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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-08-08 10:31:56 UTC

Update Date

2021-09-14 15:39:04 UTC

HMDB ID

HMDB0006774

Secondary Accession Numbers

HMDB06774

Metabolite Identification

Common Name

16a-Hydroxyandrost-4-ene-3,17-dione

Description

16a-Hydroxyandrost-4-ene-3,17-dione, also known as 4-androsten-16alpha-ol-3,17-dione or 16alpha-ohad, 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. Thus, 16a-hydroxyandrost-4-ene-3,17-dione is considered to be a steroid lipid molecule. 16a-Hydroxyandrost-4-ene-3,17-dione is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02231220512D          

 25 28  0  0  1  0            999 V2000
   13.3590  -11.1822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8979  -11.1822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0246  -10.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0567   -8.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9315  -12.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6036  -11.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6803  -11.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6967   -9.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3525  -10.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3688   -9.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5090  -12.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0027  -10.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1812  -11.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7586  -11.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5254  -10.7418    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.7750  -10.3990    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.1974  -10.2634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.4222   -9.7323    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.8761   -9.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1029  -10.8774    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1192   -9.4421    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0865  -12.3127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2434   -9.6540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0554   -8.3086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4247  -10.0292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 20  3  1  1  0  0  0
 21  4  1  1  0  0  0
  5 13  1  0  0  0  0
  5  6  1  0  0  0  0
 15  6  1  0  0  0  0
  7  9  1  0  0  0  0
  7 14  1  0  0  0  0
 16  8  1  0  0  0  0
  8 10  1  0  0  0  0
  9 20  1  0  0  0  0
 10 21  1  0  0  0  0
 11 14  1  0  0  0  0
 11 13  2  0  0  0  0
 17 12  1  0  0  0  0
 12 18  1  0  0  0  0
 13 20  1  0  0  0  0
 14 22  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 18 23  1  6  0  0  0
 18 19  1  0  0  0  0
 19 21  1  0  0  0  0
 19 24  2  0  0  0  0
 16  2  1  6  0  0  0
 17  1  1  6  0  0  0
 15 25  1  1  0  0  0
M  END


  Mrv0541 02231220512D          

 25 28  0  0  1  0            999 V2000
   13.3590  -11.1822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8979  -11.1822    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0246  -10.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0567   -8.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9315  -12.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6036  -11.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6803  -11.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6967   -9.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3525  -10.5346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3688   -9.0992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5090  -12.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0027  -10.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1812  -11.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7586  -11.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5254  -10.7418    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.7750  -10.3990    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.1974  -10.2634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.4222   -9.7323    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.8761   -9.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1029  -10.8774    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1192   -9.4421    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0865  -12.3127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2434   -9.6540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0554   -8.3086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4247  -10.0292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 20  3  1  1  0  0  0
 21  4  1  1  0  0  0
  5 13  1  0  0  0  0
  5  6  1  0  0  0  0
 15  6  1  0  0  0  0
  7  9  1  0  0  0  0
  7 14  1  0  0  0  0
 16  8  1  0  0  0  0
  8 10  1  0  0  0  0
  9 20  1  0  0  0  0
 10 21  1  0  0  0  0
 11 14  1  0  0  0  0
 11 13  2  0  0  0  0
 17 12  1  0  0  0  0
 12 18  1  0  0  0  0
 13 20  1  0  0  0  0
 14 22  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 18 23  1  6  0  0  0
 18 19  1  0  0  0  0
 19 21  1  0  0  0  0
 19 24  2  0  0  0  0
 16  2  1  6  0  0  0
 17  1  1  6  0  0  0
 15 25  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0006774

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O3/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/h9,13-16,21H,3-8,10H2,1-2H3/t13-,14+,15+,16-,18+,19+/m1/s1

> <INCHI_KEY>
SSBCZTXGVMMZOT-NBBHSKLNSA-N

> <FORMULA>
C19H26O3

> <MOLECULAR_WEIGHT>
302.4079

> <EXACT_MASS>
302.188194698

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.991129403085495

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10R,11S,13R,15S)-13-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14-dione

> <ALOGPS_LOGP>
2.32

> <JCHEM_LOGP>
3.0578850826666675

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.083368691594035

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.382230868379793

> <JCHEM_PKA_STRONGEST_BASIC>
-3.506411838826353

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
85.09969999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-androsten-16α-ol-3,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D12C%5BC@@H%5D(O...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:47})
 48 51  0  0  0  0  0  0  0  0999 V2000
   -1.6334    0.6481   -1.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6995    0.6048   -0.2757 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7488    1.5979    0.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0848    0.8744   -0.0811 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8065    1.0511    0.7165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6074    1.3426   -1.3260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638   -0.6138   -0.1749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5225   -1.5039   -0.4756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3132   -0.7457    0.1828 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1675   -0.8885    1.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5350   -1.8508   -0.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0945   -1.7915    0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5381   -0.4243   -0.2100 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6533   -0.2644   -1.2820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3204    0.7269    0.3468 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4191    0.6211    1.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3260    2.0698    0.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6957    2.1801    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5173    0.9734    0.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7222    1.1689   -0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5020    0.0057   -0.7111 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7134    0.0296   -0.7736 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7019   -1.2269   -1.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7719   -1.5505    0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9126   -0.3719    0.4579 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6507   -0.4845    1.9611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6408    1.7517    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6824    2.5446   -0.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4424    0.9280   -1.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6829   -1.7901    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1110   -0.9582    1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6051   -0.0190    2.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9784   -2.8183   -0.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5384   -1.6924   -1.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1026   -1.9971    1.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5025   -2.5526   -0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4511    2.1471   -1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3166    2.8790    0.3527 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1938    3.0959    0.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5716    2.1832    1.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1214    2.1674   -0.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1141   -1.0261   -1.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3759   -2.0646   -1.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1295   -2.3852   -0.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3743   -1.8448    0.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5991   -0.4615    2.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0294    0.3504    2.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1370   -1.4227    2.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  2 15  1  0  0  0  0
  3  4  1  0  0  0  0
  3 27  1  0  0  0  0
  3 28  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  6 29  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 10 30  1  0  0  0  0
 10 31  1  0  0  0  0
 10 32  1  0  0  0  0
 11 12  1  0  0  0  0
 11 33  1  0  0  0  0
 11 34  1  0  0  0  0
 12 13  1  0  0  0  0
 12 35  1  0  0  0  0
 12 36  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 13 25  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 37  1  0  0  0  0
 17 38  1  0  0  0  0
 18 19  1  0  0  0  0
 18 39  1  0  0  0  0
 18 40  1  0  0  0  0
 19 20  2  0  0  0  0
 19 25  1  0  0  0  0
 20 21  1  0  0  0  0
 20 41  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 42  1  0  0  0  0
 23 43  1  0  0  0  0
 24 25  1  0  0  0  0
 24 44  1  0  0  0  0
 24 45  1  0  0  0  0
 25 26  1  1  0  0  0
 26 46  1  0  0  0  0
 26 47  1  0  0  0  0
 26 48  1  0  0  0  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  H   UNK     0      24.937 -20.873   0.000  0.00  0.00           H+0
HETATM    2  H   UNK     0      22.209 -20.873   0.000  0.00  0.00           H+0
HETATM    3  C   UNK     0      20.579 -18.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.373 -16.090   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.272 -22.477   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.527 -21.584   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.070 -20.558   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.834 -17.878   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.325 -19.665   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.088 -16.985   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.617 -22.731   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.138 -19.493   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.872 -21.838   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.216 -22.091   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.381 -20.051   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.980 -19.411   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.635 -19.158   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.921 -18.167   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.902 -17.013   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      20.725 -20.304   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.489 -17.625   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      16.961 -22.984   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      28.454 -18.021   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      26.237 -15.509   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0      23.193 -18.721   0.000  0.00  0.00           H+0
CONECT    1   17                                                            
CONECT    2   16                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5   13    6                                                       
CONECT    6    5   15                                                       
CONECT    7    9   14                                                       
CONECT    8   16   10                                                       
CONECT    9    7   20                                                       
CONECT   10    8   21                                                       
CONECT   11   14   13                                                       
CONECT   12   17   18                                                       
CONECT   13    5   11   20                                                  
CONECT   14    7   11   22                                                  
CONECT   15    6   16   17   25                                             
CONECT   16    8   15   20    2                                             
CONECT   17   12   15   21    1                                             
CONECT   18   12   23   19                                                  
CONECT   19   18   21   24                                                  
CONECT   20    3    9   13   16                                             
CONECT   21    4   10   17   19                                             
CONECT   22   14                                                            
CONECT   23   18                                                            
CONECT   24   19                                                            
CONECT   25   15                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D12C%5BC@@H%5D(O... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
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HETATM    2  C   UNL     1      -1.700   0.605  -0.276  1.00  0.00           C  
HETATM    3  C   UNL     1      -2.749   1.598   0.241  1.00  0.00           C  
HETATM    4  C   UNL     1      -4.085   0.874  -0.081  1.00  0.00           C  
HETATM    5  H   UNL     1      -4.806   1.051   0.717  1.00  0.00           H  
HETATM    6  O   UNL     1      -4.607   1.343  -1.326  1.00  0.00           O  
HETATM    7  C   UNL     1      -3.764  -0.614  -0.175  1.00  0.00           C  
HETATM    8  O   UNL     1      -4.522  -1.504  -0.476  1.00  0.00           O  
HETATM    9  C   UNL     1      -2.313  -0.746   0.183  1.00  0.00           C  
HETATM   10  C   UNL     1      -2.167  -0.888   1.699  1.00  0.00           C  
HETATM   11  C   UNL     1      -1.535  -1.851  -0.504  1.00  0.00           C  
HETATM   12  C   UNL     1      -0.095  -1.792   0.029  1.00  0.00           C  
HETATM   13  C   UNL     1       0.538  -0.424  -0.210  1.00  0.00           C  
HETATM   14  H   UNL     1       0.653  -0.264  -1.282  1.00  0.00           H  
HETATM   15  C   UNL     1      -0.320   0.727   0.347  1.00  0.00           C  
HETATM   16  H   UNL     1      -0.419   0.621   1.427  1.00  0.00           H  
HETATM   17  C   UNL     1       0.326   2.070   0.005  1.00  0.00           C  
HETATM   18  C   UNL     1       1.696   2.180   0.686  1.00  0.00           C  
HETATM   19  C   UNL     1       2.517   0.973   0.265  1.00  0.00           C  
HETATM   20  C   UNL     1       3.722   1.169  -0.264  1.00  0.00           C  
HETATM   21  C   UNL     1       4.502   0.006  -0.711  1.00  0.00           C  
HETATM   22  O   UNL     1       5.713   0.030  -0.774  1.00  0.00           O  
HETATM   23  C   UNL     1       3.702  -1.227  -1.089  1.00  0.00           C  
HETATM   24  C   UNL     1       2.772  -1.550   0.080  1.00  0.00           C  
HETATM   25  C   UNL     1       1.913  -0.372   0.458  1.00  0.00           C  
HETATM   26  C   UNL     1       1.651  -0.484   1.961  1.00  0.00           C  
HETATM   27  H   UNL     1      -2.641   1.752   1.314  1.00  0.00           H  
HETATM   28  H   UNL     1      -2.682   2.545  -0.296  1.00  0.00           H  
HETATM   29  H   UNL     1      -5.442   0.928  -1.583  1.00  0.00           H  
HETATM   30  H   UNL     1      -2.683  -1.790   2.030  1.00  0.00           H  
HETATM   31  H   UNL     1      -1.111  -0.958   1.958  1.00  0.00           H  
HETATM   32  H   UNL     1      -2.605  -0.019   2.190  1.00  0.00           H  
HETATM   33  H   UNL     1      -1.978  -2.818  -0.268  1.00  0.00           H  
HETATM   34  H   UNL     1      -1.538  -1.692  -1.582  1.00  0.00           H  
HETATM   35  H   UNL     1      -0.103  -1.997   1.100  1.00  0.00           H  
HETATM   36  H   UNL     1       0.502  -2.553  -0.473  1.00  0.00           H  
HETATM   37  H   UNL     1       0.451   2.147  -1.075  1.00  0.00           H  
HETATM   38  H   UNL     1      -0.317   2.879   0.353  1.00  0.00           H  
HETATM   39  H   UNL     1       2.194   3.096   0.367  1.00  0.00           H  
HETATM   40  H   UNL     1       1.572   2.183   1.768  1.00  0.00           H  
HETATM   41  H   UNL     1       4.121   2.167  -0.364  1.00  0.00           H  
HETATM   42  H   UNL     1       3.114  -1.026  -1.984  1.00  0.00           H  
HETATM   43  H   UNL     1       4.376  -2.065  -1.268  1.00  0.00           H  
HETATM   44  H   UNL     1       2.130  -2.385  -0.201  1.00  0.00           H  
HETATM   45  H   UNL     1       3.374  -1.845   0.939  1.00  0.00           H  
HETATM   46  H   UNL     1       2.599  -0.462   2.498  1.00  0.00           H  
HETATM   47  H   UNL     1       1.029   0.350   2.285  1.00  0.00           H  
HETATM   48  H   UNL     1       1.137  -1.423   2.171  1.00  0.00           H  
CONECT    1    2                                                      
CONECT    2    1    3    9   15                                       
CONECT    3    2    4   27   28                                       
CONECT    4    3    5    6    7                                       
CONECT    5    4                                                      
CONECT    6    4   29                                                 
CONECT    7    4    8    8    9                                       
CONECT    8    7    7                                                 
CONECT    9    7    2   10   11                                       
CONECT   10    9   30   31   32                                       
CONECT   11    9   12   33   34                                       
CONECT   12   11   13   35   36                                       
CONECT   13   12   14   15   25                                       
CONECT   14   13                                                      
CONECT   15   13    2   16   17                                       
CONECT   16   15                                                      
CONECT   17   15   18   37   38                                       
CONECT   18   17   19   39   40                                       
CONECT   19   18   20   20   25                                       
CONECT   20   19   19   21   41                                       
CONECT   21   20   22   22   23                                       
CONECT   22   21   21                                                 
CONECT   23   21   24   42   43                                       
CONECT   24   23   25   44   45                                       
CONECT   25   24   13   19   26                                       
CONECT   26   25   46   47   48                                       
CONECT   27    3                                                      
CONECT   28    3                                                      
CONECT   29    6                                                      
CONECT   30   10                                                      
CONECT   31   10                                                      
CONECT   32   10                                                      
CONECT   33   11                                                      
CONECT   34   11                                                      
CONECT   35   12                                                      
CONECT   36   12                                                      
CONECT   37   17                                                      
CONECT   38   17                                                      
CONECT   39   18                                                      
CONECT   40   18                                                      
CONECT   41   20                                                      
CONECT   42   23                                                      
CONECT   43   23                                                      
CONECT   44   24                                                      
CONECT   45   24                                                      
CONECT   46   26                                                      
CONECT   47   26                                                      
CONECT   48   26                                                      
MASTER        0    0    0    0    0    0    0    0   48    0   48    0
END

https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D12C%5BC@@H%5D(O...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:47})
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M  END
$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Androsten-16alpha-ol-3,17-dione	ChEBI
4-Androsten-16a-ol-3,17-dione	Generator
4-Androsten-16α-ol-3,17-dione	Generator
16alpha-Hydroxyandrost-4-ene-3,17-dione	HMDB
16alpha-Hydroxyandrostenedione	HMDB
16-Hydroxyandrost-4-en-3,17-dione	HMDB
16 alpha-Hydroxyandrost-4-en-3,17-dione	HMDB
16-Hydroxyandrost-4-en-3,17-dione, (16alpha)-isomer	HMDB
16-Hydroxyandrost-4-en-3,17-dione, (16beta)-isomer	HMDB
16alpha-OHAD	HMDB
16a-Hydroxyandrost-4-ene-3,17-dione	Generator
16Α-hydroxyandrost-4-ene-3,17-dione	Generator

Chemical Formula

C₁₉H₂₆O₃

Average Molecular Weight

302.4079

Monoisotopic Molecular Weight

302.188194698

IUPAC Name

(1S,2R,10R,11S,13R,15S)-13-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14-dione

Traditional Name

4-androsten-16α-ol-3,17-dione

CAS Registry Number

63-02-5

SMILES

[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C19H26O3/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/h9,13-16,21H,3-8,10H2,1-2H3/t13-,14+,15+,16-,18+,19+/m1/s1

InChI Key

SSBCZTXGVMMZOT-NBBHSKLNSA-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-oxo-delta-4-steroid
3-oxosteroid
16-hydroxysteroid
16-alpha-hydroxysteroid
Oxosteroid
17-oxosteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
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

3-oxo steroid (CHEBI:27582 )
17-oxo steroid (CHEBI:27582 )
androstanoid (CHEBI:27582 )
16alpha-hydroxy steroid (CHEBI:27582 )
C19 steroids (androgens) and derivatives (C05140 )
C19 steroids (androgens) and derivatives (LMST02020065 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Biofluid and excreta:

Urine

Subcellular:

Source:

Biological:

Animal

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

System process:

Reproduction

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Molecular messenger:

Signaling molecule

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.067 g/L	ALOGPS
logP	2.32	ALOGPS
logP	3.06	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	13.38	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.1 m³·mol⁻¹	ChemAxon
Polarizability	33.99 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

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-0190000000-333d436ce8b783dec900	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0ldj-1029000000-d779bb8112f47f4675a3	2017-10-06	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-006x-0190000000-333d436ce8b783dec900	2021-09-05	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0169000000-552881f7e148e949c2d5	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fi9-0191000000-5bba772cd2498247059b	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ldl-3390000000-dcf95e7ad7d31a7b2345	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-0e8dc36bc54906d11cd2	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0029000000-e08d062d1b3fb4e55267	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05bo-1090000000-86e6dcdcc4e4babac09e	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0049000000-79630e98940a556508ff	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-114s-0972000000-fef31191241a5fee6d7a	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-06r7-1910000000-e9b6c3405a956f782301	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-4360bacaf95498925fe5	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0039000000-479f11c50b787985f7d5	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0091000000-9edb0c3dd24f9aa0965b	2021-09-07	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	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

FDB024076

KNApSAcK ID

Not Available

Chemspider ID

389474

KEGG Compound ID

C05140

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440574

PDB ID

Not Available

ChEBI ID

27582

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1

General function:: Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:: 3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids. Efficiently catalyzes the transformation of pregnenolone to progesterone, 17-alpha-hydroxypregnenolone to 17-alpha-hydroxyprogesterone, DHEA to 4-androstenedione, dihydrotestosterone to 5-alpha-androstane-3 beta,17 beta-diol, dehydroepiandrosterone to androstenedione and 5-alpha-androstan-3 beta,17 beta-diol to 5-alpha-dihydrotestosterone.
Gene Name:: HSD3B1
Uniprot ID:: P14060
Molecular weight:: 42251.25

Reactions

16a-Hydroxyandrost-4-ene-3,17-dione + Hydrogen Ion + NADH → 16a-Hydroxydehydroisoandrosterone + NAD	details

Enzyme Details

2. 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2

General function:: Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:: 3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids.
Gene Name:: HSD3B2
Uniprot ID:: P26439
Molecular weight:: 42051.845

Reactions

16a-Hydroxyandrost-4-ene-3,17-dione + Hydrogen Ion + NADH → 16a-Hydroxydehydroisoandrosterone + NAD	details

Showing metabocard for 16a-Hydroxyandrost-4-ene-3,17-dione (HMDB0006774)

MOL for HMDB0006774 (16a-Hydroxyandrost-4-ene-3,17-dione)

3D MOL for HMDB0006774 (16a-Hydroxyandrost-4-ene-3,17-dione)

3D SDF for HMDB0006774 (16a-Hydroxyandrost-4-ene-3,17-dione)

3D-SDF for HMDB0006774 (16a-Hydroxyandrost-4-ene-3,17-dione)

PDB for HMDB0006774 (16a-Hydroxyandrost-4-ene-3,17-dione)

3D PDB for HMDB0006774 (16a-Hydroxyandrost-4-ene-3,17-dione)

SMILES for HMDB0006774 (16a-Hydroxyandrost-4-ene-3,17-dione)

INCHI for HMDB0006774 (16a-Hydroxyandrost-4-ene-3,17-dione)

Structure for HMDB0006774 (16a-Hydroxyandrost-4-ene-3,17-dione)

3D Structure for HMDB0006774 (16a-Hydroxyandrost-4-ene-3,17-dione)

GC-MS

LC-MS/MS

Enzymes

Reactions

Reactions