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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:48:59 UTC
HMDB IDHMDB0000031
Secondary Accession Numbers
  • HMDB00031
Metabolite Identification
Common NameAndrosterone
DescriptionAndrosterone is an inactive breakdown metabolite of testosterone, the product of a reaction mediated by the enzyme oxidative 17beta-hydroxysteroid dehydrogenase (EC 1.1.1.51, 17beta-HSD). Androsterone can also be metabolized from other adrenal androgens such as dehydroepiandrosterone, dihydrotestosterone, or androstenedione, and is considered an inactive end product. However, it can be a physiological effector in its own right. Androsterone might be converted back to dihydrotestosterone. Humans (and other primates) are unique among mammals in having high levels of circulating androsterone glucuronide, a process that is the major role of uridine-diphospho-glucuronosyltransferase enzymes (EC 2.4.1.17, UGT) for glucuronidation of steroid metabolism in humans. Conjugation of androsterone is a pathway found in all vertebrates and it is widely recognized that the liver is a major site of glucuronidation. However, it is now clear that extrahepatic tissues are also involved in the conjugation of compounds to which these tissues are exposed. High levels of androsterone glucuronide found in the human prostate, breast cyst fluid, and ovary follicular fluid suggest that glucuronidation of 5alpha-reduced C19 steroids occurs in these tissues as well. In doping control, the ratio of androsterone/etiocholanolone provides valuable information that allows the assignment of a urine specimen to a particular person or the identification of urine samples with identical steroid profiles; this is particularly important to detect attempts of urine manipulation including urine alteration and substitution (PMID: 9188497 , 17017935 , 14643063 , 12943709 , 9699884 , 17260133 ).
Structure
Data?1582752108
Synonyms
ValueSource
(3alpha,5alpha)-3-Hydroxyandrostan-17-oneChEBI
3-Epihydroxyetioallocholan-17-oneChEBI
3alpha-Hydroxy-5alpha-androstan-17-oneChEBI
3alpha-Hydroxyetioallocholan-17-oneChEBI
5alpha-Androstane-3alpha-ol-17-oneChEBI
5alpha-AndrosteroneChEBI
AndrokinineChEBI
AndrotineChEBI
cis-AndrosteroneChEBI
(3a,5a)-3-Hydroxyandrostan-17-oneGenerator
(3Α,5α)-3-hydroxyandrostan-17-oneGenerator
3a-Hydroxy-5a-androstan-17-oneGenerator
3Α-hydroxy-5α-androstan-17-oneGenerator
3a-Hydroxyetioallocholan-17-oneGenerator
3Α-hydroxyetioallocholan-17-oneGenerator
5a-Androstane-3a-ol-17-oneGenerator
5Α-androstane-3α-ol-17-oneGenerator
5a-AndrosteroneGenerator
5Α-androsteroneGenerator
3-alpha-Hydroxy-5-alpha-androstan-17-oneHMDB
3 alpha Hydroxy 5 alpha androstan 17 oneHMDB
5 alpha Androstan 3 alpha ol 17 oneHMDB
5 alpha-Androstan-3 alpha-ol-17-oneHMDB
EpiandrosteroneHMDB
3-alpha-Hydroxy-17-androstanoneHMDB
3-alpha-Hydroxy-5-alpha-androstane-17-oneHMDB
3-alpha-Hydroxy-5alpha-androstan-17-oneHMDB
3-alpha-Hydroxyetioallocholan-17-oneHMDB
3-Hydroxy-(3-alpha,5-alpha)-androstan-17-oneHMDB
3-Hydroxyandrostan-17-oneHMDB
3alpha-Hydroxy-17-androstanoneHMDB
5-alpha-Androstan-3-alpha-ol-17-oneHMDB
5-alpha-Androstane-3alpha-ol-17-oneHMDB
5-alpha-AndrosteroneHMDB
Androstanon-3-alpha-ol-17-oneHMDB
Atromide iciHMDB
3Α-hydroxy-17-androstanoneHMDB
3Α-hydroxy-5α-androstane-17-oneHMDB
5Α-androstan-17-one-3α-olHMDB
5Α-androstan-3α-ol-17-oneHMDB
3alpha-Hydroxy-5alpha-androstane-17-oneHMDB
5alpha-Androstan-17-one-3alpha-olHMDB
5alpha-Androstan-3alpha-ol-17-oneHMDB
AndrosteroneHMDB
Chemical FormulaC19H30O2
Average Molecular Weight290.4403
Monoisotopic Molecular Weight290.224580204
IUPAC Name(1S,2S,5R,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
Traditional Name(1S,2S,5R,7S,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-one
CAS Registry Number53-41-8
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18-,19-/m0/s1
InChI KeyQGXBDMJGAMFCBF-HLUDHZFRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 3-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point185 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.012 mg/mL at 23 °CNot Available
LogP3.69HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0063 g/LALOGPS
logP3.71ALOGPS
logP3.77ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.81 m³·mol⁻¹ChemAxon
Polarizability34.56 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+175.90232859911
AllCCS[M-H]-178.96832859911
DeepCCS[M-2H]-203.92130932474
DeepCCS[M+Na]+178.77430932474
AllCCS[M+H]+175.932859911
AllCCS[M+H-H2O]+172.832859911
AllCCS[M+NH4]+178.832859911
AllCCS[M+Na]+179.632859911
AllCCS[M-H]-179.032859911
AllCCS[M+Na-2H]-179.232859911
AllCCS[M+HCOO]-179.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Androsterone[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C2294.0Standard polar33892256
Androsterone[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C2445.5Standard non polar33892256
Androsterone[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C2635.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Androsterone,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2=O2570.6Semi standard non polar33892256
Androsterone,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2576.5Semi standard non polar33892256
Androsterone,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2600.9Semi standard non polar33892256
Androsterone,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2517.3Standard non polar33892256
Androsterone,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C2936.0Standard polar33892256
Androsterone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@H]3[C@@H]4CCC(=O)[C@@]4(C)CC[C@@H]32)C12814.7Semi standard non polar33892256
Androsterone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C2849.6Semi standard non polar33892256
Androsterone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3133.8Semi standard non polar33892256
Androsterone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C2774.2Standard non polar33892256
Androsterone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3181.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Androsterone GC-MS (1 TMS)splash10-056u-6920000000-1d886b76fe1f65860afb2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Androsterone GC-MS (1 MEOX; 1 TMS)splash10-00al-9820000000-321baddda5ac4f8adaa72014-06-16HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Androsterone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Androsterone GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Androsterone GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Androsterone GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Androsterone GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Androsterone 40V, Positive-QTOFsplash10-0536-7900000000-8cce10a8e140584407c32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Androsterone 10V, Negative-QTOFsplash10-000i-0090000000-fbea13833f57d0820cd82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Androsterone 40V, Negative-QTOFsplash10-052r-6490000000-d9f8bf6f9bc4664ccad22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Androsterone 20V, Negative-QTOFsplash10-000i-0090000000-f56a880ba97983c7e0212021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Androsterone 30V, Positive-QTOFsplash10-0bta-0930000000-49751ee4f183943f62fa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Androsterone 10V, Positive-QTOFsplash10-0006-0090000000-f81b1315d55db1d47ec42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Androsterone 35V, Positive-QTOFsplash10-001c-7190000000-e870cf89a876e5f81d312021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Androsterone 20V, Positive-QTOFsplash10-0a4i-0390000000-85c48da18cebca66ba3c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Androsterone 55V, Positive-QTOFsplash10-00di-0090000000-4a8b942c855c025559692021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Androsterone 30V, Positive-QTOFsplash10-0bta-0930000000-078d7455103eab0cf1ee2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Androsterone 10V, Positive-QTOFsplash10-05fr-0390000000-905b691e9dad87bc603c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Androsterone 35V, Positive-QTOFsplash10-00di-0090000000-514df1ac9844abce75a92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Androsterone 20V, Positive-QTOFsplash10-0a4j-1930000000-b9c49a039799b0a23e042021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Androsterone 40V, Positive-QTOFsplash10-08gj-0900000000-9f326ea5c1c454997fd32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Androsterone 50V, Positive-QTOFsplash10-02cv-0900000000-9d78808dd524e4ca6c502021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androsterone 10V, Positive-QTOFsplash10-00dl-0090000000-42eb8c941695a061666d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androsterone 20V, Positive-QTOFsplash10-00dl-0290000000-1a37c17eb6ea7be9211c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androsterone 40V, Positive-QTOFsplash10-06u7-2790000000-d6e7cebd4af538181f772016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androsterone 10V, Negative-QTOFsplash10-000i-0090000000-9e9f9de3b33af0311acd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androsterone 20V, Negative-QTOFsplash10-000i-0090000000-5ba62f51f815ded160022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androsterone 40V, Negative-QTOFsplash10-0596-2190000000-513ad65531fff88b9f692016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androsterone 10V, Negative-QTOFsplash10-000i-0090000000-c8c452fd99c6bb4f36312021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androsterone 20V, Negative-QTOFsplash10-000i-0090000000-c8c452fd99c6bb4f36312021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androsterone 40V, Negative-QTOFsplash10-000i-0090000000-00c0e7de4e528b98df5c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androsterone 10V, Positive-QTOFsplash10-0006-0090000000-afb176951034ef62419f2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Locations
  • Intestine
  • Prostate
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.00065 (0.00053-0.00088) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.12 +/- 0.014 uMAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.69-96.48 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
details
UrineDetected and Quantified0.27 (0.23-0.33) umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0.16 (0.11-0.18) umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.66 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified6.69 +/- 1.65 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.36 (0.11-0.67) umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Schizophrenia
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00007167 +/- 0.000119 uMAdult (>18 years old)Not SpecifiedLeuprolide acetate-induced hypogonadism details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000142 +/- 0.00009475 uMAdult (>18 years old)Not SpecifiedLeuprolide acetate-induced hypogonadism with testosterone replacment details
UrineDetected and Quantified0.000092 +/- 0.000082 umol/mmol creatinineAdult (>18 years old)BothStress urinary incontinence details
UrineDetected and Quantified0.77 +/- 0.08 umol/mmol creatinineAdult (>18 years old)FemaleHirsutism 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 ]
Hirsutism
  1. Gilad S, Chayen R, Tordjman K, Kisch E, Stern N: Assessment of 5 alpha-reductase activity in hirsute women: comparison of serum androstanediol glucuronide with urinary androsterone and aetiocholanolone excretion. Clin Endocrinol (Oxf). 1994 Apr;40(4):459-64. [PubMed:8187312 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021881
KNApSAcK IDNot Available
Chemspider ID5668
KEGG Compound IDC00523
BioCyc IDNot Available
BiGG ID35244
Wikipedia LinkAndrosterone
METLIN ID2797
PubChem Compound5879
PDB IDNot Available
ChEBI ID16032
Food Biomarker OntologyNot Available
VMH IDANDRSTRN
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceMarker, Russell E. Androsterone. Journal of the American Chemical Society (1935), 57 1755-6.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Biswas MG, Russell DW: Expression cloning and characterization of oxidative 17beta- and 3alpha-hydroxysteroid dehydrogenases from rat and human prostate. J Biol Chem. 1997 Jun 20;272(25):15959-66. [PubMed:9188497 ]
  2. Muller L, Phillipou G: Quantification of 5 alpha- and 5 beta-androstanediols in urine by gas chromatography-mass spectrometry. Clin Chem. 1987 Feb;33(2 Pt 1):256-60. [PubMed:3802509 ]
  3. Schonberger W, Benes P, Morsches B, Zabel B, Scheidt E: [Improvement in the longitudinal growth in Ullrich-Turner syndrome with oxandrolone. Function of urinary excretion of steroid hormones]. Dtsch Med Wochenschr. 1982 Jul 2;107(26):1008-11. [PubMed:6211346 ]
  4. Kim YS, Zhang H, Kim HY: Profiling neurosteroids in cerebrospinal fluids and plasma by gas chromatography/electron capture negative chemical ionization mass spectrometry. Anal Biochem. 2000 Jan 15;277(2):187-95. [PubMed:10625505 ]
  5. Labows JN, Preti G, Hoelzle E, Leyden J, Kligman A: Steroid analysis of human apocrine secretion. Steroids. 1979 Sep;34(3):249-58. [PubMed:158859 ]
  6. Raju U, Kadner S, Levitz M, Kaganowicz A, Blaustein A: Glucosiduronidation and esterification of androsterone by human breast tumors in vitro. Steroids. 1981 Apr;37(4):399-407. [PubMed:7245287 ]
  7. Kaminski RM, Marini H, Kim WJ, Rogawski MA: Anticonvulsant activity of androsterone and etiocholanolone. Epilepsia. 2005 Jun;46(6):819-27. [PubMed:15946323 ]
  8. Grosse J, Anielski P, Hemmersbach P, Lund H, Mueller RK, Rautenberg C, Thieme D: Formation of 19-norsteroids by in situ demethylation of endogenous steroids in stored urine samples. Steroids. 2005 Jul;70(8):499-506. Epub 2005 Mar 29. [PubMed:15894033 ]
  9. Toth I, Faredin I: Steroids excreted by human skin. II. C19-steroid sulphates in human axillary sweat. Acta Med Hung. 1985;42(1-2):21-8. [PubMed:3162156 ]
  10. Teller WM, Homoki J, Wudy S, Schlickenrieder JH: Adrenarche is dissociated from gonadarche--studies in patients with Turner's syndrome. Acta Endocrinol Suppl (Copenh). 1986;279:232-40. [PubMed:2946134 ]
  11. Mitamura K, Setaka M, Shimada K, Honma S, Namiki M, Koh E, Mizokami A: Determination of sulfates of androsterone and epiandrosterone in human serum using isotope diluted liquid chromatography-electrospray ionization-mass spectrometry. Biomed Chromatogr. 2005 Dec;19(10):796-801. [PubMed:15954157 ]
  12. Tchedam Ngatcha B, Luu-The V, Labrie F, Poirier D: Androsterone 3alpha-ether-3beta-substituted and androsterone 3beta-substituted derivatives as inhibitors of type 3 17beta-hydroxysteroid dehydrogenase: chemical synthesis and structure-activity relationship. J Med Chem. 2005 Aug 11;48(16):5257-68. [PubMed:16078844 ]
  13. Hammond GL: Endogenous steroid levels in the human prostate from birth to old age: a comparison of normal and diseased tissues. J Endocrinol. 1978 Jul;78(1):7-19. [PubMed:79632 ]
  14. Thevis M, Geyer H, Mareck U, Sigmund G, Henke J, Henke L, Schanzer W: Detection of manipulation in doping control urine sample collection: a multidisciplinary approach to determine identical urine samples. Anal Bioanal Chem. 2007 Aug;388(7):1539-43. Epub 2007 Jan 27. [PubMed:17260133 ]
  15. Matsuzaki Y, Honda A: Dehydroepiandrosterone and its derivatives: potentially novel anti-proliferative and chemopreventive agents. Curr Pharm Des. 2006;12(26):3411-21. [PubMed:17017935 ]
  16. Belanger A, Pelletier G, Labrie F, Barbier O, Chouinard S: Inactivation of androgens by UDP-glucuronosyltransferase enzymes in humans. Trends Endocrinol Metab. 2003 Dec;14(10):473-9. [PubMed:14643063 ]
  17. Barbier O, Belanger A: The cynomolgus monkey (Macaca fascicularis) is the best animal model for the study of steroid glucuronidation. J Steroid Biochem Mol Biol. 2003 Jun;85(2-5):235-45. [PubMed:12943709 ]
  18. Belanger A, Hum DW, Beaulieu M, Levesque E, Guillemette C, Tchernof A, Belanger G, Turgeon D, Dubois S: Characterization and regulation of UDP-glucuronosyltransferases in steroid target tissues. J Steroid Biochem Mol Biol. 1998 Apr;65(1-6):301-10. [PubMed:9699884 ]
  19. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  20. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  21. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  22. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  23. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Only showing the first 10 proteins. There are 29 proteins in total.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:
AKR1C4
Uniprot ID:
P17516
Molecular weight:
37094.57
Reactions
Androsterone + NAD → Androstanedione + NADH + Hydrogen Iondetails
Androsterone + NADP → Androstanedione + NADPH + Hydrogen Iondetails
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
Gene Name:
SULT2A1
Uniprot ID:
Q06520
Molecular weight:
33779.57
References
  1. Chang HJ, Shi R, Rehse P, Lin SX: Identifying androsterone (ADT) as a cognate substrate for human dehydroepiandrosterone sulfotransferase (DHEA-ST) important for steroid homeostasis: structure of the enzyme-ADT complex. J Biol Chem. 2004 Jan 23;279(4):2689-96. Epub 2003 Oct 21. [PubMed:14573603 ]
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone.
Gene Name:
AKR1C3
Uniprot ID:
P42330
Molecular weight:
36866.91
General function:
Involved in oxidoreductase activity
Specific function:
Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:
AKR1C1
Uniprot ID:
Q04828
Molecular weight:
36788.02
General function:
Involved in oxidoreductase activity
Specific function:
Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent androgen 5-alpha-dihydrotestosterone (5-alpha-DHT) to 5-alpha-androstane-3-alpha,17-beta-diol (3-alpha-diol). Has a high bile-binding ability.
Gene Name:
AKR1C2
Uniprot ID:
P52895
Molecular weight:
15747.91
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Molecular weight:
38742.9
Reactions
Androsterone + Uridine diphosphate glucuronic acid → Androsterone glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:
UGT2B4
Uniprot ID:
P06133
Molecular weight:
60512.035
Reactions
Androsterone + Uridine diphosphate glucuronic acid → Androsterone glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular weight:
60024.535
Reactions
Androsterone + Uridine diphosphate glucuronic acid → Androsterone glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:
UGT2B10
Uniprot ID:
P36537
Molecular weight:
60773.485
Reactions
Androsterone + Uridine diphosphate glucuronic acid → Androsterone glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular weight:
60720.15
Reactions
Androsterone + Uridine diphosphate glucuronic acid → Androsterone glucuronide + Uridine 5'-diphosphatedetails
References
  1. Coffman BL, King CD, Rios GR, Tephly TR: The glucuronidation of opioids, other xenobiotics, and androgens by human UGT2B7Y(268) and UGT2B7H(268). Drug Metab Dispos. 1998 Jan;26(1):73-7. [PubMed:9443856 ]

Only showing the first 10 proteins. There are 29 proteins in total.