metabolites. I]. Problemy endokrinologii. 1980; 26(6):46-50. doi: NULL. [PMID: 7005892]
  • M K Samson, R L Stephens, S Rivkin, M Opipari, T Maloney, C W Groppe, R Fisher. Vinblastine, bleomycin, and cis-dichlorodiammineplatinum(II) in disseminated testicular cancer: preliminary report of a Southwest Oncology Group Study. Cancer treatment reports. 1979 Sep; 63(9-10):1663-7. doi: . [PMID: 91435]