Nandrolone (CHEM016798)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:43:59 UTC
Update Date2016-11-09 01:15:28 UTC
Accession NumberCHEM016798
Identification
Common NameNandrolone
ClassSmall Molecule
DescriptionA 3-oxo Delta(4)-steroid that is estr-4-en-3-one substituted by a beta-hydroxy group at position 17.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(17beta)-17-Hydroxyestr-4-en-3-oneChEBI
17beta-Hydroxy-19-nor-4-androsten-3-oneChEBI
17beta-Hydroxy-4-estren-3-oneChEBI
17beta-Hydroxyestr-4-en-3-oneChEBI
19-NorandrostenoloneChEBI
19-NortestosteroneChEBI
4-Estren-17beta-ol-3-oneChEBI
DecaduraKegg
(17b)-17-Hydroxyestr-4-en-3-oneGenerator
(17Β)-17-hydroxyestr-4-en-3-oneGenerator
17b-Hydroxy-19-nor-4-androsten-3-oneGenerator
17Β-hydroxy-19-nor-4-androsten-3-oneGenerator
17b-Hydroxy-4-estren-3-oneGenerator
17Β-hydroxy-4-estren-3-oneGenerator
17b-Hydroxyestr-4-en-3-oneGenerator
17Β-hydroxyestr-4-en-3-oneGenerator
4-Estren-17b-ol-3-oneGenerator
4-Estren-17β-ol-3-oneGenerator
(17-beta)-17-Hydroxyestr-4-en-3-oneHMDB
17-beta-Hydroestr-4-en-3-oneHMDB
Deca-durabolinHMDB
DurabolinHMDB
MenidrabolHMDB
NandrolonHMDB
NandrolonaHMDB
Nandrolone baseHMDB
Nandrolone decanoateHMDB
Nandrolone decanoic acidHMDB
Nandrolone phenpropionateHMDB
NandrolonumHMDB
NorandrostenolonHMDB
NorandrostenoloneHMDB
NortestonateHMDB
NortestosteroneHMDB
NortestosteronumHMDB
OestrenolonHMDB
17-Hydroxy-estr-4-ene-3-oneMeSH, HMDB
EstrenoloneMeSH, HMDB
17beta Hydroxy 19 nor 4 androsten 3 oneMeSH, HMDB
Chemical FormulaC18H26O2
Average Molecular Mass274.398 g/mol
Monoisotopic Mass274.193 g/mol
CAS Registry Number434-22-0
IUPAC Name(1S,2R,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
Traditional Name(1S,2R,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
SMILES[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]
InChI IdentifierInChI=1S/C18H26O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-17,20H,2-9H2,1H3/t13-,14+,15+,16-,17-,18-/m0/s1
InChI KeyNPAGDVCDWIYMMC-IZPLOLCNSA-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
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.056 g/LALOGPS
logP2.6ALOGPS
logP3.07ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)19.28ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.95 m³·mol⁻¹ChemAxon
Polarizability32.27 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i3-8950000000-2aca1e24a2ef4acf545fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i3-8950000000-2aca1e24a2ef4acf545fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i3-8950000000-2aca1e24a2ef4acf545fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i3-8950000000-2aca1e24a2ef4acf545fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i3-8950000000-2aca1e24a2ef4acf545fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i3-8950000000-2aca1e24a2ef4acf545fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i3-8950000000-2aca1e24a2ef4acf545fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i3-8950000000-2aca1e24a2ef4acf545fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-1390000000-ccec1d79f2682b0d6bcdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-014i-3459000000-2c9e474d4fe483963de2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0090000000-494e848349f5e9b86582Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0570-1980000000-e03a1bc79e9f4e2d8260Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-2900000000-e8dd93d5cf0dff8b90e4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a5c-7900000000-71f3c599cf3161ab0eb7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-057l-9500000000-ab3f2a34ef86ef591844Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0490000000-ef50b9f0fd0a9e2b7c03Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-494e848349f5e9b86582Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0570-1890000000-f1ef53c89897edb937bdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a5c-7900000000-3fcbdc990804e86cea69Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-3900000000-38204908207e3c492f31Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-057l-9500000000-f8e3f1dca618b5773382Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0a70-1950000000-3deed21a74589392a1e6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-057l-9500000000-1532de517e04b6798dffSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0570-1890000000-c97321edf7f62a485d35Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-3900000000-e3fa79b994c641358e40Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a5c-7900000000-05b21f3048b9a15fd44cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-0090000000-a68cb7a4b0cf987e8757Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-0390000000-3e5a09a8ce0262c4d8ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-3930000000-0e574177891b374ec885Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-d6ac133b0193eab1624eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0090000000-7b428460d9c77da1b323Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-1190000000-31322ef34e235f8b8e8fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-5809628d56891b262e6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-0950000000-ff92f819e00b54e35c1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-2900000000-8fa1a18a876d0904eb9eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB13169
HMDB IDHMDB0002725
FooDB IDFDB023054
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID1434
PDB IDNot Available
Wikipedia LinkNandrolone
Chemspider ID9520
ChEBI ID7466
PubChem Compound ID9904
Kegg Compound IDC07254
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11888015
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19055689
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20020363
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24405322
5. Nomine Gerard, Bertin Daniel, Tessier Jean, Pierdet Andre, Bucourt Robert. Process for the preparation of 19-nortestosterone and compounds used in this process. 1963, US Patent 3101354A (https://patents.google.com/patent/US3101354)
6. Nomine Gerard, Bertin Daniel, Tessier Jean, Pierdet Andre, Bucourt Robert. Process for the preparation of 19-nortestosterone and compounds used in this process. 1963, US Patent 3101354A (https://patents.google.com/patent/US3101354)
7. Segura J, Pichini S, Peng SH, de la Torre X: Hair analysis and detectability of single dose administration of androgenic steroid esters. Forensic Sci Int. 2000 Jan 10;107(1-3):347-59.
8. Venken K, Boonen S, Van Herck E, Vandenput L, Kumar N, Sitruk-Ware R, Sundaram K, Bouillon R, Vanderschueren D: Bone and muscle protective potential of the prostate-sparing synthetic androgen 7alpha-methyl-19-nortestosterone: evidence from the aged orchidectomized male rat model. Bone. 2005 Apr;36(4):663-70.
9. Noorafshan A, Karbalay-Doust S, Ardekani FM: High doses of nandrolone decanoate reduce volume of testis and length of seminiferous tubules in rats. APMIS. 2005 Feb;113(2):122-5.
10. Tai SS, Xu B, Sniegoski LT, Welch MJ: Development and evaluation of a candidate reference measurement procedure for the determination of 19-norandrosterone in human urine using isotope-dilution liquid chromatography/tandem mass spectrometry. Anal Chem. 2006 May 15;78(10):3393-8.
11. Summerfield AE, Diaz Cruz PJ, Dolenga MP, Smith HE, Strader CD, Toney JH: Tissue-specific pharmacology of testosterone and 5 alpha-dihydrotestosterone analogues: characterization of a novel canine liver androgen-binding protein. Mol Pharmacol. 1995 May;47(5):1080-8.
12. Schmitt N, Flament MM, Goubault C, Legros P, Grenier-Loustalot MF, Denjean A: Nandrolone excretion is not increased by exhaustive exercise in trained athletes. Med Sci Sports Exerc. 2002 Sep;34(9):1436-9.
13. Hold KM, Borges CR, Wilkins DG, Rollins DE, Joseph RE Jr: Detection of nandrolone, testosterone, and their esters in rat and human hair samples. J Anal Toxicol. 1999 Oct;23(6):416-23.
14. Silberzahn P, Gaillard JL, Quincey D, Dintinger T, Al-Timimi I: Aromatization of testosterone and 19-nortestosterone by a single enzyme from equine testicular microsomes. Differences from human placental aromatase. J Steroid Biochem. 1988 Jan;29(1):119-25.
15. Foreman MI, Clanachan I, Kelly IP: The diffusion of nandrolone through occluded and non-occluded human skin. J Pharm Pharmacol. 1978 Mar;30(3):152-7.
16. Foreman MI, Kelly I: The diffusion of nandrolone through hydrated human cadaver skin. Br J Dermatol. 1976 Sep;95(3):265-70.
17. Baume N, Avois L, Schweizer C, Cardis C, Dvorak J, Cauderay M, Mangin P, Saugy M: [13C]Nandrolone excretion in trained athletes: interindividual variability in metabolism. Clin Chem. 2004 Feb;50(2):355-64. Epub 2003 Nov 21.
18. Frisoli A Jr, Chaves PH, Pinheiro MM, Szejnfeld VL: The effect of nandrolone decanoate on bone mineral density, muscle mass, and hemoglobin levels in elderly women with osteoporosis: a double-blind, randomized, placebo-controlled clinical trial. J Gerontol A Biol Sci Med Sci. 2005 May;60(5):648-53.
19. Farjam A, Vreuls JJ, Cuppen WJ, Brinkman UA, de Jong GJ: Direct introduction of large-volume urine samples into an on-line immunoaffinity sample pretreatment-capillary gas chromatography system. Anal Chem. 1991 Nov 1;63(21):2481-7.
20. Kintz P, Cirimele V, Dumestre-Toulet V, Ludes B: Doping control for nandrolone using hair analysis. J Pharm Biomed Anal. 2001 Mar;24(5-6):1125-30.