Cholesterol sulfate (BioDeep_00000012044)
Secondary id: BioDeep_00000229589, BioDeep_00000638235
human metabolite Endogenous blood metabolite natural product
代谢物信息卡片
化学式: C27H46O4S (466.3117)
中文名称: 胆甾醇硫酸盐, 硫酸化胆固醇, 胆固醇硫酸酯
谱图信息:
最多检出来源 Homo sapiens(blood) 14.48%
Last reviewed on 2024-07-15.
Cite this Page
Cholesterol sulfate. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China.
https://query.biodeep.cn/s/cholesterol_sulfate (retrieved
2024-12-22) (BioDeep RN: BioDeep_00000012044). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
分子结构信息
SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OS(=O)(=O)O)C)C
InChI: InChI=1S/C27H46O4S/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(31-32(28,29)30)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25H,6-8,10-17H2,1-5H3,(H,28,29,30)/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
描述信息
Cholesterol sulfate, or cholest-5-en-3beta-ol sulfate, is an endogenous steroid and the C3beta sulfate ester of cholesterol. It is formed from cholesterol by steroid sulfotransferases (SSTs) such as SULT2B1b (also known as cholesterol sulfotransferase) and is converted back into cholesterol by steroid sulfatase (STS). Accumulation of cholesterol sulfate in the skin is implicated in the pathophysiology of X-linked ichthyosis, a congenital disorder in which STS is non-functional and the body cannot convert cholesterol sulfate back into cholesterol. Cholesterol sulfate is quantitatively the most important known sterol sulfate in human plasma, where it is present in a concentration that overlaps that of the other abundant circulating steroid sulfate, dehydroepiandrosterone (DHEA) sulfate (PMID 12730293). Cholesterol sulfate has a stabilizing function on the membrane, supports platelet adhesion and is involved in signal transduction (PMID 12730293). It plays a role in protecting erythrocytes from osmotic lysis and regulating sperm capacitation. Cholesterol sulfate can regulate the activity of serine proteases, e.g., those involved in blood clotting, fibrinolysis, and epidermal cell adhesion (PMID 12730293). As a result of its ability to regulate the activity of selective protein kinase C isoforms and modulate the specificity of phosphatidylinositol 3-kinase, cholesterol sulfate is involved in signal transduction (PMID 12730293). Cholesterol sulfate functions in keratinocyte differentiation, inducing genes that encode for key components involved in development of the barrier (PMID 12730293).
Cholesterol sulfate is a sterol sulfate in human plasma. It is a component of cell membrane and has a regulatory function. It has a stabilizing function on the membrane, supports platelet adhesion and involves in signal transduction. (PMID 12730293) [HMDB]
D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors > D015842 - Serine Proteinase Inhibitors
D020011 - Protective Agents > D016588 - Anticarcinogenic Agents
D000970 - Antineoplastic Agents
同义名列表
44 个代谢物同义名
[(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid; Cholesteryl sulfate, potassium salt, (3beta)-isomer; Cholesteryl sulfate, ammonium salt, (3beta)-isomer; Cholesteryl sulfate, sodium salt, 26-(14)C-labeled; Cholesteryl sulfate, sodium salt, (3beta)-isomer; Cholesteryl sulfate, 3H-labeled, (3beta)-isomer; CHOLEST-5-en-3-yl hydrogen sulphuric acid; CHOLEST-5-en-3-yl hydrogen sulfuric acid; cholest-5-en-3beta-yl hydrogen sulfate; Cholest-5-en-3beta-ol sulphuric acid; CHOLEST-5-en-3-yl hydrogen sulphate; Cholesterol hydrogen sulphuric acid; Cholest-5-en-3beta-ol sulfuric acid; Cholesterol hydrogen sulfuric acid; CHOLEST-5-EN-3-YL HYDROGEN SULFATE; Cholest-5-en-3β-ol sulphuric acid; Cholest-5-en-3b-ol sulphuric acid; Cholest-5-en-3b-ol sulfuric acid; Cholest-5-en-3β-ol sulfuric acid; Cholest-5-en-3beta-ol sulphate; Cholesterol hydrogen sulphate; Cholest-5-en-3beta-ol sulfate; Cholesterol hydrogen sulfate; Cholesterol 3-sulphuric acid; Cholesterol 3-sulfuric acid; Cholest-5-en-3β-ol sulphate; Cholest-5-en-3b-ol sulphate; Cholest-5-en-3β-ol sulfate; Cholest-5-en-3b-ol sulfate; Cholesterol sulphuric acid; Cholesteryl sulphuric acid; 5-Cholesten-3b-yl sulphate; 5-Cholesten-3b-yl sulfate; Cholesteryl sulfuric acid; Cholesterol sulfuric acid; Cholesterol 3-sulphate; Cholesterol 3-sulfate; Cholesterol sulphate; Cholesteryl sulphate; cholesteryl sulfate; cholesterol sulfate; DTXSID70401323; Cholesterol sulfate; Cholesterol sulfate
数据库引用编号
20 个数据库交叉引用编号
- ChEBI: CHEBI:41321
- KEGG: C18043
- PubChem: 65076
- HMDB: HMDB0000653
- Metlin: METLIN5625
- DrugBank: DB01990
- ChEMBL: CHEMBL1231592
- Wikipedia: Cholesterol sulfate
- KNApSAcK: C00055763
- foodb: FDB022164
- chemspider: 58586
- CAS: 1256-86-6
- PMhub: MS000026315
- LipidMAPS: LMST05020016
- PDB-CCD: C3S
- NIKKAJI: J324.075D
- RefMet: Cholesterol sulfate
- LOTUS: LTS0244060
- PubChem: 96024263
- KNApSAcK: 41321
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
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)
25 个相关的物种来源信息
- 7586 - Echinodermata: LTS0244060
- 33682 - Euglenozoa: LTS0244060
- 2759 - Eukaryota: LTS0244060
- 42393 - Eupentacta: LTS0244060
- 1774088 - Eupentacta fraudatrix: 10.1016/0039-128X(93)90026-J
- 1774088 - Eupentacta fraudatrix: LTS0244060
- 105882 - Gorgonocephalidae: LTS0244060
- 105880 - Gorgonocephalus: LTS0244060
- 105881 - Gorgonocephalus eucnemis: 10.1007/BF00630137
- 105881 - Gorgonocephalus eucnemis: LTS0244060
- 7705 - Holothuroidea: LTS0244060
- 9606 - Homo sapiens: -
- 9606 - Homo sapiens: 10.1007/S11306-016-1051-4
- 5653 - Kinetoplastea: LTS0244060
- 33208 - Metazoa: LTS0244060
- 48547 - Ophiura: LTS0244060
- 861515 - Ophiura sarsii: 10.1007/BF00598993
- 861515 - Ophiura sarsii: LTS0244060
- 35054 - Ophiuridae: LTS0244060
- 7618 - Ophiuroidea: LTS0244060
- 42392 - Sclerodactylidae: LTS0244060
- 5690 - Trypanosoma: LTS0244060
- 5691 - Trypanosoma brucei: 10.1371/JOURNAL.PNTD.0001618
- 5691 - Trypanosoma brucei: LTS0244060
- 5654 - Trypanosomatidae: LTS0244060
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
- S Tokoro, T Ogawa, S Hayashi, K Igawa. High-resolution mass spectrometry imaging reveals skin lipid changes and the cholesterol sulphate cycle during keratinization.
Journal of the European Academy of Dermatology and Venereology : JEADV.
2024 Jun; 38(6):e456-e458. doi:
10.1111/jdv.19621
. [PMID: 37909310] - Yunling Wang, Jinyue Yang, Yuming Wang, Yaoguang Chang, Changhu Xue, Tiantian Zhang. Preparation and properties of fucoxanthin-loaded liposomes stabilized by sea cucumber derived cholesterol sulfate instead of cholesterol.
Journal of bioscience and bioengineering.
2023 Feb; 135(2):160-166. doi:
10.1016/j.jbiosc.2022.11.004
. [PMID: 36494249] - Kenji Morino, Kazufumi Kunimura, Yuki Sugiura, Yoshihiro Izumi, Keisuke Matsubara, Sayaka Akiyoshi, Rae Maeda, Kenichiro Hirotani, Daiji Sakata, Seiya Mizuno, Satoru Takahashi, Takeshi Bamba, Takehito Uruno, Yoshinori Fukui. Cholesterol sulfate limits neutrophil recruitment and gut inflammation during mucosal injury.
Frontiers in immunology.
2023; 14(?):1131146. doi:
10.3389/fimmu.2023.1131146
. [PMID: 37006281] - Fumika Mi-Ichi, Hiroshi Tsugawa, Makoto Arita, Hiroki Yoshida. Pleiotropic Roles of Cholesteryl Sulfate during Entamoeba Encystation: Involvement in Cell Rounding and Development of Membrane Impermeability.
mSphere.
2022 08; 7(4):e0029922. doi:
10.1128/msphere.00299-22
. [PMID: 35943216] - Takaaki Tatsuguchi, Takehito Uruno, Yuki Sugiura, Daiji Sakata, Yoshihiro Izumi, Tetsuya Sakurai, Yuko Hattori, Eiji Oki, Naoto Kubota, Koshiro Nishimoto, Masafumi Oyama, Kazufumi Kunimura, Takuto Ohki, Takeshi Bamba, Hideaki Tahara, Michiie Sakamoto, Masafumi Nakamura, Makoto Suematsu, Yoshinori Fukui. Cancer-derived cholesterol sulfate is a key mediator to prevent tumor infiltration by effector T cells.
International immunology.
2022 04; 34(5):277-289. doi:
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Journal of lipid research.
2022 03; 63(3):100177. doi:
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Journal of molecular biology.
2021 12; 433(24):167328. doi:
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Experimental dermatology.
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Analytical chemistry.
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Brain research.
2019 11; 1723(?):146378. doi:
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Scientific reports.
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The Journal of steroid biochemistry and molecular biology.
2018 05; 179(?):45-54. doi:
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Metabolomics : Official journal of the Metabolomic Society.
2018 02; 14(4):38. doi:
10.1007/s11306-018-1334-z
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Biophysical chemistry.
2017 05; 224(?):20-31. doi:
10.1016/j.bpc.2017.03.004
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Pharmaceutical development and technology.
2017 May; 22(3):436-444. doi:
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Langmuir : the ACS journal of surfaces and colloids.
2017 03; 33(11):2890-2899. doi:
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Archives of toxicology.
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Artificial cells, nanomedicine, and biotechnology.
2016 Nov; 44(7):1684-93. doi:
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Journal of microencapsulation.
2016 Aug; 33(5):427-37. doi:
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. [PMID: 27388548] - Matthew G K Benesch, Ruthven N A H Lewis, Ronald N McElhaney. A calorimetric and spectroscopic comparison of the effects of cholesterol and its sulfur-containing analogs thiocholesterol and cholesterol sulfate on the thermotropic phase behavior and organization of dipalmitoylphosphatidylcholine bilayer membranes.
Biochimica et biophysica acta.
2016 Feb; 1858(2):168-80. doi:
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. [PMID: 26585353] - Peter J Milianta, Michelle Muzzio, Jacqueline Denver, Geoffrey Cawley, Sunghee Lee. Water Permeability across Symmetric and Asymmetric Droplet Interface Bilayers: Interaction of Cholesterol Sulfate with DPhPC.
Langmuir : the ACS journal of surfaces and colloids.
2015 Nov; 31(44):12187-96. doi:
10.1021/acs.langmuir.5b02748
. [PMID: 26492572] - Alberto Sánchez-Guijo, Vinzenz Oji, Michaela F Hartmann, Heiko Traupe, Stefan A Wudy. Simultaneous quantification of cholesterol sulfate, androgen sulfates, and progestagen sulfates in human serum by LC-MS/MS.
Journal of lipid research.
2015 Sep; 56(9):1843-51. doi:
10.1194/jlr.d061499
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Langmuir : the ACS journal of surfaces and colloids.
2015 Jul; 31(29):8042-51. doi:
10.1021/acs.langmuir.5b01365
. [PMID: 26139630] - Stephanie Seneff, Robert M Davidson, Ann Lauritzen, Anthony Samsel, Glyn Wainwright. A novel hypothesis for atherosclerosis as a cholesterol sulfate deficiency syndrome.
Theoretical biology & medical modelling.
2015 May; 12(?):9. doi:
10.1186/s12976-015-0006-1
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Journal of lipid research.
2015 Feb; 56(2):403-12. doi:
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2015 Feb; 56(2):413-22. doi:
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The journal of physical chemistry. B.
2014 Sep; 118(35):10460-70. doi:
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The FEBS journal.
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The international journal of biochemistry & cell biology.
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2014 May; 30(19):5527-35. doi:
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2014 Mar; 1841(3):353-61. doi:
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Pharmaceutical development and technology.
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Talanta.
2013 Nov; 116(?):115-21. doi:
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Drug delivery.
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Physical chemistry chemical physics : PCCP.
2012 Nov; 14(42):14523-33. doi:
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Journal of photochemistry and photobiology. B, Biology.
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Biology of reproduction.
2012 Jun; 86(6):181. doi:
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ACS chemical neuroscience.
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