Cholesterol sulfate (BioCAD00000008425)
Metabolite Card
Formula: C27H46O4S (466.3117)
SMILES: [H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](CC[C@]12C)OS(O)(=O)=O
Synonyms [en]
cholesterol sulfate; CHOLEST-5-EN-3-YL HYDROGEN SULFATE; cholest-5-en-3beta-yl hydrogen sulfate; cholesteryl sulfate; Cholest-5-en-3beta-ol sulfate; cholesterol sulphate
Last reviewed on 2024-06-28.
Cite this Page
Cholesterol sulfate. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China.
https://biocad_registry.innovation.ac.cn/s/(-)-arctiin
(retrieved
2026-01-03) (CAD Registry RN: BioCAD00000008425). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
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).
DBLinks
- CAS Registry Number: 1256-86-6
- PubChem CID: 65076
- ChEBI: 41321
- HMDB: HMDB0000653
- LipidMaps: LMST05020016
- KEGG: C18043
- BioCyc:
- NCBI MeSH: cholesteryl sulfate
- Wikipedia: Cholesterol sulfate
Other DBLinks
- CAS Registry Number: 1256-86-6
- PubChem: 65076
- ChEBI: ChEBI:41321
- HMDB: HMDB0000653
- HMDB: HMDB00653
- LipidMaps: LMST05020016
- KEGG: C18043
- NCBI MeSH: cholesteryl sulfate
- Wikipedia: Cholesterol sulfate
- Wikipedia: Cholesterol_sulfate
- DrugBank: DB01990
- RefMet: RM0135845
- MoNA: HMDB0000653_ms_ms_891
- MoNA: HMDB0000653_ms_ms_892
- MoNA: HMDB0000653_ms_ms_893
- Metlin: METLIN_5625
- Coconut NaturalProduct: CNP0230675.1
Class / Ontology
- WishartLab ClassyFire: [Cholestane steroids] Cholestane steroids
- RefMet: [Cholesterols] Cholesterols
- LipidMaps: [Sulfates [ST0502]] Sulfates [ST0502]
- ChEBI: [CHEBI:41321] cholesterol sulfate
- Coconut NaturalProduct: [Cholestane steroids] Cholestane steroids
| ID | EC Number | Name |
|---|---|---|
| KEGG:R08941 | 3.1.6.2 | cholesterol-sulfate sulfohydrolase; |
| KEGG:R08977 | 2.8.2.2 | 3'-phosphoadenylyl-sulfate:cholesterol sulfotransferase |