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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-08 10:31:56 UTC
Update Date2022-03-07 02:49:33 UTC
HMDB IDHMDB0006774
Secondary Accession Numbers
  • HMDB06774
Metabolite Identification
Common Name16a-Hydroxyandrost-4-ene-3,17-dione
Description16a-Hydroxyandrost-4-ene-3,17-dione, also known as 4-androsten-16alpha-ol-3,17-dione or 16alpha-ohad, 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. Thus, 16a-hydroxyandrost-4-ene-3,17-dione is considered to be a steroid lipid molecule. 16a-Hydroxyandrost-4-ene-3,17-dione is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1582752405
Synonyms
ValueSource
4-Androsten-16alpha-ol-3,17-dioneChEBI
4-Androsten-16a-ol-3,17-dioneGenerator
4-Androsten-16α-ol-3,17-dioneGenerator
16alpha-Hydroxyandrost-4-ene-3,17-dioneHMDB
16alpha-HydroxyandrostenedioneHMDB
16-Hydroxyandrost-4-en-3,17-dioneHMDB
16 alpha-Hydroxyandrost-4-en-3,17-dioneHMDB
16-Hydroxyandrost-4-en-3,17-dione, (16alpha)-isomerHMDB
16-Hydroxyandrost-4-en-3,17-dione, (16beta)-isomerHMDB
16alpha-OHADHMDB
16a-Hydroxyandrost-4-ene-3,17-dioneGenerator
16Α-hydroxyandrost-4-ene-3,17-dioneGenerator
Chemical FormulaC19H26O3
Average Molecular Weight302.4079
Monoisotopic Molecular Weight302.188194698
IUPAC Name(1S,2R,10R,11S,13R,15S)-13-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14-dione
Traditional Name4-androsten-16α-ol-3,17-dione
CAS Registry Number63-02-5
SMILES
[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C19H26O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h9,13-16,21H,3-8,10H2,1-2H3/t13-,14+,15+,16-,18+,19+/m1/s1
InChI KeySSBCZTXGVMMZOT-NBBHSKLNSA-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-oxo-delta-4-steroid
  • 3-oxosteroid
  • 16-hydroxysteroid
  • 16-alpha-hydroxysteroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

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 Solubility0.067 g/LALOGPS
logP2.32ALOGPS
logP3.06ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)13.38ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.1 m³·mol⁻¹ChemAxon
Polarizability33.99 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]+174.99231661259
DarkChem[M-H]-170.41931661259
DeepCCS[M-2H]-208.83430932474
DeepCCS[M+Na]+183.42730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
16a-Hydroxyandrost-4-ene-3,17-dione[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C3527.0Standard polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C2628.3Standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C2826.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
16a-Hydroxyandrost-4-ene-3,17-dione,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1C[C@@H](O[Si](C)(C)C)C2=O2916.4Semi standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC(O)=C2O[Si](C)(C)C2880.0Semi standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,1TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1C[C@@H](O)C2=O2806.2Semi standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C2940.8Semi standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C2663.1Standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C3143.8Standard polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1C[C@@H](O[Si](C)(C)C)C2=O2851.5Semi standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1C[C@@H](O[Si](C)(C)C)C2=O2771.6Standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1C[C@@H](O[Si](C)(C)C)C2=O3197.6Standard polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC(O)=C2O[Si](C)(C)C2847.2Semi standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC(O)=C2O[Si](C)(C)C2679.8Standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC(O)=C2O[Si](C)(C)C3142.4Standard polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,3TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C2879.1Semi standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,3TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C2837.9Standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,3TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C3126.0Standard polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]2(C)C1=O3167.2Semi standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C(O)C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C3133.2Semi standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3C[C@@H](O)C(=O)[C@@]3(C)CC[C@@H]123075.9Semi standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]2C13437.4Semi standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]2C13127.6Standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]2C13365.3Standard polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)[C@@]3(C)CC[C@@H]123369.6Semi standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)[C@@]3(C)CC[C@@H]123265.3Standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)[C@@]3(C)CC[C@@H]123430.8Standard polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC(O)=C(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]123357.1Semi standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC(O)=C(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]123098.4Standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC(O)=C(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]123392.2Standard polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]123594.0Semi standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]123402.2Standard non polar33892256
16a-Hydroxyandrost-4-ene-3,17-dione,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]123424.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-0190000000-333d436ce8b783dec9002017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione GC-MS (1 TMS) - 70eV, Positivesplash10-0ldj-1029000000-d779bb8112f47f4675a32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 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 - 16a-Hydroxyandrost-4-ene-3,17-dione 10V, Positive-QTOFsplash10-0udi-0169000000-552881f7e148e949c2d52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 20V, Positive-QTOFsplash10-0fi9-0191000000-5bba772cd2498247059b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 40V, Positive-QTOFsplash10-0ldl-3390000000-dcf95e7ad7d31a7b23452017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 10V, Negative-QTOFsplash10-0udi-0009000000-0e8dc36bc54906d11cd22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 20V, Negative-QTOFsplash10-0udi-0029000000-e08d062d1b3fb4e552672017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 40V, Negative-QTOFsplash10-05bo-1090000000-86e6dcdcc4e4babac09e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 10V, Positive-QTOFsplash10-0udi-0049000000-79630e98940a556508ff2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 20V, Positive-QTOFsplash10-114s-0972000000-fef31191241a5fee6d7a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 40V, Positive-QTOFsplash10-06r7-1910000000-e9b6c3405a956f7823012021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 10V, Negative-QTOFsplash10-0udi-0009000000-4360bacaf95498925fe52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 20V, Negative-QTOFsplash10-0udi-0039000000-479f11c50b787985f7d52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 40V, Negative-QTOFsplash10-0006-0091000000-9edb0c3dd24f9aa0965b2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB024076
KNApSAcK IDNot Available
Chemspider ID389474
KEGG Compound IDC05140
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440574
PDB IDNot Available
ChEBI ID27582
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 ReferencesNot Available

Enzymes

General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. Efficiently catalyzes the transformation of pregnenolone to progesterone, 17-alpha-hydroxypregnenolone to 17-alpha-hydroxyprogesterone, DHEA to 4-androstenedione, dihydrotestosterone to 5-alpha-androstane-3 beta,17 beta-diol, dehydroepiandrosterone to androstenedione and 5-alpha-androstan-3 beta,17 beta-diol to 5-alpha-dihydrotestosterone.
Gene Name:
HSD3B1
Uniprot ID:
P14060
Molecular weight:
42251.25
Reactions
16a-Hydroxyandrost-4-ene-3,17-dione + Hydrogen Ion + NADH → 16a-Hydroxydehydroisoandrosterone + NADdetails
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids.
Gene Name:
HSD3B2
Uniprot ID:
P26439
Molecular weight:
42051.845
Reactions
16a-Hydroxyandrost-4-ene-3,17-dione + Hydrogen Ion + NADH → 16a-Hydroxydehydroisoandrosterone + NADdetails