Desmosterol (BioDeep_00000004760)

 

Secondary id: BioDeep_00000419037

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

化学式: C27H44O (384.3391974)
中文名称: 3β-羟基-5,24-胆甾二烯
谱图信息: 最多检出来源 Homo sapiens(blood) 0.6%

分子结构信息

SMILES: C/C(C)=C\CC[C@@H](C)[C@H]1CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C
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/h7,9,19,21-25,28H,6,8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

描述信息

Desmosterol is an intermediate in the synthesis of cholesterol. Desmosterolosis is a rare autosomal recessive inborn errors of cholesterol synthesis that is caused by defective activity of desmosterol reductase which results in an accumulation of demosterol (DHCR24, EC 1.3.1.72), combines a severe osteosclerotic skeletal dysplasia and includes 2-3 toe syndactyly with Smith-Lemli-Opitz syndrome (SLOS; the biochemical block in SLOS results in decreased cholesterol levels and increased 7-dehydrocholesterol levels). Desmosterolosis is caused by mutation of the 24-dehydrocholesterol reductase gene (DHCR24). Many of the malformations in SLOS and desmosterolosis are consistent with impaired hedgehog function. The hedgehog proteins include Sonic hedgehog (SHH), which plays a major role in midline patterning and limb development. Desmosterolosis, caused by defective activity of desmosterol reductase, combines a severe osteosclerotic skeletal dysplasia. 7-dehydrocholesterol reductase (DHCR7, EC 1.3.1.21) reduces the C7-C8 double bond in the sterol B ring to form cholesterol or desmosterol depending upon the precursor. Desmosterol can be converted to cholesterol by DHCR24. Therefore, SLOS and Desmosterolosis patients invariably have elevated levels of cholesterol precursors 7-dehydrocholesterol (and its spontaneous isomer 8-dehydrocholesterol) and absent desmosterol. (PMID: 14631207, 16207203). Desmosterol is found in many foods, some of which are fig, sago palm, mexican groundcherry, and pepper (c. frutescens).
Desmosterol is an intermediate in the synthesis of cholesterol. Desmosterolosis is a rare autosomal recessive inborn errors of cholesterol synthesis that is caused by defective activity of desmosterol reductase which results in an accumulation of demosterol (DHCR24, EC 1.3.1.72), combines a severe osteosclerotic skeletal dysplasia and includes 2-3 toe syndactyly with Smith-Lemli-Opitz syndrome (SLOS; the biochemical block in SLOS results in decreased cholesterol levels and increased 7-dehydrocholesterol levels). Desmosterolosis is caused by mutation of the 24-dehydrocholesterol reductase gene (DHCR24). Many of the malformations in SLOS and desmosterolosis are consistent with impaired hedgehog function. The hedgehog proteins include Sonic hedgehog (SHH), which plays a major role in midline patterning and limb development. Desmosterolosis, caused by defective activity of desmosterol reductase, combines a severe osteosclerotic skeletal dysplasia. 7-dehydrocholesterol reductase (DHCR7, EC 1.3.1.21) reduces the C7-C8 double bond in the sterol B ring to form cholesterol or desmosterol depending upon the precursor. Desmosterol can be converted to cholesterol by DHCR24. Therefore, SLOS and Desmosterolosis patients invariably have elevated levels of cholesterol precursors 7-dehydrocholesterol (and its spontaneous isomer 8-dehydrocholesterol) and absent desmosterol. (PMID: 14631207, 16207203).
Desmosterol is a molecule similar to cholesterol. Desmosterol is the immediate precursor of cholesterol in the Bloch pathway of cholesterol biosynthesis. Desmosterol, as an endogenous metabolite, used to study cholesterol metabolism[1].
Desmosterol is a molecule similar to cholesterol. Desmosterol is the immediate precursor of cholesterol in the Bloch pathway of cholesterol biosynthesis. Desmosterol, as an endogenous metabolite, used to study cholesterol metabolism[1].

同义名列表

20 个代谢物同义名

(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; (1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol; 3β-Hydroxy-5,24-cholestadiene, 5,24-Cholestadien-3β-ol; (3beta)-Cholesta-5,24-dien-3-ol; Cholesta-5,24-dien-3.beta.-ol; 3beta-Cholesta-5,24-dien-3-ol; (3Β)-cholesta-5,24-dien-3-ol; Cholesta-5,24-dien-3beta-ol; 3b-Cholesta-5,24-dien-3-ol; 3Β-cholesta-5,24-dien-3-ol; cholest-5,24-dien-3beta-ol; Cholesta-5,24-dien-3b-ol; Cholesta-5,24-dien-3β-ol; 24,25-Dehydrocholesterol; Cholesta-5,24-dien-3-ol; 24-Dehydrocholesterol; 24 Dehydrocholesterol; Desmesterol; Desmosterol; Demosterol



数据库引用编号

22 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

BioCyc(3)

PlantCyc(0)

代谢反应

342 个相关的代谢反应过程信息。

Reactome(65)

BioCyc(11)

WikiPathways(4)

Plant Reactome(3)

INOH(0)

PlantCyc(205)

COVID-19 Disease Map(0)

PathBank(54)

PharmGKB(0)

78 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。



文献列表

  • Enchen Zhou, Xiaoke Ge, Hiroyuki Nakashima, Rumei Li, Hendrik J P van der Zande, Cong Liu, Zhuang Li, Christoph Müller, Franz Bracher, Yassene Mohammed, Jan Freark de Boer, Folkert Kuipers, Bruno Guigas, Christopher K Glass, Patrick C N Rensen, Martin Giera, Yanan Wang. Inhibition of DHCR24 activates LXRα to ameliorate hepatic steatosis and inflammation. EMBO molecular medicine. 2023 Jun; ?(?):e16845. doi: 10.15252/emmm.202216845. [PMID: 37357756]
  • Haozhen Wang, Ziyin Lu, Yang Li, Ting Liu, Linlin Zhao, Tianqi Gao, Xiuli Lu, Bing Gao. Virtual Screening of Novel 24-Dehydroxysterol Reductase (DHCR24) Inhibitors and the Biological Evaluation of Irbesartan in Cholesterol-Lowering Effect. Molecules (Basel, Switzerland). 2023 Mar; 28(6):. doi: 10.3390/molecules28062643. [PMID: 36985615]
  • Valéria Sutti Nunes, Edite Vieira Silva de Campos, Jamal Baracat, Victor França, Érica Ivana Lázaro Gomes, Raissa Peres Coelho, Edna Regina Nakandakare, Vanessa Helena Souza Zago, Eliana Cotta de Faria, Eder Carlos Rocha Quintão. Plasma Campesterol Is Positively Associated with Carotid Plaques in Asymptomatic Subjects. International journal of molecular sciences. 2022 Oct; 23(19):. doi: 10.3390/ijms231911997. [PMID: 36233298]
  • Yonas Mulat Simachew, Tamara Antonić, Tamara Gojković, Sandra Vladimirov, Marija Mihajlović, Sanja Vujčić, Gordana Miloševski-Lomić, Jelena Vekić, Aleksandra Zeljković, Vesna Spasojević-Kalimanovska, Amira Peco-Antić, Dušan Paripović, Aleksandra Stefanović. Lipoproteins and cholesterol homeostasis in paediatric nephrotic syndrome patients. Biochemia medica. 2022 Jun; 32(2):020706. doi: 10.11613/bm.2022.020706. [PMID: 35799985]
  • Roubi Abuobeid, Javier Sánchez-Marco, María J Felices, Carmen Arnal, Juan Carlos Burillo, Roberto Lasheras, Rebeca Busto, Miguel A Lasunción, María Jesús Rodríguez-Yoldi, Roberto Martínez-Beamonte, Jesús Osada. Squalene through Its Post-Squalene Metabolites Is a Modulator of Hepatic Transcriptome in Rabbits. International journal of molecular sciences. 2022 Apr; 23(8):. doi: 10.3390/ijms23084172. [PMID: 35456988]
  • 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]
  • Zhi-Zhao Li, Qiong Huang, Xiao-Li Yang, Jieqiong Zeng, Qi-Hui Wang, Hai-Ming Tang, Zhen-Qiu Yu, Yu-Qing Song, Yang Liu. Cholesterol Metabolic Markers for Differential Evaluation of Patients with Hyperlipidemia and Familial Hypercholesterolemia. Disease markers. 2022; 2022(?):2008556. doi: 10.1155/2022/2008556. [PMID: 35493299]
  • Christoph Müller, Emily Hank, Martin Giera, Franz Bracher. Dehydrocholesterol Reductase 24 (DHCR24): Medicinal Chemistry, Pharmacology and Novel Therapeutic Options. Current medicinal chemistry. 2022; 29(23):4005-4025. doi: 10.2174/0929867328666211115121832. [PMID: 34781860]
  • Xinbo Zhang, Jeffrey G McDonald, Binod Aryal, Alberto Canfrán-Duque, Emily L Goldberg, Elisa Araldi, Wen Ding, Yuhua Fan, Bonne M Thompson, Abhishek K Singh, Qian Li, George Tellides, Jose Ordovás-Montanes, Rolando García Milian, Vishwa Deep Dixit, Elina Ikonen, Yajaira Suárez, Carlos Fernández-Hernando. Desmosterol suppresses macrophage inflammasome activation and protects against vascular inflammation and atherosclerosis. Proceedings of the National Academy of Sciences of the United States of America. 2021 11; 118(47):. doi: 10.1073/pnas.2107682118. [PMID: 34782454]
  • Stefan A Berghoff, Lena Spieth, Ting Sun, Leon Hosang, Lennart Schlaphoff, Constanze Depp, Tim Düking, Jan Winchenbach, Jonathan Neuber, David Ewers, Patricia Scholz, Franziska van der Meer, Ludovico Cantuti-Castelvetri, Andrew O Sasmita, Martin Meschkat, Torben Ruhwedel, Wiebke Möbius, Roman Sankowski, Marco Prinz, Inge Huitinga, Michael W Sereda, Francesca Odoardi, Till Ischebeck, Mikael Simons, Christine Stadelmann-Nessler, Julia M Edgar, Klaus-Armin Nave, Gesine Saher. Microglia facilitate repair of demyelinated lesions via post-squalene sterol synthesis. Nature neuroscience. 2021 01; 24(1):47-60. doi: 10.1038/s41593-020-00757-6. [PMID: 33349711]
  • P Simonen, S Li, N K Chua, A-M Lampi, V Piironen, J Lommi, J Sinisalo, A J Brown, E Ikonen, H Gylling. Amiodarone disrupts cholesterol biosynthesis pathway and causes accumulation of circulating desmosterol by inhibiting 24-dehydrocholesterol reductase. Journal of internal medicine. 2020 11; 288(5):560-569. doi: 10.1111/joim.13095. [PMID: 32415867]
  • María de Las Mercedes Carro, Daniel A Peñalva, Silvia S Antollini, Federico A Hozbor, Jorgelina Buschiazzo. Cholesterol and desmosterol incorporation into ram sperm membrane before cryopreservation: Effects on membrane biophysical properties and sperm quality. Biochimica et biophysica acta. Biomembranes. 2020 09; 1862(9):183357. doi: 10.1016/j.bbamem.2020.183357. [PMID: 32416195]
  • Valéria Sutti Nunes, Isabela M Bensenor, Paulo A Lotufo, Marisa Passarelli, Edna Regina Nakandakare, Eder Carlos Rocha Quintão. The coronary artery calcium score is linked to plasma cholesterol synthesis and absorption markers: Brazilian Longitudinal Study of Adult Health. Bioscience reports. 2020 07; 40(7):. doi: 10.1042/bsr20201094. [PMID: 32579186]
  • Luke B Allen, Thiago C Genaro-Mattos, Allison Anderson, Ned A Porter, Károly Mirnics, Zeljka Korade. Amiodarone Alters Cholesterol Biosynthesis through Tissue-Dependent Inhibition of Emopamil Binding Protein and Dehydrocholesterol Reductase 24. ACS chemical neuroscience. 2020 05; 11(10):1413-1423. doi: 10.1021/acschemneuro.0c00042. [PMID: 32286791]
  • Luke B Allen, Thiago C Genaro-Mattos, Ned A Porter, Károly Mirnics, Zeljka Korade. Desmosterolosis and desmosterol homeostasis in the developing mouse brain. Journal of inherited metabolic disease. 2019 09; 42(5):934-943. doi: 10.1002/jimd.12088. [PMID: 30891795]
  • Maite M Schroor, Henriette P Sennels, Jan Fahrenkrug, Henrik L Jørgensen, Jogchum Plat, Ronald P Mensink. Diurnal Variation of Markers for Cholesterol Synthesis, Cholesterol Absorption, and Bile Acid Synthesis: A Systematic Review and the Bispebjerg Study of Diurnal Variations. Nutrients. 2019 Jun; 11(7):. doi: 10.3390/nu11071439. [PMID: 31247945]
  • Seung Mi Lee, Ju-Yeon Moon, Byeong-Yun Lim, Sun Min Kim, Chan-Wook Park, Byoung Jae Kim, Jong Kwan Jun, Errol R Norwitz, Man Ho Choi, Joong Shin Park. Increased biosynthesis and accumulation of cholesterol in maternal plasma, but not amniotic fluid in pre-eclampsia. Scientific reports. 2019 02; 9(1):1550. doi: 10.1038/s41598-018-37757-3. [PMID: 30733456]
  • Sultan Mashnafi, Jogchum Plat, Ronald P Mensink, Sabine Baumgartner. Non-Cholesterol Sterol Concentrations as Biomarkers for Cholesterol Absorption and Synthesis in Different Metabolic Disorders: A Systematic Review. Nutrients. 2019 Jan; 11(1):. doi: 10.3390/nu11010124. [PMID: 30634478]
  • Elijah J Weber, Kevin A Lidberg, Lu Wang, Theo K Bammler, James W MacDonald, Mavis J Li, Michelle Redhair, William M Atkins, Cecilia Tran, Kelly M Hines, Josi Herron, Libin Xu, Maria Beatriz Monteiro, Susanne Ramm, Vishal Vaidya, Martti Vaara, Timo Vaara, Jonathan Himmelfarb, Edward J Kelly. Human kidney on a chip assessment of polymyxin antibiotic nephrotoxicity. JCI insight. 2018 12; 3(24):. doi: 10.1172/jci.insight.123673. [PMID: 30568031]
  • Phillip A Wages, Hye-Young H Kim, Zeljka Korade, Ned A Porter. Identification and characterization of prescription drugs that change levels of 7-dehydrocholesterol and desmosterol. Journal of lipid research. 2018 10; 59(10):1916-1926. doi: 10.1194/jlr.m086991. [PMID: 30087204]
  • Ai Ushiyama, Atsushi Tajima, Naoto Ishikawa, Atsushi Asano. Modification of membrane cholesterol and desmosterol in chicken spermatozoa improves post-thaw survival and prevents impairment of sperm function after cryopreservation. Reproduction, fertility, and development. 2018 Mar; 30(4):591-599. doi: 10.1071/rd17076. [PMID: 28945984]
  • P Simonen, J Lehtonen, A-M Lampi, V Piironen, U-H Stenman, M Kupari, H Gylling. Desmosterol accumulation in users of amiodarone. Journal of internal medicine. 2018 01; 283(1):93-101. doi: 10.1111/joim.12682. [PMID: 28861933]
  • Christoph Müller, Sandra Hemmers, Nicholas Bartl, Alois Plodek, Andreas Körner, Valbona Mirakaj, Martin Giera, Franz Bracher. New chemotype of selective and potent inhibitors of human delta 24-dehydrocholesterol reductase. European journal of medicinal chemistry. 2017 Nov; 140(?):305-320. doi: 10.1016/j.ejmech.2017.08.011. [PMID: 28964935]
  • Islam J A Hamdan, Lorena Claumarchirant, Guadalupe Garcia-Llatas, Amparo Alegría, María Jesús Lagarda. Sterols in infant formulas: validation of a gas chromatographic method. International journal of food sciences and nutrition. 2017 Sep; 68(6):695-703. doi: 10.1080/09637486.2017.1287883. [PMID: 28276904]
  • Ole G Mouritsen, Luis A Bagatolli, Lars Duelund, Olav Garvik, John H Ipsen, Adam Cohen Simonsen. Effects of seaweed sterols fucosterol and desmosterol on lipid membranes. Chemistry and physics of lipids. 2017 06; 205(?):1-10. doi: 10.1016/j.chemphyslip.2017.03.010. [PMID: 28365392]
  • Deirdre A Costello, Valerie A Villareal, Priscilla L Yang. Desmosterol Increases Lipid Bilayer Fluidity during Hepatitis C Virus Infection. ACS infectious diseases. 2016 11; 2(11):852-862. doi: 10.1021/acsinfecdis.6b00086. [PMID: 27933788]
  • Valerie A Villareal, Dan Fu, Deirdre A Costello, Xiaoliang Sunney Xie, Priscilla L Yang. Hepatitis C Virus Selectively Alters the Intracellular Localization of Desmosterol. ACS chemical biology. 2016 07; 11(7):1827-33. doi: 10.1021/acschembio.6b00324. [PMID: 27128812]
  • Lei Yin, Kevin Shengyang Yu, Kun Lu, Xiaozhong Yu. Benzyl butyl phthalate promotes adipogenesis in 3T3-L1 preadipocytes: A High Content Cellomics and metabolomic analysis. Toxicology in vitro : an international journal published in association with BIBRA. 2016 Apr; 32(?):297-309. doi: 10.1016/j.tiv.2016.01.010. [PMID: 26820058]
  • Isabel Andrade, Lèlita Santos, Fernando Ramos. Cholesterol absorption and synthesis markers in Portuguese hypercholesterolemic adults: A cross-sectional study. European journal of internal medicine. 2016 Mar; 28(?):85-90. doi: 10.1016/j.ejim.2015.10.022. [PMID: 26577223]
  • Ryoko Kiyotake, Masatsugu Oh-Hora, Eri Ishikawa, Tomofumi Miyamoto, Tatsuro Ishibashi, Sho Yamasaki. Human Mincle Binds to Cholesterol Crystals and Triggers Innate Immune Responses. The Journal of biological chemistry. 2015 Oct; 290(42):25322-32. doi: 10.1074/jbc.m115.645234. [PMID: 26296894]
  • Matthew G K Benesch, Ruthven N A H Lewis, Ronald N McElhaney. A calorimetric and spectroscopic comparison of the effects of cholesterol and its immediate biosynthetic precursors 7-dehydrocholesterol and desmosterol on the thermotropic phase behavior and organization of dipalmitoylphosphatidylcholine bilayer membranes. Chemistry and physics of lipids. 2015 Oct; 191(?):123-35. doi: 10.1016/j.chemphyslip.2015.09.002. [PMID: 26368000]
  • Katarzyna Hąc-Wydro, Karolina Węder, Marzena Mach, Michał Flasiński, Paweł Wydro. The influence of cholesterol precursor--desmosterol--on artificial lipid membranes. Biochimica et biophysica acta. 2015 Aug; 1848(8):1639-45. doi: 10.1016/j.bbamem.2015.04.017. [PMID: 25960185]
  • Cisem Altunayar, Ipek Sahin, Nadide Kazanci. A comparative study of the effects of cholesterol and desmosterol on zwitterionic DPPC model membranes. Chemistry and physics of lipids. 2015 May; 188(?):37-45. doi: 10.1016/j.chemphyslip.2015.03.006. [PMID: 25847673]
  • Isabel Mendiara, Karim Bentayeb, Cristina Nerín, Celia Domeño. Online solid-phase extraction-liquid chromatography-mass spectrometry to determine free sterols in human serum. Talanta. 2015 Jan; 132(?):690-7. doi: 10.1016/j.talanta.2014.10.029. [PMID: 25476366]
  • Sandeep Goyal, Yi Xiao, Ned A Porter, Libin Xu, F Peter Guengerich. Oxidation of 7-dehydrocholesterol and desmosterol by human cytochrome P450 46A1. Journal of lipid research. 2014 Sep; 55(9):1933-43. doi: 10.1194/jlr.m051508. [PMID: 25017465]
  • Lucía Baila-Rueda, Rocío Mateo-Gallego, Estibaliz Jarauta, Isabel de Castro-Orós, Ana M Bea, Ana Cenarro, Fernando Civeira. Bile acid synthesis precursors in familial combined hyperlipidemia: the oxysterols 24S-hydroxycholesterol and 27-hydroxycholesterol. Biochemical and biophysical research communications. 2014 Apr; 446(3):731-5. doi: 10.1016/j.bbrc.2013.12.131. [PMID: 24406166]
  • Winnie Luu, Eser J Zerenturk, Ika Kristiana, Martin P Bucknall, Laura J Sharpe, Andrew J Brown. Signaling regulates activity of DHCR24, the final enzyme in cholesterol synthesis. Journal of lipid research. 2014 Mar; 55(3):410-20. doi: 10.1194/jlr.m043257. [PMID: 24363437]
  • Kazuo Sugiyama, Hirotoshi Ebinuma, Nobuhiro Nakamoto, Noriko Sakasegawa, Yuko Murakami, Po-Sung Chu, Shingo Usui, Yuka Ishibashi, Yuko Wakayama, Nobuhito Taniki, Hiroko Murata, Yoshimasa Saito, Masayoshi Fukasawa, Kyoko Saito, Yoshiyuki Yamagishi, Takaji Wakita, Hiroshi Takaku, Toshifumi Hibi, Hidetsugu Saito, Takanori Kanai. Prominent steatosis with hypermetabolism of the cell line permissive for years of infection with hepatitis C virus. PloS one. 2014; 9(4):e94460. doi: 10.1371/journal.pone.0094460. [PMID: 24718268]
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