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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 21:47:21 UTC
Update Date2022-03-07 02:49:21 UTC
HMDB IDHMDB0004590
Secondary Accession Numbers
  • HMDB04590
Metabolite Identification
Common Name19-Nor-5-androstenediol
Description19-Nor-5-androstenediol is an androgen steroid that has been found to be part of nutritional supplements that are commercialized as nandrolone-free. Some reports regarding nandrolone-positive cases have been related to intake of some of these supplements. Nandrolone is the most frequently abused substance in doping control because it does not convert to estrogens and does not have and androgenic side effects. For this reason, one the major metabolites of nandrolone, 19-norandrosterone (19-NA) have been used as determinants for doping of nandrolone. However, there are situations where the occurrence of nandrolone metabolites is a phenomenon not necessarily associated with doping: a) in human ovarian follicular fluid is a possible intermediate in the multistep enzymatic conversion of androgen to estrogen, b) during the course of pregnancy, 19-NA increases in urine, c) human chorionic gonadotropin (hCG) also stimulates 19-NA excretion in urine, d) exercise has been shown to affect the urinary excretion of nandrolone metabolites such as 19-NA, e) 19-NA is a minor metabolite of oral contraceptives such as norethisterone. Furthermore, 19-NA is the main urinary metabolite of 19-Nor-5-androstenediol. Nevertheless, the prevalence of nandrolone abuse is evident; internationally, 212 cases were found in 1995 and 232 cases were found in 1996. From 1998 to 2001, nandrolone-positive findings reported by the IOC-accredited laboratories ranged from 0.17% to 0.65%. (PMID: 15902981 ).
Structure
Thumb
Synonyms
ValueSource
(3b,17b)-Estr-5-ene-3,17-diolHMDB
19-Nor-5-androstene-3b,17b-diolHMDB
D5-Estrene-3b,17b-diolHMDB
Estr-5-ene-3b,17b-diolHMDB
Chemical FormulaC18H28O2
Average Molecular Weight276.4137
Monoisotopic Molecular Weight276.20893014
IUPAC Name(1S,2R,5S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-diol
Traditional Nameestr-5-ene-3b,17b-diol
CAS Registry Number25975-59-1
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CC[C@H](O)CC3=CC[C@@]21[H]
InChI Identifier
InChI=1S/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2,12-17,19-20H,3-10H2,1H3/t12-,13-,14+,15+,16-,17-,18-/m0/s1
InChI KeyVVUQRXPUVKXAIO-XFUVECHXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • 17-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • 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 IDDB01455
Phenol Explorer Compound IDNot Available
FooDB IDFDB023379
KNApSAcK IDNot Available
Chemspider ID8075901
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link19-Nor-5-androstenediol
METLIN IDNot Available
PubChem Compound9900246
PDB IDNot Available
ChEBI ID529214
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceHartman, John A. The preparation of four 3,17b-dihydroxyestrenes. Journal of the American Chemical Society (1955), 77 5151-4.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tseng YL, Kuo FH, Sun KH: Quantification and profiling of 19-norandrosterone and 19-noretiocholanolone in human urine after consumption of a nutritional supplement and norsteroids. J Anal Toxicol. 2005 Mar;29(2):124-34. [PubMed:15902981 ]