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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:03 UTC
HMDB IDHMDB0000495
Secondary Accession Numbers
  • HMDB00495
Metabolite Identification
Common NameAndrostanediol
DescriptionAndrostanediol is a metabolite of dihydrotestosterone, itself a metabolite of testosterone. Androstanediol is implicated in the regulation of gonadotropin secretion. As a metabolite of dihydroxytestosterone formed in the peripheral tissues, androstanediol and androstnediol-glucuronide can be used to estimate peripheral androgen activity. Androstanediol is a potential GABA (A) receptor-modulating neurosteroid with anticonvulsant properties and hence could act as a key neuromodulator in the central nervous system. It is considered that androstanediol has hedonic effects; therefore it is anticipated that androgens that are readily metabolized to androstanediol may have higher abuse potential than androgens that are not as easily metabolized to androstanediol. These results add to the growing literature indicating that athletes and non-athletes may be at considerable risk when they abuse androgens. (PMID: 11500254 , 16040068 , 11744084 ).
Structure
Data?1582752135
Synonyms
ValueSource
Androstane-3,17-diolKEGG
3-a-AndrostanediolHMDB
3-alpha-AndrostanediolHMDB
3alpha-AndrostanediolHMDB
5 a-Androstane-3 a, 17 b-diolHMDB
5 alpha-Androstane-3 alpha, 17 beta-diolHMDB
5-a-Androstane-3-a, 17-b-diolHMDB
5-alpha-Androstan-3-alpha,17-beta-diolHMDB
5-alpha-Androstane-3-a, 17-beta-diolHMDB
5-alpha-Androstane-3-alpha-17-beta-diolHMDB
5 Androstane 3,17 diolMeSH, HMDB
5 alpha Androstane 3 alpha,17 beta diolMeSH, HMDB
5 alpha Androstane 3 beta,17 alpha diolMeSH, HMDB
5 alpha Androstane 3 beta,17 beta diolMeSH, HMDB
5 alpha Androstane 3alpha,17 beta diolMeSH, HMDB
5 alpha-Androstane-3 alpha,17 beta-diolMeSH, HMDB
5 alpha-Androstane-3 beta,17 alpha-diolMeSH, HMDB
5 alpha-Androstane-3 beta,17 beta-diolMeSH, HMDB
5 alpha-Androstane-3alpha,17 beta-diolMeSH, HMDB
5 beta Androstane 3 alpha,17 beta diolMeSH, HMDB
5 beta-Androstane-3 alpha,17 beta-diolMeSH, HMDB
5-Androstane-3,17-diolMeSH, HMDB
5alpha Androstane 3beta,17alpha diolMeSH, HMDB
5alpha-Androstane-3beta,17alpha-diolMeSH, HMDB
Androstane 3,17 diolMeSH, HMDB
Chemical FormulaC19H32O2
Average Molecular Weight292.4562
Monoisotopic Molecular Weight292.240230268
IUPAC Name(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol
Traditional Name(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,14-diol
CAS Registry Number25126-76-5
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/C19H32O2/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/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17?,18-,19-/m0/s1
InChI KeyCBMYJHIOYJEBSB-UNPXRYTGSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentPhosphatidylcholines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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 Solubility0.019 g/LALOGPS
logP3.56ALOGPS
logP3.2ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-0.76ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.63 m³·mol⁻¹ChemAxon
Polarizability35.34 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]+170.66331661259
DarkChem[M-H]-166.24731661259
AllCCS[M+H]+177.83932859911
AllCCS[M-H]-179.13632859911
DeepCCS[M-2H]-206.36930932474
DeepCCS[M+Na]+181.62730932474
AllCCS[M+H]+177.832859911
AllCCS[M+H-H2O]+174.832859911
AllCCS[M+NH4]+180.632859911
AllCCS[M+Na]+181.532859911
AllCCS[M-H]-179.132859911
AllCCS[M+Na-2H]-179.432859911
AllCCS[M+HCOO]-179.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Androstanediol[H][C@@]12CCC(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C2444.0Standard polar33892256
Androstanediol[H][C@@]12CCC(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C2471.5Standard non polar33892256
Androstanediol[H][C@@]12CCC(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C2611.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Androstanediol,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](O)CC[C@@]43C)[C@@H]1CCC2O[Si](C)(C)C2596.8Semi standard non polar33892256
Androstanediol,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC[C@H]4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CCC2O2582.8Semi standard non polar33892256
Androstanediol,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]1CCC2O[Si](C)(C)C2601.9Semi standard non polar33892256
Androstanediol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C2876.1Semi standard non polar33892256
Androstanediol,1TBDMS,isomer #2CC(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)C12839.6Semi standard non polar33892256
Androstanediol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CC[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@]12C3155.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Androstanediol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03gi-0290000000-ef7ce05726cbec3a35bd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Androstanediol GC-MS (2 TMS) - 70eV, Positivesplash10-05fr-2237900000-35be1627cada18777db82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Androstanediol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Androstanediol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Androstanediol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Androstanediol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Androstanediol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Androstanediol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanediol 10V, Positive-QTOFsplash10-004l-0090000000-22d60c19836ea8b4c2912016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanediol 20V, Positive-QTOFsplash10-056r-0390000000-edb0fb77b27575b4b7292016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanediol 40V, Positive-QTOFsplash10-00mk-2980000000-cd6eafa93f3164ed780a2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanediol 10V, Negative-QTOFsplash10-0006-0090000000-bc689c3cdfdf044c011e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanediol 20V, Negative-QTOFsplash10-006x-0090000000-bfbc140857bbdb62bcff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanediol 40V, Negative-QTOFsplash10-06vm-1290000000-bced1e06a8686f3501af2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanediol 10V, Negative-QTOFsplash10-0006-0090000000-11452f48ce72555f1f282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanediol 20V, Negative-QTOFsplash10-0006-0090000000-11452f48ce72555f1f282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanediol 40V, Negative-QTOFsplash10-000l-0090000000-ac9e93370094e8aebfa12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanediol 10V, Positive-QTOFsplash10-002f-0090000000-36f4d97265b0d994d6282021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanediol 20V, Positive-QTOFsplash10-052b-3940000000-b87bad8b672cc5fb32b02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Androstanediol 40V, Positive-QTOFsplash10-0aos-3900000000-0f8ce10c286f165d6e0f2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected and Quantified0.022 +/- 0.0043 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.019 +/- 0.0029 umol/mmol creatinineAdult (>18 years old)BothBenign prostatic hypertrophy (BPH) details
UrineDetected and Quantified0.10 +/- 0.04 umol/mmol creatinineAdult (>18 years old)BothProstate cancer details
Associated Disorders and Diseases
Disease References
Benign prostatic hyperplasia
  1. Puah CM, Williams G, Ghanadian R: Urinary unconjugated 5 alpha-androstane-3 alpha, 17 beta-diol in patients with prostatic tumours. Urol Res. 1982;10(2):81-4. [PubMed:6180540 ]
Prostate cancer
  1. Puah CM, Williams G, Ghanadian R: Urinary unconjugated 5 alpha-androstane-3 alpha, 17 beta-diol in patients with prostatic tumours. Urol Res. 1982;10(2):81-4. [PubMed:6180540 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB025706
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000176
Good Scents IDNot Available
References
Synthesis ReferenceVierhapper H Formation of androstanediol from 13C-labeled testosterone in humans. Steroids (1990), 55(4), 177-80.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chetyrkin SV, Hu J, Gough WH, Dumaual N, Kedishvili NY: Further characterization of human microsomal 3alpha-hydroxysteroid dehydrogenase. Arch Biochem Biophys. 2001 Feb 1;386(1):1-10. [PubMed:11360992 ]
  2. Karlsson T, Vahlquist A, Kedishvili N, Torma H: 13-cis-retinoic acid competitively inhibits 3 alpha-hydroxysteroid oxidation by retinol dehydrogenase RoDH-4: a mechanism for its anti-androgenic effects in sebaceous glands? Biochem Biophys Res Commun. 2003 Mar 28;303(1):273-8. [PubMed:12646198 ]
  3. Thompson JA, Miles BS, Fennessey PV: Urinary organic acids quantitated by age groups in a healthy pediatric population. Clin Chem. 1977 Sep;23(9):1734-8. [PubMed:890917 ]
  4. Gupta MK, Guryev OL, Auchus RJ: 5alpha-reduced C21 steroids are substrates for human cytochrome P450c17. Arch Biochem Biophys. 2003 Oct 15;418(2):151-60. [PubMed:14522586 ]
  5. Secreto G, Toniolo P, Berrino F, Recchione C, Cavalleri A, Pisani P, Totis A, Fariselli G, Di Pietro S: Serum and urinary androgens and risk of breast cancer in postmenopausal women. Cancer Res. 1991 May 15;51(10):2572-6. [PubMed:2021938 ]
  6. Gratterola R: Anovulation and increased androgenic activity as breast cancer risk in women with fibrocystic disease of the breast. Cancer Res. 1978 Sep;38(9):3051-4. [PubMed:679211 ]
  7. Leszczynski DE, Schafer RM: Characterization of steroid hormone association with human plasma lipoproteins. Steroids. 1989 Jul;54(1):37-53. [PubMed:2815156 ]
  8. Thompson DL, Rittmaster RS, Rodriguez AM, Moore PH Jr, Rao PN: Synthesis of new steroid haptens for radioimmunoassay--VIII. Development and validation of a specific radioimmunoassay for serum 5 alpha-androstane-3 alpha, 17 beta-diol 17-glucuronide. J Steroid Biochem. 1990 Jul 4;36(4):345-9. [PubMed:2391963 ]
  9. Secreto G, Toniolo P, Berrino F, Recchione C, Di Pietro S, Fariselli G, Decarli A: Increased androgenic activity and breast cancer risk in premenopausal women. Cancer Res. 1984 Dec;44(12 Pt 1):5902-5. [PubMed:6498847 ]
  10. Ivell R, Balvers M, Anand RJ, Paust HJ, McKinnell C, Sharpe R: Differentiation-dependent expression of 17beta-hydroxysteroid dehydrogenase, type 10, in the rodent testis: effect of aging in Leydig cells. Endocrinology. 2003 Jul;144(7):3130-7. [PubMed:12810569 ]
  11. Wudy SA, Dorr HG, Solleder C, Djalali M, Homoki J: Profiling steroid hormones in amniotic fluid of midpregnancy by routine stable isotope dilution/gas chromatography-mass spectrometry: reference values and concentrations in fetuses at risk for 21-hydroxylase deficiency. J Clin Endocrinol Metab. 1999 Aug;84(8):2724-8. [PubMed:10443667 ]
  12. Keel BA, Abney TO: Oestrogenic regulation of testicular androgen production during development in the rat. J Endocrinol. 1985 May;105(2):211-8. [PubMed:2985727 ]
  13. Klemm W, Liebich HM, Gupta D: Plasma levels of 5alpha-androstane-3alpha,17beta-diol in boys during adolescent growth. J Clin Endocrinol Metab. 1976 Mar;42(3):514-9. [PubMed:1254692 ]
  14. Frye CA, Park D, Tanaka M, Rosellini R, Svare B: The testosterone metabolite and neurosteroid 3alpha-androstanediol may mediate the effects of testosterone on conditioned place preference. Psychoneuroendocrinology. 2001 Oct;26(7):731-50. [PubMed:11500254 ]
  15. Reddy DS, Venkatarangan L, Chien B, Ramu K: A high-performance liquid chromatography-tandem mass spectrometry assay of the androgenic neurosteroid 3alpha-androstanediol (5alpha-androstane-3alpha,17beta-diol) in plasma. Steroids. 2005 Dec 1;70(13):879-85. Epub 2005 Jul 22. [PubMed:16040068 ]
  16. Rosellini RA, Svare BB, Rhodes ME, Frye CA: The testosterone metabolite and neurosteroid 3alpha-androstanediol may mediate the effects of testosterone on conditioned place preference. Brain Res Brain Res Rev. 2001 Nov;37(1-3):162-71. [PubMed:11744084 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Oxidoreductase with a preference for NAD. Oxidizes all- trans-retinol and 13-cis-retinol to the corresponding aldehydes. Has higher activity towards CRBP-bound retinol than with free retinol. Oxidizes 3-alpha-hydroxysteroids. Oxidizes androstanediol and androsterone to dihydrotestosterone and androstanedione. Can also catalyze the reverse reaction
Gene Name:
RDH16
Uniprot ID:
O75452
Molecular weight:
35673.1