Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-22 21:03:43 UTC
Update Date2021-09-14 15:40:13 UTC
HMDB IDHMDB0006278
Secondary Accession Numbers
  • HMDB06278
Metabolite Identification
Common Name5a-Dihydrotestosterone sulfate
Description5a-Dihydrotestosterone sulfate is a sulfate derivative of 5a-Dihydrotestosterone produced through phase II metabolism. 5a-dihydrotestosterone (DHT) is a steroid similar to testosterone and androstenedione, that belongs to a class called androgens. DHT is a C19 steroid and possesses androgenic activity. Androgen production takes place mainly in the Leydig cells of the testes. Androgens circulate in the blood bound to proteins, especially sex hormone binding globulin (SHBG) and albumin. A trace amount of these steroids circulate in the unbound form in the blood and are referred to as the free fractions. DHT has at least three times the binding affinity for SHBG than testosterone. About 70% of DHT is derived from peripheral conversion of testosterone in males, while most of the DHT is derived from androstenedione in females.
Structure
Data?1582752378
Synonyms
ValueSource
(5alpha,17beta)-3-Oxoandrostan-17-yl hydrogen sulfateChEBI
5alpha-Dihydrotestosterone 17-sulfateChEBI
DHT-SulfateChEBI
DHT-SulphateChEBI
Dihydrotestosterone sulfateChEBI
Dihydrotestosterone sulphateChEBI
(5a,17b)-3-Oxoandrostan-17-yl hydrogen sulfateGenerator
(5a,17b)-3-Oxoandrostan-17-yl hydrogen sulfuric acidGenerator
(5a,17b)-3-Oxoandrostan-17-yl hydrogen sulphateGenerator
(5a,17b)-3-Oxoandrostan-17-yl hydrogen sulphuric acidGenerator
(5alpha,17beta)-3-Oxoandrostan-17-yl hydrogen sulfuric acidGenerator
(5alpha,17beta)-3-Oxoandrostan-17-yl hydrogen sulphateGenerator
(5alpha,17beta)-3-Oxoandrostan-17-yl hydrogen sulphuric acidGenerator
(5Α,17β)-3-oxoandrostan-17-yl hydrogen sulfateGenerator
(5Α,17β)-3-oxoandrostan-17-yl hydrogen sulfuric acidGenerator
(5Α,17β)-3-oxoandrostan-17-yl hydrogen sulphateGenerator
(5Α,17β)-3-oxoandrostan-17-yl hydrogen sulphuric acidGenerator
5a-Dihydrotestosterone 17-sulfateGenerator
5a-Dihydrotestosterone 17-sulfuric acidGenerator
5a-Dihydrotestosterone 17-sulphateGenerator
5a-Dihydrotestosterone 17-sulphuric acidGenerator
5alpha-Dihydrotestosterone 17-sulfuric acidGenerator
5alpha-Dihydrotestosterone 17-sulphateGenerator
5alpha-Dihydrotestosterone 17-sulphuric acidGenerator
5Α-dihydrotestosterone 17-sulfateGenerator
5Α-dihydrotestosterone 17-sulfuric acidGenerator
5Α-dihydrotestosterone 17-sulphateGenerator
5Α-dihydrotestosterone 17-sulphuric acidGenerator
DHT-Sulfuric acidGenerator
DHT-Sulphuric acidGenerator
Dihydrotestosterone sulfuric acidGenerator
Dihydrotestosterone sulphuric acidGenerator
5a-Dihydrotestosterone sulfuric acidGenerator
5a-Dihydrotestosterone sulphateGenerator
5a-Dihydrotestosterone sulphuric acidGenerator
5alpha-Dihydrotestosterone sulfateHMDB
5alpha-Dihydrotestosterone sulphateHMDB
Chemical FormulaC19H30O5S
Average Molecular Weight370.504
Monoisotopic Molecular Weight370.18139476
IUPAC Name[(1S,2S,7S,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]oxidanesulfonic acid
Traditional Name5α-dihydrotestosterone sulfate
CAS Registry NumberNot Available
SMILES
[H][C@@]12CC[C@H](OS(O)(=O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C19H30O5S/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(24-25(21,22)23)19(15,2)10-8-16(14)18/h12,14-17H,3-11H2,1-2H3,(H,21,22,23)/t12-,14-,15-,16-,17-,18-,19-/m0/s1
InChI KeyKYVPWJSGFKNNLD-ABEVXSGRSA-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
  • Androgen-skeleton
  • Androstane-skeleton
  • 3-oxosteroid
  • Oxosteroid
  • 3-oxo-5-alpha-steroid
  • Sulfuric acid ester
  • Sulfuric acid monoester
  • Sulfate-ester
  • Alkyl sulfate
  • Organic sulfuric acid or derivatives
  • Cyclic ketone
  • Ketone
  • Organooxygen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
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 PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0053 g/LALOGPS
logP0.27ALOGPS
logP3.47ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)-1.3ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity93.59 m³·mol⁻¹ChemAxon
Polarizability40.41 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]+188.38331661259
DarkChem[M-H]-182.01331661259
DeepCCS[M-2H]-217.530932474
DeepCCS[M+Na]+191.77530932474
AllCCS[M+H]+189.832859911
AllCCS[M+H-H2O]+187.332859911
AllCCS[M+NH4]+192.032859911
AllCCS[M+Na]+192.632859911
AllCCS[M-H]-187.632859911
AllCCS[M+Na-2H]-188.132859911
AllCCS[M+HCOO]-188.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5a-Dihydrotestosterone sulfate[H][C@@]12CC[C@H](OS(O)(=O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C3251.4Standard polar33892256
5a-Dihydrotestosterone sulfate[H][C@@]12CC[C@H](OS(O)(=O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C2905.7Standard non polar33892256
5a-Dihydrotestosterone sulfate[H][C@@]12CC[C@H](OS(O)(=O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C3182.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5a-Dihydrotestosterone sulfate,1TMS,isomer #1C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@H]123088.1Semi standard non polar33892256
5a-Dihydrotestosterone sulfate,1TMS,isomer #1C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@H]123069.4Standard non polar33892256
5a-Dihydrotestosterone sulfate,1TMS,isomer #1C[C@]12CCC(=O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@H]123744.1Standard polar33892256
5a-Dihydrotestosterone sulfate,1TMS,isomer #2C[C@]12CC=C(O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O)CC[C@@H]123112.9Semi standard non polar33892256
5a-Dihydrotestosterone sulfate,1TMS,isomer #2C[C@]12CC=C(O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O)CC[C@@H]122989.9Standard non polar33892256
5a-Dihydrotestosterone sulfate,1TMS,isomer #2C[C@]12CC=C(O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O)CC[C@@H]123847.5Standard polar33892256
5a-Dihydrotestosterone sulfate,1TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O3107.0Semi standard non polar33892256
5a-Dihydrotestosterone sulfate,1TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O3007.0Standard non polar33892256
5a-Dihydrotestosterone sulfate,1TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O3839.7Standard polar33892256
5a-Dihydrotestosterone sulfate,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O[Si](C)(C)C3108.3Semi standard non polar33892256
5a-Dihydrotestosterone sulfate,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O[Si](C)(C)C3208.4Standard non polar33892256
5a-Dihydrotestosterone sulfate,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C=C(O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2OS(=O)(=O)O[Si](C)(C)C3794.7Standard polar33892256
5a-Dihydrotestosterone sulfate,2TMS,isomer #2C[C@]12CC=C(O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@H]123115.4Semi standard non polar33892256
5a-Dihydrotestosterone sulfate,2TMS,isomer #2C[C@]12CC=C(O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@H]123192.5Standard non polar33892256
5a-Dihydrotestosterone sulfate,2TMS,isomer #2C[C@]12CC=C(O[Si](C)(C)C)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C)CC[C@@H]123796.6Standard polar33892256
5a-Dihydrotestosterone sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C3308.3Semi standard non polar33892256
5a-Dihydrotestosterone sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C3377.8Standard non polar33892256
5a-Dihydrotestosterone sulfate,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OS(=O)(=O)O[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C3864.4Standard polar33892256
5a-Dihydrotestosterone sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O)CC[C@@H]32)C13396.2Semi standard non polar33892256
5a-Dihydrotestosterone sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O)CC[C@@H]32)C13285.8Standard non polar33892256
5a-Dihydrotestosterone sulfate,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O)CC[C@@H]32)C13987.1Standard polar33892256
5a-Dihydrotestosterone sulfate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC13375.5Semi standard non polar33892256
5a-Dihydrotestosterone sulfate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC13311.7Standard non polar33892256
5a-Dihydrotestosterone sulfate,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC13980.2Standard polar33892256
5a-Dihydrotestosterone sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@@H]32)C13589.0Semi standard non polar33892256
5a-Dihydrotestosterone sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@@H]32)C13749.7Standard non polar33892256
5a-Dihydrotestosterone sulfate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)CC[C@@H]32)C13954.5Standard polar33892256
5a-Dihydrotestosterone sulfate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC13559.9Semi standard non polar33892256
5a-Dihydrotestosterone sulfate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC13774.4Standard non polar33892256
5a-Dihydrotestosterone sulfate,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](OS(=O)(=O)O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC13951.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5a-Dihydrotestosterone sulfate GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-0359000000-149485897a60b61396e32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5a-Dihydrotestosterone 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 - 5a-Dihydrotestosterone sulfate 10V, Positive-QTOFsplash10-00di-0039000000-dbc19fa747f37f7212032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Dihydrotestosterone sulfate 20V, Positive-QTOFsplash10-00di-0191000000-bb7a78b507be8c3547bc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Dihydrotestosterone sulfate 40V, Positive-QTOFsplash10-002f-3595000000-0842465a9970bd04f71b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Dihydrotestosterone sulfate 10V, Negative-QTOFsplash10-014i-0029000000-b2c6c394ba2ce2ee8c152016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Dihydrotestosterone sulfate 20V, Negative-QTOFsplash10-000i-1092000000-887ce248e8af997371372016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Dihydrotestosterone sulfate 40V, Negative-QTOFsplash10-00ei-6090000000-c03f985254acf33f9b4f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Dihydrotestosterone sulfate 10V, Negative-QTOFsplash10-014i-0009000000-0295bc1386cdfbdd92bf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Dihydrotestosterone sulfate 20V, Negative-QTOFsplash10-014i-0009000000-0295bc1386cdfbdd92bf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Dihydrotestosterone sulfate 40V, Negative-QTOFsplash10-000t-9011000000-eaffe80174b9298493e92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Dihydrotestosterone sulfate 10V, Positive-QTOFsplash10-00di-0009000000-f30493f615f831a2b06f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Dihydrotestosterone sulfate 20V, Positive-QTOFsplash10-0mb9-0982000000-fbfefafbafb34eb8849d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5a-Dihydrotestosterone sulfate 40V, Positive-QTOFsplash10-0a4i-1910000000-7cd7f432c40e91f1db592021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023873
KNApSAcK IDNot Available
Chemspider ID18915389
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2794980
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound18665256
PDB IDNot Available
ChEBI ID138026
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Purvis K, Saksena SK, Landgren BM, Cekan Z, Diczfalusy E: Steroid conjugates in human seminal plasma. Clin Endocrinol (Oxf). 1976 May;5(3):253-61. [PubMed:133773 ]
  2. Purvis K, Saksena SK, Cekan Z, Diczfalusy E, Giner J: Endocrine effects of vasectomy. Clin Endocrinol (Oxf). 1976 May;5(3):263-72. [PubMed:133774 ]
  3. Zhao X, Xu F, Qi B, Hao S, Li Y, Li Y, Zou L, Lu C, Xu G, Hou L: Serum metabolomics study of polycystic ovary syndrome based on liquid chromatography-mass spectrometry. J Proteome Res. 2014 Feb 7;13(2):1101-11. doi: 10.1021/pr401130w. Epub 2014 Jan 24. [PubMed:24428203 ]
  4. Sanchez-Guijo A, Oji V, Hartmann MF, Traupe H, Wudy SA: Simultaneous quantification of cholesterol sulfate, androgen sulfates, and progestagen sulfates in human serum by LC-MS/MS. J Lipid Res. 2015 Sep;56(9):1843-51. doi: 10.1194/jlr.D061499. Epub 2015 Aug 2. [PubMed:26239050 ]
  5. Xu H, Zheng X, Qian Y, Guan J, Yi H, Zou J, Wang Y, Meng L, Zhao A, Yin S, Jia W: Metabolomics Profiling for Obstructive Sleep Apnea and Simple Snorers. Sci Rep. 2016 Aug 2;6:30958. doi: 10.1038/srep30958. [PubMed:27480913 ]
  6. Dehennin L, Jondet M, Scholler R: Androgen and 19-norsteroid profiles in human preovulatory follicles from stimulated cycles: an isotope dilution-mass spectrometric study. J Steroid Biochem. 1987 Mar;26(3):399-405. [PubMed:3586654 ]
  7. Gibb W, Jeffery J: 5 -dihydrotestosterone sulphate and cortisone reductase. Biochim Biophys Acta. 1972 Dec 8;280(4):646-51. [PubMed:4648789 ]