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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:09 UTC
HMDB IDHMDB00653
Secondary Accession NumbersNone
Metabolite Identification
Common NameCholesterol sulfate
DescriptionCholesterol 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 ).
Structure
Thumb
Synonyms
ValueSource
CHOLEST-5-en-3-yl hydrogen sulfATEChEBI
Cholest-5-en-3beta-ol sulfateChEBI
Cholesteryl sulfateChEBI
CHOLEST-5-en-3-yl hydrogen sulfuric acidGenerator
CHOLEST-5-en-3-yl hydrogen sulphateGenerator
CHOLEST-5-en-3-yl hydrogen sulphuric acidGenerator
5-Cholesten-3b-yl sulfateHMDB
5-Cholesten-3b-yl sulphateHMDB
Cholest-5-en-3b-ol sulfateHMDB
Cholest-5-en-3b-ol sulphateHMDB
Cholesterol 3-sulfateHMDB
Cholesterol 3-sulphateHMDB
Cholesterol hydrogen sulfateHMDB
Cholesterol hydrogen sulphateHMDB
Cholesterol sulphateHMDB
Cholesteryl sulphateHMDB
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[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxidanesulfonic acid
Traditional Namecholesterol sulfate
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 KeyInChIKey=BHYOQNUELFTYRT-DPAQBDIFSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cholesterols and derivatives. These 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
  • 3-sulfated steroid
  • Sulfated steroid skeleton
  • Delta-5-steroid
  • Sulfuric acid monoester
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Organic sulfuric acid or derivatives
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.48e-05 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity130.61 m3·mol-1ChemAxon
Polarizability56.43 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-014i-0000900000-548706c8c2ce9f09a548View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-014i-0000900000-7a511fae1b9c9c3ae716View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-014i-1000900000-c804c1920be98c205e26View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
Tissue Location
  • Adrenal Gland
  • Platelet
  • Skin
  • Stratum Corneum
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified5.40 +/- 0.52 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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. [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. [8231659 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022164
KNApSAcK IDNot Available
Chemspider ID58586
KEGG Compound IDC18043
BioCyc IDNot Available
BiGG ID2705326
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00653
Metagene LinkHMDB00653
METLIN ID5625
PubChem Compound65076
PDB IDC3S
ChEBI ID41321
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. [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. [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. [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. [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. [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. [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. [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. [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. [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. [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