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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-04-12 16:49:34 UTC
Update Date2019-01-11 19:19:00 UTC
HMDB IDHMDB0005886
Secondary Accession Numbers
  • HMDB05886
Metabolite Identification
Common Name19-Noretiocholanolone
Description19-noretiocholanolone (19-NE) is one of the two main indicators used to prove the illegal use of nandrolone by humans. Recent studies showed that 19-NE can be endogenously produced in some individuals. The mediated cases observed over the last years generated some questions about the appropriateness of the official International Olympic Committee cutoff level, which is 2 ng/mL of 19-NA in male urine samples. In 1997, in France, quite a few sportsmen had concentrations of nandrolone metabolites very close to the IOC cut off limit (2ng/ml). At that time, a debate took place about the capability of the human male body to produce by itself these metabolites without any intake of nandrolone or related compounds. The International Football Federation (FIFA) was very concerned with this problem, especially because the World Cup was about to start in France. Concentrations of 19- noretiocholanolone after a game are generally higher than those before games. Recent studies demonstrated the endogenous production of these compounds in man at concentrations very close to the threshold of the International Olympic Committee (IOC), i.e. 2 ng/ml. Because the possibility of reaching or exceeding this fateful limit is difficult to exclude, a complementary biochemical parameter is necessary for the differentiation of endogenous 19-NE production from residues resulting from nandrolone consumption. (PMID: 11888015 , 11755174 ).
Structure
Data?1547234340
Synonyms
ValueSource
(3a,5b)-3-Hydroxy-estran-17-oneHMDB
19-Noretiocholan-3a-ol-17-oneHMDB
3a-Hydroxy-5b-estran-17-oneHMDB
5b-Estran-3a-ol-17-oneHMDB
19-Norandrosterone, (3alpha,5beta)-isomerMeSH
19-Norandrosterone, (3alpha,5alpha)-isomerMeSH
19-Norandrosterone, (3beta,5beta)-isomerMeSH
19-Norandrosterone, (3beta,5alpha,8alpha,9beta,10alpha,13alpha,14beta)-isomerMeSH
19-NorandrosteroneMeSH
19-Norandrosterone, (3beta)-isomerMeSH
19-Norandrosterone, (3beta,5alpha)-isomerMeSH
3-Hydroxyestran-17-oneMeSH
19-NoreoiandrosteroneMeSH
2,2,3,4,4,-D5-19-Nor-5alpha-androsteroneMeSH
Chemical FormulaC18H28O2
Average Molecular Weight276.4137
Monoisotopic Molecular Weight276.20893014
IUPAC Name(1R,2S,5R,7R,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-one
Traditional Name(1R,2S,5R,7R,10R,11S,15S)-5-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-one
CAS Registry Number33036-33-8
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12[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/h11-16,19H,2-10H2,1H3/t11-,12-,13+,14-,15-,16+,18+/m1/s1
InChI KeyUOUIARGWRPHDBX-DHMVHTBWSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 17-oxosteroid
  • Oxosteroid
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP3.34ALOGPS
logP3.47ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)18.31ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.33 m³·mol⁻¹ChemAxon
Polarizability32.65 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00l2-0390000000-3e9d3cc01211fe3f2e0cJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0g1r-2269000000-927e4978162cfa2c72d4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0090000000-cbc92b8361a51e9f9374JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05r0-0390000000-8f98ba1efcc73acea899JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f92-5980000000-22ddcd9c3181e54f339eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-020f4653853c30d0fb3eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-fbcac4cd1c51b535f3d3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-1190000000-8e893b5bd8d4088c8a09JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.0025 (0.000047-0.005) umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB023785
    KNApSAcK IDNot Available
    Chemspider ID19347817
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound14009228
    PDB IDNot Available
    ChEBI ID36412
    References
    Synthesis ReferenceCounsell, R. E. Isomeric estrane derivatives. Tetrahedron (1961), 15 202-11.
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Le BB, Bryand F, Gaudin I, Monteau F, Poulain F, Andre F: Endogenous nandrolone metabolites in human urine. Two-year monitoring of male professional soccer players. J Anal Toxicol. 2002 Jan-Feb;26(1):43-7. [PubMed:11888015 ]
    2. Le Bizec B, Bryand F, Gaudin I, Monteau F, Poulain F, Andre F: Endogenous nandrolone metabolites in human urine: preliminary results to discriminate between endogenous and exogenous origin. Steroids. 2002 Feb;67(2):105-10. [PubMed:11755174 ]