Lathosterol (BioDeep_00000636703)

Main id: BioDeep_00000004609

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


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

化学式: C27H46O (386.3548)
中文名称: 5α-胆固醇-7-烯-3ß-醇
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)CCCC(C)C)CC[C@@]4([H])C3=CC[C@@]2([H])C[C@@H](O)C1
InChI: InChI=1S/C27H46O/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/h10,18-21,23-25,28H,6-9,11-17H2,1-5H3/t19-,20+,21+,23-,24+,25+,26+,27-/m1/s1

描述信息

Lathosterol is a cholesterol-like molecule. Serum Lathosterol concentration is an indicator of whole-body cholesterol synthesis.
Lathosterol is a cholesterol-like molecule. Serum Lathosterol concentration is an indicator of whole-body cholesterol synthesis.

同义名列表

18 个代谢物同义名

Lathosterol; (3S,5S,9R,10S,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; (3S,5S,9R,10S,13R,14R,17R)-17-[(1R)-1,5-dimethylhexyl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; Cholest-7-en-3-ol, (3-beta,5-alpha)- (9CI); (3-beta,5-alpha)-Cholest-7-en-3-ol; 5-alpha-Cholest-7-en-3-beta-ol; 5alpha-Cholest-7-en-3beta-ol; delta(sup 7)-Cholestenol; 7-Cholesten-3-beta-ol; cholest-7-en-3beta-ol; Cholesterin [German]; gamma-Cholesterol; LMST01010089; CHEBI:17168; ST5331314; C01189; ST 27:1;O; Lathosterol



数据库引用编号

15 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(3)

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)

237 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 5 APOB, APOE, HTT, PCSK9, SREBF2
Peripheral membrane protein 1 CYP27A1
Endosome membrane 3 APOB, HTT, LDLR
Endoplasmic reticulum membrane 6 ABCA1, APOB, CYP7A1, DHCR7, HMGCR, SREBF2
Mitochondrion membrane 1 CYP27A1
Nucleus 3 APOE, HTT, SREBF2
autophagosome 1 HTT
cytosol 4 APOA1, APOB, HTT, SREBF2
dendrite 2 APOE, HTT
phagocytic vesicle 1 ABCA1
nucleoplasm 2 HTT, SREBF2
Cell membrane 6 ABCA1, ABCG5, ABCG8, DPP4, HTT, LDLR
lamellipodium 1 DPP4
Multi-pass membrane protein 7 ABCA1, ABCG5, ABCG8, DHCR7, HMGCR, HTT, SREBF2
Golgi apparatus membrane 1 SREBF2
Synapse 1 HTT
cell junction 1 DPP4
cell surface 3 DPP4, LDLR, PCSK9
glutamatergic synapse 1 APOE
Golgi apparatus 5 ABCA1, APOE, HTT, LDLR, PCSK9
Golgi membrane 2 INS, SREBF2
lysosomal membrane 2 DPP4, PCSK9
mitochondrial inner membrane 1 CYP27A1
neuronal cell body 2 APOB, APOE
presynaptic membrane 1 HTT
smooth endoplasmic reticulum 1 APOB
Lysosome 2 LDLR, PCSK9
endosome 2 ABCA1, PCSK9
plasma membrane 10 ABCA1, ABCG5, ABCG8, APOA1, APOB, APOE, DPP4, HTT, LDLR, PCSK9
Membrane 8 ABCA1, ABCG5, ABCG8, APOE, DHCR7, DPP4, HMGCR, LDLR
apical plasma membrane 3 ABCG5, ABCG8, DPP4
axon 1 HTT
basolateral plasma membrane 2 ABCA1, LDLR
extracellular exosome 6 APOA1, APOB, APOC3, APOE, CETP, DPP4
endoplasmic reticulum 6 APOE, DHCR7, HMGCR, HTT, PCSK9, SREBF2
extracellular space 9 APOA1, APOB, APOC3, APOE, CETP, CRP, INS, LPA, PCSK9
lysosomal lumen 1 APOB
perinuclear region of cytoplasm 3 ABCA1, HTT, PCSK9
intercellular canaliculus 1 DPP4
mitochondrion 1 CYP27A1
protein-containing complex 1 HTT
intracellular membrane-bounded organelle 4 ABCA1, APOB, CYP7A1, SREBF2
Microsome membrane 1 CYP7A1
Single-pass type I membrane protein 1 LDLR
Secreted 9 APOA1, APOB, APOC3, APOE, CETP, CRP, DPP4, INS, PCSK9
extracellular region 10 APOA1, APOB, APOC3, APOE, CETP, CRP, DPP4, INS, LPA, PCSK9
Single-pass membrane protein 3 CYP7A1, DPP4, LDLR
mitochondrial matrix 1 CYP27A1
anchoring junction 1 DPP4
external side of plasma membrane 2 ABCA1, LDLR
Endosome, multivesicular body 1 APOE
Extracellular vesicle 2 APOA1, APOE
Secreted, extracellular space, extracellular matrix 1 APOE
chylomicron 4 APOA1, APOB, APOC3, APOE
high-density lipoprotein particle 3 APOA1, APOE, CETP
low-density lipoprotein particle 4 APOA1, APOB, APOE, LDLR
multivesicular body 1 APOE
very-low-density lipoprotein particle 4 APOA1, APOB, APOC3, APOE
cytoplasmic vesicle 1 APOA1
Early endosome 7 APOA1, APOB, APOC3, APOE, HTT, 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
Single-pass type II membrane protein 1 DPP4
vesicle 1 CETP
postsynaptic membrane 1 HTT
Apical cell membrane 3 ABCG5, ABCG8, DPP4
Mitochondrion inner membrane 1 CYP27A1
Membrane raft 3 ABCA1, DPP4, HTT
Cell junction, focal adhesion 1 HTT
focal adhesion 2 DPP4, HTT
extracellular matrix 1 APOE
intracellular vesicle 1 ABCA1
peroxisomal membrane 1 HMGCR
collagen-containing extracellular matrix 3 APOA1, APOC3, APOE
nuclear outer membrane 1 DHCR7
Late endosome 3 HTT, LDLR, PCSK9
receptor complex 3 ABCG5, ABCG8, LDLR
Cell projection, neuron projection 1 HTT
neuron projection 1 HTT
chromatin 1 SREBF2
centriole 1 HTT
Secreted, extracellular space 1 APOE
blood microparticle 2 APOA1, APOE
Endomembrane system 3 DPP4, HTT, LDLR
endosome lumen 2 APOB, INS
sorting endosome 1 LDLR
Lipid droplet 1 APOB
Cytoplasmic vesicle membrane 1 HTT
Melanosome 1 APOE
Peroxisome membrane 1 HMGCR
secretory granule lumen 2 APOA1, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 5 APOA1, APOB, APOE, INS, PCSK9
endocytic vesicle 3 ABCA1, APOA1, DPP4
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
endoplasmic reticulum exit site 1 APOB
ER to Golgi transport vesicle membrane 1 SREBF2
ATP-binding cassette (ABC) transporter complex 2 ABCG5, ABCG8
clathrin-coated endocytic vesicle membrane 3 APOB, APOE, LDLR
synaptic cleft 1 APOE
endolysosome membrane 2 LDLR, PCSK9
SREBP-SCAP-Insig complex 1 SREBF2
postsynaptic cytosol 1 HTT
somatodendritic compartment 1 LDLR
extrinsic component of external side of plasma membrane 1 PCSK9
Cytoplasmic vesicle, COPII-coated vesicle membrane 1 SREBF2
presynaptic cytosol 1 HTT
discoidal high-density lipoprotein particle 1 APOE
spherical high-density lipoprotein particle 2 APOA1, APOC3
lamellipodium membrane 1 DPP4
endocytic vesicle lumen 3 APOA1, APOB, APOE
PCSK9-LDLR complex 2 LDLR, PCSK9
chylomicron remnant 2 APOB, APOE
intermediate-density lipoprotein particle 3 APOB, APOC3, APOE
lipoprotein particle 1 APOE
multivesicular body, internal vesicle 1 APOE
mature chylomicron 1 APOB
inclusion body 1 HTT
Cell projection, lamellipodium membrane 1 DPP4
Cell projection, invadopodium membrane 1 DPP4
PCSK9-AnxA2 complex 1 PCSK9
plasma lipoprotein particle 1 LPA
[Dipeptidyl peptidase 4 soluble form]: Secreted 1 DPP4
serotonergic synapse 1 HTT
[Huntingtin]: Cytoplasm 1 HTT
[Huntingtin, myristoylated N-terminal fragment]: Cytoplasmic vesicle, autophagosome 1 HTT
[Sterol regulatory element-binding protein 2]: Endoplasmic reticulum membrane 1 SREBF2
[Processed sterol regulatory element-binding protein 2]: Nucleus 1 SREBF2


文献列表

  • Valéria Sutti Nunes, Angela de Oliveira Godoy Ilha, Guilherme da Silva Ferreira, Renata de Paula Assis Bombo, Milessa Silva Afonso, Maria Silvia Ferrari Lavrador, Roberta Marcondes Machado, Edna Regina Nakandakare, Eder Carlos Rocha Quintão, Ana Maria Lottenberg. Plasma lathosterol measures rates of cholesterol synthesis and efficiency of dietary phytosterols in reducing the plasma cholesterol concentration. Clinics (Sao Paulo, Brazil). 2022; 77(?):100028. doi: 10.1016/j.clinsp.2022.100028. [PMID: 35397367]
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  • Ivana Semova, Amy E Levenson, Joanna Krawczyk, Kevin Bullock, Kathryn A Williams, R Paul Wadwa, Philip R Khoury, Thomas R Kimball, Elaine M Urbina, Sarah D de Ferranti, David M Maahs, Lawrence M Dolan, Amy S Shah, Clary B Clish, Sudha B Biddinger. Markers of cholesterol synthesis are elevated in adolescents and young adults with type 2 diabetes. Pediatric diabetes. 2020 11; 21(7):1126-1131. doi: 10.1111/pedi.13097. [PMID: 32738021]
  • 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]
  • Hiroshi Yoshida, Hayato Tada, Kumie Ito, Yoshimi Kishimoto, Hidekatsu Yanai, Tomonori Okamura, Katsunori Ikewaki, Kyoko Inagaki, Tetsuo Shoji, Hideaki Bujo, Takashi Miida, Masayuki Yoshida, Masafumi Kuzuya, Shizuya Yamashita. Reference Intervals of Serum Non-Cholesterol Sterols by Gender in Healthy Japanese Individuals. Journal of atherosclerosis and thrombosis. 2020 May; 27(5):409-417. doi: 10.5551/jat.50187. [PMID: 31484845]
  • Hammad Ullah, Ajmal Khan, Najeeb Ur Rehman, Sobia Ahsan Halim, Haroon Khan, Imran Khan, Rene Csuk, Ahmed Al-Rawahi, Saif Al-Hatmi, Ahmed Al-Harrasi. Lophenol and lathosterol from resin of Commiphora kua possess hepatoprotective effects in vivo. Journal of ethnopharmacology. 2020 Apr; 252(?):112558. doi: 10.1016/j.jep.2020.112558. [PMID: 31926985]
  • Monica Gelzo, Maria Donata Di Taranto, Concetta Sica, Antonio Boscia, Francesco Papagni, Giuliana Fortunato, Gaetano Corso, Antonio Dello Russo. Age-related changes of cholestanol and lathosterol plasma concentrations: an explorative study. Lipids in health and disease. 2019 Dec; 18(1):235. doi: 10.1186/s12944-019-1176-3. [PMID: 31888647]
  • Oliver Weingärtner, Dieter Lütjohann, Sven Meyer, Arne Fuhrmann, Bodo Cremers, Sarah Seiler-Mußler, Hans-F Schött, Anja Kerksiek, Silvia Friedrichs, Ursula Ulbricht, Adam Zawada, Ulrich Laufs, P Christian Schulze, Bruno Scheller, Danilo Fliser, Michael Böhm, Eric Sijbrands, Gunnar H Heine. Low serum lathosterol levels associate with fatal cardiovascular disease and excess all-cause mortality: a prospective cohort study. Clinical research in cardiology : official journal of the German Cardiac Society. 2019 Dec; 108(12):1381-1385. doi: 10.1007/s00392-019-01474-2. [PMID: 30949753]
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  • Elizabeth A Babawale, Peter Jh Jones, Kelly E Mercer, Haixia Lin, Laxmi Yeruva, Fabiana Bar Yoseph, Shane M Rutherfurd. Modulating Sterol Concentrations in Infant Formula Influences Cholesterol Absorption and Synthesis in the Neonatal Piglet. Nutrients. 2018 Dec; 10(12):. doi: 10.3390/nu10121848. [PMID: 30513717]
  • Natalia Mast, Ilya R Bederman, Irina A Pikuleva. Retinal Cholesterol Content Is Reduced in Simvastatin-Treated Mice Due to Inhibited Local Biosynthesis Albeit Increased Uptake of Serum Cholesterol. Drug metabolism and disposition: the biological fate of chemicals. 2018 11; 46(11):1528-1537. doi: 10.1124/dmd.118.083345. [PMID: 30115644]
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  • 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]
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  • Akinori Sawamura, Takahiro Okumura, Hiroaki Hiraiwa, Soichiro Aoki, Toru Kondo, Takeo Ichii, Kenji Furusawa, Naoki Watanabe, Naoaki Kano, Kenji Fukaya, Ryota Morimoto, Yasuko K Bando, Toyoaki Murohara. Cholesterol metabolism as a prognostic marker in patients with mildly symptomatic nonischemic dilated cardiomyopathy. Journal of cardiology. 2017 Jun; 69(6):888-894. doi: 10.1016/j.jjcc.2016.08.012. [PMID: 27686044]
  • Frans Stellaard, Klaus von Bergmann, Thomas Sudhop, Dieter Lütjohann. The value of surrogate markers to monitor cholesterol absorption, synthesis and bioconversion to bile acids under lipid lowering therapies. The Journal of steroid biochemistry and molecular biology. 2017 05; 169(?):111-122. doi: 10.1016/j.jsbmb.2016.03.030. [PMID: 27060336]
  • Oliver Weingärtner, Ivan Bogeski, Carsten Kummerow, Stephan H Schirmer, Constanze Husche, Tim Vanmierlo, Gudrun Wagenpfeil, Markus Hoth, Michael Böhm, Dieter Lütjohann, Ulrich Laufs. Plant sterol ester diet supplementation increases serum plant sterols and markers of cholesterol synthesis, but has no effect on total cholesterol levels. The Journal of steroid biochemistry and molecular biology. 2017 05; 169(?):219-225. doi: 10.1016/j.jsbmb.2016.07.016. [PMID: 27473562]
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  • Eva Herzog, Ingo Pragst, Marcel Waelchli, Andreas Gille, Sabrina Schenk, Jochen Mueller-Cohrs, Svetlana Diditchenko, Paolo Zanoni, Marina Cuchel, Andreas Seubert, Daniel J Rader, Samuel D Wright. Reconstituted high-density lipoprotein can elevate plasma alanine aminotransferase by transient depletion of hepatic cholesterol: role of the phospholipid component. Journal of applied toxicology : JAT. 2016 08; 36(8):1038-47. doi: 10.1002/jat.3264. [PMID: 26651060]
  • Piia Simonen, Jukka Lehtonen, Helena Gylling, Markku Kupari. Cholesterol metabolism in cardiac sarcoidosis. Atherosclerosis. 2016 May; 248(?):210-5. doi: 10.1016/j.atherosclerosis.2016.03.018. [PMID: 27035112]
  • Wendy Whiteside, Meng Tan, Richard E Ostlund, Sunkyung Yu, Lina Ma, Albert Rocchini. Altered Cholesterol Metabolism and Hypocholesterolemia in Patients with Single Ventricle following Fontan Palliation. The Journal of pediatrics. 2016 Apr; 171(?):73-7. doi: 10.1016/j.jpeds.2015.12.038. [PMID: 26806364]
  • R T Ras, W P Koppenol, U Garczarek, A Otten-Hofman, D Fuchs, F Wagner, E A Trautwein. Increases in plasma plant sterols stabilize within four weeks of plant sterol intake and are independent of cholesterol metabolism. Nutrition, metabolism, and cardiovascular diseases : NMCD. 2016 Apr; 26(4):302-9. doi: 10.1016/j.numecd.2015.11.007. [PMID: 26806045]
  • 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]
  • Andrea Mignarri, Alessandro Magni, Marina Del Puppo, Gian Nicola Gallus, Ingemar Björkhem, Antonio Federico, Maria Teresa Dotti. Evaluation of cholesterol metabolism in cerebrotendinous xanthomatosis. Journal of inherited metabolic disease. 2016 Jan; 39(1):75-83. doi: 10.1007/s10545-015-9873-1. [PMID: 26153518]
  • Dylan S MacKay, Peter K Eck, Sarah K Gebauer, David J Baer, Peter Jh Jones. CYP7A1-rs3808607 and APOE isoform associate with LDL cholesterol lowering after plant sterol consumption in a randomized clinical trial. The American journal of clinical nutrition. 2015 Oct; 102(4):951-7. doi: 10.3945/ajcn.115.109231. [PMID: 26333513]
  • Valerio Leoni, Claudio Caccia. The impairment of cholesterol metabolism in Huntington disease. Biochimica et biophysica acta. 2015 Aug; 1851(8):1095-105. doi: 10.1016/j.bbalip.2014.12.018. [PMID: 25596342]
  • Suzy A A Comhair, Jonathan McDunn, Carole Bennett, Jade Fettig, Serpil C Erzurum, Satish C Kalhan. Metabolomic Endotype of Asthma. Journal of immunology (Baltimore, Md. : 1950). 2015 Jul; 195(2):643-50. doi: 10.4049/jimmunol.1500736. [PMID: 26048149]
  • Fredrik Rosqvist, Annika Smedman, Helena Lindmark-Månsson, Marie Paulsson, Paul Petrus, Sara Straniero, Mats Rudling, Ingrid Dahlman, Ulf Risérus. Potential role of milk fat globule membrane in modulating plasma lipoproteins, gene expression, and cholesterol metabolism in humans: a randomized study. The American journal of clinical nutrition. 2015 Jul; 102(1):20-30. doi: 10.3945/ajcn.115.107045. [PMID: 26016870]
  • Hyun-Hwa Son, Shin Hye Kim, Ju-Yeon Moon, Bong Chul Chung, Mi Jung Park, Man Ho Choi. Serum sterol profiling reveals increased cholesterol biosynthesis in childhood obesity. The Journal of steroid biochemistry and molecular biology. 2015 May; 149(?):138-45. doi: 10.1016/j.jsbmb.2015.02.012. [PMID: 25725317]
  • Dylan S Mackay, Sarah K Gebauer, Peter K Eck, David J Baer, Peter J H Jones. Lathosterol-to-cholesterol ratio in serum predicts cholesterol-lowering response to plant sterol consumption in a dual-center, randomized, single-blind placebo-controlled trial. The American journal of clinical nutrition. 2015 Mar; 101(3):432-9. doi: 10.3945/ajcn.114.095356. [PMID: 25733626]
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