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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:06 UTC

Update Date

2022-09-22 17:43:49 UTC

HMDB ID

HMDB0002725

Secondary Accession Numbers

HMDB02725

Metabolite Identification

Common Name

Nandrolone

Description

Nandrolone is a C18 steroid with androgenic and anabolic properties. It is generally prepared from alkyl ethers of estradiol to resemble testosterone, but it has one less carbon atom 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0002725
     RDKit          3D
Nandrolone
 46 49  0  0  0  0  0  0  0  0999 V2000
   -2.6324    1.0837   -1.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1597    0.5800    0.2698 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2545    1.5082    0.9517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0549    0.9482    1.4119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7308    0.0263    0.4906 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9486    0.5432   -0.1928 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8320    1.3451    0.6868 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2577    1.4268    0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7725    0.0219    0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8587   -0.3240    0.6869 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9216   -0.8897   -0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6257   -0.6647   -0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8645   -1.6421   -1.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4079   -1.6850   -1.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1939   -0.5303   -0.6060 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4471   -0.7732    0.1205 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5041   -1.5716   -0.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7402   -1.1532    0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3573    0.1166    1.0218 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3942    1.0362    1.0544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3560    2.1674   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2416    0.4987   -1.9226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7434    1.0644   -1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0310    2.3684    0.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7685    1.9479    1.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7238    1.8077    1.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1383    0.4727    2.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0443   -0.8920    1.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6297    1.1492   -1.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4325    2.4010    0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8137    1.0315    1.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8254    1.9744    1.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3811    1.8622   -0.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3985   -1.7833   -1.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0983   -1.4509   -2.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2889   -2.6728   -1.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1170   -2.6160   -0.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1123   -1.7956   -2.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2987    0.3258   -1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3014   -1.1276    1.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3069   -2.6622   -0.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6314   -1.4736   -1.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9955   -1.9276    1.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5802   -0.9794   -0.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0588   -0.1466    2.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7809    1.0539    1.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 16  2  1  0
 19  2  1  0
 15  5  1  0
 12  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  1
  6 29  1  6
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  6
 16 40  1  1
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  1
 20 46  1  0
M  END

Untitled Document-2
  Mrv1652305171817122D          

 24 27  0  0  0  0            999 V2000
   -2.0637   -0.5198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0637   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3492   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348   -0.5198    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3492   -0.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0796   -1.7573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942   -0.5198    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0796   -0.1073    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5086   -0.1073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5086    0.7177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7942    1.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0796    0.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933   -0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7782    0.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2933    0.9726    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7782   -1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6348    0.3052    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    0.3052    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086    1.5427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0796   -0.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5086   -0.9323    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5482    1.7572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
  2 18  2  0  0  0  0
  5 19  1  1  0  0  0
  9 20  1  1  0  0  0
 12 21  1  1  0  0  0
 10 22  1  6  0  0  0
 11 23  1  6  0  0  0
 17 24  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0002725

> <DATABASE_NAME>
hmdb

> <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_KEY>
NPAGDVCDWIYMMC-IZPLOLCNSA-N

> <FORMULA>
C18H26O2

> <MOLECULAR_WEIGHT>
274.3978

> <EXACT_MASS>
274.193280076

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
32.27342735561857

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
3.065376177666667

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.377705301929787

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.278891158439862

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8839295273296058

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
79.95469999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0002725
     RDKit          3D
Nandrolone
 46 49  0  0  0  0  0  0  0  0999 V2000
   -2.6324    1.0837   -1.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1597    0.5800    0.2698 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2545    1.5082    0.9517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0549    0.9482    1.4119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7308    0.0263    0.4906 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9486    0.5432   -0.1928 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8320    1.3451    0.6868 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2577    1.4268    0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7725    0.0219    0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8587   -0.3240    0.6869 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9216   -0.8897   -0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6257   -0.6647   -0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8645   -1.6421   -1.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4079   -1.6850   -1.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1939   -0.5303   -0.6060 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4471   -0.7732    0.1205 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5041   -1.5716   -0.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7402   -1.1532    0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3573    0.1166    1.0218 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3942    1.0362    1.0544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3560    2.1674   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2416    0.4987   -1.9226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7434    1.0644   -1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0310    2.3684    0.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7685    1.9479    1.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7238    1.8077    1.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1383    0.4727    2.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0443   -0.8920    1.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6297    1.1492   -1.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4325    2.4010    0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8137    1.0315    1.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8254    1.9744    1.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3811    1.8622   -0.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3985   -1.7833   -1.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0983   -1.4509   -2.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2889   -2.6728   -1.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1170   -2.6160   -0.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1123   -1.7956   -2.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2987    0.3258   -1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3014   -1.1276    1.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3069   -2.6622   -0.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6314   -1.4736   -1.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9955   -1.9276    1.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5802   -0.9794   -0.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0588   -0.1466    2.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7809    1.0539    1.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 16  2  1  0
 19  2  1  0
 15  5  1  0
 12  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  1
  6 29  1  6
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  6
 16 40  1  1
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  1
 20 46  1  0
M  END

HEADER    PROTEIN                                 17-MAY-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-2                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAY-18         0                                  
HETATM    1  C   UNK     0      -3.852  -0.970   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.852  -2.510   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.519  -3.280   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.185  -2.510   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.185  -0.970   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.519  -0.200   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.149  -3.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.483  -2.510   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.483  -0.970   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.149  -0.200   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.816  -0.200   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.816   1.340   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.483   2.110   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.149   1.340   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.281  -0.676   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.186   0.570   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.281   1.816   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.186  -3.280   0.000  0.00  0.00           O+0
HETATM   19  H   UNK     0      -1.185   0.570   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       1.483   0.570   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       2.816   2.880   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       0.149  -1.740   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.816  -1.740   0.000  0.00  0.00           H+0
HETATM   24  O   UNK     0       4.757   3.280   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   19                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   20                                             
CONECT   10    9    5   14   22                                             
CONECT   11    9   12   15   23                                             
CONECT   12   11   13   17   21                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   24                                                  
CONECT   18    2                                                            
CONECT   19    5                                                            
CONECT   20    9                                                            
CONECT   21   12                                                            
CONECT   22   10                                                            
CONECT   23   11                                                            
CONECT   24   17                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0002725
HETATM    1  C1  UNL     1      -2.632   1.084  -1.089  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.160   0.580   0.270  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.255   1.508   0.952  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.055   0.948   1.412  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.731   0.026   0.491  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.949   0.543  -0.193  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.832   1.345   0.687  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.258   1.427   0.260  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.773   0.022   0.155  1.00  0.00           C  
HETATM   10  O1  UNL     1       5.859  -0.324   0.687  1.00  0.00           O  
HETATM   11  C10 UNL     1       3.922  -0.890  -0.602  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.626  -0.665  -0.770  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.865  -1.642  -1.546  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.408  -1.685  -1.310  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.194  -0.530  -0.606  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.447  -0.773   0.121  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.504  -1.572  -0.504  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.740  -1.153   0.281  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.357   0.117   1.022  1.00  0.00           C  
HETATM   20  O2  UNL     1      -4.394   1.036   1.054  1.00  0.00           O  
HETATM   21  H1  UNL     1      -2.356   2.167  -1.130  1.00  0.00           H  
HETATM   22  H2  UNL     1      -2.242   0.499  -1.923  1.00  0.00           H  
HETATM   23  H3  UNL     1      -3.743   1.064  -1.171  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.031   2.368   0.279  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.768   1.948   1.844  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.724   1.808   1.636  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.138   0.473   2.419  1.00  0.00           H  
HETATM   28  H8  UNL     1       1.044  -0.892   1.070  1.00  0.00           H  
HETATM   29  H9  UNL     1       1.630   1.149  -1.079  1.00  0.00           H  
HETATM   30  H10 UNL     1       2.432   2.401   0.694  1.00  0.00           H  
HETATM   31  H11 UNL     1       2.814   1.031   1.754  1.00  0.00           H  
HETATM   32  H12 UNL     1       4.825   1.974   1.028  1.00  0.00           H  
HETATM   33  H13 UNL     1       4.381   1.862  -0.757  1.00  0.00           H  
HETATM   34  H14 UNL     1       4.399  -1.783  -1.034  1.00  0.00           H  
HETATM   35  H15 UNL     1       2.098  -1.451  -2.634  1.00  0.00           H  
HETATM   36  H16 UNL     1       2.289  -2.673  -1.360  1.00  0.00           H  
HETATM   37  H17 UNL     1       0.117  -2.616  -0.748  1.00  0.00           H  
HETATM   38  H18 UNL     1      -0.112  -1.796  -2.301  1.00  0.00           H  
HETATM   39  H19 UNL     1      -0.299   0.326  -1.326  1.00  0.00           H  
HETATM   40  H20 UNL     1      -1.301  -1.128   1.176  1.00  0.00           H  
HETATM   41  H21 UNL     1      -2.307  -2.662  -0.285  1.00  0.00           H  
HETATM   42  H22 UNL     1      -2.631  -1.474  -1.578  1.00  0.00           H  
HETATM   43  H23 UNL     1      -3.996  -1.928   1.017  1.00  0.00           H  
HETATM   44  H24 UNL     1      -4.580  -0.979  -0.417  1.00  0.00           H  
HETATM   45  H25 UNL     1      -3.059  -0.147   2.075  1.00  0.00           H  
HETATM   46  H26 UNL     1      -4.781   1.054   1.979  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   16   19
CONECT    3    4   24   25
CONECT    4    5   26   27
CONECT    5    6   15   28
CONECT    6    7   12   29
CONECT    7    8   30   31
CONECT    8    9   32   33
CONECT    9   10   10   11
CONECT   11   12   12   34
CONECT   12   13
CONECT   13   14   35   36
CONECT   14   15   37   38
CONECT   15   16   39
CONECT   16   17   40
CONECT   17   18   41   42
CONECT   18   19   43   44
CONECT   19   20   45
CONECT   20   46
END

HMDB0002725
     RDKit          3D
Nandrolone
 46 49  0  0  0  0  0  0  0  0999 V2000
   -2.6324    1.0837   -1.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1597    0.5800    0.2698 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2545    1.5082    0.9517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0549    0.9482    1.4119 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7308    0.0263    0.4906 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9486    0.5432   -0.1928 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8320    1.3451    0.6868 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2577    1.4268    0.2599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7725    0.0219    0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8587   -0.3240    0.6869 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9216   -0.8897   -0.6018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6257   -0.6647   -0.7700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8645   -1.6421   -1.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4079   -1.6850   -1.3104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1939   -0.5303   -0.6060 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4471   -0.7732    0.1205 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5041   -1.5716   -0.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7402   -1.1532    0.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3573    0.1166    1.0218 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3942    1.0362    1.0544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3560    2.1674   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2416    0.4987   -1.9226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7434    1.0644   -1.1710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0310    2.3684    0.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7685    1.9479    1.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7238    1.8077    1.6362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1383    0.4727    2.4190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0443   -0.8920    1.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6297    1.1492   -1.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4325    2.4010    0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8137    1.0315    1.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8254    1.9744    1.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3811    1.8622   -0.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3985   -1.7833   -1.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0983   -1.4509   -2.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2889   -2.6728   -1.3604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1170   -2.6160   -0.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1123   -1.7956   -2.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2987    0.3258   -1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3014   -1.1276    1.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3069   -2.6622   -0.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6314   -1.4736   -1.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9955   -1.9276    1.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5802   -0.9794   -0.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0588   -0.1466    2.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7809    1.0539    1.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 16  2  1  0
 19  2  1  0
 15  5  1  0
 12  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  1
  6 29  1  6
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
 11 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  6
 16 40  1  1
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  1
 20 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(17beta)-17-Hydroxyestr-4-en-3-one	ChEBI
17beta-Hydroxy-19-nor-4-androsten-3-one	ChEBI
17beta-Hydroxy-4-estren-3-one	ChEBI
17beta-Hydroxyestr-4-en-3-one	ChEBI
19-Norandrostenolone	ChEBI
19-Nortestosterone	ChEBI
4-Estren-17beta-ol-3-one	ChEBI
Decadura	Kegg
(17b)-17-Hydroxyestr-4-en-3-one	Generator
(17Β)-17-hydroxyestr-4-en-3-one	Generator
17b-Hydroxy-19-nor-4-androsten-3-one	Generator
17Β-hydroxy-19-nor-4-androsten-3-one	Generator
17b-Hydroxy-4-estren-3-one	Generator
17Β-hydroxy-4-estren-3-one	Generator
17b-Hydroxyestr-4-en-3-one	Generator
17Β-hydroxyestr-4-en-3-one	Generator
4-Estren-17b-ol-3-one	Generator
4-Estren-17β-ol-3-one	Generator
(17-beta)-17-Hydroxyestr-4-en-3-one	HMDB
17-beta-Hydroestr-4-en-3-one	HMDB
Deca-durabolin	HMDB
Durabolin	HMDB
Menidrabol	HMDB
Nandrolon	HMDB
Nandrolona	HMDB
Nandrolone base	HMDB
Nandrolone decanoate	HMDB
Nandrolone decanoic acid	HMDB
Nandrolone phenpropionate	HMDB
Nandrolonum	HMDB
Norandrostenolon	HMDB
Norandrostenolone	HMDB
Nortestonate	HMDB
Nortestosterone	HMDB
Nortestosteronum	HMDB
Oestrenolon	HMDB
17-Hydroxy-estr-4-ene-3-one	MeSH, HMDB
Estrenolone	MeSH, HMDB
17beta Hydroxy 19 nor 4 androsten 3 one	MeSH, HMDB

Chemical Formula

C₁₈H₂₆O₂

Average Molecular Weight

274.3978

Monoisotopic Molecular Weight

274.193280076

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

CAS Registry Number

434-22-0

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 Key

NPAGDVCDWIYMMC-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrogens 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 Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo Delta(4)-steroid (CHEBI:7466 )
17beta-hydroxy steroid (CHEBI:7466 )
anabolic androgenic steroid (CHEBI:7466 )
Estrane and derivatives (C07254 )
C18 steroids (estrogens) and derivatives (LMST02010044 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16714373)

Cellular substructure

Tissue substructure

Muscle (HMDB: HMDB0002725)
Hair (HMDB: HMDB0002725)

Organ

Gland

Adrenal Gland (HMDB: HMDB0002725)
Adrenal Gland (HMDB: HMDB0002725)

Testicle (HMDB: HMDB0002725)
Testicle (HMDB: HMDB0002725)

Tissue

Epithelium

Epidermis (HMDB: HMDB0002725)

Muscle tissue

Skeletal muscle (HMDB: HMDB0002725)

Nervous tissue

Hepatic tissue (HMDB: HMDB0002725)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0002725)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002725)

Source

Exogenous

Exogenous (HMDB: HMDB0002725)

Food

Food (HMDB: HMDB0002725)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0002725)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0002725)

Molecular messenger

Signaling molecule (HMDB: HMDB0002725)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002725)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0002725)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	118 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3.09 mg/mL at 25 °C	Not Available
LogP	2.62	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	167.5	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.056 g/L	ALOGPS
logP	2.6	ALOGPS
logP	3.07	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	19.28	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.95 m³·mol⁻¹	ChemAxon
Polarizability	32.27 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	167.347	31661259
DarkChem	[M-H]-	164.453	31661259
DeepCCS	[M-2H]-	205.396	30932474
DeepCCS	[M+Na]+	179.459	30932474
AllCCS	[M+H]+	170.4	32859911
AllCCS	[M+H-H2O]+	167.1	32859911
AllCCS	[M+NH4]+	173.5	32859911
AllCCS	[M+Na]+	174.3	32859911
AllCCS	[M-H]-	174.9	32859911
AllCCS	[M+Na-2H]-	174.9	32859911
AllCCS	[M+HCOO]-	175.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.08 minutes	32390414
Predicted by Siyang on May 30, 2022	15.0844 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.32 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2466.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	397.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	196.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	188.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	413.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	597.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	619.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	102.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1232.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	435.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1419.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	374.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	412.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	312.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	423.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	47.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nandrolone	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]	3459.4	Standard polar	33892256
Nandrolone	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]	2522.7	Standard non polar	33892256
Nandrolone	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]	2699.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nandrolone,1TMS,isomer #1	C[C@]12CC[C@@H]3[C@H]4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C	2677.8	Semi standard non polar	33892256
Nandrolone,1TMS,isomer #2	C[C@]12CC[C@@H]3[C@H]4CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O	2555.6	Semi standard non polar	33892256
Nandrolone,2TMS,isomer #1	C[C@]12CC[C@@H]3[C@H]4CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C	2621.6	Semi standard non polar	33892256
Nandrolone,2TMS,isomer #1	C[C@]12CC[C@@H]3[C@H]4CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C	2657.8	Standard non polar	33892256
Nandrolone,2TMS,isomer #1	C[C@]12CC[C@@H]3[C@H]4CC=C(O[Si](C)(C)C)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O[Si](C)(C)C	2953.7	Standard polar	33892256
Nandrolone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@]12C	2935.8	Semi standard non polar	33892256
Nandrolone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12	2856.6	Semi standard non polar	33892256
Nandrolone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]12	3182.6	Semi standard non polar	33892256
Nandrolone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]12	3140.1	Standard non polar	33892256
Nandrolone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@H]12	3196.8	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Adrenal Gland
Epidermis
Hair
Skeletal Muscle
Testis

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0145 +/- 0.0094 uM	Adult (>18 years old)	Both	Normal	16714373	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13169

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023054

KNApSAcK ID

Not Available

Chemspider ID

9520

KEGG Compound ID

C07254

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nandrolone

METLIN ID

1434

PubChem Compound

9904

PDB ID

Not Available

ChEBI ID

7466

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

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)

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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. [PubMed:10689586 ]
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. [PubMed:15784189 ]
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. [PubMed:15723686 ]
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. [PubMed:16689542 ]
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. [PubMed:7746275 ]
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. [PubMed:12218735 ]
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. [PubMed:10517545 ]
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. [PubMed:3347045 ]
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. [PubMed:24687 ]
Foreman MI, Kelly I: The diffusion of nandrolone through hydrated human cadaver skin. Br J Dermatol. 1976 Sep;95(3):265-70. [PubMed:974017 ]
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. [PubMed:14633920 ]
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. [PubMed:15972619 ]
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. [PubMed:1763806 ]
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. [PubMed:11248508 ]

Enzymes

Enzyme Details

1. Androgen receptor

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

Showing metabocard for Nandrolone (HMDB0002725)

MOL for HMDB0002725 (Nandrolone)

3D MOL for HMDB0002725 (Nandrolone)

3D SDF for HMDB0002725 (Nandrolone)

3D-SDF for HMDB0002725 (Nandrolone)

PDB for HMDB0002725 (Nandrolone)

3D PDB for HMDB0002725 (Nandrolone)

SMILES for HMDB0002725 (Nandrolone)

INCHI for HMDB0002725 (Nandrolone)

Structure for HMDB0002725 (Nandrolone)

3D Structure for HMDB0002725 (Nandrolone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes