3beta-hydroxy-5-cholestenoate (BioDeep_00000011647)
Secondary id: BioDeep_00001869641
human metabolite Endogenous blood metabolite
代谢物信息卡片
化学式: C27H44O3 (416.329)
中文名称: 3β-羟基-5-胆甾烯酸
谱图信息:
最多检出来源 Homo sapiens(blood) 8.34%
Last reviewed on 2024-09-14.
Cite this Page
3beta-hydroxy-5-cholestenoate. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China.
https://query.biodeep.cn/s/3beta-hydroxy-5-cholestenoate (retrieved
2024-12-22) (BioDeep RN: BioDeep_00000011647). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
分子结构信息
SMILES: CC(CCCC(C)C(=O)O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
InChI: InChI=1S/C27H44O3/c1-17(6-5-7-18(2)25(29)30)22-10-11-23-21-9-8-19-16-20(28)12-14-26(19,3)24(21)13-15-27(22,23)4/h8,17-18,20-24,28H,5-7,9-16H2,1-4H3,(H,29,30)/t17-,18-,20+,21+,22-,23+,24+,26+,27-/m1/s1
描述信息
3beta-Hydroxy-5-cholestenoic acid (CAS: 6561-58-6) belongs to the class of organic compounds known as monohydroxy bile acids, alcohols, and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. 3beta-Hydroxy-5-cholestenoic acid is found in the primary bile acid biosynthesis pathway. 3beta-Hydroxy-5-cholestenoic acid is created from cholest-5-ene-3 beta,26-diol through the action of CYP27A (EC 1.14.13.15). 3beta-Hydroxy-5-cholestenoic acid is then converted into 3beta,7alpha-dihydroxy-5-cholestenoic acid by the action of CYP7B (EC 1.14.13.100). 3beta-Hydroxy-5-cholestenoic acid was identified as one of forty plasma metabolites that could be used to predict gut microbiome Shannon diversity (PMID: 31477923). Shannon diversity is a metric that summarizes both species abundance and evenness, and it has been suggested as a marker for microbiome health.
同义名列表
25 个代谢物同义名
(2R,6R)-6-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]-2-methylheptanoic acid; (3beta,25R)-3-Hydroxycholest-5-en-26-oic acid; (3β,25R)-3-Hydroxycholest-5-en-26-oic acid; (3beta)-3-Hydroxycholest-5-en-26-oic acid; (25R)-3b-Hydroxycholest-5-en-26-Oic acid; (25R)-3Β-hydroxycholest-5-en-26-Oic acid; (25R)-3beta-Hydroxycholest-5-en-26-Oate; 3β-Hydroxycholest-5-en-26-oic acid; (3β)-3-Hydroxycholest-5-en-26-oic acid; 3beta-Hydroxycholest-5-en-27-oic acid; 3beta-Hydroxycholest-5-en-26-oic acid; (25R)-3Β-hydroxycholest-5-en-26-Oate; (25R)-3b-Hydroxycholest-5-en-26-Oate; 5-Cholesten-3-ol-25-carboxylic acid; 3β-Hydroxycholest-5-en-26-oic acid; 3β-Hydroxycholest-5-en-27-oic acid; 3beta-hydroxy-5-cholestenoic acid; 3b-Hydroxy-5-cholestenoic acid; 3Β-hydroxy-5-cholestenoic acid; 3beta-Hydroxy-5-cholestenoate; 3Β-hydroxy-5-cholestenoate; 3b-Hydroxy-5-cholestenoate; Cholestenoic acid; SCHEMBL10106699; 3beta-Hydroxy-5-cholestenoate
数据库引用编号
15 个数据库交叉引用编号
- ChEBI: CHEBI:86378
- ChEBI: CHEBI:81014
- KEGG: C17333
- PubChem: 40579073
- PubChem: 9909847
- PubChem: 165511
- HMDB: HMDB0012453
- Metlin: METLIN43082
- foodb: FDB111635
- chemspider: 25942571
- CAS: 6561-58-6
- PMhub: MS000025717
- PubChem: 96023695
- NIKKAJI: J676.103H
- KNApSAcK: 81014
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
1 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
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。
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
- Yaping Wang, William M Pandak, Phillip B Hylemon, Hae-Ki Min, John Min, Michael Fuchs, Arun J Sanyal, Shunlin Ren. Cholestenoic Acid as Endogenous Epigenetic Regulator Decreases Hepatocyte Lipid Accumulation in Vitro and in Vivo.
American journal of physiology. Gastrointestinal and liver physiology.
2023 Nov; ?(?):. doi:
10.1152/ajpgi.00184.2023. [PMID: 37961761] - Lautaro D Alvarez, María V Dansey, María F Ogara, Carina I Peña, René Houtman, Adriana S Veleiro, Adali Pecci, Gerardo Burton. Cholestenoic acid analogues as inverse agonists of the liver X receptors.
The Journal of steroid biochemistry and molecular biology.
2020 05; 199(?):105585. doi:
10.1016/j.jsbmb.2020.105585. [PMID: 31931135] - Peter J Crick, Eylan Yutuc, Jonas Abdel-Khalik, Ahmed Saeed, Christer Betsholtz, Guillem Genove, Ingemar Björkhem, Yuqin Wang, William J Griffiths. Formation and metabolism of oxysterols and cholestenoic acids found in the mouse circulation: Lessons learnt from deuterium-enrichment experiments and the CYP46A1 transgenic mouse.
The Journal of steroid biochemistry and molecular biology.
2019 12; 195(?):105475. doi:
10.1016/j.jsbmb.2019.105475. [PMID: 31541728] - Yunlu He, Yanbo Luo, Huan Chen, Jian Chen, Yaning Fu, Hongwei Hou, Qingyuan Hu. Profiling of carboxyl-containing metabolites in smokers and non-smokers by stable isotope labeling combined with LC-MS/MS.
Analytical biochemistry.
2019 03; 569(?):1-9. doi:
10.1016/j.ab.2018.12.006. [PMID: 30543805] - William J Griffiths, Peter J Crick, Anna Meljon, Spyridon Theofilopoulos, Jonas Abdel-Khalik, Eylan Yutuc, Josie E Parker, Diane E Kelly, Steven L Kelly, Ernest Arenas, Yuqin Wang. Additional pathways of sterol metabolism: Evidence from analysis of Cyp27a1-/- mouse brain and plasma.
Biochimica et biophysica acta. Molecular and cell biology of lipids.
2019 02; 1864(2):191-211. doi:
10.1016/j.bbalip.2018.11.006. [PMID: 30471425] - Cristian R Rodriguez, Lautaro D Alvarez, M Virginia Dansey, Luciano S Paolo, Adriana S Veleiro, Adali Pecci, Gerardo Burton. Fluorinated oxysterol analogues: Synthesis, molecular modelling and LXRβ activity.
The Journal of steroid biochemistry and molecular biology.
2017 01; 165(Pt B):268-276. doi:
10.1016/j.jsbmb.2016.07.001. [PMID: 27452335] - Lautaro D Álvarez, M Virginia Dansey, Diego Y Grinman, Daniela Navalesi, Gisela A Samaja, M Celeste Del Fueyo, Niek Bastiaensen, René Houtman, Darío A Estrin, Adriana S Veleiro, Adali Pecci, Gerardo Burton. Destabilization of the torsioned conformation of a ligand side chain inverts the LXRβ activity.
Biochimica et biophysica acta.
2015 Dec; 1851(12):1577-86. doi:
10.1016/j.bbalip.2015.09.007. [PMID: 26434697] - Joo In Jung, Ashleigh R Price, Thomas B Ladd, Yong Ran, Hyo-Jin Park, Carolina Ceballos-Diaz, Lisa A Smithson, Günther Hochhaus, Yufei Tang, Rajender Akula, Saritha Ba, Edward H Koo, Gideon Shapiro, Kevin M Felsenstein, Todd E Golde. Cholestenoic acid, an endogenous cholesterol metabolite, is a potent γ-secretase modulator.
Molecular neurodegeneration.
2015 Jul; 10(?):29. doi:
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Steroids.
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10.1016/j.steroids.2015.02.021. [PMID: 25759118] - Spyridon Theofilopoulos, William J Griffiths, Peter J Crick, Shanzheng Yang, Anna Meljon, Michael Ogundare, Satish Srinivas Kitambi, Andrew Lockhart, Karin Tuschl, Peter T Clayton, Andrew A Morris, Adelaida Martinez, M Ashwin Reddy, Andrea Martinuzzi, Maria T Bassi, Akira Honda, Tatsuki Mizuochi, Akihiko Kimura, Hiroshi Nittono, Giuseppe De Michele, Rosa Carbone, Chiara Criscuolo, Joyce L Yau, Jonathan R Seckl, Rebecca Schüle, Ludger Schöls, Andreas W Sailer, Jens Kuhle, Matthew J Fraidakis, Jan-Åke Gustafsson, Knut R Steffensen, Ingemar Björkhem, Patrik Ernfors, Jan Sjövall, Ernest Arenas, Yuqin Wang. Cholestenoic acids regulate motor neuron survival via liver X receptors.
The Journal of clinical investigation.
2014 Nov; 124(11):4829-42. doi:
10.1172/jci68506. [PMID: 25271621] - William J Griffiths, Peter J Crick, Yuchen Wang, Michael Ogundare, Karin Tuschl, Andrew A Morris, Brian W Bigger, Peter T Clayton, Yuqin Wang. Analytical strategies for characterization of oxysterol lipidomes: liver X receptor ligands in plasma.
Free radical biology & medicine.
2013 Jun; 59(?):69-84. doi:
10.1016/j.freeradbiomed.2012.07.027. [PMID: 22846477] - Cun S Fang, Ying C Wang, Tao H Zhang, Jing Wu, Wei Wang, Chun Wang, Ming Y Zhang. Clinical significance of serum lipids in idiopathic pulmonary alveolar proteinosis.
Lipids in health and disease.
2012 Jan; 11(?):12. doi:
10.1186/1476-511x-11-12. [PMID: 22252101] - Xinlun Tian, Jinmei Luo, Kai-Feng Xu, Lan Wang, Jiong Zhou, Ruie Feng, Yaosong Gui, Juan Wang, Wenbing Xu, Yi Xiao, Yuanjue Zhu. Impaired lipid metabolism in idiopathic pulmonary alveolar proteinosis.
Lipids in health and disease.
2011 Apr; 10(?):54. doi:
10.1186/1476-511x-10-54. [PMID: 21486485] - David N Douda, Nicole Farmakovski, Sharon Dell, Hartmut Grasemann, Nades Palaniyar. SP-D counteracts GM-CSF-mediated increase of granuloma formation by alveolar macrophages in lysinuric protein intolerance.
Orphanet journal of rare diseases.
2009 Dec; 4(?):29. doi:
10.1186/1750-1172-4-29. [PMID: 20030831] - William J Griffiths, Martin Hornshaw, Gary Woffendin, Sharon F Baker, Andrew Lockhart, Sibylle Heidelberger, Magnus Gustafsson, Jan Sjövall, Yuqin Wang. Discovering oxysterols in plasma: a window on the metabolome.
Journal of proteome research.
2008 Aug; 7(8):3602-12. doi:
10.1021/pr8001639. [PMID: 18605750] - A Babiker, S Dzeletovic, B Wiklund, N Pettersson, J Salonen, K Nyyssönen, M Eriksson, U Diczfalusy, I Björkhem. Patients with atherosclerosis may have increased circulating levels of 27-hydroxycholesterol and cholestenoic acid.
Scandinavian journal of clinical and laboratory investigation.
2005; 65(5):365-75. doi:
10.1080/00365510510025746. [PMID: 16081359] - Steve Meaney, Tracey L Bonfield, Magnus Hansson, Amir Babiker, Mani S Kavuru, Mary Jane Thomassen. Serum cholestenoic acid as a potential marker of pulmonary cholesterol homeostasis: increased levels in patients with pulmonary alveolar proteinosis.
Journal of lipid research.
2004 Dec; 45(12):2354-60. doi:
10.1194/jlr.m400302-jlr200. [PMID: 15466366] - Akira Honda, Tadashi Yoshida, Guorong Xu, Yasushi Matsuzaki, Sugano Fukushima, Naomi Tanaka, Mikio Doy, Sarah Shefer, Gerald Salen. Significance of plasma 7alpha-hydroxy-4-cholesten-3-one and 27-hydroxycholesterol concentrations as markers for hepatic bile acid synthesis in cholesterol-fed rabbits.
Metabolism: clinical and experimental.
2004 Jan; 53(1):42-8. doi:
10.1016/j.metabol.2003.07.018. [PMID: 14681840] - Steve Meaney, Amir Babiker, Dieter Lütjohann, Ulf Diczfalusy, Magnus Axelson, Ingemar Björkhem. On the origin of the cholestenoic acids in human circulation.
Steroids.
2003 Sep; 68(7-8):595-601. doi:
10.1016/s0039-128x(03)00081-3. [PMID: 12957664] - Magnus Hansson, Ewa Ellis, Mary C Hunt, Gerd Schmitz, Amir Babiker. Marked induction of sterol 27-hydroxylase activity and mRNA levels during differentiation of human cultured monocytes into macrophages.
Biochimica et biophysica acta.
2003 Feb; 1593(2-3):283-9. doi:
10.1016/s0167-4889(02)00398-1. [PMID: 12581873] - X Fu, J G Menke, Y Chen, G Zhou, K L MacNaul, S D Wright, C P Sparrow, E G Lund. 27-hydroxycholesterol is an endogenous ligand for liver X receptor in cholesterol-loaded cells.
The Journal of biological chemistry.
2001 Oct; 276(42):38378-87. doi:
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Endocrinology.
2000 Nov; 141(11):4180-4. doi:
10.1210/endo.141.11.7772. [PMID: 11089551] - A Babiker, U Diczfalusy. Transport of side-chain oxidized oxysterols in the human circulation.
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