Desmosterol (BioDeep_00000004760)

 

Secondary id: BioDeep_00000419037

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019 natural product


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 (384.3392)
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) 24.29%

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

21 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; Desmosterol



数据库引用编号

26 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)

350 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 6 ALB, APOB, APOE, DHCR24, NR1H2, PCSK9
Peripheral membrane protein 2 CYP1B1, CYP27A1
Endosome membrane 3 ABCG4, APOB, LDLR
Endoplasmic reticulum membrane 7 ABCA1, ABCG1, APOB, CYP1B1, DHCR24, DHCR7, HMGCR
Mitochondrion membrane 1 CYP27A1
Nucleus 4 ALB, APOE, DHCR24, NR1H2
cytosol 4 ALB, APOA1, APOB, NR1H2
dendrite 1 APOE
phagocytic vesicle 1 ABCA1
centrosome 1 ALB
nucleoplasm 1 NR1H2
RNA polymerase II transcription regulator complex 1 NR1H2
Cell membrane 6 ABCA1, ABCG1, ABCG4, ABCG8, LDLR, TNF
Multi-pass membrane protein 6 ABCA1, ABCG1, ABCG4, ABCG8, DHCR7, HMGCR
Golgi apparatus membrane 2 ABCG1, DHCR24
cell surface 3 LDLR, PCSK9, TNF
glutamatergic synapse 1 APOE
Golgi apparatus 6 ABCA1, ABCG1, ALB, APOE, LDLR, PCSK9
Golgi membrane 3 ABCG1, DHCR24, INS
lysosomal membrane 1 PCSK9
mitochondrial inner membrane 1 CYP27A1
neuronal cell body 3 APOB, APOE, TNF
smooth endoplasmic reticulum 1 APOB
Lysosome 2 LDLR, PCSK9
endosome 3 ABCA1, ABCG1, PCSK9
plasma membrane 10 ABCA1, ABCG1, ABCG4, ABCG8, APOA1, APOB, APOE, LDLR, PCSK9, TNF
Membrane 11 ABCA1, ABCG1, ABCG4, ABCG8, APOE, CYP1B1, DHCR24, DHCR7, HMGCR, LCAT, LDLR
apical plasma membrane 1 ABCG8
basolateral plasma membrane 2 ABCA1, LDLR
extracellular exosome 5 ALB, APOA1, APOB, APOE, LCAT
endoplasmic reticulum 6 ALB, APOE, DHCR24, DHCR7, HMGCR, PCSK9
extracellular space 9 ALB, APOA1, APOB, APOE, IL6, INS, LCAT, PCSK9, TNF
lysosomal lumen 1 APOB
perinuclear region of cytoplasm 2 ABCA1, PCSK9
mitochondrion 3 ABCG1, CYP1B1, CYP27A1
protein-containing complex 1 ALB
intracellular membrane-bounded organelle 3 ABCA1, APOB, CYP1B1
Microsome membrane 1 CYP1B1
Single-pass type I membrane protein 1 LDLR
Secreted 8 ALB, APOA1, APOB, APOE, IL6, INS, LCAT, PCSK9
extracellular region 9 ALB, APOA1, APOB, APOE, IL6, INS, LCAT, PCSK9, TNF
Single-pass membrane protein 2 DHCR24, LDLR
mitochondrial matrix 1 CYP27A1
anchoring junction 1 ALB
external side of plasma membrane 4 ABCA1, ABCG1, LDLR, TNF
Endosome, multivesicular body 1 APOE
Extracellular vesicle 2 APOA1, APOE
Secreted, extracellular space, extracellular matrix 1 APOE
chylomicron 3 APOA1, APOB, APOE
high-density lipoprotein particle 3 APOA1, APOE, LCAT
low-density lipoprotein particle 4 APOA1, APOB, APOE, LDLR
multivesicular body 1 APOE
very-low-density lipoprotein particle 3 APOA1, APOB, APOE
cytoplasmic vesicle 2 ABCG4, APOA1
Early endosome 5 APOA1, APOB, APOE, LDLR, PCSK9
Membrane, clathrin-coated pit 1 LDLR
apical part of cell 1 LDLR
clathrin-coated pit 1 LDLR
COPII-coated ER to Golgi transport vesicle 1 PCSK9
recycling endosome 2 ABCG1, TNF
Single-pass type II membrane protein 1 TNF
Apical cell membrane 1 ABCG8
Mitochondrion inner membrane 1 CYP27A1
Membrane raft 2 ABCA1, TNF
extracellular matrix 1 APOE
intracellular vesicle 1 ABCA1
peroxisomal membrane 1 HMGCR
collagen-containing extracellular matrix 2 APOA1, APOE
nuclear outer membrane 1 DHCR7
Late endosome 2 LDLR, PCSK9
receptor complex 2 ABCG8, LDLR
ciliary basal body 1 ALB
chromatin 1 NR1H2
phagocytic cup 1 TNF
centriole 1 ALB
Secreted, extracellular space 1 APOE
spindle pole 1 ALB
blood microparticle 3 ALB, APOA1, APOE
Endomembrane system 1 LDLR
endosome lumen 2 APOB, INS
sorting endosome 1 LDLR
Lipid droplet 1 APOB
Cytoplasmic vesicle membrane 1 ABCG4
Melanosome 1 APOE
Peroxisome membrane 1 HMGCR
secretory granule lumen 2 APOA1, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 7 ALB, APOA1, APOB, APOE, IL6, INS, PCSK9
platelet alpha granule lumen 1 ALB
endocytic vesicle 2 ABCA1, APOA1
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
endoplasmic reticulum exit site 1 APOB
ATP-binding cassette (ABC) transporter complex 1 ABCG8
clathrin-coated endocytic vesicle membrane 3 APOB, APOE, LDLR
synaptic cleft 1 APOE
endolysosome membrane 2 LDLR, PCSK9
somatodendritic compartment 1 LDLR
extrinsic component of external side of plasma membrane 1 PCSK9
discoidal high-density lipoprotein particle 1 APOE
spherical high-density lipoprotein particle 1 APOA1
endocytic vesicle lumen 3 APOA1, APOB, APOE
PCSK9-LDLR complex 2 LDLR, PCSK9
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
chylomicron remnant 2 APOB, APOE
intermediate-density lipoprotein particle 2 APOB, APOE
lipoprotein particle 1 APOE
multivesicular body, internal vesicle 1 APOE
mature chylomicron 1 APOB
interleukin-6 receptor complex 1 IL6
PCSK9-AnxA2 complex 1 PCSK9
ciliary transition fiber 1 ALB
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


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]
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  • 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]
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  • 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]
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  • 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]
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  • 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]
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  • 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]
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