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Showing metabocard for Androstanediol (HMDB0000495)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-08-16 03:20:41 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
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
5 alpha Androstane 3 alpha,17 beta diolMeSH
5 alpha Androstane 3 beta,17 alpha diolMeSH
5 alpha Androstane 3 beta,17 beta diolMeSH
5 alpha Androstane 3alpha,17 beta diolMeSH
5 alpha-Androstane-3 alpha,17 beta-diolMeSH
5 alpha-Androstane-3 beta,17 alpha-diolMeSH
5 alpha-Androstane-3 beta,17 beta-diolMeSH
5 alpha-Androstane-3alpha,17 beta-diolMeSH
5 beta Androstane 3 alpha,17 beta diolMeSH
5 beta-Androstane-3 alpha,17 beta-diolMeSH
5-Androstane-3,17-diolMeSH
5alpha Androstane 3beta,17alpha diolMeSH
5alpha-Androstane-3beta,17alpha-diolMeSH
Androstane 3,17 diolMeSH
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
DescriptionThis compound 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
  • 17-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • C19 steroids (androgens) and derivatives (C07632 )
  • Androstane and derivatives (C07632 )
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
  • Extracellular
  • Membrane (predicted from logP)
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 Solubility0.019 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.63 m3·mol-1ChemAxon
Polarizability35.34 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Testes
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    		 details
    UrineDetected and Quantified0.022 +/- 0.0043 umol/mmol creatinineAdult (>18 years old)MaleNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    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
    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
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB022074
    KNApSAcK IDNot Available
    Chemspider ID390064
    KEGG Compound IDC07632
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    NuGOwiki LinkHMDB0000495
    METLIN ID5481
    PubChem Compound441301
    PDB IDNot Available
    ChEBI ID428186
    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

    Enzyme Details
    1. Retinol dehydrogenase 16
    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