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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-08-08 10:31:56 UTC

Update Date

2022-03-07 02:49:33 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. Based on a literature review a significant number of articles have been published on 16a-Hydroxyandrost-4-ene-3,17-dione.

Structure

MOL 3D 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

HMDB0006774
     RDKit          3D
16a-Hydroxyandrost-4-ene-3,17-dione
 48 51  0  0  0  0  0  0  0  0999 V2000
   -2.7054   -1.6253    0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4007   -0.4227   -0.7118 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5012   -0.6584   -1.8846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1250   -1.0703   -1.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4599   -0.0010   -0.5003 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4846    0.1368    0.6537 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0920    0.9325    1.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1994    0.0563    2.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2337    0.0043    1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5146    0.1712    1.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4900    0.1178    0.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5961   -0.4605    0.6072 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1454    0.7694   -0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7126    0.6053   -1.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8963   -0.2297   -0.1576 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2460   -1.6933   -0.4570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7513    0.7031    0.1075 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8161    1.0442    1.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0793    0.9807    0.1905 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4152    2.2901   -0.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6733    0.2464   -1.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3016    0.2433   -2.0956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1087   -2.5147   -0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7791   -1.9395   -0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6451   -1.4449    1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9162   -1.4994   -2.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4149    0.2683   -2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2768   -1.9950   -0.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5172   -1.2865   -2.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3422    0.9573   -1.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6929   -0.8837    1.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7081    1.1236    2.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5848    1.8774    1.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8014   -0.9757    2.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381    0.4449    3.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8322    0.3426    2.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7508    0.3419   -1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    1.8723   -0.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2556    1.6456   -1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6127    0.2208   -2.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3424   -1.8166   -1.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155   -1.9071    0.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5243   -2.3868    0.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5550    1.5287   -0.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8976    0.4344    1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6613    2.1053    1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8879    0.4659    0.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6030    2.8807   -0.1762 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  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  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  6
  6 31  1  1
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  6
 18 45  1  0
 18 46  1  0
 19 47  1  1
 20 48  1  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

$$$$

HMDB0006774
     RDKit          3D
16a-Hydroxyandrost-4-ene-3,17-dione
 48 51  0  0  0  0  0  0  0  0999 V2000
   -2.7054   -1.6253    0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4007   -0.4227   -0.7118 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5012   -0.6584   -1.8846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1250   -1.0703   -1.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4599   -0.0010   -0.5003 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4846    0.1368    0.6537 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0920    0.9325    1.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1994    0.0563    2.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2337    0.0043    1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5146    0.1712    1.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4900    0.1178    0.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5961   -0.4605    0.6072 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1454    0.7694   -0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7126    0.6053   -1.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8963   -0.2297   -0.1576 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2460   -1.6933   -0.4570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7513    0.7031    0.1075 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8161    1.0442    1.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0793    0.9807    0.1905 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4152    2.2901   -0.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6733    0.2464   -1.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3016    0.2433   -2.0956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1087   -2.5147   -0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7791   -1.9395   -0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6451   -1.4449    1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9162   -1.4994   -2.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4149    0.2683   -2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2768   -1.9950   -0.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5172   -1.2865   -2.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3422    0.9573   -1.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6929   -0.8837    1.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7081    1.1236    2.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5848    1.8774    1.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8014   -0.9757    2.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381    0.4449    3.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8322    0.3426    2.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7508    0.3419   -1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    1.8723   -0.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2556    1.6456   -1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6127    0.2208   -2.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3424   -1.8166   -1.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155   -1.9071    0.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5243   -2.3868    0.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5550    1.5287   -0.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8976    0.4344    1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6613    2.1053    1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8879    0.4659    0.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6030    2.8807   -0.1762 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  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  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  6
  6 31  1  1
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  6
 18 45  1  0
 18 46  1  0
 19 47  1  1
 20 48  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  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    HMDB0006774
HETATM    1  C1  UNL     1      -2.705  -1.625   0.107  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.401  -0.423  -0.712  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.501  -0.658  -1.885  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.125  -1.070  -1.409  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.460  -0.001  -0.500  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.485   0.137   0.654  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.092   0.933   1.795  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.199   0.056   2.347  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.234   0.004   1.246  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.515   0.171   1.538  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.490   0.118   0.467  1.00  0.00           C  
HETATM   12  O1  UNL     1       5.596  -0.461   0.607  1.00  0.00           O  
HETATM   13  C12 UNL     1       4.145   0.769  -0.808  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.713   0.605  -1.123  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.896  -0.230  -0.158  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.246  -1.693  -0.457  1.00  0.00           C  
HETATM   17  C16 UNL     1      -1.751   0.703   0.108  1.00  0.00           C  
HETATM   18  C17 UNL     1      -2.816   1.044   1.051  1.00  0.00           C  
HETATM   19  C18 UNL     1      -4.079   0.981   0.191  1.00  0.00           C  
HETATM   20  O2  UNL     1      -4.415   2.290  -0.172  1.00  0.00           O  
HETATM   21  C19 UNL     1      -3.673   0.246  -1.057  1.00  0.00           C  
HETATM   22  O3  UNL     1      -4.302   0.243  -2.096  1.00  0.00           O  
HETATM   23  H1  UNL     1      -2.109  -2.515  -0.101  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.779  -1.939  -0.059  1.00  0.00           H  
HETATM   25  H3  UNL     1      -2.645  -1.445   1.205  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.916  -1.499  -2.468  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.415   0.268  -2.452  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.277  -1.995  -0.818  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.517  -1.287  -2.279  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.342   0.957  -1.091  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.693  -0.884   1.037  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.708   1.124   2.522  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.585   1.877   1.447  1.00  0.00           H  
HETATM   34  H12 UNL     1       0.801  -0.976   2.429  1.00  0.00           H  
HETATM   35  H13 UNL     1       1.638   0.445   3.260  1.00  0.00           H  
HETATM   36  H14 UNL     1       3.832   0.343   2.584  1.00  0.00           H  
HETATM   37  H15 UNL     1       4.751   0.342  -1.648  1.00  0.00           H  
HETATM   38  H16 UNL     1       4.397   1.872  -0.746  1.00  0.00           H  
HETATM   39  H17 UNL     1       2.256   1.646  -1.208  1.00  0.00           H  
HETATM   40  H18 UNL     1       2.613   0.221  -2.169  1.00  0.00           H  
HETATM   41  H19 UNL     1       2.342  -1.817  -1.542  1.00  0.00           H  
HETATM   42  H20 UNL     1       3.216  -1.907   0.035  1.00  0.00           H  
HETATM   43  H21 UNL     1       1.524  -2.387   0.020  1.00  0.00           H  
HETATM   44  H22 UNL     1      -1.555   1.529  -0.577  1.00  0.00           H  
HETATM   45  H23 UNL     1      -2.898   0.434   1.958  1.00  0.00           H  
HETATM   46  H24 UNL     1      -2.661   2.105   1.404  1.00  0.00           H  
HETATM   47  H25 UNL     1      -4.888   0.466   0.724  1.00  0.00           H  
HETATM   48  H26 UNL     1      -3.603   2.881  -0.176  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   34   35
CONECT    9   10   10   15
CONECT   10   11   36
CONECT   11   12   12   13
CONECT   13   14   37   38
CONECT   14   15   39   40
CONECT   15   16
CONECT   16   41   42   43
CONECT   17   18   44
CONECT   18   19   45   46
CONECT   19   20   21   47
CONECT   20   48
CONECT   21   22   22
END

HMDB0006774
     RDKit          3D
16a-Hydroxyandrost-4-ene-3,17-dione
 48 51  0  0  0  0  0  0  0  0999 V2000
   -2.7054   -1.6253    0.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4007   -0.4227   -0.7118 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5012   -0.6584   -1.8846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1250   -1.0703   -1.4092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4599   -0.0010   -0.5003 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4846    0.1368    0.6537 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0920    0.9325    1.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1994    0.0563    2.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2337    0.0043    1.2461 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5146    0.1712    1.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4900    0.1178    0.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5961   -0.4605    0.6072 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1454    0.7694   -0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7126    0.6053   -1.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8963   -0.2297   -0.1576 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2460   -1.6933   -0.4570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7513    0.7031    0.1075 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8161    1.0442    1.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0793    0.9807    0.1905 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4152    2.2901   -0.1717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6733    0.2464   -1.0566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3016    0.2433   -2.0956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1087   -2.5147   -0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7791   -1.9395   -0.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6451   -1.4449    1.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9162   -1.4994   -2.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4149    0.2683   -2.4515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2768   -1.9950   -0.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5172   -1.2865   -2.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3422    0.9573   -1.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6929   -0.8837    1.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7081    1.1236    2.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5848    1.8774    1.4465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8014   -0.9757    2.4286 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381    0.4449    3.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8322    0.3426    2.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7508    0.3419   -1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    1.8723   -0.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2556    1.6456   -1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6127    0.2208   -2.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3424   -1.8166   -1.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2155   -1.9071    0.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5243   -2.3868    0.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5550    1.5287   -0.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8976    0.4344    1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6613    2.1053    1.4039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8879    0.4659    0.7243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6030    2.8807   -0.1762 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  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  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  6
  6 31  1  1
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  6
 18 45  1  0
 18 46  1  0
 19 47  1  1
 20 48  1  0
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
16 alpha-Hydroxyandrost-4-en-3,17-dione	MeSH
16-Hydroxyandrost-4-en-3,17-dione	MeSH
16-Hydroxyandrost-4-en-3,17-dione, (16alpha)-isomer	MeSH
16-Hydroxyandrost-4-en-3,17-dione, (16beta)-isomer	MeSH
16alpha-OHAD	MeSH
16alpha-Hydroxyandrost-4-ene-3,17-dione	HMDB
16alpha-Hydroxyandrostenedione	MeSH, 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

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006774)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0006774)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006774)

Source

Endogenous

Endogenous (HMDB: HMDB0006774)

Animal

Animal (HMDB: HMDB0006774)

Exogenous

Food

Food (HMDB: HMDB0006774)

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: HMDB0006774)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0006774)

Molecular messenger

Signaling molecule (HMDB: HMDB0006774)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006774)

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	174.992	31661259
DarkChem	[M-H]-	170.419	31661259
DeepCCS	[M-2H]-	208.834	30932474
DeepCCS	[M+Na]+	183.427	30932474
AllCCS	[M+H]+	176.0	32859911
AllCCS	[M+H-H2O]+	173.0	32859911
AllCCS	[M+NH4]+	178.9	32859911
AllCCS	[M+Na]+	179.7	32859911
AllCCS	[M-H]-	180.1	32859911
AllCCS	[M+Na-2H]-	180.1	32859911
AllCCS	[M+HCOO]-	180.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
16a-Hydroxyandrost-4-ene-3,17-dione	[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	3527.0	Standard polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione	[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	2628.3	Standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione	[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	2826.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
16a-Hydroxyandrost-4-ene-3,17-dione,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1C[C@@H](O[Si](C)(C)C)C2=O	2916.4	Semi standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,1TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC(O)=C2O[Si](C)(C)C	2880.0	Semi standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,1TMS,isomer #3	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1C[C@@H](O)C2=O	2806.2	Semi standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2940.8	Semi standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2663.1	Standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	3143.8	Standard polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1C[C@@H](O[Si](C)(C)C)C2=O	2851.5	Semi standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1C[C@@H](O[Si](C)(C)C)C2=O	2771.6	Standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1C[C@@H](O[Si](C)(C)C)C2=O	3197.6	Standard polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TMS,isomer #3	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC(O)=C2O[Si](C)(C)C	2847.2	Semi standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TMS,isomer #3	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC(O)=C2O[Si](C)(C)C	2679.8	Standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TMS,isomer #3	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC(O)=C2O[Si](C)(C)C	3142.4	Standard polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,3TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2879.1	Semi standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,3TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	2837.9	Standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,3TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC(O[Si](C)(C)C)=C2O[Si](C)(C)C	3126.0	Standard polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]2(C)C1=O	3167.2	Semi standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(O)C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	3133.2	Semi standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3C[C@@H](O)C(=O)[C@@]3(C)CC[C@@H]12	3075.9	Semi standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]2C1	3437.4	Semi standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]2C1	3127.6	Standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C(O[Si](C)(C)C(C)(C)C)[C@@]2(C)CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]2C1	3365.3	Standard polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)[C@@]3(C)CC[C@@H]12	3369.6	Semi standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)[C@@]3(C)CC[C@@H]12	3265.3	Standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)[C@@]3(C)CC[C@@H]12	3430.8	Standard polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC(O)=C(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12	3357.1	Semi standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC(O)=C(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12	3098.4	Standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC(O)=C(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12	3392.2	Standard polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12	3594.0	Semi standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12	3402.2	Standard non polar	33892256
16a-Hydroxyandrost-4-ene-3,17-dione,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12	3424.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-0190000000-333d436ce8b783dec900	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione GC-MS (1 TMS) - 70eV, Positive	splash10-0ldj-1029000000-d779bb8112f47f4675a3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 10V, Positive-QTOF	splash10-0udi-0169000000-552881f7e148e949c2d5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 20V, Positive-QTOF	splash10-0fi9-0191000000-5bba772cd2498247059b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 40V, Positive-QTOF	splash10-0ldl-3390000000-dcf95e7ad7d31a7b2345	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 10V, Negative-QTOF	splash10-0udi-0009000000-0e8dc36bc54906d11cd2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 20V, Negative-QTOF	splash10-0udi-0029000000-e08d062d1b3fb4e55267	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 40V, Negative-QTOF	splash10-05bo-1090000000-86e6dcdcc4e4babac09e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 10V, Positive-QTOF	splash10-0udi-0049000000-79630e98940a556508ff	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 20V, Positive-QTOF	splash10-114s-0972000000-fef31191241a5fee6d7a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 40V, Positive-QTOF	splash10-06r7-1910000000-e9b6c3405a956f782301	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 10V, Negative-QTOF	splash10-0udi-0009000000-4360bacaf95498925fe5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 20V, Negative-QTOF	splash10-0udi-0039000000-479f11c50b787985f7d5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16a-Hydroxyandrost-4-ene-3,17-dione 40V, Negative-QTOF	splash10-0006-0091000000-9edb0c3dd24f9aa0965b	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

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

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

Good Scents 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)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions