7-Dehydrocholesterol (BioDeep_00000004599)

 

Secondary id: BioDeep_00000405188, BioDeep_00000636699

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019 natural product


代谢物信息卡片


(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol

化学式: C27H44O (384.3392)
中文名称: Δ5,7-胆固醇
谱图信息: 最多检出来源 Homo sapiens(blood) 25.27%

分子结构信息

SMILES: C1[C@@H](CC2=CC=C3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC[C@@H]1[C@@H](CCCC(C)C)C)C)O
InChI: InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1

描述信息

7-Dehydrocholesterol (7-DHC), also known as provitamin D3 or 5,7-cholestadien-3-b-ol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 7-dehydrocholesterol is also classified as a sterol. 7-Dehydrocholesterol is known as a zoosterol, meaning that it is a sterol isolated from animals (to distinguish those sterols isolated from plants which are called phytosterols). 7-DHC functions in the serum as a cholesterol precursor and is photochemically converted to vitamin D3 in the skin. Therefore 7-DHC functions as provitamin-D3. The presence of 7-DHC in human skin enables humans and other mammals to manufacture vitamin D3 (cholecalciferol) from ultraviolet rays in the sun light, via an intermediate isomer pre-vitamin D3. 7-DHC absorbs UV light most effectively at wavelengths between 290 and 320 nm and, thus, the production of vitamin D3 will occur primarily at those wavelengths (PMID: 9625080). The two most important factors that govern the generation of pre-vitamin D3 are the quantity (intensity) and quality (appropriate wavelength) of the UVB irradiation reaching the 7-dehydrocholesterol deep in the stratum basale and stratum spinosum (PMID: 9625080). 7-DHC is also found in the milk of several mammalian species, including cows (PMID: 10999630; PMID: 225459). It was discovered by Nobel-laureate organic chemist Adolf Windaus. 7-DHC can be produced by animals and plants via different pathways (PMID: 23717318). It is not produced by fungi in significant amounts. 7-DHC is made by some algae and can also be produced by some bacteria.
7-Dehydrocholesterol is a zoosterol (a sterol produced by animals rather than plants). It is a provitamin-D. The presence of this compound in skin enables humans to manufacture vitamin D3 from ultra-violet rays in the sun light, via an intermediate isomer provitamin D3. It is also found in breast milk. [HMDB]
D018977 - Micronutrients > D014815 - Vitamins > D000072664 - Provitamins
7-Dehydrocholesterol is biosynthetic precursor of cholesterol and vitamin D3.
7-Dehydrocholesterol is biosynthetic precursor of cholesterol and vitamin D3.

同义名列表

46 个代谢物同义名

(1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol; 17-(1,5-Dimethylhexyl)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; 10,13-Dimethyl-17-(6-methylheptan-2-yl)-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol; 7-Dehydrocholesterol, (3beta,9beta,10alpha)-isomer; 7-Dehydrocholesterol, (3beta,10alpha)-isomer; 7-Dehydrocholesterol, (3beta,9beta)-isomer; Provitamin D3,Cholesta-5,7-dien-3beta-ol; 7-Dehydrocholesterol, (3alpha)-isomer; 3β-Hydroxy-5,7-cholestadiene; Delta5,7-Cholestadien-3beta-ol; (3beta)-Cholesta-5,7-dien-3-ol; Cholesta-5,7-dien-3 beta -ol; (3b)-Cholesta-5,7-dien-3-ol; Cholesta-5,7-dien-3 beta-ol; Cholesta-5,7-dien-3-beta-ol; (3Β)-cholesta-5,7-dien-3-ol; 5,7-Cholestadien-3β-ol; 5,7-Cholestandien-3beta-ol; 5,7-Cholestadien-3-beta-ol; cholesta-5,7-dien-3beta-ol; (3β)-7-Dehydro Cholesterol; 5,7-Cholestadien-3beta-ol; 7,8-Didehydrocholesterol; (-)-7-Dehydrocholesterol; Cholesta-5,7-dien-3β-ol; Cholesta-5,7-dien-3b-ol; 5,7-Cholestadien-3-b-ol; 5,7-Cholestadien-3-β-ol; 7,8-Dehydro-cholesterol; Cholesta-5,7-dien-3-ol; 5,7-Cholestadien-3β-ol; 5,7-Cholestandien-3-ol; 5,7-Cholestadien-3b-ol; 7-Dehydro-cholesterol; Delta5,7-Cholesterol; 7-Dehydrocholesterol; 7-Dehydrocholesterin; Delta7-Cholesterol; Dehydrocholesterin; Dehydrocholesterol; Provitamin D(3); Provitamin-D3; Provitamin D3; 7-DHC; 7DHC; 7-Dehydrocholesterol



数据库引用编号

24 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(5)

BioCyc(3)

PlantCyc(3)

代谢反应

180 个相关的代谢反应过程信息。

Reactome(76)

BioCyc(6)

WikiPathways(12)

Plant Reactome(4)

INOH(2)

PlantCyc(31)

COVID-19 Disease Map(0)

PathBank(49)

PharmGKB(0)

67 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 7 AKT1, CYP27B1, CYP2R1, DHCR24, IDI1, SMO, VDR
Peripheral membrane protein 4 CYP11A1, CYP1B1, CYP27A1, FDXR
Endoplasmic reticulum membrane 9 CYP1B1, CYP2R1, CYP7A1, DHCR24, DHCR7, EBP, FDFT1, HMGCR, SC5D
Mitochondrion membrane 3 CYP11A1, CYP27A1, CYP27B1
Nucleus 4 AKT1, DHCR24, SMO, VDR
cytosol 4 AKT1, IDI1, SMO, VDR
dendrite 1 SMO
nucleoplasm 3 AKT1, SMO, VDR
RNA polymerase II transcription regulator complex 1 VDR
Cell membrane 3 AKT1, GPRC5A, SMO
lamellipodium 1 AKT1
Multi-pass membrane protein 7 DHCR7, EBP, FDFT1, GPRC5A, HMGCR, SC5D, SMO
Golgi apparatus membrane 1 DHCR24
cell cortex 1 AKT1
glutamatergic synapse 1 AKT1
Golgi apparatus 1 SMO
Golgi membrane 1 DHCR24
mitochondrial inner membrane 4 CYP11A1, CYP24A1, CYP27A1, FDXR
postsynapse 1 AKT1
plasma membrane 3 AKT1, GPRC5A, SMO
Membrane 8 AKT1, CYP11A1, CYP1B1, DHCR24, DHCR7, FDFT1, HMGCR, SC5D
extracellular exosome 2 GPRC5A, SMO
endoplasmic reticulum 7 DHCR24, DHCR7, EBP, FDFT1, HMGCR, SC5D, SMO
extracellular space 1 PTH
mitochondrion 6 CYP11A1, CYP1B1, CYP24A1, CYP27A1, CYP27B1, FDXR
protein-containing complex 1 AKT1
intracellular membrane-bounded organelle 5 CYP1B1, CYP2R1, CYP7A1, GPRC5A, SMO
Microsome membrane 3 CYP1B1, CYP2R1, CYP7A1
extracellular region 1 PTH
Single-pass membrane protein 2 CYP7A1, DHCR24
mitochondrial outer membrane 1 CYP27B1
mitochondrial matrix 3 CYP11A1, CYP27A1, FDXR
Cell projection, cilium 1 SMO
ciliary membrane 1 SMO
nuclear membrane 2 EBP, SMO
cytoplasmic vesicle 1 EBP
microtubule cytoskeleton 1 AKT1
nucleolus 1 GPRC5A
cell-cell junction 1 AKT1
vesicle 2 AKT1, GPRC5A
Mitochondrion inner membrane 3 CYP11A1, CYP27A1, FDXR
spindle 1 AKT1
Peroxisome 1 IDI1
peroxisomal membrane 1 HMGCR
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
ciliary tip 1 SMO
nuclear outer membrane 1 DHCR7
Late endosome 1 SMO
receptor complex 2 GPRC5A, VDR
ciliary basal body 1 AKT1
cilium 1 SMO
chromatin 1 VDR
centriole 1 SMO
nuclear envelope 1 EBP
Nucleus envelope 1 EBP
Cytoplasmic vesicle membrane 1 GPRC5A
Peroxisome membrane 1 HMGCR
endocytic vesicle membrane 1 SMO
9+0 non-motile cilium 1 SMO
endoplasmic reticulum-Golgi intermediate compartment 1 SMO


文献列表

  • Shaojie Cui, Jin Ye. 7-Dehydrocholesterol: A sterol shield against an iron sword. Molecular cell. 2024 Apr; 84(7):1183-1185. doi: 10.1016/j.molcel.2024.03.003. [PMID: 38579675]
  • Thiago C Genaro-Mattos, Zeljka Korade, Namood-E Sahar, Jose Pedro Friedmann Angeli, Károly Mirnics, Eric S Peeples. Enhancing 7-dehydrocholesterol suppresses brain ferroptosis and tissue injury after neonatal hypoxia-ischemia. Scientific reports. 2024 04; 14(1):7924. doi: 10.1038/s41598-024-58579-6. [PMID: 38575644]
  • Florencio Porto Freitas, Hamed Alborzinia, Ancély Ferreira Dos Santos, Palina Nepachalovich, Lohans Pedrera, Omkar Zilka, Alex Inague, Corinna Klein, Nesrine Aroua, Kamini Kaushal, Bettina Kast, Svenja M Lorenz, Viktoria Kunz, Helene Nehring, Thamara N Xavier da Silva, Zhiyi Chen, Sena Atici, Sebastian G Doll, Emily L Schaefer, Ifedapo Ekpo, Werner Schmitz, Aline Horling, Peter Imming, Sayuri Miyamoto, Ann M Wehman, Thiago C Genaro-Mattos, Karoly Mirnics, Lokender Kumar, Judith Klein-Seetharaman, Svenja Meierjohann, Isabel Weigand, Matthias Kroiss, Georg W Bornkamm, Fernando Gomes, Luis Eduardo Soares Netto, Manjima B Sathian, David B Konrad, Douglas F Covey, Bernhard Michalke, Kurt Bommert, Ralf C Bargou, Ana Garcia-Saez, Derek A Pratt, Maria Fedorova, Andreas Trumpp, Marcus Conrad, José Pedro Friedmann Angeli. 7-Dehydrocholesterol is an endogenous suppressor of ferroptosis. Nature. 2024 Jan; ?(?):. doi: 10.1038/s41586-023-06878-9. [PMID: 38297129]
  • Xia Ke, Zi-Hao Pan, Hong-Fei Du, Yi Shen, Ji-Dong Shen, Zhi-Qiang Liu, Yu-Guo Zheng. Secretory Production of 7-dehydrocholesterol by Engineered Saccharomyces cerevisiae. Biotechnology journal. 2023 Sep; ?(?):e2300056. doi: 10.1002/biot.202300056. [PMID: 37688450]
  • Yitao Luo, Chengqiang Zhang, Li Ma, Yuxiao Zhang, Zhengyuan Liu, Li Chen, Rui Wang, Yujing Luan, Yulan Rao. Measurement of 7-dehydrocholesterol and cholesterol in hair can be used in the diagnosis of Smith-Lemli-Opitz syndrome. Journal of lipid research. 2022 06; 63(6):100228. doi: 10.1016/j.jlr.2022.100228. [PMID: 35577137]
  • Erik Stokstad. Engineered tomatoes get a healthy dose of vitamin D. Science (New York, N.Y.). 2022 05; 376(6596):907. doi: 10.1126/science.add1587. [PMID: 35617417]
  • Basar Cenik, Jayme M Palka, Bonne M Thompson, Jeffrey G McDonald, Carol A Tamminga, Can Cenik, E Sherwood Brown. Desmosterol and 7-dehydrocholesterol concentrations in post mortem brains of depressed people: The role of trazodone. Translational psychiatry. 2022 04; 12(1):139. doi: 10.1038/s41398-022-01903-3. [PMID: 35379782]
  • Ian Delahunty, Jianwen Li, Wen Jiang, Chaebin Lee, Xueyuan Yang, Anil Kumar, Zhi Liu, Weizhong Zhang, Jin Xie. 7-Dehydrocholesterol Encapsulated Polymeric Nanoparticles As a Radiation-Responsive Sensitizer for Enhancing Radiation Therapy. Small (Weinheim an der Bergstrasse, Germany). 2022 04; 18(17):e2200710. doi: 10.1002/smll.202200710. [PMID: 35304816]
  • Yitao Luo, Zhengyuan Liu, Yujie Zeng, Yuxiao Zhang, Yujing Luan, Li Ma, Li Chen, Lin Zou, Jingmin Yang, Zhibin Huang, Yulan Rao, Chengqiang Zhang. A reliable tool for detecting 7-dehydrocholesterol and cholesterol in human plasma and its use in diagnosis of Smith-Lemli-Opitz syndrome. Journal of separation science. 2022 Mar; 45(5):1080-1093. doi: 10.1002/jssc.202100594. [PMID: 34962712]
  • Katalin Koczok, László Horváth, Zeljka Korade, Zoltán András Mezei, Gabriella P Szabó, Ned A Porter, Eszter Kovács, Károly Mirnics, István Balogh. Biochemical and Clinical Effects of Vitamin E Supplementation in Hungarian Smith-Lemli-Opitz Syndrome Patients. Biomolecules. 2021 08; 11(8):. doi: 10.3390/biom11081228. [PMID: 34439893]
  • Tatsunosuke Tomita, Renu Wadhwa, Sunil C Kaul, Ryoji Kurita, Naoshi Kojima, Yoshiaki Onishi. Withanolide Derivative 2,3-Dihydro-3β-methoxy Withaferin-A Modulates the Circadian Clock via Interaction with RAR-Related Orphan Receptor α (RORa). Journal of natural products. 2021 07; 84(7):1882-1888. doi: 10.1021/acs.jnatprod.0c01276. [PMID: 34152143]
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  • Danielle L Sofferman, Arkaprabha Konar, Kenneth G Spears, Roseanne J Sension. Ultrafast excited state dynamics of provitamin D3 and analogs in solution and in lipid bilayers. The Journal of chemical physics. 2021 Mar; 154(9):094309. doi: 10.1063/5.0041375. [PMID: 33685160]
  • Jonas Abdel-Khalik, Thomas Hearn, Alison L Dickson, Peter J Crick, Eylan Yutuc, Karl Austin-Muttitt, Brian W Bigger, Andrew A Morris, Cedric H Shackleton, Peter T Clayton, Takashi Iida, Ria Sircar, Rajat Rohatgi, Hanns-Ulrich Marschall, Jan Sjövall, Ingemar Björkhem, Jonathan G L Mullins, William J Griffiths, Yuqin Wang. Bile acid biosynthesis in Smith-Lemli-Opitz syndrome bypassing cholesterol: Potential importance of pathway intermediates. The Journal of steroid biochemistry and molecular biology. 2021 02; 206(?):105794. doi: 10.1016/j.jsbmb.2020.105794. [PMID: 33246156]
  • Maurizio Cutolo, Stefano Soldano, Alberto Sulli, Vanessa Smith, Emanuele Gotelli. Influence of Seasonal Vitamin D Changes on Clinical Manifestations of Rheumatoid Arthritis and Systemic Sclerosis. Frontiers in immunology. 2021; 12(?):683665. doi: 10.3389/fimmu.2021.683665. [PMID: 34267753]
  • Mikis Kiourtzidis, Julia Kühn, Corinna Brandsch, Gabriele I Stangl. Vitamin D Status of Mice Deficient in Scavenger Receptor Class B Type 1, Cluster Determinant 36 and ATP-Binding Cassette Proteins G5/G8. Nutrients. 2020 Jul; 12(8):. doi: 10.3390/nu12082169. [PMID: 32707802]
  • Hiroshi Iwasaki, Masaki Wakamatsu, Kazunari Sugihara, Kyohei Kamio, Satoshi Tsuji, Junya Morita, Yasuhiro Kurihara, Tomoko Izumi, Tomohiro Nishimoto, Kohnosuke Kinoshita, Yutaka Nakanishi, Minoru Sasaki. Drug-induced lenticular opacity and accumulation of cholesterol-related substances in the lens cortex of dogs. The Journal of toxicological sciences. 2020; 45(4):201-218. doi: 10.2131/jts.45.201. [PMID: 32238695]
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