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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:39:09 UTC
HMDB IDHMDB0000309
Secondary Accession Numbers
  • HMDB00309
Metabolite Identification
Common Name3alpha,16beta-Dihydroxyandrostenone
Description3alpha,16beta-Dihydroxyandrostenone belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favour the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, 3alpha,16beta-dihydroxyandrostenone is considered to be a steroid lipid molecule. 3alpha,16beta-Dihydroxyandrostenone is an unusual steroid found in the urinary excretion of a subject having a virilizing malignant adrenocortical tumor; apparent 21-steroid hydroxylase deficiency is discussed in the light of these results as well as the hormonogenesis enzymatic induction of the tumour biopsy (PMID: 198067 ).
Structure
Data?1600360541
Synonyms
ValueSource
3a,16b-DihydroxyandrostenoneGenerator
3Α,16β-dihydroxyandrostenoneGenerator
(3alpha,16beta)-3,16-Dihydroxyandrost-5-en-17-oneHMDB
(3Α,16β)-3,16-dihydroxyandrost-5-en-17-oneHMDB
3alpha,16beta-Dihydroxyandrost-5-en-17-oneHMDB
3Α,16β-dihydroxyandrost-5-en-17-oneHMDB
3alpha,16beta-DihydroxyandrostenoneHMDB
Chemical FormulaC19H28O3
Average Molecular Weight304.43
Monoisotopic Molecular Weight304.203844762
IUPAC Name(1S,2R,5R,10R,11S,13S,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one
Traditional Name(1S,2R,5R,10R,11S,13S,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-one
CAS Registry Number60828-06-0
SMILES
[H][C@@]12C[C@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C19H28O3/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/h3,12-16,20-21H,4-10H2,1-2H3/t12-,13-,14+,15+,16+,18+,19+/m1/s1
InChI KeyQQIVKFZWLZJXJT-BNSUEQOYSA-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-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 16-hydroxysteroid
  • 16-beta-hydroxysteroid
  • Oxosteroid
  • 17-oxosteroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • 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

Source

Route of exposure

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 Solubility0.079 g/LALOGPS
logP10(2.42) g/LALOGPS
logP10(2.49) g/LChemAxon
logS10(-3.4) g/LALOGPS
pKa (Strongest Acidic)13.38ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.15 m³·mol⁻¹ChemAxon
Polarizability34.94 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3alpha,16beta-Dihydroxyandrostenone[H][C@@]12C[C@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](O)CC[C@]12C2709.5Standard polar33892256
3alpha,16beta-Dihydroxyandrostenone[H][C@@]12C[C@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](O)CC[C@]12C2602.5Standard non polar33892256
3alpha,16beta-Dihydroxyandrostenone[H][C@@]12C[C@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](O)CC[C@]12C2716.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3alpha,16beta-Dihydroxyandrostenone,1TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](O)CC[C@@]43C)[C@@H]1C[C@H](O[Si](C)(C)C)C2=O2802.3Semi standard non polar33892256
3alpha,16beta-Dihydroxyandrostenone,1TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1C[C@H](O)C2=O2769.5Semi standard non polar33892256
3alpha,16beta-Dihydroxyandrostenone,1TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](O)CC[C@@]43C)[C@@H]1CC(O)=C2O[Si](C)(C)C2759.1Semi standard non polar33892256
3alpha,16beta-Dihydroxyandrostenone,2TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1C[C@H](O[Si](C)(C)C)C2=O2828.4Semi standard non polar33892256
3alpha,16beta-Dihydroxyandrostenone,2TMS,isomer #2C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](O)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C2833.8Semi standard non polar33892256
3alpha,16beta-Dihydroxyandrostenone,2TMS,isomer #3C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC(O)=C2O[Si](C)(C)C2765.2Semi standard non polar33892256
3alpha,16beta-Dihydroxyandrostenone,3TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C2825.9Semi standard non polar33892256
3alpha,16beta-Dihydroxyandrostenone,3TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C2812.9Standard non polar33892256
3alpha,16beta-Dihydroxyandrostenone,3TMS,isomer #1C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C3081.8Standard polar33892256
3alpha,16beta-Dihydroxyandrostenone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1C[C@H]2[C@@H]3CC=C4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]2(C)C1=O3073.1Semi standard non polar33892256
3alpha,16beta-Dihydroxyandrostenone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1CC[C@@]2(C)C(=CC[C@H]3[C@@H]4C[C@H](O)C(=O)[C@@]4(C)CC[C@@H]32)C13042.6Semi standard non polar33892256
3alpha,16beta-Dihydroxyandrostenone,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C(O)C[C@H]2[C@@H]3CC=C4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C3042.9Semi standard non polar33892256
3alpha,16beta-Dihydroxyandrostenone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1C[C@H]2[C@@H]3CC=C4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]2(C)C1=O3340.0Semi standard non polar33892256
3alpha,16beta-Dihydroxyandrostenone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@H]3[C@@H](CC=C4C[C@H](O)CC[C@@]43C)[C@@H]2C13384.5Semi standard non polar33892256
3alpha,16beta-Dihydroxyandrostenone,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=C(O)C[C@H]2[C@@H]3CC=C4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C3308.8Semi standard non polar33892256
3alpha,16beta-Dihydroxyandrostenone,3TBDMS,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](CC=C4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@@]43C)[C@@H]2C13579.4Semi standard non polar33892256
3alpha,16beta-Dihydroxyandrostenone,3TBDMS,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](CC=C4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@@]43C)[C@@H]2C13382.3Standard non polar33892256
3alpha,16beta-Dihydroxyandrostenone,3TBDMS,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](CC=C4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@@]43C)[C@@H]2C13374.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone 10V, Negative-QTOFsplash10-0udi-0009000000-93986d59045cc7fce5512021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone 20V, Negative-QTOFsplash10-0udi-0039000000-af52444aa96638a90cb72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone 40V, Negative-QTOFsplash10-0uk9-1094000000-48ce674daa94d6aea6fb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone 10V, Positive-QTOFsplash10-0a4r-0069000000-057040f4b3850a0663672021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone 20V, Positive-QTOFsplash10-0670-0982000000-202e2a5dcedc0d7b97b12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3alpha,16beta-Dihydroxyandrostenone 40V, Positive-QTOFsplash10-0005-1910000000-6544390a129e44d961062021-09-25Wishart 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 IDFDB021936
KNApSAcK IDNot Available
Chemspider ID24850099
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44263333
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. Dubost M, Begue RJ, Desgres J, Rifle C, Putelat R, Moriniere M, Padieu P: [Study of a virilizing adrenal cortical tumor. Analysis of urinary steroids by gas-liquid chromatography and mass spectrometry]. C R Seances Soc Biol Fil. 1977;171(1):67-72. [PubMed:198067 ]