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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:00 UTC

HMDB ID

HMDB0000322

Secondary Accession Numbers

HMDB00322

Metabolite Identification

Common Name

16-Oxoandrostenediol

Description

16-Oxoandrostenediol is a naturally occurring androgenic steroid hormone generated by the adrenal glands. It has been found in the urine of newborn infants. Secretion of this steroid is suppressed by dexamethasone. Levels of this hormone are almost absent by 5 months of age. ((Steroids (1964), 3(1), 77-83.) ). 16-Oxoandrostenediol is a natural hormone with androgenic activity and that two potent antiandrogens: hydroxyflutamide (Eulexin) and bicalutamide (Casodex).

Structure

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

HMDB0000322
     RDKit          3D
16-Oxoandrostenediol
 50 53  0  0  0  0  0  0  0  0999 V2000
   -3.9205    0.0436    1.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8012   -0.1239    0.4256 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9985   -1.3243    0.8206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7678   -1.4802   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0462   -0.2318   -0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5297    0.9376    0.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713    2.2105    0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5682    1.9892   -0.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1935    0.8416   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6065    0.7876   -0.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3463   -0.4438   -0.2957 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1023   -0.1926    0.8719 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5516   -1.6962   -0.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1337   -1.5092   -0.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837   -0.4181    0.2339 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7196   -0.7885    1.6493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0020    1.1312    0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2770    1.7124   -1.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5325    1.0488   -1.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4212    1.5330   -2.1028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4943   -0.3216   -0.9126 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7720   -0.8525   -0.7222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4477    0.1299    2.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6315   -0.7794    1.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3761    1.0345    1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6354   -2.2223    0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7713   -1.2889    1.8909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0976   -1.8877   -1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1724   -2.3186    0.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0468    0.0449   -1.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4726    0.8151    1.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3937    2.7121   -0.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1200    2.9350    1.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1196    2.8711   -0.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6684    0.9166   -1.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1487    1.6628   -0.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1407   -0.6305   -1.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4538    0.7202    0.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9876   -2.5353   -0.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355   -2.0567    0.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6123   -2.4667   -0.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1507   -1.1236   -1.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9051   -0.5257    2.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7937   -1.9062    1.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6367   -0.3057    2.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3683    1.8637    1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4936    1.4601   -1.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3914    2.8229   -0.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9003   -0.9824   -1.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6739   -1.8118   -0.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 17  2  1  0
 21  2  1  0
 15  5  1  0
 15  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  6
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 21 49  1  6
 22 50  1  0
M  END


  Mrv0541 02231218272D          

 22 25  0  0  1  0            999 V2000
    9.1142   -7.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0043   -5.5824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1774   -9.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8089   -8.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8510   -8.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7458   -6.6566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4826   -7.7181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3774   -6.1258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7703   -9.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1137   -7.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4019   -8.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9948   -9.0613    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.6651   -7.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8896   -7.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2967   -7.2197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4749   -6.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8809   -6.0195    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2580   -7.9997    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1528   -6.4074    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3632   -9.5921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2872   -6.4483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9952   -5.2025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 18  1  1  1  0  0  0
 19  2  1  1  0  0  0
  3 11  2  0  0  0  0
  3  4  1  0  0  0  0
 13  4  1  0  0  0  0
  5  7  1  0  0  0  0
  5 12  1  0  0  0  0
 14  6  1  0  0  0  0
  6  8  1  0  0  0  0
  7 18  1  0  0  0  0
  8 19  1  0  0  0  0
  9 12  1  0  0  0  0
  9 11  1  0  0  0  0
 15 10  1  0  0  0  0
 10 16  1  0  0  0  0
 11 18  1  0  0  0  0
 12 20  1  1  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 21  2  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
 17 22  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0000322

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@]34C)C1CC(=O)[C@@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-15,17,20,22H,4-10H2,1-2H3/t12-,13?,14?,15?,17-,18-,19-/m0/s1

> <INCHI_KEY>
AKRBLZKRYPEVIK-IACDPKRHSA-N

> <FORMULA>
C19H28O3

> <MOLECULAR_WEIGHT>
304.4238

> <EXACT_MASS>
304.203844762

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.655713738506456

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,5S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-one

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
2.134612230666667

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.204289505503088

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.966629576546968

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972436515563893

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
85.94529999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-androsten-3b,17b-diol-16-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000322
     RDKit          3D
16-Oxoandrostenediol
 50 53  0  0  0  0  0  0  0  0999 V2000
   -3.9205    0.0436    1.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8012   -0.1239    0.4256 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9985   -1.3243    0.8206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7678   -1.4802   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0462   -0.2318   -0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5297    0.9376    0.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713    2.2105    0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5682    1.9892   -0.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1935    0.8416   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6065    0.7876   -0.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3463   -0.4438   -0.2957 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1023   -0.1926    0.8719 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5516   -1.6962   -0.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1337   -1.5092   -0.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837   -0.4181    0.2339 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7196   -0.7885    1.6493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0020    1.1312    0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2770    1.7124   -1.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5325    1.0488   -1.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4212    1.5330   -2.1028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4943   -0.3216   -0.9126 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7720   -0.8525   -0.7222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4477    0.1299    2.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6315   -0.7794    1.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3761    1.0345    1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6354   -2.2223    0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7713   -1.2889    1.8909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0976   -1.8877   -1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1724   -2.3186    0.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0468    0.0449   -1.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4726    0.8151    1.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3937    2.7121   -0.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1200    2.9350    1.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1196    2.8711   -0.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6684    0.9166   -1.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1487    1.6628   -0.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1407   -0.6305   -1.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4538    0.7202    0.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9876   -2.5353   -0.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355   -2.0567    0.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6123   -2.4667   -0.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1507   -1.1236   -1.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9051   -0.5257    2.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7937   -1.9062    1.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6367   -0.3057    2.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3683    1.8637    1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4936    1.4601   -1.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3914    2.8229   -0.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9003   -0.9824   -1.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6739   -1.8118   -0.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 17  2  1  0
 21  2  1  0
 15  5  1  0
 15  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  6
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 21 49  1  6
 22 50  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      17.013 -13.416   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.541 -10.420   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.998 -16.975   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.177 -15.984   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.655 -15.398   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.192 -12.426   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.834 -14.407   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.371 -11.435   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.371 -17.440   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.612 -13.690   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.550 -16.449   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.924 -16.914   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.908 -14.468   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.461 -13.942   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.087 -13.477   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      23.286 -12.305   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.178 -11.236   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.282 -14.933   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      20.819 -11.960   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      13.745 -17.905   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      24.803 -12.037   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      22.391  -9.711   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   19                                                            
CONECT    3   11    4                                                       
CONECT    4    3   13                                                       
CONECT    5    7   12                                                       
CONECT    6   14    8                                                       
CONECT    7    5   18                                                       
CONECT    8    6   19                                                       
CONECT    9   12   11                                                       
CONECT   10   15   16                                                       
CONECT   11    3    9   18                                                  
CONECT   12    5    9   20                                                  
CONECT   13    4   14   15                                                  
CONECT   14    6   13   18                                                  
CONECT   15   10   13   19                                                  
CONECT   16   10   21   17                                                  
CONECT   17   16   19   22                                                  
CONECT   18    1    7   11   14                                             
CONECT   19    2    8   15   17                                             
CONECT   20   12                                                            
CONECT   21   16                                                            
CONECT   22   17                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0000322
HETATM    1  C1  UNL     1      -3.921   0.044   1.459  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.801  -0.124   0.426  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.998  -1.324   0.821  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.768  -1.480  -0.026  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.046  -0.232  -0.147  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.530   0.938   0.578  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.171   2.211   0.256  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.568   1.989  -0.170  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.194   0.842  -0.195  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.606   0.788  -0.653  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.346  -0.444  -0.296  1.00  0.00           C  
HETATM   12  O1  UNL     1       5.102  -0.193   0.872  1.00  0.00           O  
HETATM   13  C12 UNL     1       3.552  -1.696  -0.186  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.134  -1.509  -0.630  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.484  -0.418   0.234  1.00  0.00           C  
HETATM   16  C15 UNL     1       1.720  -0.788   1.649  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.002   1.131   0.290  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.277   1.712  -1.054  1.00  0.00           C  
HETATM   19  C18 UNL     1      -3.532   1.049  -1.455  1.00  0.00           C  
HETATM   20  O2  UNL     1      -4.421   1.533  -2.103  1.00  0.00           O  
HETATM   21  C19 UNL     1      -3.494  -0.322  -0.913  1.00  0.00           C  
HETATM   22  O3  UNL     1      -4.772  -0.852  -0.722  1.00  0.00           O  
HETATM   23  H1  UNL     1      -3.448   0.130   2.471  1.00  0.00           H  
HETATM   24  H2  UNL     1      -4.631  -0.779   1.388  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.376   1.034   1.251  1.00  0.00           H  
HETATM   26  H4  UNL     1      -2.635  -2.222   0.633  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.771  -1.289   1.891  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.098  -1.888  -1.015  1.00  0.00           H  
HETATM   29  H7  UNL     1      -0.172  -2.319   0.434  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.047   0.045  -1.241  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.473   0.815   1.700  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.394   2.712  -0.582  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.120   2.935   1.097  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.120   2.871  -0.491  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.668   0.917  -1.775  1.00  0.00           H  
HETATM   36  H14 UNL     1       4.149   1.663  -0.229  1.00  0.00           H  
HETATM   37  H15 UNL     1       5.141  -0.631  -1.081  1.00  0.00           H  
HETATM   38  H16 UNL     1       5.454   0.720   0.856  1.00  0.00           H  
HETATM   39  H17 UNL     1       3.988  -2.535  -0.801  1.00  0.00           H  
HETATM   40  H18 UNL     1       3.635  -2.057   0.859  1.00  0.00           H  
HETATM   41  H19 UNL     1       1.612  -2.467  -0.543  1.00  0.00           H  
HETATM   42  H20 UNL     1       2.151  -1.124  -1.667  1.00  0.00           H  
HETATM   43  H21 UNL     1       0.905  -0.526   2.352  1.00  0.00           H  
HETATM   44  H22 UNL     1       1.794  -1.906   1.718  1.00  0.00           H  
HETATM   45  H23 UNL     1       2.637  -0.306   2.068  1.00  0.00           H  
HETATM   46  H24 UNL     1      -2.368   1.864   1.065  1.00  0.00           H  
HETATM   47  H25 UNL     1      -1.494   1.460  -1.810  1.00  0.00           H  
HETATM   48  H26 UNL     1      -2.391   2.823  -0.980  1.00  0.00           H  
HETATM   49  H27 UNL     1      -2.900  -0.982  -1.592  1.00  0.00           H  
HETATM   50  H28 UNL     1      -4.674  -1.812  -0.604  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   17   21
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   15   30
CONECT    6    7   17   31
CONECT    7    8   32   33
CONECT    8    9    9   34
CONECT    9   10   15
CONECT   10   11   35   36
CONECT   11   12   13   37
CONECT   12   38
CONECT   13   14   39   40
CONECT   14   15   41   42
CONECT   15   16
CONECT   16   43   44   45
CONECT   17   18   46
CONECT   18   19   47   48
CONECT   19   20   20   21
CONECT   21   22   49
CONECT   22   50
END

HMDB0000322
     RDKit          3D
16-Oxoandrostenediol
 50 53  0  0  0  0  0  0  0  0999 V2000
   -3.9205    0.0436    1.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8012   -0.1239    0.4256 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9985   -1.3243    0.8206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7678   -1.4802   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0462   -0.2318   -0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5297    0.9376    0.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713    2.2105    0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5682    1.9892   -0.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1935    0.8416   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6065    0.7876   -0.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3463   -0.4438   -0.2957 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1023   -0.1926    0.8719 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5516   -1.6962   -0.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1337   -1.5092   -0.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837   -0.4181    0.2339 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7196   -0.7885    1.6493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0020    1.1312    0.2900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2770    1.7124   -1.0538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5325    1.0488   -1.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4212    1.5330   -2.1028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4943   -0.3216   -0.9126 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7720   -0.8525   -0.7222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4477    0.1299    2.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6315   -0.7794    1.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3761    1.0345    1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6354   -2.2223    0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7713   -1.2889    1.8909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0976   -1.8877   -1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1724   -2.3186    0.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0468    0.0449   -1.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4726    0.8151    1.6997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3937    2.7121   -0.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1200    2.9350    1.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1196    2.8711   -0.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6684    0.9166   -1.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1487    1.6628   -0.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1407   -0.6305   -1.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4538    0.7202    0.8564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9876   -2.5353   -0.8011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355   -2.0567    0.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6123   -2.4667   -0.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1507   -1.1236   -1.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9051   -0.5257    2.3521 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7937   -1.9062    1.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6367   -0.3057    2.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3683    1.8637    1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4936    1.4601   -1.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3914    2.8229   -0.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9003   -0.9824   -1.5918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6739   -1.8118   -0.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  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  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 17  2  1  0
 21  2  1  0
 15  5  1  0
 15  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 11 37  1  6
 12 38  1  0
 13 39  1  0
 13 40  1  0
 14 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 21 49  1  6
 22 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3b,17b)-3b,17b-Dihydroxyandrost-5-en-16-one	HMDB
3b,17b-Dihydroxy-androst-5-en-16-one	HMDB
3b,17b-Dihydroxyandrost-5-en-16-one	HMDB
3beta,17beta-Dihydroxy-androst-5-en-16-one	HMDB
5-Androsten-3b,17b-diol-16-one	HMDB
Androst-5-ene-3b,17b-diol-16-one	HMDB

Chemical Formula

C₁₉H₂₈O₃

Average Molecular Weight

304.4238

Monoisotopic Molecular Weight

304.203844762

IUPAC Name

(2R,5S,14R,15S)-5,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-one

Traditional Name

5-androsten-3b,17b-diol-16-one

CAS Registry Number

1159-66-6

SMILES

C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@]34C)C1CC(=O)[C@@H]2O

InChI Identifier

InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-15,17,20,22H,4-10H2,1-2H3/t12-,13?,14?,15?,17-,18-,19-/m0/s1

InChI Key

AKRBLZKRYPEVIK-IACDPKRHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
3-hydroxy-delta-5-steroid
3-hydroxysteroid
17-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Oxosteroid
16-oxosteroid
Hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organ

Gland

Adrenal Gland (HMDB: HMDB0000322)
Adrenal Gland (HMDB: HMDB0000322)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000322)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000322)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000322)

Source

Endogenous

Endogenous (HMDB: HMDB0000322)

Animal

Animal (HMDB: HMDB0000322)

Exogenous

Food

Food (HMDB: HMDB0000322)

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)

Exogenous (HMDB: HMDB0000322)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000322)

Molecular messenger

Hormone (HMDB: HMDB0000322)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000322)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	203 - 205 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	2.39	ALOGPS
logP	2.13	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	12.97	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.95 m³·mol⁻¹	ChemAxon
Polarizability	34.66 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	169.054	31661259
DarkChem	[M-H]-	165.559	31661259
AllCCS	[M+H]+	177.887	32859911
AllCCS	[M-H]-	180.559	32859911
DeepCCS	[M-2H]-	209.39	30932474
DeepCCS	[M+Na]+	184.618	30932474
AllCCS	[M+H]+	177.9	32859911
AllCCS	[M+H-H2O]+	174.9	32859911
AllCCS	[M+NH4]+	180.7	32859911
AllCCS	[M+Na]+	181.5	32859911
AllCCS	[M-H]-	180.6	32859911
AllCCS	[M+Na-2H]-	180.7	32859911
AllCCS	[M+HCOO]-	180.9	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.	5.57 minutes	32390414
Predicted by Siyang on May 30, 2022	12.905 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.26 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2408.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	251.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	182.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	173.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	278.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	531.0 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	586.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	97.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1041.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	417.6 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	1392.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	333.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	398.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	333.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	337.1 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	42.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
16-Oxoandrostenediol	C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@]34C)C1CC(=O)[C@@H]2O	2822.0	Standard polar	33892256
16-Oxoandrostenediol	C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@]34C)C1CC(=O)[C@@H]2O	2636.0	Standard non polar	33892256
16-Oxoandrostenediol	C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@]34C)C1CC(=O)[C@@H]2O	2701.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
16-Oxoandrostenediol,1TMS,isomer #1	C[C@]12CCC3C(CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)C1CC(=O)[C@@H]2O	2797.5	Semi standard non polar	33892256
16-Oxoandrostenediol,1TMS,isomer #2	C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@@]43C)C1CC(=O)[C@@H]2O[Si](C)(C)C	2835.0	Semi standard non polar	33892256
16-Oxoandrostenediol,1TMS,isomer #3	C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@@]43C)C1CC(O[Si](C)(C)C)=C2O	2759.1	Semi standard non polar	33892256
16-Oxoandrostenediol,1TMS,isomer #4	C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@@]43C)C1C=C(O[Si](C)(C)C)[C@@H]2O	2723.2	Semi standard non polar	33892256
16-Oxoandrostenediol,2TMS,isomer #1	C[C@]12CCC3C(CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)C1CC(=O)[C@@H]2O[Si](C)(C)C	2842.5	Semi standard non polar	33892256
16-Oxoandrostenediol,2TMS,isomer #2	C[C@]12CCC3C(CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)C1CC(O[Si](C)(C)C)=C2O	2755.8	Semi standard non polar	33892256
16-Oxoandrostenediol,2TMS,isomer #3	C[C@]12CCC3C(CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)C1C=C(O[Si](C)(C)C)[C@@H]2O	2731.2	Semi standard non polar	33892256
16-Oxoandrostenediol,2TMS,isomer #4	C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@@]43C)C1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2821.3	Semi standard non polar	33892256
16-Oxoandrostenediol,2TMS,isomer #5	C[C@]12CCC3C(CC=C4C[C@@H](O)CC[C@@]43C)C1C=C(O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C	2793.6	Semi standard non polar	33892256
16-Oxoandrostenediol,3TMS,isomer #1	C[C@]12CCC3C(CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)C1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2800.2	Semi standard non polar	33892256
16-Oxoandrostenediol,3TMS,isomer #1	C[C@]12CCC3C(CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)C1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2783.4	Standard non polar	33892256
16-Oxoandrostenediol,3TMS,isomer #1	C[C@]12CCC3C(CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)C1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	3101.4	Standard polar	33892256
16-Oxoandrostenediol,3TMS,isomer #2	C[C@]12CCC3C(CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)C1C=C(O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C	2781.5	Semi standard non polar	33892256
16-Oxoandrostenediol,3TMS,isomer #2	C[C@]12CCC3C(CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)C1C=C(O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C	2776.6	Standard non polar	33892256
16-Oxoandrostenediol,3TMS,isomer #2	C[C@]12CCC3C(CC=C4C[C@@H](O[Si](C)(C)C)CC[C@@]43C)C1C=C(O[Si](C)(C)C)[C@@H]2O[Si](C)(C)C	3082.4	Standard polar	33892256
16-Oxoandrostenediol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CCC3C4CC(=O)[C@H](O)[C@@]4(C)CCC32)C1	3063.8	Semi standard non polar	33892256
16-Oxoandrostenediol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1C(=O)CC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@@]21C	3103.4	Semi standard non polar	33892256
16-Oxoandrostenediol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C(O)[C@@]2(C)CCC3C(CC=C4C[C@@H](O)CC[C@@]43C)C2C1	3027.4	Semi standard non polar	33892256
16-Oxoandrostenediol,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]2(C)[C@H]1O	3010.5	Semi standard non polar	33892256
16-Oxoandrostenediol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@@]2(C)C(=CCC3C4CC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@]4(C)CCC32)C1	3339.2	Semi standard non polar	33892256
16-Oxoandrostenediol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(O)[C@@]2(C)CCC3C(CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@]43C)C2C1	3243.7	Semi standard non polar	33892256
16-Oxoandrostenediol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC2C3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]2(C)[C@H]1O	3225.6	Semi standard non polar	33892256
16-Oxoandrostenediol,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CCC3C(CC=C4C[C@@H](O)CC[C@@]43C)C2C1	3352.1	Semi standard non polar	33892256
16-Oxoandrostenediol,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]2(C)[C@H]1O[Si](C)(C)C(C)(C)C	3322.2	Semi standard non polar	33892256
16-Oxoandrostenediol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CCC3C(CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@]43C)C2C1	3490.8	Semi standard non polar	33892256
16-Oxoandrostenediol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CCC3C(CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@]43C)C2C1	3381.6	Standard non polar	33892256
16-Oxoandrostenediol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CCC3C(CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@@]43C)C2C1	3388.2	Standard polar	33892256
16-Oxoandrostenediol,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2C3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]2(C)[C@H]1O[Si](C)(C)C(C)(C)C	3482.2	Semi standard non polar	33892256
16-Oxoandrostenediol,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2C3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]2(C)[C@H]1O[Si](C)(C)C(C)(C)C	3300.3	Standard non polar	33892256
16-Oxoandrostenediol,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2C3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]2(C)[C@H]1O[Si](C)(C)C(C)(C)C	3373.2	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Adrenal Gland

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021948

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5311

PubChem Compound

53477682

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Aoki, Terumi; Yamamura, Hiroko; Takei, Kyoko; Mori, Hiromu. Synthesis of 16-oxygenated androst-5-en-3b-ol derivatives. Chemical & Pharmaceutical Bulletin (1964), 12(7), 808-12.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 16-Oxoandrostenediol (HMDB0000322)

MOL for HMDB0000322 (16-Oxoandrostenediol)

3D MOL for HMDB0000322 (16-Oxoandrostenediol)

3D SDF for HMDB0000322 (16-Oxoandrostenediol)

3D-SDF for HMDB0000322 (16-Oxoandrostenediol)

PDB for HMDB0000322 (16-Oxoandrostenediol)

3D PDB for HMDB0000322 (16-Oxoandrostenediol)

SMILES for HMDB0000322 (16-Oxoandrostenediol)

INCHI for HMDB0000322 (16-Oxoandrostenediol)

Structure for HMDB0000322 (16-Oxoandrostenediol)

3D Structure for HMDB0000322 (16-Oxoandrostenediol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized