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Record Information
Version3.6
Creation Date2006-05-22 15:12:06 UTC
Update Date2016-02-11 01:05:46 UTC
HMDB IDHMDB02725
Secondary Accession NumbersNone
Metabolite Identification
Common NameNandrolone
DescriptionNandrolone is a C18 steroid with androgenic and anabolic properties. It is generally prepared from alkyl ethers of estradiol to resemble testosterone but less one carbon at the 19 position. -- Pubchem; Nandrolone is an anabolic steroid occurring naturally in the human body, albeit in small quantities. Nandrolone is most commonly sold commercially as its decanoate ester (Deca-Durabolin) and less commonly as a phenylpropionate ester (Durabolin). Nandrolone use is indirectly detectable in urine tests by testing for the presence of 19-norandrosterone, a metabolism product of this molecule. The International Olympic Committee has set a limit of 2 ng per ml of urine as the upper limit, beyond which an athlete is suspected of doping. -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
(17beta)-17-Hydroxyestr-4-en-3-oneChEBI
17beta-Hydroxy-19-nor-4-androsten-3-oneChEBI
17beta-Hydroxy-4-estren-3-oneChEBI
19-NorandrostenoloneChEBI
19-NortestosteroneChEBI
4-Estren-17beta-ol-3-oneChEBI
(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
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
Chemical FormulaC18H26O2
Average Molecular Weight274.3978
Monoisotopic Molecular Weight274.193280076
IUPAC Name(1S,2R,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
Traditional Namenandrolone
CAS Registry Number434-22-0
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 Identifier
InChI=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 KeyInChIKey=NPAGDVCDWIYMMC-IZPLOLCNSA-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
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point118 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.09 mg/mL at 25 °CNot Available
LogP2.62HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.056 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.95 m3·mol-1ChemAxon
Polarizability32.19 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
Tissue Location
  • Adrenal Gland
  • Epidermis
  • Hair
  • Muscle
  • Stratum Corneum
  • Testes
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0145 +/- 0.0094 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023054
KNApSAcK IDNot Available
Chemspider ID9520
KEGG Compound IDC07254
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNandrolone
NuGOwiki LinkHMDB02725
Metagene LinkHMDB02725
METLIN ID1434
PubChem Compound9904
PDB IDNot Available
ChEBI ID7466
References
Synthesis ReferenceBucourt, Robert; Vignau, Michel; Raynal, Jean. 19-Nortestosterone. Fr. (1967), 9 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [10689586 ]
  2. 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. [15784189 ]
  3. 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. [15723686 ]
  4. 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. [16689542 ]
  5. 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. [7746275 ]
  6. 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. [12218735 ]
  7. 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. [10517545 ]
  8. 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. [3347045 ]
  9. 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. [24687 ]
  10. Foreman MI, Kelly I: The diffusion of nandrolone through hydrated human cadaver skin. Br J Dermatol. 1976 Sep;95(3):265-70. [974017 ]
  11. 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. [14633920 ]
  12. 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. [15972619 ]
  13. 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. [1763806 ]
  14. 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. [11248508 ]

Enzymes

General function:
Involved in DNA binding
Specific function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3
Gene Name:
AR
Uniprot ID:
P10275
Molecular weight:
98987.9