Tachysterol 3 (BioDeep_00000028229)

   

human metabolite Endogenous


代谢物信息卡片


(1S)-3-[(E)-2-[(1R,3aR,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethenyl]-4-methylcyclohex-3-en-1-ol

化学式: C27H44O (384.3392)
中文名称:
谱图信息: 最多检出来源 not specific(not specific) 0%

分子结构信息

SMILES: CC(C)CCC[C@@H](C)[C@@]1([H])CC[C@@]2([H])C(=CCC[C@]12C)\C=C\C1=C(C)CC[C@H](O)C1
InChI: InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h10,12-13,19,21,24-26,28H,6-9,11,14-18H2,1-5H3/b13-12+/t21-,24+,25-,26+,27-/m1/s1

描述信息

Tachysterol 3 is a normal human secosterooid metabolite from the class of vitamin D3 photoisomer derivatives. It is synthesized from 7-Dehydrocholesterol in the epidermis in response to ultraviolet irradiation. When human skin is exposed to ultraviolet radiation, epidermal 7-dehydrocholesterol is converted to previtamin D, and during prolonged exposure, the synthesis of previtamin D3 reaches a plateau at about 10 to 15 percent of the original 7-dehydrocholesterol content, and previtamin D3 is photoisomerized to two biologically inert isomers and tachysterol 3 is one of them (the other one being lumisterol 3). Therefore, tachysterol is a metabolite to chronic exposure to sunlight. Tachysterol 3, as well as other photoisomers of vitamin D3 and previtamin D3 has been demonstrated to have inhibited keratinocyte proliferation. Thus, sunlight provides vitamin D3 photoproducts that may act directly to regulate epidermal proliferation and differentiation under physiologic conditions. (PMID 6256855, 10876100) [HMDB]
Tachysterol 3 is a normal human secosterooid metabolite from the class of vitamin D3 photoisomer derivatives. It is synthesized from 7-Dehydrocholesterol in the epidermis in response to ultraviolet irradiation. When human skin is exposed to ultraviolet radiation, epidermal 7-dehydrocholesterol is converted to previtamin D, and during prolonged exposure, the synthesis of previtamin D3 reaches a plateau at about 10 to 15 percent of the original 7-dehydrocholesterol content, and previtamin D3 is photoisomerized to two biologically inert isomers and tachysterol 3 is one of them (the other one being lumisterol 3). Therefore, tachysterol is a metabolite to chronic exposure to sunlight. Tachysterol 3, as well as other photoisomers of vitamin D3 and previtamin D3 has been demonstrated to have inhibited keratinocyte proliferation. Thus, sunlight provides vitamin D3 photoproducts that may act directly to regulate epidermal proliferation and differentiation under physiologic conditions. (PMID 6256855, 10876100).

同义名列表

22 个代谢物同义名

(1S)-3-[(E)-2-[(1R,3aR,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethenyl]-4-methylcyclohex-3-en-1-ol; (3beta,6E)-9,10-Secocholesta-5(10),6,8-trien-3-ol; (6E)-(3S)-9,10-seco-5(10),6,8-cholestatrien-3-ol; (6E)-9,10-Secocholesta-5(10),6,8-trien-3beta-ol; (3Β,6E)-9,10-secocholesta-5(10),6,8-trien-3-ol; (3b,6E)-9,10-Secocholesta-5(10),6,8-trien-3-ol; (6E)-9,10-Secocholesta-5(10),6,8-trien-3b-ol; (6E)-9,10-Secocholesta-5(10),6,8-trien-3β-ol; 1,25-Dihydroxy-3-epi-19-nor-previtamin D3; Previtamin D(3), (3alpha,6Z)-isomer; Previtamin D(3), (3beta,6E)-isomer; 14-Epi-19-nortachysterol; Precholecalciferol; Previtamin D(3); (6E)-Tacalciol; Tachysterol(3); Precalciferol; Tachysterol 3; Previtamin D3; Tachysterol_3; tachysterol3; Tacalciol



数据库引用编号

6 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

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PharmGKB(0)

1 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。

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亚细胞结构定位 关联基因列表


文献列表

  • Andrzej T Slominski, Tae-Kang Kim, Radomir M Slominski, Yuwei Song, Zorica Janjetovic, Ewa Podgorska, Sivani B Reddy, Yuhua Song, Chander Raman, Edith K Y Tang, Adrian Fabisiak, Pawel Brzeminski, Rafal R Sicinski, Venkatram Atigadda, Anton M Jetten, Michael F Holick, Robert C Tuckey. Metabolic activation of tachysterol3 to biologically active hydroxyderivatives that act on VDR, AhR, LXRs, and PPARγ receptors. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2022 08; 36(8):e22451. doi: 10.1096/fj.202200578r. [PMID: 35838947]
  • Danielle L Sofferman, Arkaprabha Konar, Joseph N Mastron, Kenneth G Spears, Cecilia Cisneros, Adam C Smith, Enrico Tapavicza, Roseanne J Sension. Probing the Formation and Conformational Relaxation of Previtamin D3 and Analogues in Solution and in Lipid Bilayers. The journal of physical chemistry. B. 2021 09; 125(36):10085-10096. doi: 10.1021/acs.jpcb.1c04376. [PMID: 34473504]
  • Robert C Tuckey, Wei Li, Dejian Ma, Chloe Y S Cheng, Katie M Wang, Tae-Kang Kim, Saowanee Jeayeng, Andrzej T Slominski. CYP27A1 acts on the pre-vitamin D3 photoproduct, lumisterol, producing biologically active hydroxy-metabolites. The Journal of steroid biochemistry and molecular biology. 2018 07; 181(?):1-10. doi: 10.1016/j.jsbmb.2018.02.008. [PMID: 29452159]
  • Julia Wranicz, Dorota Szostak-Węgierek. Health outcomes of vitamin D. Part I. characteristics and classic role. Roczniki Panstwowego Zakladu Higieny. 2014; 65(3):179-84. doi: . [PMID: 25247796]
  • Tetiana Orlova, Johan Moan, Zoya Lagunova, Lage Aksnes, Irina Terenetskaya, Asta Juzeniene. Increase in serum 25-hydroxyvitamin-D3 in humans after sunbed exposures compared to previtamin D3 synthesis in vitro. Journal of photochemistry and photobiology. B, Biology. 2013 May; 122(?):32-6. doi: 10.1016/j.jphotobiol.2013.03.006. [PMID: 23591142]
  • Gordon L Klein, Tai C Chen, Michael F Holick, Craig B Langman, Heather Price, Mario M Celis, David N Herndon. Synthesis of vitamin D in skin after burns. Lancet (London, England). 2004 Jan; 363(9405):291-2. doi: 10.1016/s0140-6736(03)15388-3. [PMID: 14751703]
  • L Y Matsuoka, L Ide, J Wortsman, J A MacLaughlin, M F Holick. Sunscreens suppress cutaneous vitamin D3 synthesis. The Journal of clinical endocrinology and metabolism. 1987 Jun; 64(6):1165-8. doi: 10.1210/jcem-64-6-1165. [PMID: 3033008]
  • M F Holick. The cutaneous photosynthesis of previtamin D3: a unique photoendocrine system. The Journal of investigative dermatology. 1981 Jul; 77(1):51-8. doi: 10.1111/1523-1747.ep12479237. [PMID: 6265564]