Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:37 UTC
Update Date2022-03-07 02:49:18 UTC
HMDB IDHMDB0003166
Secondary Accession Numbers
  • HMDB03166
Metabolite Identification
Common Name16b-Hydroxystanozolol
Description16b-Hydroxystanozolol is the major metabolite of stanozolol. Stanozolol is an anabolic steroid illicitly used for growth promoting purposes in animal production. For reasons of public health the use of anabolic steroids as growth promoters is officially banned in Europe in animals intended for consumption. Stanozolol is an anabolic steroid banned in competing athletes. Doping control screening for the analysis of anabolic steroids in human urine or the detection of anabolic steroid residues in cattle's urine is achieved using liquid and gas chromatography time-of-flight mass spectrometry, liquid chromatography-tandem mass spectrometry or through a combination of liquid chromatography/tandem mass spectrometry and gas chromatography/mass spectrometry. Androgenic anabolic steroids are defined as natural, synthetic or semi-synthetic drugs chemicals derived from testosterone, used with the aim to improve physical performance by increasing both muscle strength and mass. Despite their reported toxicological effects on the cardiovascular, hepatic and neuro-endocrine systems, the AAS have been extensively used in sports activities. (PMID: 15782394 , 17610244 , 17724580 ).
Structure
Data?1582752265
Synonyms
ValueSource
(5a,16b,17b)-17-Methyl-'h-androst-2-eno[3,2-c]pyrazole-16,17-diolHMDB
16b-OH-StanozololHMDB
16beta-HydroxystanozololHMDB
Cyclopenta[7,8]phenanthro[2,3-c]pyrazole, 2'H-androst-2-eno[3,2-c]pyrazole-16,17-diol deriv.HMDB
16-Hydroxystanozolol, (5alpha,16alpha,17beta)-isomerHMDB
16-HydroxystanozololHMDB
16-Hydroxystanozolol, (5alpha,16alpha,17alpha)-isomerHMDB
Chemical FormulaC21H32N2O2
Average Molecular Weight344.491
Monoisotopic Molecular Weight344.246378278
IUPAC Name(1S,2S,10S,13R,14S,16S,17R,18S)-2,17,18-trimethyl-6,7-diazapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icosa-4(8),5-diene-16,17-diol
Traditional Name(1S,2S,10S,13R,14S,16S,17R,18S)-2,17,18-trimethyl-6,7-diazapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icosa-4(8),5-diene-16,17-diol
CAS Registry Number125590-76-3
SMILES
[H][C@@]12C[C@H](O)[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC3=C(C[C@]12C)C=NN3
InChI Identifier
InChI=1S/C21H32N2O2/c1-19-10-12-11-22-23-17(12)8-13(19)4-5-14-15(19)6-7-20(2)16(14)9-18(24)21(20,3)25/h11,13-16,18,24-25H,4-10H2,1-3H3,(H,22,23)/t13-,14+,15-,16-,18-,19-,20-,21-/m0/s1
InChI KeyIZGBPAAEPVNBGA-BWPSUJIGSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrane steroids
Alternative Parents
Substituents
  • Estrane-skeleton
  • Hydroxysteroid
  • 16-beta-hydroxysteroid
  • 16-hydroxysteroid
  • 17-hydroxysteroid
  • Azole
  • Cyclic alcohol
  • Pyrazole
  • Tertiary alcohol
  • Heteroaromatic compound
  • 1,2-diol
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.801Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.022 g/LALOGPS
logP3.14ALOGPS
logP2.62ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)13.49ChemAxon
pKa (Strongest Basic)2.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity98.61 m³·mol⁻¹ChemAxon
Polarizability40.12 ųChemAxon
Number of Rings5ChemAxon
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]+180.78231661259
DarkChem[M-H]-177.27131661259
DeepCCS[M-2H]-219.50630932474
DeepCCS[M+Na]+193.79930932474
AllCCS[M+H]+186.332859911
AllCCS[M+H-H2O]+183.632859911
AllCCS[M+NH4]+188.832859911
AllCCS[M+Na]+189.532859911
AllCCS[M-H]-191.032859911
AllCCS[M+Na-2H]-191.332859911
AllCCS[M+HCOO]-191.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
16b-Hydroxystanozolol[H][C@@]12C[C@H](O)[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC3=C(C[C@]12C)C=NN34045.5Standard polar33892256
16b-Hydroxystanozolol[H][C@@]12C[C@H](O)[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC3=C(C[C@]12C)C=NN33149.8Standard non polar33892256
16b-Hydroxystanozolol[H][C@@]12C[C@H](O)[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC3=C(C[C@]12C)C=NN33356.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
16b-Hydroxystanozolol,1TMS,isomer #1C[C@]12CC3=C(C[C@@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C[C@H](O[Si](C)(C)C)[C@]2(C)O)[NH]N=C33215.3Semi standard non polar33892256
16b-Hydroxystanozolol,1TMS,isomer #2C[C@]12CC3=C(C[C@@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C[C@H](O)[C@]2(C)O[Si](C)(C)C)[NH]N=C33224.1Semi standard non polar33892256
16b-Hydroxystanozolol,1TMS,isomer #3C[C@]12CC3=C(C[C@@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C[C@H](O)[C@]2(C)O)N([Si](C)(C)C)N=C33238.4Semi standard non polar33892256
16b-Hydroxystanozolol,2TMS,isomer #1C[C@]12CC3=C(C[C@@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C[C@H](O[Si](C)(C)C)[C@]2(C)O[Si](C)(C)C)[NH]N=C33266.1Semi standard non polar33892256
16b-Hydroxystanozolol,2TMS,isomer #2C[C@]12CC3=C(C[C@@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C[C@H](O[Si](C)(C)C)[C@]2(C)O)N([Si](C)(C)C)N=C33243.7Semi standard non polar33892256
16b-Hydroxystanozolol,2TMS,isomer #3C[C@]12CC3=C(C[C@@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C[C@H](O)[C@]2(C)O[Si](C)(C)C)N([Si](C)(C)C)N=C33230.8Semi standard non polar33892256
16b-Hydroxystanozolol,3TMS,isomer #1C[C@]12CC3=C(C[C@@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C[C@H](O[Si](C)(C)C)[C@]2(C)O[Si](C)(C)C)N([Si](C)(C)C)N=C33288.4Semi standard non polar33892256
16b-Hydroxystanozolol,3TMS,isomer #1C[C@]12CC3=C(C[C@@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C[C@H](O[Si](C)(C)C)[C@]2(C)O[Si](C)(C)C)N([Si](C)(C)C)N=C33267.9Standard non polar33892256
16b-Hydroxystanozolol,3TMS,isomer #1C[C@]12CC3=C(C[C@@H]1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1C[C@H](O[Si](C)(C)C)[C@]2(C)O[Si](C)(C)C)N([Si](C)(C)C)N=C33363.2Standard polar33892256
16b-Hydroxystanozolol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1C[C@H]2[C@@H]3CC[C@H]4CC5=C(C=N[NH]5)C[C@]4(C)[C@H]3CC[C@]2(C)[C@@]1(C)O3470.8Semi standard non polar33892256
16b-Hydroxystanozolol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@]1(C)[C@@H](O)C[C@H]2[C@@H]3CC[C@H]4CC5=C(C=N[NH]5)C[C@]4(C)[C@H]3CC[C@@]21C3476.7Semi standard non polar33892256
16b-Hydroxystanozolol,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1N=CC2=C1C[C@@H]1CC[C@@H]3[C@H](CC[C@@]4(C)[C@H]3C[C@H](O)[C@]4(C)O)[C@@]1(C)C23455.5Semi standard non polar33892256
16b-Hydroxystanozolol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1C[C@H]2[C@@H]3CC[C@H]4CC5=C(C=N[NH]5)C[C@]4(C)[C@H]3CC[C@]2(C)[C@@]1(C)O[Si](C)(C)C(C)(C)C3758.8Semi standard non polar33892256
16b-Hydroxystanozolol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1C[C@H]2[C@@H]3CC[C@H]4CC5=C(C=NN5[Si](C)(C)C(C)(C)C)C[C@]4(C)[C@H]3CC[C@]2(C)[C@@]1(C)O3678.0Semi standard non polar33892256
16b-Hydroxystanozolol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@]1(C)[C@@H](O)C[C@H]2[C@@H]3CC[C@H]4CC5=C(C=NN5[Si](C)(C)C(C)(C)C)C[C@]4(C)[C@H]3CC[C@@]21C3666.1Semi standard non polar33892256
16b-Hydroxystanozolol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1C[C@H]2[C@@H]3CC[C@H]4CC5=C(C=NN5[Si](C)(C)C(C)(C)C)C[C@]4(C)[C@H]3CC[C@]2(C)[C@@]1(C)O[Si](C)(C)C(C)(C)C3920.9Semi standard non polar33892256
16b-Hydroxystanozolol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1C[C@H]2[C@@H]3CC[C@H]4CC5=C(C=NN5[Si](C)(C)C(C)(C)C)C[C@]4(C)[C@H]3CC[C@]2(C)[C@@]1(C)O[Si](C)(C)C(C)(C)C4035.8Standard non polar33892256
16b-Hydroxystanozolol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1C[C@H]2[C@@H]3CC[C@H]4CC5=C(C=NN5[Si](C)(C)C(C)(C)C)C[C@]4(C)[C@H]3CC[C@]2(C)[C@@]1(C)O[Si](C)(C)C(C)(C)C3610.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxystanozolol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uxs-1298000000-e5922c5f2c2da69632b52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxystanozolol GC-MS (2 TMS) - 70eV, Positivesplash10-00di-3236900000-157d8d09efaeaf84d26b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16b-Hydroxystanozolol 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 - 16b-Hydroxystanozolol 10V, Positive-QTOFsplash10-0002-0009000000-3dce83afdfd62c3562f72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxystanozolol 20V, Positive-QTOFsplash10-0ar0-0093000000-d8197d56bb13cd018ce92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxystanozolol 40V, Positive-QTOFsplash10-0ldi-7987000000-c63f25f5fb379062b1782017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxystanozolol 10V, Negative-QTOFsplash10-0006-0009000000-d62368294f0bd1560d222017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxystanozolol 20V, Negative-QTOFsplash10-00mo-0009000000-1b482a36251fc401712a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxystanozolol 40V, Negative-QTOFsplash10-004i-2049000000-6cd31c36847fe353db022017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxystanozolol 10V, Positive-QTOFsplash10-0002-0029000000-eecedc58c6f30dab76902021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxystanozolol 20V, Positive-QTOFsplash10-000j-0964000000-f58bdd1b840402e74de42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxystanozolol 40V, Positive-QTOFsplash10-0udi-0590000000-c98f4d460e53eb3a27b02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxystanozolol 10V, Negative-QTOFsplash10-0006-0009000000-f0c9f6f6d6de10398e832021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxystanozolol 20V, Negative-QTOFsplash10-0006-0049000000-0ebdb8c09f289f5ce0bb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16b-Hydroxystanozolol 40V, Negative-QTOFsplash10-0006-0029000000-60ec668969053e23118d2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023118
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14299609
PDB IDNot Available
ChEBI IDNot Available
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. Masse R, Ayotte C, Bi HG, Dugal R: Studies on anabolic steroids. III. Detection and characterization of stanozolol urinary metabolites in humans by gas chromatography-mass spectrometry. J Chromatogr. 1989 Dec 29;497:17-37. [PubMed:2625454 ]
  2. Georgakopoulos CG, Vonaparti A, Stamou M, Kiousi P, Lyris E, Angelis YS, Tsoupras G, Wuest B, Nielen MW, Panderi I, Koupparis M: Preventive doping control analysis: liquid and gas chromatography time-of-flight mass spectrometry for detection of designer steroids. Rapid Commun Mass Spectrom. 2007;21(15):2439-46. [PubMed:17610244 ]
  3. Pozo OJ, Van Eenoo P, Deventer K, Delbeke FT: Development and validation of a qualitative screening method for the detection of exogenous anabolic steroids in urine by liquid chromatography-tandem mass spectrometry. Anal Bioanal Chem. 2007 Oct;389(4):1209-24. Epub 2007 Aug 28. [PubMed:17724580 ]
  4. Van Poucke C, Van De Velde M, Van Peteghem C: Combination of liquid chromatography/tandem mass spectrometry and gas chromatography/mass spectrometry for the detection of 21 anabolic steroid residues in bovine urine. J Mass Spectrom. 2005 Jun;40(6):731-8. [PubMed:15782394 ]