16-Dehydropregnenolone (BioDeep_00000006139)

 

Secondary id: BioDeep_00000172114, BioDeep_00000637539

natural product


代谢物信息卡片


1-[(3S,8R,9S,10R,13S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone

化学式: C21H30O2 (314.2246)
中文名称: 16-妊娠双烯醇酮
谱图信息: 最多检出来源 Macaca mulatta(otcml) 7.59%

分子结构信息

SMILES: CC(=O)C1=CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
InChI: InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,6,15-16,18-19,23H,5,7-12H2,1-3H3/t15-,16-,18-,19-,20-,21+/m0/s1

描述信息

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones

同义名列表

8 个代谢物同义名

16-Dehydropregnenolone; 1-[(3S,8R,9S,10R,13S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone; 1-(3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone; (3beta)-3-hydroxypregna-5,16-dien-20-one; 3beta-hydroxypregna-5,16-dien-20-one; 5,16-pregnadien-3beta-ol-20-one; 16,17-didehydropregnenolone; Delta(16)-pregnenolone



数据库引用编号

13 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

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)

11 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 11 AR, ATM, BCL2, CASP3, CASP8, CASP9, CHEK2, CYP2E1, DHPS, MSMP, SGCB
Peripheral membrane protein 1 CYP2E1
Endoplasmic reticulum membrane 4 BCL2, CYP1A2, CYP2E1, CYP7A1
Nucleus 8 AR, ATM, BCL2, CASP3, CASP8, CASP9, CHEK2, PPARA
cytosol 8 AR, ATM, BCL2, CASP3, CASP8, CASP9, DHPS, NGF
dendrite 1 NGF
centrosome 1 ATM
nucleoplasm 6 AR, ATM, CASP3, CASP8, CHEK2, PPARA
lamellipodium 1 CASP8
glutamatergic synapse 1 CASP3
Golgi apparatus 1 CHEK2
mitochondrial inner membrane 1 CYP2E1
neuronal cell body 1 CASP3
sarcolemma 1 SGCB
synaptic vesicle 1 NGF
plasma membrane 2 AR, SGCB
Membrane 2 AR, BCL2
axon 1 NGF
endoplasmic reticulum 1 BCL2
extracellular space 2 MSMP, NGF
mitochondrion 3 BCL2, CASP8, CASP9
protein-containing complex 4 AR, BCL2, CASP8, CASP9
intracellular membrane-bounded organelle 4 ATM, CYP1A2, CYP2E1, CYP7A1
Microsome membrane 3 CYP1A2, CYP2E1, CYP7A1
postsynaptic density 1 CASP3
Secreted 2 MSMP, NGF
extracellular region 1 NGF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 2 BCL2, CYP7A1
mitochondrial outer membrane 2 BCL2, CASP8
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 ATM
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
cytoplasmic vesicle 1 ATM
nucleolus 1 ATM
Single-pass type II membrane protein 1 SGCB
Cell membrane, sarcolemma 1 SGCB
Cell projection, lamellipodium 1 CASP8
Mitochondrion inner membrane 1 CYP2E1
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 SGCB
spindle 1 ATM
Peroxisome matrix 1 ATM
peroxisomal matrix 1 ATM
PML body 1 CHEK2
nuclear speck 1 AR
chromatin 2 AR, PPARA
cytoskeleton 2 CASP8, SGCB
site of double-strand break 1 ATM
endosome lumen 1 NGF
cell body 1 CASP8
myelin sheath 1 BCL2
Golgi lumen 1 NGF
extrinsic component of synaptic vesicle membrane 1 ATM
apoptosome 1 CASP9
CD95 death-inducing signaling complex 1 CASP8
death-inducing signaling complex 2 CASP3, CASP8
ripoptosome 1 CASP8
dystrophin-associated glycoprotein complex 1 SGCB
sarcoglycan complex 1 SGCB
DNA repair complex 1 ATM
BAD-BCL-2 complex 1 BCL2
caspase complex 1 CASP9


文献列表

  • Rachumallu Ramakrishna, Durgesh Kumar, Manisha Bhateria, Anil Nilkanth Gaikwad, Rabi Sankar Bhatta. 16-Dehydropregnenolone lowers serum cholesterol by up-regulation of CYP7A1 in hyperlipidemic male hamsters. The Journal of steroid biochemistry and molecular biology. 2017 04; 168(?):110-117. doi: 10.1016/j.jsbmb.2017.02.013. [PMID: 28232149]
  • Yangyang Sun, Lili Jia, Hui Zhou, Mengqian Mao, Xiaobo Wang, Lan Wei, Lixin Sun. Pharmacokinetics of 16-dehydropregnenolone hydroxypropyl-β-cyclodextrin inclusion complex following peroral administration. Pharmaceutical development and technology. 2017 Mar; 22(2):218-228. doi: 10.1080/10837450.2016.1193192. [PMID: 27269370]
  • Zhenxue Deng, Xiaobo Wang, Fang Wang, Zheng Qin, Yuqi Cui, Yangyang Sun, Lixin Sun. Pharmacokinetics and tissue distribution study of 16-dehydropregnenolone liposome in female mice after intravenous administration. Drug delivery. 2016 Oct; 23(8):2787-2795. doi: 10.3109/10717544.2015.1088596. [PMID: 26366505]
  • Rachumallu Ramakrishna, Manisha Bhateria, Rajbir Singh, Rabi Sankar Bhatta. Evaluation of the impact of 16-dehydropregnenolone on the activity and expression of rat hepatic cytochrome P450 enzymes. The Journal of steroid biochemistry and molecular biology. 2016 10; 163(?):183-92. doi: 10.1016/j.jsbmb.2016.05.018. [PMID: 27224941]
  • A Misra, H N Kushwaha, N Gautam, B Singh, P C Verma, R Pratap, S K Singh. Bioanalytical LC-MS/MS method development and validation of novel antidiabetic candidate S007-1261 in rat plasma and its application to pharmacokinetic and oral bioavailability studies. Drug research. 2014 Aug; 64(8):399-405. doi: 10.1055/s-0033-1358739. [PMID: 24258707]
  • Devendra Kumar, Ashok K Khanna, Ram Pratap, Jitendra K Sexana, Rabi S Bhatta. Dose escalation pharmacokinetics and lipid lowering activity of a novel farnesoid X receptor modulator: 16-Dehydropregnenolone. Indian journal of pharmacology. 2012 Jan; 44(1):57-62. doi: 10.4103/0253-7613.91868. [PMID: 22345871]
  • Satyendra Suryawanshi, Wahajuddin, Ram Chandra Gupta, Shio Kumar Singh. Preclinical pharmacokinetics, dose proportionality, gender difference and protein binding study of 16-dehydropregnenolone, an antihyperlipidemic agent, in rats. The Journal of pharmacy and pharmacology. 2011 Jan; 63(1):41-8. doi: 10.1111/j.2042-7158.2010.01158.x. [PMID: 21155814]
  • Li-Xin Sun, Wen-Wei Fu, Jing Ren, Liang Xu, Kai-Shun Bi, Min-Wei Wang. Cytotoxic constituents from Solanum lyratum. Archives of pharmacal research. 2006 Feb; 29(2):135-9. doi: 10.1007/bf02974274. [PMID: 16526277]
  • Satyendra Suryawanshi, S K Singh, R C Gupta. A sensitive and selective HPLC/ESI-MS/MS assay for the simultaneous quantification of 16-dehydropregnenolone and its major metabolites in rabbit plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2006 Jan; 830(1):54-63. doi: 10.1016/j.jchromb.2005.10.012. [PMID: 16290073]
  • S K Singh, Nitin Mehrotra, S Sabarinath, R C Gupta. HPLC-UV method development and validation for 16-dehydropregnenolone, a novel oral hypolipidaemic agent, in rat biological matrices for application to pharmacokinetic studies. Journal of pharmaceutical and biomedical analysis. 2003 Nov; 33(4):755-64. doi: 10.1016/s0731-7085(03)00308-x. [PMID: 14623602]
  • N Tagawa, K Saiki, Y Kobayashi. Development of an enzyme immunoassay for serum 16-dehydropregnenolone. Biological & pharmaceutical bulletin. 2001 Aug; 24(8):867-71. doi: 10.1248/bpb.24.867. [PMID: 11510475]
  • N Tagawa, S Kusuda, Y Kobayashi. 16-Dehydropregnenolone 3-sulfate, its source and metabolism in the feto-placental unit. Biological & pharmaceutical bulletin. 1999 Dec; 22(12):1262-5. doi: 10.1248/bpb.22.1262. [PMID: 10746151]
  • N Tagawa, Y Nakata, S Kusuda, Y Kobayashi, F Watanabe. Serum levels of 16-dehydropregnenolone sulfate during the early neonatal period. Biological & pharmaceutical bulletin. 1997 Jan; 20(1):76-8. doi: 10.1248/bpb.20.76. [PMID: 9013811]
  • Y Kobayashi, N Tagawa, K Saiki, F Watanabe. Studies on steroids in fetuses and neonates: identification of 16-dehydropregnenolone in the circulation of pre-term neonates. Biological & pharmaceutical bulletin. 1994 Nov; 17(11):1501-4. doi: 10.1248/bpb.17.1501. [PMID: 7703972]