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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-16 15:27:09 UTC
HMDB IDHMDB0000653
Secondary Accession Numbers
  • HMDB00653
Metabolite Identification
Common NameCholesterol sulfate
DescriptionCholesterol 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 ).
Structure
Data?1582752147
Synonyms
ValueSource
CHOLEST-5-en-3-yl hydrogen sulfATEChEBI
Cholest-5-en-3beta-ol sulfateChEBI
Cholesterol 3-sulfateChEBI
Cholesterol 3-sulphateChEBI
Cholesterol hydrogen sulfateChEBI
Cholesterol hydrogen sulphateChEBI
Cholesterol sulphateChEBI
Cholesteryl sulfateChEBI
Cholesteryl sulphateChEBI
CHOLEST-5-en-3-yl hydrogen sulfuric acidGenerator
CHOLEST-5-en-3-yl hydrogen sulphateGenerator
CHOLEST-5-en-3-yl hydrogen sulphuric acidGenerator
Cholest-5-en-3b-ol sulfateGenerator
Cholest-5-en-3b-ol sulfuric acidGenerator
Cholest-5-en-3b-ol sulphateGenerator
Cholest-5-en-3b-ol sulphuric acidGenerator
Cholest-5-en-3beta-ol sulfuric acidGenerator
Cholest-5-en-3beta-ol sulphateGenerator
Cholest-5-en-3beta-ol sulphuric acidGenerator
Cholest-5-en-3β-ol sulfateGenerator
Cholest-5-en-3β-ol sulfuric acidGenerator
Cholest-5-en-3β-ol sulphateGenerator
Cholest-5-en-3β-ol sulphuric acidGenerator
Cholesterol 3-sulfuric acidGenerator
Cholesterol 3-sulphuric acidGenerator
Cholesterol hydrogen sulfuric acidGenerator
Cholesterol hydrogen sulphuric acidGenerator
Cholesterol sulfuric acidGenerator
Cholesterol sulphuric acidGenerator
Cholesteryl sulfuric acidGenerator
Cholesteryl sulphuric acidGenerator
5-Cholesten-3b-yl sulfateHMDB
5-Cholesten-3b-yl sulphateHMDB
Cholesteryl sulfate, sodium salt, (3beta)-isomerMeSH, HMDB
Cholesteryl sulfate, ammonium salt, (3beta)-isomerMeSH, HMDB
Cholesteryl sulfate, sodium salt, 26-(14)C-labeledMeSH, HMDB
Cholesteryl sulfate, 3H-labeled, (3beta)-isomerMeSH, HMDB
Cholesteryl sulfate, potassium salt, (3beta)-isomerMeSH, HMDB
Chemical FormulaC27H46O4S
Average Molecular Weight466.717
Monoisotopic Molecular Weight466.31168065
IUPAC Name[(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
Traditional Name[(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
CAS Registry Number1256-86-6
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
InChI Identifier
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
InChI KeyBHYOQNUELFTYRT-DPAQBDIFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol
  • Sulfated steroid skeleton
  • Delta-5-steroid
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Sulfuric acid monoester
  • Organic sulfuric acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.5e-05 g/LALOGPS
logP3.27ALOGPS
logP7.17ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)-1.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity130.61 m³·mol⁻¹ChemAxon
Polarizability56.55 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available212.33431661259
DarkChem[M-H]-PredictedNot Available208.77231661259
AllCCS[M+H]+PredictedNot Available216.92532859911
AllCCS[M-H]-PredictedNot Available210.96832859911

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-2117900000-d2dc1d52c2c6b6024f0f2017-09-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-014i-0000900000-548706c8c2ce9f09a5482012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-014i-0000900000-7a511fae1b9c9c3ae7162012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-014i-1000900000-c804c1920be98c205e262012-07-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0004900000-3e084b0869dec1511e5a2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2019000000-7af1b592431ae5367f0f2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-7259200000-0958e602876ec6735f352017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0002900000-4bf9e43838ae87b487602017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-1009200000-cefbd199aabf735755c72017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0159-5009000000-5d0bf7cb45e64f0239da2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-e3ecb40a540de289ba8b2021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1000900000-76ef4296ff82739218242021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-9002600000-9ad23ecad6099c20e1482021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0002900000-b9275f9e554fed1edbf32021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ar0-3279000000-9c38d5fd98e2387d950d2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3494000000-282974a841618bfa049a2021-09-07View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)2012-12-04View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, 100%_DMSO, predicted)2012-12-05View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Adrenal Gland
  • Epidermis
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified5.40 +/- 0.52 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified9.52 +/- 1.10 uMAdult (>18 years old)BothCirrhosis details
BloodDetected and Quantified8.86 +/- 0.95 uMAdult (>18 years old)BothHypercholesterolemia details
Associated Disorders and Diseases
Disease References
Cirrhosis
  1. Tamasawa N, Tamasawa A, Takebe K: Higher levels of plasma cholesterol sulfate in patients with liver cirrhosis and hypercholesterolemia. Lipids. 1993 Sep;28(9):833-6. [PubMed:8231659 ]
Hypercholesterolemia
  1. Tamasawa N, Tamasawa A, Takebe K: Higher levels of plasma cholesterol sulfate in patients with liver cirrhosis and hypercholesterolemia. Lipids. 1993 Sep;28(9):833-6. [PubMed:8231659 ]
Associated OMIM IDsNone
DrugBank IDDB01990
Phenol Explorer Compound IDNot Available
FooDB IDFDB022164
KNApSAcK IDC00055763
Chemspider ID58586
KEGG Compound IDC18043
BioCyc IDNot Available
BiGG ID2705326
Wikipedia LinkCholesterol sulfate
METLIN ID5625
PubChem Compound65076
PDB IDNot Available
ChEBI ID41321
Food Biomarker OntologyNot Available
VMH IDCHSTEROLS
MarkerDB IDMDB00000209
References
Synthesis ReferenceDrayer, N. M.; Lieberman, S. Isolation of cholesterol sulfate from human blood and gallstones. Biochemical and Biophysical Research Communications (1965), 18(1), 126-30.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Mason JI, Hemsell PG: Cholesterol sulfate metabolism in human fetal adrenal mitochondria. Endocrinology. 1982 Jul;111(1):208-13. [PubMed:7084110 ]
  2. Marinkovic-Ilsen A, Wolthers BG, Jansen G, de Bruijn HW, van der Loos C: Early diagnosis of recessive X-linked ichthyosis: elevation of cholesterol sulfate levels in placental sulfatase deficiency before the onset of skin symptoms. Pediatr Dermatol. 1985 Nov;3(1):59-64. [PubMed:4070088 ]
  3. Bedin M, Pointis G: [Steroid sulfatase and placental deficiency. Current data as instigators of new research]. Ann Endocrinol (Paris). 1987;48(4):323-33. [PubMed:3477995 ]
  4. Strott CA, Higashi Y: Cholesterol sulfate in human physiology: what's it all about? J Lipid Res. 2003 Jul;44(7):1268-78. Epub 2003 May 1. [PubMed:12730293 ]
  5. Serizawa S, Nagai T, Sato Y: Simplified method of determination of serum cholesterol sulfate by reverse phase thin-layer chromatography. J Invest Dermatol. 1987 Dec;89(6):580-7. [PubMed:2960747 ]
  6. Sion B, Grizard G, Boucher D: Quantitative analysis of desmosterol, cholesterol and cholesterol sulfate in semen by high-performance liquid chromatography. J Chromatogr A. 2001 Nov 23;935(1-2):259-65. [PubMed:11762778 ]
  7. Zettersten E, Man MQ, Sato J, Denda M, Farrell A, Ghadially R, Williams ML, Feingold KR, Elias PM: Recessive x-linked ichthyosis: role of cholesterol-sulfate accumulation in the barrier abnormality. J Invest Dermatol. 1998 Nov;111(5):784-90. [PubMed:9804339 ]
  8. Serizawa S, Nagai T, Ito M, Sato Y: Simplified determination of serum cholesterol sulfate by gas-liquid chromatography combined with cyclohexylsilane-bonded phase column purification. Arch Dermatol Res. 1989;281(6):411-6. [PubMed:2531994 ]
  9. Marinkovic-Ilsen A, van den Ende A, Wolthers BG: Excretion of (sulfated) steroids in the urine and excretion of cholesterol sulfate in the feces of boys with recessive X-linked ichthyosis. Arch Dermatol Res. 1984;276(6):364-9. [PubMed:6542768 ]
  10. Iwamori M, Suzuki H, Kimura T, Iwamori Y: Shedding of sulfated lipids into gastric fluid and inhibition of pancreatic DNase I by cholesterol sulfate in concert with bile acids. Biochim Biophys Acta. 2000 Sep 27;1487(2-3):268-74. [PubMed:11018478 ]

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Cholesterol + Phosphoadenosine phosphosulfate → Cholesterol sulfate + Adenosine 3',5'-diphosphatedetails
General function:
Involved in catalytic activity
Specific function:
Conversion of sulfated steroid precursors to estrogens during pregnancy.
Gene Name:
STS
Uniprot ID:
P08842
Molecular weight:
65491.72
Reactions
Cholesterol + Oat gum → Cholesterol sulfate + Waterdetails