Dehydroepiandrosterone (BioDeep_00000001231)

 

Secondary id: BioDeep_00000398237, BioDeep_00000422634

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019 natural product


代谢物信息卡片


(1S,2R,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one

化学式: C19H28O2 (288.2089)
中文名称: 去氢表雄酮
谱图信息: 最多检出来源 Homo sapiens(blood) 26.36%

分子结构信息

SMILES: C1[C@]2(C)[C@@]3([H])CC[C@]4(C)C(=O)CC[C@@]4([H])[C@]3([H])CC=C2C[C@@H](O)C1
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/h3,13-16,20H,4-11H2,1-2H3

描述信息

Dehydroepiandrosterone (DHEA) is a natural steroid hormone produced from cholesterol by the adrenal glands. DHEA is also produced in the gonads, adipose tissue and the brain. DHEA is structurally similar to, and is a precursor of, androstenedione, testosterone, estradiol, estrone and estrogen. It is the most abundant hormone in the human body. Most of DHEA is sulfated (dehydroepiandrosterone sulfate- DEHAS) before secretion. DHEAS is the sulfated version of DHEA; - this conversion is reversibly catalyzed by sulfotransferase (SULT2A1) primarily in the adrenals, the liver, and small intestines. In blood, most DHEA is found as DHEAS with levels that are about 300 times higher than free DHEA. Blood measurements of DHEAS/DHEA are useful to detect excess adrenal activity as seen in adrenal cancer or hyperplasia, including certain forms of congenital adrenal hyperplasia. Women with polycystic ovary syndrome tend to have normal or mildly elevated levels of DHEAS. [HMDB]. Dehydroepiandrosterone is found in many foods, some of which are summer grape, quinoa, calabash, and chinese chives.
Dehydroepiandrosterone (DHEA) is a natural steroid hormone produced from cholesterol by the adrenal glands. DHEA is also produced in the gonads, adipose tissue, and the brain. DHEA is structurally similar to and is a precursor of, androstenedione, testosterone, estradiol, estrone, and estrogen. It is the most abundant hormone in the human body. Most of DHEA is sulfated (dehydroepiandrosterone sulfate or DHEA-S) before secretion. DHEA-S is the sulfated version of DHEA; this conversion is reversibly catalyzed by sulfotransferase (SULT2A1) primarily in the adrenals, the liver, and small intestines. In blood, most DHEA is found as DHEA-S with levels that are about 300 times higher than free DHEA. Blood measurements of DHEA-S/DHEA are useful to detect excess adrenal activity as seen in adrenal cancer or hyperplasia, including certain forms of congenital adrenal hyperplasia. Women with polycystic ovary syndrome tend to have normal or mildly elevated levels of DHEA-S.
A - Alimentary tract and metabolism > A14 - Anabolic agents for systemic use > A14A - Anabolic steroids > A14AA - Androstan derivatives
G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
CONFIDENCE standard compound; EAWAG_UCHEM_ID 3085
D007155 - Immunologic Factors

同义名列表

61 个代谢物同义名

(1S,2R,5S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one; (3beta,16alpha)-3,16-Dihydroxy-androst-5-en-17-one; (3-beta)-3-Hydroxyandrost-5-en-17-one; (3beta)-3-Hydroxy-androst-5-en-17-one; 3beta-Hydroxy-androst-5-en-17-one; 3-BETA-HYDROXY-5-androsten-17-one; 5-Androsten-3-beta-hydroxy-17-one; 3beta-Hydroxy-D5-androsten-17-one; 5 Androsten 3 beta hydroxy 17 one; 3-beta-Hydroxyandrost-5-en-17-one; 3beta-Hydroxy-5-androsten-17-one; 3beta-hydroxyandrost-5-en-17-one; 3-b-HYDROXY-5-androsten-17-one; 3-Β-hydroxy-5-androsten-17-one; 3b-Hydroxy-D5-androsten-17-one; 3b-Hydroxyandrost-5-en-17-one; 3Β-hydroxyandrost-5-en-17-one; Androst-5-ene-3beta-ol-17-one; Dehydroepiandrosterone (DHEA); 3-Hydroxyandrost-5-en-17-one; 5,6-Didehydroisoandrosterone; 5-Androsten-3-beta-ol-17-one; D5-Androsten-3beta-ol-17-one; 5-Androsten-3beta-ol-17-one; Prasterone, 3 alpha-isomer; Prasterone, 3 alpha isomer; Androst-5-ene-3b-ol-17-one; (+)-Dehydroisoandrosterone; 5,6-Dehydroisoandrosterone; Androsten-3beta-ol-17-one; D5-Androsten-3b-ol-17-one; EM-760Dehydroandrosterone; trans-Dehydroandrosterone; 5-Dehydro-epiandrosterone; 5-Androsten-3b-ol-17-one; 5-Dehydroepiandrosterone; Dehydro-epi-androsterone; 5 Androsten 3 ol 17 one; 5-Androsten-3-ol-17-one; Dehydroepiandrosterone; Dehydroisoandrosterone; Hydroxyandrostenone; Androstenolone; 17-Hormoforin; Psicosterone; 17-Chetovis; Andrestenol; Prasteronum; Prasterone; Prasterona; ST 19:2;O2; Diandrone; Intrarosa; Astenile; Deandros; Diandron; Prestara; Biolaif; DHEA; DHA; Dehydroepiandrosterone



数据库引用编号

34 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(7)

BioCyc(1)

PlantCyc(0)

代谢反应

105 个相关的代谢反应过程信息。

Reactome(86)

BioCyc(3)

  • androgen biosynthesis: 17-α-hydroxypregnenolone + O2 + a reduced [NADPH-hemoprotein reductase] ⟶ 3-β-hydroxyandrost-5-en-17-one + H+ + H2O + acetate + an oxidized [NADPH-hemoprotein reductase]
  • androgen biosynthesis: NADP+ + testosterone ⟶ H+ + NADPH + androst-4-ene-3,17-dione
  • androgen biosynthesis: NAD+ + dehydroepiandrosterone ⟶ 5-androstene-3,17-dione + H+ + NADH

WikiPathways(4)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(12)

PharmGKB(0)

19 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 AKT1, AR, BDNF, BGLAP, CAT, G6PD, PIK3CA, PRL
Peripheral membrane protein 3 CYP11A1, CYP1B1, G6PD
Endoplasmic reticulum membrane 4 CYP17A1, CYP1B1, STAR, STS
Mitochondrion membrane 1 CYP11A1
Nucleus 3 AKT1, AR, PRL
cytosol 7 AKT1, AR, CAT, G6PD, LEP, PIK3CA, SLC2A4
dendrite 2 BDNF, BGLAP
trans-Golgi network 1 SLC2A4
nucleoplasm 3 AKT1, AR, PRL
RNA polymerase II transcription regulator complex 1 PRL
Cell membrane 3 AKT1, SLC2A4, STAR
lamellipodium 2 AKT1, PIK3CA
Multi-pass membrane protein 1 SLC2A4
cell cortex 1 AKT1
glutamatergic synapse 1 AKT1
Golgi apparatus 1 STS
mitochondrial inner membrane 1 CYP11A1
neuronal cell body 1 CYP17A1
postsynapse 1 AKT1
sarcolemma 1 SLC2A4
synaptic vesicle 1 BDNF
Cytoplasm, cytosol 1 G6PD
Lysosome 1 STS
Presynapse 1 SLC2A4
endosome 1 STS
plasma membrane 7 AKT1, AR, PIK3CA, REN, SLC2A4, STAR, STS
Membrane 10 AKT1, AR, BDNF, CAT, CYP11A1, CYP1B1, G6PD, REN, SLC2A4, STS
axon 2 BDNF, CYP17A1
extracellular exosome 3 CAT, G6PD, SLC2A4
endoplasmic reticulum 2 CYP17A1, STS
extracellular space 9 AMH, BDNF, BGLAP, CRP, GNRH1, IL2, LEP, PRL, REN
perinuclear region of cytoplasm 3 BDNF, PIK3CA, SLC2A4
intercalated disc 1 PIK3CA
mitochondrion 4 CAT, CYP11A1, CYP1B1, STAR
protein-containing complex 3 AKT1, AR, CAT
intracellular membrane-bounded organelle 4 CAT, CYP1B1, G6PD, STS
Microsome membrane 2 CYP17A1, CYP1B1
Single-pass type I membrane protein 1 STAR
Secreted 8 AMH, BDNF, BGLAP, CRP, IL2, LEP, PRL, REN
extracellular region 10 AMH, BDNF, BGLAP, CAT, CRP, GNRH1, IL2, LEP, PRL, REN
cytoplasmic side of plasma membrane 1 G6PD
mitochondrial matrix 3 CAT, CYP11A1, STAR
centriolar satellite 1 G6PD
external side of plasma membrane 1 SLC2A4
multivesicular body 1 SLC2A4
T-tubule 1 SLC2A4
perikaryon 1 BGLAP
microtubule cytoskeleton 1 AKT1
apical part of cell 1 REN
cell-cell junction 1 AKT1
clathrin-coated pit 1 SLC2A4
vesicle 2 AKT1, BGLAP
Cytoplasm, perinuclear region 1 SLC2A4
Mitochondrion inner membrane 1 CYP11A1
Membrane raft 1 SLC2A4
focal adhesion 1 CAT
spindle 1 AKT1
Peroxisome 1 CAT
sarcoplasmic reticulum 1 SLC2A4
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 2 AKT1, STAR
nuclear speck 1 AR
ciliary basal body 1 AKT1
chromatin 2 AR, PRL
Endomembrane system 1 SLC2A4
endosome lumen 1 PRL
Cytoplasmic vesicle membrane 1 SLC2A4
clathrin-coated vesicle 1 SLC2A4
trans-Golgi network transport vesicle 1 SLC2A4
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
Golgi lumen 1 BGLAP
endoplasmic reticulum lumen 3 BDNF, BGLAP, STS
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
vesicle membrane 1 SLC2A4
catalase complex 1 CAT
Cytoplasmic vesicle, secretory vesicle, microneme membrane 1 STS
microneme membrane 1 STS
insulin-responsive compartment 1 SLC2A4
[Neurotrophic factor BDNF precursor form]: Secreted 1 BDNF
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA


文献列表

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  • Yi-Fen Chiang, I-Cheng Lin, Ko-Chieh Huang, Hsin-Yuan Chen, Mohamed Ali, Yun-Ju Huang, Shih-Min Hsia. Caffeic acid's role in mitigating polycystic ovary syndrome by countering apoptosis and ER stress triggered by oxidative stress. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2023 Oct; 166(?):115327. doi: 10.1016/j.biopha.2023.115327. [PMID: 37619480]
  • Tingting Zhang, Huimin Gao, Yali Fan, Shuya Chen, Yingying Li, Ruixia Liu, Tianhe Li, Chenghong Yin. Gut microbiota disorder induces liver dysfunction in polycystic ovary syndrome rats' model by regulating metabolite rosmarinic acid. Life sciences. 2023 Oct; 330(?):121912. doi: 10.1016/j.lfs.2023.121912. [PMID: 37423380]
  • Mengqing Gu, Han Cai, Weinan Deng, Yedong Tang, Shuailin Du, Peiran Wang, Wenbo Deng, Haibin Wang, Aijun Sun, Shuangbo Kong. Dingkun pill alleviates metabolic abnormalities in polycystic ovary syndrome through brown adipose tissue activation. Journal of ovarian research. 2023 Aug; 16(1):176. doi: 10.1186/s13048-023-01215-0. [PMID: 37633943]
  • Fengya Zhu, Shao Yin, Bin Yang, Siyun Li, Xia Feng, Tianyu Wang, Deya Che. TEAS, DHEA, CoQ10, and GH for poor ovarian response undergoing IVF-ET: a systematic review and network meta-analysis. Reproductive biology and endocrinology : RB&E. 2023 Jul; 21(1):64. doi: 10.1186/s12958-023-01119-0. [PMID: 37464357]
  • Rama Satya Sri Kotipalli, Samata Sai Patnaik, Jerald Mahesh Kumar, Sistla Ramakrishna, Kathirvel Muralidharan. Biochanin-A attenuates DHEA-induced polycystic ovary syndrome via upregulation of GDF9 and BMP15 signaling in vivo. Life sciences. 2023 May; 326(?):121795. doi: 10.1016/j.lfs.2023.121795. [PMID: 37230376]
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  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Ritu Rani, Havagiray R Chitme, Neha Kukreti, Pankaj Pant, Basel A Abdel-Wahab, Masood Medleri Khateeb, Mohammed Shafiuddin Habeeb, Marwa B Bakir. Regulation of Insulin Resistance, Lipid Profile and Glucose Metabolism Associated with Polycystic Ovary Syndrome by Tinospora cordifolia. Nutrients. 2023 May; 15(10):. doi: 10.3390/nu15102238. [PMID: 37242122]
  • Samuel D Offei, Hadi D Arman, Francis K Yoshimoto. Synthesis of menarandroside A from dehydroepiandrosterone. Organic & biomolecular chemistry. 2023 Mar; ?(?):. doi: 10.1039/d3ob00054k. [PMID: 36950968]
  • Yijie Jiang, Jianshu Yang, Ke Du, Kaiming Luo, Xin Yuan, Fei Hua. 1,25-Dihydroxyvitamin D3 alleviates hyperandrogen-induced ferroptosis in KGN cells. Hormones (Athens, Greece). 2023 Mar; ?(?):. doi: 10.1007/s42000-023-00439-5. [PMID: 36884209]
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  • Neşe Başak Türkmen, Hande Yüce, Muhterem Aydın, Aslı Taşlıdere, Ayşegül Doğan, Dilan Aşkın Özek, Taha Bartu Hayal, Şeyma Yaşar, Osman Çiftçi, Songül Ünüvar. Nerolidol attenuates dehydroepiandrosterone-induced polycystic ovary syndrome in rats by regulating oxidative stress and decreasing apoptosis. Life sciences. 2023 Feb; 315(?):121380. doi: 10.1016/j.lfs.2023.121380. [PMID: 36640898]
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