Androst-5-ene-3beta,17beta-diol (BioDeep_00000005470)

human metabolite Endogenous

代谢物信息卡片

(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-diol

化学式: C19H30O2 (290.224568)
中文名称: 5-雄烯二醇, 雄烯二醇
谱图信息: 最多检出来源 Homo sapiens(feces) 4.98%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

Androst-5-ene-3beta,17beta-diol. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/androst-5-ene-3beta,17beta-diol (retrieved 2024-11-03) (BioDeep RN: BioDeep_00000005470). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC12CCC(O)CC1=CCC1C2CCC2(C)C(O)CCC12
InChI: InChI=1S/C19H30O2/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/h3,13-17,20-21H,4-11H2,1-2H3

描述信息

5-Androstenediol is a direct metabolite of the most abundant steroid produced by the human adrenal cortex, dehydroepiandrosterone (DHEA). 5-Androstenediol is less androgenic than 4-androstenediol, and stimulates the immune system. When administered to rats in vivo, 5-androstenediol has approximately 1/70 the androgenicity of DHEA, 1/185 the androgenicity of androstenedione, and 1/475 the androgenicity of testosterone (Wikipedia). Because it induces production of white blood cells and platelets, 5-androstenediol is being developed as a radiation countermeasure as Neumune (HE2100). An intermediate in testosterone biosynthesis, found in the testis or the adrenal glands. 5-Androstenediol, derived from dehydroepiandrosterone by the reduction of the 17-keto group (17-hydroxysteroid dehydrogenases), is converted to testosterone by the oxidation of the 3-beta hydroxyl group to a 3-keto group (3-fydroxysteroid dehydrogenase).
Androstenediol is a term used to refer to two different steroids with molecular weights of 290.44: 4-androstenediol (4-androstene-3beta,17beta-diol) and 5-androstenediol (5-androstene-3beta,17beta-diol). 4-Androstenediol is closer to testosterone structurally, and has androgenic effects. 5-Androstenediol is a direct metabolite of the most abundant steroid produced by the human adrenal cortex, dehydroepiandrosterone (DHEA). 5-Androstenediol is less androgenic than 4-androstenediol, and stimulates the immune system. When administered to rats in vivo, 5-androstenediol has approximately 1/70 the androgenicity of DHEA, 1/185 the androgenicity of androstenedione, and 1/475 the androgenicity of testosterone (Coffey, 1988). Because it induces production of white blood cells and platelets, 5-androstenediol is being developed as a radiation countermeasure as Neumune(HE2100).
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D045930 - Anabolic Agents
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C2360 - Anabolic Steroid

同义名列表

39 个代谢物同义名

(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-diol; .DELTA.5-Androstene-3.beta.,17.beta.-diol; delta 5 Androstene 3 beta,17 beta diol; (3beta,17beta)-Androst-5-ene-3,17-diol; delta 5-Androstene-3 beta,17 beta-diol; Parke davis brand OF androstenediol; 3beta,17beta-Dihydroxy-5-androstene; 3beta,17beta-Dihydroxyandrost-5-ene; Androst-5-ene-3 beta,17 beta-diol; Androst 5 ene 3 beta,17 beta diol; (3Β,17β)-androst-5-ene-3,17-diol; (3b,17b)-Androst-5-ene-3,17-diol; Androst-5-ene-3beta,17beta-diol; 5-Androstene-3beta-17beta-diol; 5 Androstene 3beta 17beta diol; androst-5-en-3beta,17beta-diol; 3Β,17β-dihydroxyandrost-5-ene; 3b,17b-Dihydroxy-5-androstene; 3Β,17β-dihydroxy-5-androstene; 3b,17b-Dihydroxyandrost-5-ene; Androst-5-ene-3β,17β-diol; Androst-5-ene-3b,17b-diol; Androst-5-en-3β,17β-diol; Androst-5-en-3b,17b-diol; Androst-5-ene-3,17-diol; Androst 5 ene 3,17 diol; delta-5-Androstenediol; Delta 5 Androstenediol; Delta 5-Androstenediol; 5-Androstene-3,17-diol; 5 Androstene 3,17 diol; Delta5-Androstenediol; Androst-5-enediol; 5-ANDROSTENEDIOL; Androstenediol; Hermaphrodiol; Bisexovister; b,17b-Diol; Tetrabol

数据库引用编号

21 个数据库交叉引用编号

ChEBI: CHEBI:2710
KEGG: C04295
KEGGdrug: D00179
PubChem: 223407
PubChem: 10634
HMDB: HMDB0003818
Metlin: METLIN41835
DrugBank: DB01524
ChEMBL: CHEMBL4755638
ChEMBL: CHEMBL440283
Wikipedia: Androstenediol
MeSH: Androstenediol
foodb: FDB023228
chemspider: 10188
CAS: 521-17-5
PMhub: MS000018286
PubChem: 6955
LipidMAPS: LMST02020005
PDB-CCD: B81
3DMET: B01731
NIKKAJI: J6.611G

分类词条

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)

2 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

Benedikt A Gasser, Samuel F Buerki, Johann Kurz, Markus G Mohaupt. Hyperandrogenism? Increased 17, 20-Lyase Activity? A Metanalysis and Systematic Review of Altered Androgens in Boys and Girls with Autism. International journal of molecular sciences. 2021 Nov; 22(22):. doi: 10.3390/ijms222212324. [PMID: 34830216]
Takako Kawakita, Toshiyuki Yasui, Kanako Yoshida, Sumika Matsui, Takeshi Iwasa. Correlations of androstenediol with reproductive hormones and cortisol according to stages during the menopausal transition in Japanese women. The Journal of steroid biochemistry and molecular biology. 2021 11; 214(?):106009. doi: 10.1016/j.jsbmb.2021.106009. [PMID: 34571175]
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Haruka Tanabe, Hitoshi Mutai, Daimei Sasayama, Hidehiko Sasamoto, Yoshimichi Miyashiro, Nobuhiro Sugiyama, Shinsuke Washizuka. Sex differences in serum levels of 5α-androstane-3β, 17β-diol, and androstenediol in the young adults: A liquid chromatography-tandem mass spectrometry study. PloS one. 2021; 16(12):e0261440. doi: 10.1371/journal.pone.0261440. [PMID: 34910781]
Joanne F Dorgan, Seungyoun Jung, Cher M Dallal, Min Zhan, Christina A Stennett, Yuji Zhang, Richard L Eckert, Linda G Snetselaar, Linda Van Horn. Alcohol consumption and serum metabolite concentrations in young women. Cancer causes & control : CCC. 2020 Feb; 31(2):113-126. doi: 10.1007/s10552-019-01256-1. [PMID: 31828464]
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