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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 IDHMDB0000322
Secondary Accession Numbers
  • HMDB00322
Metabolite Identification
Common Name16-Oxoandrostenediol
Description16-Oxoandrostenediol is a naturally occurring androgenic steroid hormone generated by the adrenal glands. It has been found in the urine of newborn infants. Secretion of this steroid is suppressed by dexamethasone. Levels of this hormone are almost absent by 5 months of age. ((Steroids (1964), 3(1), 77-83.) ). 16-Oxoandrostenediol is a natural hormone with androgenic activity and that two potent antiandrogens: hydroxyflutamide (Eulexin) and bicalutamide (Casodex).
Structure
Thumb
Synonyms
ValueSource
(3b,17b)-3b,17b-Dihydroxyandrost-5-en-16-oneHMDB
3b,17b-Dihydroxy-androst-5-en-16-oneHMDB
3b,17b-Dihydroxyandrost-5-en-16-oneHMDB
3beta,17beta-Dihydroxy-androst-5-en-16-oneHMDB
5-Androsten-3b,17b-diol-16-oneHMDB
Androst-5-ene-3b,17b-diol-16-oneHMDB
Chemical FormulaC19H28O3
Average Molecular Weight304.4238
Monoisotopic Molecular Weight304.203844762
IUPAC Name(2R,5S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-one
Traditional Name5-androsten-3b,17b-diol-16-one
CAS Registry Number1159-66-6
SMILES
C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@]34C)C1CC(=O)[C@@H]2O
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/h3,12-15,17,20,22H,4-10H2,1-2H3/t12-,13?,14?,15?,17-,18-,19-/m0/s1
InChI KeyAKRBLZKRYPEVIK-IACDPKRHSA-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
  • 17-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Oxosteroid
  • 16-oxosteroid
  • Hydroxysteroid
  • Delta-5-steroid
  • 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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point203 - 205 °CNot 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 Locations
  • Adrenal Gland
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 IDFDB021948
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5311
PubChem Compound53477682
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceAoki, Terumi; Yamamura, Hiroko; Takei, Kyoko; Mori, Hiromu. Synthesis of 16-oxygenated androst-5-en-3b-ol derivatives. Chemical & Pharmaceutical Bulletin (1964), 12(7), 808-12.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available