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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:00 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
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
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
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 ]