Determine the necessary mass, volume, or concentration for preparing a solution.
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Synonyms | Dehydroepiandrosterone | DHEA | PRASTERONE | 53-43-0 | Dehydroisoandrosterone | Androstenolone | trans-Dehydroandrosterone | Psicosterone | Diandrone | Diandron | 3beta-hydroxyandrost-5-en-17-one | Prestara | 17-Hormoforin | 17-Chetovis | Andrestenol | Intrarosa | 5-Dehydroepiandrostero |
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Specifications & Purity | Moligand™, 10mM in DMSO |
Storage Temp | Store at -80°C |
Shipped In | Ice chest + Ice pads |
Grade | Moligand™ |
ALogP | 3.2 |
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Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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IUPAC Name | (3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one |
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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/t13-,14-,15-,16-,18-,19-/m0/s1 |
InChi Key | FMGSKLZLMKYGDP-USOAJAOKSA-N |
Canonical SMILES | CC12CCC3C(C1CCC2=O)CC=C4C3(CCC(C4)O)C |
Isomeric SMILES | C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CC[C@@H](C4)O)C |
WGK Germany | 2 |
RTECS | BV8396000 |
PubChem CID | 5881 |
Molecular Weight | 288.43 |
Beilstein | 2058110 |
Enter Lot Number to search for COA:
Melt Point(°C) | 146-151°C |
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Pictogram(s) | GHS08, GHS09, GHS07 |
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Signal | Danger |
Hazard Statements | H315:Causes skin irritation H319:Causes serious eye irritation H335:May cause respiratory irritation H400:Very toxic to aquatic life H410:Very toxic to aquatic life with long lasting effects H360:May damage fertility or the unborn child H362:May cause harm to breast-fed children |
Precautionary Statements | P261:Avoid breathing dust/fume/gas/mist/vapors/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do - continue rinsing. P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of water. P321:Specific treatment (see ... on this label). P405:Store locked up. P501:Dispose of contents/container to ... P264:Wash hands [and …] thoroughly after handling. P260:Do not breathe dust/fume/gas/mist/vapors/spray. P271:Use only outdoors or in a well-ventilated area. P270:Do not eat, drink or smoke when using this product. P304+P340:IF INHALED: Remove person to fresh air and keep comfortable for breathing. P403+P233:Store in a well-ventilated place. Keep container tightly closed. P362+P364:Take off contaminated clothing and wash it before reuse. P391:Collect spillage. P263:Avoid contact during pregnancy/while nursing. P203:Obtain, read and follow all safety instructions before use. P264+P265:Wash hands [and …] thoroughly after handling. Do not touch eyes. P318:if exposed or concerned, get medical advice. P337+P317:If eye irritation persists: Get medical help. P332+P317:If skin irritation occurs: Get medical help. P319:Get medical help if you feel unwell. |
WGK Germany | 2 |
RTECS | BV8396000 |
1. Guojuan Yi, Hanlu Zou, Tao Long, Tolbert Osire, Lin Wang, Xiaoyun Wei, Mengfei Long, Zhiming Rao, Guojian Liao. (2024) Novel cytochrome P450s for various hydroxylation of steroids from filamentous fungi. BIORESOURCE TECHNOLOGY, 394 (130244). [PMID:38145763] [10.1016/j.biortech.2023.130244] |
2. Nan Li, Juan Zheng, Lu-Dan Yu, Yuan-Jun Tong, Xinying Gong, Yu Hou, Guosheng Chen, Jianqiao Xu, Fang Zhu, Gangfeng Ouyang. (2024) Green, mildly synthesized bismuth-based MOF for extraction of polar glucocorticoids in environmental water. JOURNAL OF HAZARDOUS MATERIALS, 461 (132477). [PMID:37716268] [10.1016/j.jhazmat.2023.132477] |
3. Lifeng Ding, Lili Jiang, Ze Xing, Huixu Dai, Jingzan Wei. (2023) Map4k4 is up-regulated and modulates granulosa cell injury and oxidative stress in polycystic ovary syndrome via activating JNK/c-JUN pathway: An experimental study. INTERNATIONAL IMMUNOPHARMACOLOGY, 124 (110841). [PMID:37647682] [10.1016/j.intimp.2023.110841] |
4. Tingting Yang, Jiayu Yuan, Yuting Peng, Jiale Pang, Zhen Qiu, Shangxiu Chen, Yuhan Huang, Zhenzhou Jiang, Yilin Fan, Junjie Liu, Tao Wang, Xueyan Zhou, Sitong Qian, Jinfang Song, Yi Xu, Qian Lu, Xiaoxing Yin. (2023) Metformin: A promising clinical therapeutical approach for BPH treatment via inhibiting dysregulated steroid hormones-induced prostatic epithelial cells proliferation. Journal of Pharmaceutical Analysis, [PMID:38352949] [10.1016/j.jpha.2023.08.012] |
5. Jin-Bu Xu, Jin Bi, Peng Wen, Shi-Xing Miao, Xiao-Huan Li, Feng Gao. (2023) Synthesis and Cytotoxicity Evaluation of Dehydroepiandrosterone Derivatives by Iron-Catalyzed Stereoselective Hydroamination. CHEMICAL & PHARMACEUTICAL BULLETIN, 71 (5): (349-353). [PMID:36858603] [10.1248/cpb.c22-00857] |
6. Jing Cong, Mubai Li, Yu Wang, Hongli Ma, Xinming Yang, Jingshu Gao, Long Wang, Xiaoke Wu. (2023) Protective effects of electroacupuncture on polycystic ovary syndrome in rats: Down-regulating Alas2 to inhibit apoptosis, oxidative stress, and mitochondrial dysfunction in ovarian granulosa cells. TISSUE & CELL, 82 (102090). [PMID:37075681] [10.1016/j.tice.2023.102090] |
7. Ruosi Zhang, Mingdong Yao, Haidi Ma, Wenhai Xiao, Ying Wang, Yingjin Yuan. (2023) Modular Coculture to Reduce Substrate Competition and Off-Target Intermediates in Androstenedione Biosynthesis. ACS Synthetic Biology, 12 (3): (788–799). [PMID:36857753] [10.1021/acssynbio.2c00590] |
8. Ying Wang, Jiyu Yang, Yu Wang, Yao Chen, Yiran Wang, Hongying Kuang, Xiaoling Feng. (2023) Upregulation of TXNIP contributes to granulosa cell dysfunction in polycystic ovary syndrome via activation of the NLRP3 inflammasome. MOLECULAR AND CELLULAR ENDOCRINOLOGY, 561 (111824). [PMID:36450326] [10.1016/j.mce.2022.111824] |
9. Jing Cong, Yuehui Zhang, Xinming Yang, Yu Wang, Hui He, Mengying Wang. (2022) Anti-polycystic ovary syndrome effect of electroacupuncture: IMD inhibits ER stress-mediated apoptosis and autophagy in granulosa cells. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 634 (159). [PMID:36244114] [10.1016/j.bbrc.2022.10.030] |
10. Ying Wang Yu Wang Yao Chen Qianqian Gao Lihui Hou Xiaoling Feng. (2022) HDAC5 inhibits ovarian angiogenesis in dehydroepiandrosterone-induced mouse model of polycystic ovary syndrome. FOLIA HISTOCHEMICA ET CYTOBIOLOGICA, 60 (3): (260-270). [PMID:36124413] [10.5603/FHC.a2022.0024] |
11. Xiao-San Li, Mao-Xun Yang, Yu-Hao Luo, He-Hui Zhan, Mei-Fang Chen, Yong-Mei Huang, Li Liu, Xue-Mei Yang. (2022) Design, Synthesis and Anticancer Activity of Novel Steroidal Derivatives with D-Ring Fused or Substituted N-Heterocyclic Systems. CHEMISTRY & BIODIVERSITY, 19 (10): (e202200648). [PMID:36043381] [10.1002/cbdv.202200648] |
12. Jing Xia, Shujuan Wu, Gengxiang Wu, Jing Yang. (2022) Inhibition of 8-oxoguanine DNA glycosylase (OGG1) expression suppresses polycystic ovarian syndrome via the NF-κB signaling pathway. Reproductive Biology, 22 (100679). [PMID:35961097] [10.1016/j.repbio.2022.100679] |
13. Ying-Li Cai, Feng Zhang, Xiu-Xiu Dou, Hua-Wu Zeng, Gao-Song Wu, Yan-Lin Liang, Xi-Ke Xu, Jing Zhao, Ji Ye, Wei-Dong Zhang. (2022) Integrated metabolomics and network pharmacology to reveal the therapeutic mechanism of Dingkun Pill on polycystic ovary syndrome. JOURNAL OF ETHNOPHARMACOLOGY, 295 (115442). [PMID:35688255] [10.1016/j.jep.2022.115442] |
14. Huiyi Yang, Qiyi He, Mingxia Lin, Li Ji, Leheng Zhang, Huanxin Xiao, Shijia Li, Qinglan Li, Xiping Cui, Suqing Zhao. (2022) Multifunctional Au@Pt@Ag NPs with color-photothermal-Raman properties for multimodal lateral flow immunoassay. JOURNAL OF HAZARDOUS MATERIALS, 435 (129082). [PMID:35650752] [10.1016/j.jhazmat.2022.129082] |
15. Susu Lin, Bingbing Ma, Qilin Gao, Jian Yang, Gang Lai, Runhao Lin, Bingxian Yang, Bing-Nan Han, Lian-Hua Xu. (2022) The 16α-Hydroxylation of Progesterone by Cytochrome P450 107X1 from Streptomyces avermitilis. CHEMISTRY & BIODIVERSITY, 19 (5): (e202200177). [PMID:35426465] [10.1002/cbdv.202200177] |
16. Yan Li, Jia Xu, Lingxia Li, Lu Bai, Yunping Wang, Jianfang Zhang, Haixu Wang. (2022) Inhibition of Nicotinamide adenine dinucleotide phosphate oxidase 4 attenuates cell apoptosis and oxidative stress in a rat model of polycystic ovary syndrome through the activation of Nrf-2/HO-1 signaling pathway. MOLECULAR AND CELLULAR ENDOCRINOLOGY, 550 (111645). [PMID:35413388] [10.1016/j.mce.2022.111645] |
17. Huiyi Yang, Qiyi He, Junkang Pan, Mingxia Lin, Zhiting Lao, Qinglan Li, Xiping Cui, Suqing Zhao. (2022) PtCu nanocages with superior tetra-enzyme mimics for colorimetric sensing and fluorescent sensing dehydroepiandrosterone. SENSORS AND ACTUATORS B-CHEMICAL, 351 (130905). [PMID:] [10.1016/j.snb.2021.130905] |
18. Yang Huiyi, He Qiyi, Eremin Sergei A., Pan Junkang, Zou Yikui, Cui Xiping, Zhao Suqing. (2021) Fluorescence polarization immunoassay for rapid determination of dehydroepiandrosterone in human urine. ANALYTICAL AND BIOANALYTICAL CHEMISTRY, 413 (17): (4459-4469). [PMID:34137913] [10.1007/s00216-021-03403-7] |
19. Yang Huiyi, He Qiyi, Chen Yingshan, Shen Ding, Xiao Huanxin, Eremin Sergei A., Cui Xiping, Zhao Suqing. (2020) Platinum nanoflowers with peroxidase-like property in a dual immunoassay for dehydroepiandrosterone. MICROCHIMICA ACTA, 187 (11): (1-12). [PMID:33025211] [10.1007/s00604-020-04528-9] |
20. Jun Liu, Jinli Ding, Bing Qu, Jiuying Liu, Xiaojie Song, Qingli Suo, Aifen Zhou, Jing Yang. (2020) CircPSMC3 alleviates the symptoms of PCOS by sponging miR-296-3p and regulating PTEN expression. JOURNAL OF CELLULAR AND MOLECULAR MEDICINE, 24 (18): (11001-11011). [PMID:32808450] [10.1111/jcmm.15747] |
21. Gengxiang Wu, Xue Hu, Jinli Ding, Jing Yang. (2020) The effect of glutamine on Dehydroepiandrosterone-induced polycystic ovary syndrome rats.. Journal of Ovarian Research, 13 (1): (57-57). [PMID:32386521] [10.1186/s13048-020-00650-7] |
22. Ling-Li Zheng, Guan Wen, Yun-Xin Yao, Xiao-Huan Li, Feng Gao. (2020) Design, Synthesis, and Anticancer Activity of Natural Product Hybrids With Paclitaxel Side Chain Inducing Apoptosis in Human Colon Cancer Cells. Natural Product Communications, [PMID:] [10.1177/1934578X20917298] |
23. Wu Gengxiang, Hu Xue, Ding Jinli, Yang Jing. (2019) Abnormal expression of HSP70 may contribute to PCOS pathology. Journal of Ovarian Research, 12 (1): (1-7). [PMID:31399035] [10.1186/s13048-019-0548-7] |
24. Zhou Dan-ni, Li Sai-jiao, Ding Jin-li, Yin Tai-lang, Yang Jing, Ye Hong. (2018) MIF May Participate in Pathogenesis of Polycystic Ovary Syndrome in Rats through MAPK Signalling Pathway. Current Medical Science, 38 (5): (853-860). [PMID:30341520] [10.1007/s11596-018-1953-7] |
25. Di Xu, Mengyun Wu, Xue Li, Mingyu Xia, Dongchun Liu, Yinghui Dai, Qing Yu, Bin Wu, Dong Wang. (2018) Cloning, prokaryotic expression and function of the Bufo bufo gargarizans 3β-hydroxysteroid dehydrogenase (3βHSD) gene. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 120 (673). [PMID:30170058] [10.1016/j.ijbiomac.2018.08.165] |
26. Xianzhi Qu, Jiyao Sheng, Luyan Shen, Jing Su, Yunjie Xu, Qi Xie, Yao Wu, Xuewen Zhang, Liankun Sun. (2017) Autophagy inhibitor chloroquine increases sensitivity to cisplatin in QBC939 cholangiocarcinoma cells by mitochondrial ROS. PLoS One, 12 (3): (e0173712). [PMID:28301876] [10.1371/journal.pone.0173712] |
27. Zhuang Wu, Linlang Li, Long-Tai Zheng, Zhihong Xu, Lin Guo, Xuechu Zhen. (2015) Allosteric modulation of sigma-1 receptors by SKF83959 inhibits microglia-mediated inflammation. JOURNAL OF NEUROCHEMISTRY, 134 (5): (904-914). [PMID:26031312] [10.1111/jnc.13182] |
28. Teng-Fei Yuan,Juan Le,Yan Cui,Rui Peng,Shao-Ting Wang,Yan Li. (2018-09-17) An LC-MS/MS analysis for seven sex hormones in serum.. Journal of pharmaceutical and biomedical analysis, 162 (34-40). [PMID:30219597] |
29. Teng-Fei Yuan,Juan Le,Shao-Ting Wang,Yan Li. (2020-01-23) An LC/MS/MS method for analyzing the steroid metabolome with high accuracy and from small serum samples.. Journal of lipid research, 61 ((4)): (580-586). [PMID:31964762] |
30. Zhijing Song,Huanyu Gao,Wenchun Xie,Qing Sun,Kai Liang,Yan Li. (2020-12-29) Quantitative MALDI-MS assay of steroid hormones in plasma based on hydroxylamine derivatization.. Analytical biochemistry, 616 (114089-114089). [PMID:33359147] |
31. Yunjie Xu,Weinan Gao,Yong Zhang,Shanshan Wu,Yanan Liu,Xinyue Deng,Lili Xie,Jiayan Yang,Huimei Yu,Jing Su,Liankun Sun. (2018-07-18) ABT737 reverses cisplatin resistance by targeting glucose metabolism of human ovarian cancer cells.. International journal of oncology, 53 ((3)): (1055-1068). [PMID:30015875] |
1. Guojuan Yi, Hanlu Zou, Tao Long, Tolbert Osire, Lin Wang, Xiaoyun Wei, Mengfei Long, Zhiming Rao, Guojian Liao. (2024) Novel cytochrome P450s for various hydroxylation of steroids from filamentous fungi. BIORESOURCE TECHNOLOGY, 394 (130244). [PMID:38145763] [10.1016/j.biortech.2023.130244] |
2. Nan Li, Juan Zheng, Lu-Dan Yu, Yuan-Jun Tong, Xinying Gong, Yu Hou, Guosheng Chen, Jianqiao Xu, Fang Zhu, Gangfeng Ouyang. (2024) Green, mildly synthesized bismuth-based MOF for extraction of polar glucocorticoids in environmental water. JOURNAL OF HAZARDOUS MATERIALS, 461 (132477). [PMID:37716268] [10.1016/j.jhazmat.2023.132477] |
3. Lifeng Ding, Lili Jiang, Ze Xing, Huixu Dai, Jingzan Wei. (2023) Map4k4 is up-regulated and modulates granulosa cell injury and oxidative stress in polycystic ovary syndrome via activating JNK/c-JUN pathway: An experimental study. INTERNATIONAL IMMUNOPHARMACOLOGY, 124 (110841). [PMID:37647682] [10.1016/j.intimp.2023.110841] |
4. Tingting Yang, Jiayu Yuan, Yuting Peng, Jiale Pang, Zhen Qiu, Shangxiu Chen, Yuhan Huang, Zhenzhou Jiang, Yilin Fan, Junjie Liu, Tao Wang, Xueyan Zhou, Sitong Qian, Jinfang Song, Yi Xu, Qian Lu, Xiaoxing Yin. (2023) Metformin: A promising clinical therapeutical approach for BPH treatment via inhibiting dysregulated steroid hormones-induced prostatic epithelial cells proliferation. Journal of Pharmaceutical Analysis, [PMID:38352949] [10.1016/j.jpha.2023.08.012] |
5. Jin-Bu Xu, Jin Bi, Peng Wen, Shi-Xing Miao, Xiao-Huan Li, Feng Gao. (2023) Synthesis and Cytotoxicity Evaluation of Dehydroepiandrosterone Derivatives by Iron-Catalyzed Stereoselective Hydroamination. CHEMICAL & PHARMACEUTICAL BULLETIN, 71 (5): (349-353). [PMID:36858603] [10.1248/cpb.c22-00857] |
6. Jing Cong, Mubai Li, Yu Wang, Hongli Ma, Xinming Yang, Jingshu Gao, Long Wang, Xiaoke Wu. (2023) Protective effects of electroacupuncture on polycystic ovary syndrome in rats: Down-regulating Alas2 to inhibit apoptosis, oxidative stress, and mitochondrial dysfunction in ovarian granulosa cells. TISSUE & CELL, 82 (102090). [PMID:37075681] [10.1016/j.tice.2023.102090] |
7. Ruosi Zhang, Mingdong Yao, Haidi Ma, Wenhai Xiao, Ying Wang, Yingjin Yuan. (2023) Modular Coculture to Reduce Substrate Competition and Off-Target Intermediates in Androstenedione Biosynthesis. ACS Synthetic Biology, 12 (3): (788–799). [PMID:36857753] [10.1021/acssynbio.2c00590] |
8. Ying Wang, Jiyu Yang, Yu Wang, Yao Chen, Yiran Wang, Hongying Kuang, Xiaoling Feng. (2023) Upregulation of TXNIP contributes to granulosa cell dysfunction in polycystic ovary syndrome via activation of the NLRP3 inflammasome. MOLECULAR AND CELLULAR ENDOCRINOLOGY, 561 (111824). [PMID:36450326] [10.1016/j.mce.2022.111824] |
9. Jing Cong, Yuehui Zhang, Xinming Yang, Yu Wang, Hui He, Mengying Wang. (2022) Anti-polycystic ovary syndrome effect of electroacupuncture: IMD inhibits ER stress-mediated apoptosis and autophagy in granulosa cells. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 634 (159). [PMID:36244114] [10.1016/j.bbrc.2022.10.030] |
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