Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H46O4S |
| Molecular Weight | 466.717 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)OS(O)(=O)=O
InChI
InChIKey=BHYOQNUELFTYRT-DPAQBDIFSA-N
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
| Molecular Formula | C27H46O4S |
| Molecular Weight | 466.717 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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. Cholesterol sulfate is generated in the normal epidermis by cholesterol sulfotransferase but then is desulfated in the outer epidermis as part of a 'cholesterol sulfate cycle' that is a powerful regulator of epidermal metabolism and barrier function. It accumulates in the epidermis in the human genetic disorder X-linked ichthyosis. In XLI, cholesterol sulfate levels exceed 10% of total lipid mass (≈1% of total weight). Cholesterol sulfate is a component of cell membranes where it has a stabilizing role, e.g., protecting erythrocytes from osmotic lysis and regulating sperm capacitation. It is present in platelet membranes where it supports platelet adhesion. Cholesterol sulfate can regulate the activity of serine proteases, e.g., those involved in blood clotting, fibrinolysis, and epidermal cell adhesion. Because 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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P08842 Gene ID: 412.0 Gene Symbol: STS Target Organism: Homo sapiens (Human) |
|||
Target ID: P24723 Gene ID: 5583.0 Gene Symbol: PRKCH Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Diagnostic | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Inhibition of cell invasion and protease activity by cholesterol sulfate. | 2010-11 |
|
| Lipid mapping of colonic mucosa by cluster TOF-SIMS imaging and multivariate analysis in cftr knockout mice. | 2010-10 |
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| Cholesterol sulfate alters substrate preference of matrix metalloproteinase-7 and promotes degradations of pericellular laminin-332 and fibronectin. | 2010-09-10 |
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| Formation of fluid lamellar phase and large unilamellar vesicles with octadecyl methyl sulfoxide/cholesterol mixtures. | 2010-08-03 |
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| Investigation of stratum corneum lipid model membranes with free fatty acid composition by neutron diffraction. | 2010-07 |
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| Respiratory and cutaneous water loss of temperate-zone passerine birds. | 2010-06 |
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| Modification of sphingoglycolipids and sulfolipids in kidney cell lines under heat stress: activation of monohexosylceramide synthesis as a ceramide scavenger. | 2010-06 |
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| Cholesterol sulfate imaging in human prostate cancer tissue by desorption electrospray ionization mass spectrometry. | 2010-05-01 |
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| Expression and regulation of cholesterol sulfotransferase (SULT2B1b) in human endometrium. | 2010-03-15 |
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| Modulation of retinoic acid receptor-related orphan receptor alpha and gamma activity by 7-oxygenated sterol ligands. | 2010-02-12 |
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| Determination of free and liposomal amphotericin B in human plasma by liquid chromatography-mass spectroscopy with solid phase extraction and protein precipitation techniques. | 2010-02-01 |
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| Inhibition of proteases involved in embryo implantation by cholesterol sulfate. | 2010-01 |
|
| The BSA-induced Ca2+ influx during sperm capacitation is CATSPER channel-dependent. | 2009-10-27 |
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| Steroid and protein ligand binding to cytochrome P450 46A1 as assessed by hydrogen-deuterium exchange and mass spectrometry. | 2009-05-19 |
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| Cationic detergent/sterol mixtures can form fluid lamellar phases and stable unilamellar vesicles. | 2009-05-19 |
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| Analysis of the hibernation cycle using LC-MS-based metabolomics in ground squirrel liver. | 2009-03-03 |
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| 7-Ketocholesterol is present in lipid deposits in the primate retina: potential implication in the induction of VEGF and CNV formation. | 2009-02 |
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| Regulation of sulfotransferase and UDP-glucuronosyltransferase gene expression by the PPARs. | 2009 |
|
| Liposome formation with wool lipid extracts rich in ceramides. | 2009 |
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| Retinoid-related orphan receptors (RORs): critical roles in development, immunity, circadian rhythm, and cellular metabolism. | 2009 |
|
| Identification of amino acid residues of matrix metalloproteinase-7 essential for binding to cholesterol sulfate. | 2008-12-19 |
|
| Expression of a skin cholesterol sulfotransferase, St2b2, is a trigger of epidermal cell differentiation. | 2008-12 |
|
| Pre-medication practices and incidence of infusion-related reactions in patients receiving AMPHOTEC: data from the Patient Registry of Amphotericin B Cholesteryl Sulfate Complex for Injection Clinical Tolerability (PRoACT) registry. | 2008-12 |
|
| Constitutive expression of human keratin 14 gene in mouse lung induces premalignant lesions and squamous differentiation. | 2008-12 |
|
| Biosynthesis of leukotriene B4 in human polymorphonuclear leukocytes: regulation by cholesterol and other lipids. | 2008-10 |
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| Transcriptional activation of HIF-1 by RORalpha and its role in hypoxia signaling. | 2008-10 |
|
| Placental steroids in cattle: hormones, placental growth factors or by-products of trophoblast giant cell differentiation? | 2008-07 |
|
| Inhibitory effects of cholesterol sulfate on progesterone production in human granulosa-like tumor cell line, KGN. | 2008-07 |
|
| Pathogenesis of permeability barrier abnormalities in the ichthyoses: inherited disorders of lipid metabolism. | 2008-04 |
|
| Chemical properties of epidermal lipids, especially sphingolipids, of the Antarctic minke whale. | 2008-02 |
|
| Purified NPC1 protein: II. Localization of sterol binding to a 240-amino acid soluble luminal loop. | 2008-01-11 |
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| Effect of nutritional substrate on sulfolipids metabolic turnover in isolated renal tubules from rat. | 2008 |
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| Cholesterol sulphate affects production of steroid hormones by reducing steroidogenic acute regulatory protein level in adrenocortical cells. | 2007-12 |
|
| Details of the structure determination of the sulfated steroids PSDS and PADS: new components of the sea lamprey (petromyzon marinus) migratory pheromone. | 2007-09-28 |
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| Phase behavior of palmitic acid/cholesterol/cholesterol sulfate mixtures and properties of the derived liposomes. | 2007-09-20 |
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| A new cytotoxic cholesterol sulfate from marine sponge Halichondria rugosa. | 2007-09 |
|
| Structural basis of sterol binding by NPC2, a lysosomal protein deficient in Niemann-Pick type C2 disease. | 2007-08-10 |
|
| Recognition mechanism of galectin-4 for cholesterol 3-sulfate. | 2007-07-20 |
|
| Human stratum corneum lipid organization as observed by atomic force microscopy on Langmuir-Blodgett films. | 2007-06 |
|
| Nephrotic syndrome with X-linked ichthyosis, Kallmann Syndrome and unilateral renal agenesis. | 2007-04 |
|
| Cholesterol sulfate and Ca(2+) modulate the mixing properties of lipids in stratum corneum model mixtures. | 2007-01-01 |
|
| Optimizing efficacy of Amphotericin B through nanomodification. | 2007 |
|
| [Suppression of 5-lipoxygenase activity by anionic cholesterol derivatives]. | 2006-12-22 |
|
| NPC2, the protein deficient in Niemann-Pick C2 disease, consists of multiple glycoforms that bind a variety of sterols. | 2006-12-01 |
|
| Regulation of ABCA1 expression in human keratinocytes and murine epidermis. | 2006-10 |
|
| Change in the concentration of neutrophil elastase in bronchoalveolar lavage fluid during anesthesia and its inhibition by cholesterol sulfate. | 2006-08 |
|
| An update of the defensive barrier function of skin. | 2006-06-30 |
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| Optimizing efficacy of amphotericin B through nanomodification. | 2006 |
|
| Analysis of hair lipids and tensile properties as a function of distance from scalp. | 2005-08 |
|
| FTIR spectroscopic analyses of the temperature and pH influences on stratum corneum lipid phase behaviors and interactions. | 2002-03-04 |
Sample Use Guides
Recombinant PKC isoforms were produced using baculovirus expression systems. Full-length cDNA of mouse nPKC eta was inserted into pUC1 8 and transferred into baculovirus expression vector pAcYM1 . Eta isoform of protein kinase C (nPKC eta) was activated by cholesterol sulfate in a dose-dependent manner from 1 to 100 uM. This activation was greater than that by phosphatidylserine plus phorbol ester; the Vmax for the activation by cholesterol sulfate was 3.6 times that by phosphatidylserine plus phorbol ester, while Kms were almost equal. Activation of nPKC eta by cholesterol sulfate was further demonstrated by autophosphorylation of the kinase molecule. However, the alpha and delta isoforms of protein kinase C were not activated by cholesterol sulfate.
| Substance Class |
Chemical
Created
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admin
on
Edited
Mon Mar 31 19:03:29 GMT 2025
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| Record UNII |
KU576NT9O9
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| Record Status |
Validated (UNII)
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| Record Version |
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136579
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Cholesterol sulfate
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