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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:40:12 UTC
HMDB IDHMDB0000774
Secondary Accession Numbers
  • HMDB00774
Metabolite Identification
Common NamePregnenolone sulfate
DescriptionPregnenolone sulfate is a sulfated version of the steroid hormone known as pregnenolone. Pregnenolone sulfate belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton. Pregnenolone sulfate is a neurosteroid found in the brain and central nervous system. Pregnenolone sulfate is a metabolite synthesized from pregnenolone via sulfation. It is known to have cognitive and memory-enhancing, antidepressant, anxiogenic, and proconvulsant effects (PMID: 21094889 ). As a neurosteroid, pregnenolone sulfate modulates a variety of ion channels, transporters, and enzymes. Interestingly, as a sulfated steroid, pregnenolone sulfate is not the final- or waste-product of pregnenolone being sulfated via a phase II metabolism reaction and renally excreted, as one would presume from pharmacology textbook knowledge. Pregnenolone sulfate is also the source and thereby the starting point for subsequent steroid synthesis pathways. Recently, pregnenolone sulfate has been shown to not only be a modulator of ion channels, but it is also an activating ion channel ligand (PMID: 24084011 ).
Structure
Data?1582752155
Synonyms
ValueSource
Pregnenolone sulfuric acidGenerator
Pregnenolone sulphateGenerator
Pregnenolone sulphuric acidGenerator
5-Pregnen-3b-sulfate-20-oneHMDB
5-Pregnen-3b-sulphate-20-oneHMDB
Pregn-5-en-20-on-3b-yl sulfurateHMDB
Pregn-5-en-20-on-3b-yl sulfuric acidHMDB
Pregn-5-en-20-one-3b-yl sulfateHMDB
Pregn-5-en-20-one-3b-yl sulphateHMDB
Pregnenolone 3-sulfateHMDB
Pregnenolone 3-sulphateHMDB
Pregnenolone 3b-sulfateHMDB
Pregnenolone 3b-sulphateHMDB
Pregnenolone hydrogen sulfateHMDB
Pregnenolone hydrogen sulphateHMDB
Pregnenolone monosulfateHMDB
Pregnenolone monosulphateHMDB
[(1S,2R,10S,11S,14S,15S)-14-Acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxidanesulfonateHMDB
[(1S,2R,10S,11S,14S,15S)-14-Acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxidanesulphonateHMDB
[(1S,2R,10S,11S,14S,15S)-14-Acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl]oxidanesulphonic acidHMDB
Chemical FormulaC21H32O5S
Average Molecular Weight396.541
Monoisotopic Molecular Weight396.197044824
IUPAC Name[(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid
Traditional Name[(1S,2R,10S,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl]oxidanesulfonic acid
CAS Registry Number1247-64-9
SMILES
[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(CC[C@]12C)OS(O)(=O)=O
InChI Identifier
InChI=1S/C21H32O5S/c1-13(22)17-6-7-18-16-5-4-14-12-15(26-27(23,24)25)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19H,5-12H2,1-3H3,(H,23,24,25)/t15?,16-,17+,18-,19-,20-,21+/m0/s1
InChI KeyDIJBBUIOWGGQOP-OZIWPBGVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sulfated steroids. These are sterol lipids containing a sulfate group attached to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSulfated steroids
Direct ParentSulfated steroids
Alternative Parents
Substituents
  • Sulfated steroid skeleton
  • 20-oxosteroid
  • Pregnane-skeleton
  • Oxosteroid
  • Delta-5-steroid
  • Sulfuric acid ester
  • Sulfuric acid monoester
  • Sulfate-ester
  • Alkyl sulfate
  • Organic sulfuric acid or derivatives
  • Ketone
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg203.90730932474
[M-H]-Not Available203.907http://allccs.zhulab.cn/database/detail?ID=AllCCS00000213
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0013 g/LALOGPS
logP0.98ALOGPS
logP3.64ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)-1.4ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity103.75 m³·mol⁻¹ChemAxon
Polarizability43.84 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+193.67431661259
DarkChem[M-H]-186.26931661259
AllCCS[M+H]+196.42632859911
AllCCS[M-H]-195.64432859911
DeepCCS[M-2H]-230.27130932474
DeepCCS[M+Na]+204.70430932474
AllCCS[M+H]+196.432859911
AllCCS[M+H-H2O]+194.132859911
AllCCS[M+NH4]+198.532859911
AllCCS[M+Na]+199.132859911
AllCCS[M-H]-195.632859911
AllCCS[M+Na-2H]-196.532859911
AllCCS[M+HCOO]-197.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Pregnenolone sulfate[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(CC[C@]12C)OS(O)(=O)=O3789.5Standard polar33892256
Pregnenolone sulfate[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(CC[C@]12C)OS(O)(=O)=O2958.7Standard non polar33892256
Pregnenolone sulfate[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(CC[C@]12C)OS(O)(=O)=O3338.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pregnenolone sulfate,1TMS,isomer #1CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3292.5Semi standard non polar33892256
Pregnenolone sulfate,1TMS,isomer #1CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3198.2Standard non polar33892256
Pregnenolone sulfate,1TMS,isomer #1CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3933.8Standard polar33892256
Pregnenolone sulfate,1TMS,isomer #2CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C3331.6Semi standard non polar33892256
Pregnenolone sulfate,1TMS,isomer #2CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C3148.9Standard non polar33892256
Pregnenolone sulfate,1TMS,isomer #2CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C4053.8Standard polar33892256
Pregnenolone sulfate,1TMS,isomer #3C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C3267.8Semi standard non polar33892256
Pregnenolone sulfate,1TMS,isomer #3C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C3169.0Standard non polar33892256
Pregnenolone sulfate,1TMS,isomer #3C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C4170.9Standard polar33892256
Pregnenolone sulfate,2TMS,isomer #1CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3372.2Semi standard non polar33892256
Pregnenolone sulfate,2TMS,isomer #1CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3341.5Standard non polar33892256
Pregnenolone sulfate,2TMS,isomer #1CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3954.8Standard polar33892256
Pregnenolone sulfate,2TMS,isomer #2C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3299.7Semi standard non polar33892256
Pregnenolone sulfate,2TMS,isomer #2C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3360.4Standard non polar33892256
Pregnenolone sulfate,2TMS,isomer #2C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C4054.6Standard polar33892256
Pregnenolone sulfate,1TBDMS,isomer #1CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3518.2Semi standard non polar33892256
Pregnenolone sulfate,1TBDMS,isomer #1CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3503.4Standard non polar33892256
Pregnenolone sulfate,1TBDMS,isomer #1CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C4044.1Standard polar33892256
Pregnenolone sulfate,1TBDMS,isomer #2CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C3587.8Semi standard non polar33892256
Pregnenolone sulfate,1TBDMS,isomer #2CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C3463.4Standard non polar33892256
Pregnenolone sulfate,1TBDMS,isomer #2CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C4195.1Standard polar33892256
Pregnenolone sulfate,1TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C3515.4Semi standard non polar33892256
Pregnenolone sulfate,1TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C3479.2Standard non polar33892256
Pregnenolone sulfate,1TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O)CC[C@]4(C)[C@H]3CC[C@]12C4293.7Standard polar33892256
Pregnenolone sulfate,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3825.3Semi standard non polar33892256
Pregnenolone sulfate,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3928.0Standard non polar33892256
Pregnenolone sulfate,2TBDMS,isomer #1CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C4123.8Standard polar33892256
Pregnenolone sulfate,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3743.3Semi standard non polar33892256
Pregnenolone sulfate,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3938.0Standard non polar33892256
Pregnenolone sulfate,2TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4CC(OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C4194.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pregnenolone sulfate GC-MS (Non-derivatized) - 70eV, Positivesplash10-015c-1069000000-98638a32c64bd13693bb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pregnenolone sulfate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnenolone sulfate 10V, Positive-QTOFsplash10-0002-0039000000-c29e72af13a8b1df901a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnenolone sulfate 20V, Positive-QTOFsplash10-0002-0092000000-48af0541d95515a42eca2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnenolone sulfate 40V, Positive-QTOFsplash10-0kai-5193000000-d981003b06fdf18508e32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnenolone sulfate 10V, Negative-QTOFsplash10-0002-0019000000-2cac349b15d130782aef2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnenolone sulfate 20V, Negative-QTOFsplash10-014j-1039000000-f63d28f7bec5ec72f4372016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnenolone sulfate 40V, Negative-QTOFsplash10-000t-6093000000-3f7db3bec91ec381b0602016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnenolone sulfate 10V, Negative-QTOFsplash10-0002-0009000000-5d910d6c0e79d0a64f732021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnenolone sulfate 20V, Negative-QTOFsplash10-0f6t-1009000000-9f3fbb71720d2bb163cb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnenolone sulfate 40V, Negative-QTOFsplash10-0002-9007000000-5ff2a20734539479696c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnenolone sulfate 10V, Positive-QTOFsplash10-0002-0019000000-d84db4f789aa355c64b22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnenolone sulfate 20V, Positive-QTOFsplash10-0zfs-0092000000-833a400098daed115a392021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pregnenolone sulfate 40V, Positive-QTOFsplash10-0k96-4691000000-5ee53c8e93e1765212432021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Kidney
  • Liver
  • Ovary
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.13 +/- 0.06 uMAdult (>18 years old)BothNormal
    • Tietz NW eds. Cli...
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Schizophrenia
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Schizophrenia
details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24. [PubMed:22944140 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022235
KNApSAcK IDNot Available
Chemspider ID17216005
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2705327
Wikipedia LinkPregnenolone sulfate
METLIN ID5740
PubChem Compound20845972
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDPRGNLONES
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceKillinger, Donald W.; Solomon, Samuel. Synthesis of pregnenolone sulfate, dehydroisoandrosterone sulfate, 17a-hydroxypregnenolone sulfate, and pregn-5-enetriol by the normal human adrenal gland. Journal of Clinical Endocrinology and Metabolism (1965), 25(2), 290-3.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Havlikova H, Hill M, Hampl R, Starka L: Sex- and age-related changes in epitestosterone in relation to pregnenolone sulfate and testosterone in normal subjects. J Clin Endocrinol Metab. 2002 May;87(5):2225-31. [PubMed:11994368 ]
  2. Horak M, Vlcek K, Chodounska H, Vyklicky L Jr: Subtype-dependence of N-methyl-D-aspartate receptor modulation by pregnenolone sulfate. Neuroscience. 2006;137(1):93-102. Epub 2005 Oct 28. [PubMed:16257494 ]
  3. Bicikova M, Klak J, Hill M, Zizka Z, Hampl R, Calda P: Two neuroactive steroids in midpregnancy as measured in maternal and fetal sera and in amniotic fluid. Steroids. 2002 Apr;67(5):399-402. [PubMed:11958797 ]
  4. Kamiya T, Yasui T, Yokomori H, Nakamoto H, Maruyama T, Suzuki O, Ookawa H, Kiryu Y, Yasumura K, Kakumoto Y, et al.: [2 surgically treated cases of adrenocortical carcinoma producing steroid hormones without endocrinological symptoms--case report and a review of cases in the Japanese literature]. Gan No Rinsho. 1988 Jan;34(1):97-106. [PubMed:2963158 ]
  5. Reddy DS: Neurosteroids: endogenous role in the human brain and therapeutic potentials. Prog Brain Res. 2010;186:113-37. doi: 10.1016/B978-0-444-53630-3.00008-7. [PubMed:21094889 ]
  6. Harteneck C: Pregnenolone sulfate: from steroid metabolite to TRP channel ligand. Molecules. 2013 Sep 27;18(10):12012-28. doi: 10.3390/molecules181012012. [PubMed:24084011 ]