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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2007-04-12 15:51:51 UTC

Update Date

2022-03-07 02:49:29 UTC

HMDB ID

HMDB0005849

Secondary Accession Numbers

HMDB05849

Metabolite Identification

Common Name

4-Androstenediol

Description

4-Androstenediol is a metabolite of testosterone. Conversely, the conversion of 4-androstenediol to testosterone has been demonstrated to occur in homogenates of hyperplastic human female adrenal glands. 4-Androstenediol is an anabolic agent that has been found in increased concentration in athletes suspected of doping. 4-Androstenediol has also been found in aqueous and solid nutritional supplements that are commercially available. Studies showing that non-hormonal supplements such as vitamins, minerals, and amino acids can contain anabolic androgenic steroids not declared on the labels of the products have been published. These undeclared substances (often prohormones of testosterone) can cause health risks to consumers and might lead to positive results in sports doping control. It has been demonstrated that 4-androstenediol taken by mouth is capable of producing in vivo increases in testosterone concentration in apparently healthy young men an women (PMID: 15808000 , 15103700 , 10638382 , 15370836 ).

Structure

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

HMDB0005849
     RDKit          3D
4-Androstenediol
 51 54  0  0  0  0  0  0  0  0999 V2000
    3.0176    1.2686   -0.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4900   -0.1266   -0.7488 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5677   -0.3260   -1.9261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3122    0.5098   -1.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3654   -0.1062   -0.3948 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5613    0.1510    0.7702 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0661   -0.2184    2.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1809    0.7897    2.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1968    0.4674    1.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4751    0.3709    1.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5193    0.0586    0.5105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9112    1.1155   -0.2652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9280   -1.1050   -0.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6309   -0.7622   -0.8744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7900    0.2815   -0.1932 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0513    1.6096   -0.9255 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8019   -0.6229    0.4737 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8603   -0.6429    1.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0672   -1.1763    0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6965   -1.0505   -0.7738 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7665   -0.3902   -1.3768 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0293    1.2823   -0.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3982    1.9773   -0.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1557    1.6537   -1.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273    0.1686   -2.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3321   -1.3788   -2.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7728    1.4834   -1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3237    0.6181   -2.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2930   -1.2228   -0.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7288    1.2525    0.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4501   -1.2385    2.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7167   -0.1291    2.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5992    0.6302    3.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7504    1.7868    2.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8003    0.5211    2.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4270   -0.3836    1.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7585    0.9022   -0.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7428   -1.8963    0.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6251   -1.4775   -1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0504   -1.7398   -0.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8172   -0.5049   -1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6847    1.4312   -1.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1318    2.0759   -1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4918    2.3731   -0.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4870   -1.6809    0.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0847    0.3206    1.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6223   -1.3809    2.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2006   -2.2618    0.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9321   -0.5690    0.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4809   -2.0152   -1.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9515   -0.6933   -2.2904 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  1  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
 20 21  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  6
  6 30  1  1
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 11 36  1  1
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  6
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  6
 21 51  1  0
M  END


  Mrv1652310041922032D          

 24 27  0  0  0  0            999 V2000
 9999.306610000.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.447910001.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4479 9998.9596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1658 9998.1238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.733710000.1945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.0216 9998.9596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.734510001.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.020010000.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0200 9999.7870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7345 9999.3746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.0206 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7351 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5935 9999.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8790 9999.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8790 9998.5410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.5935 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3080 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3080 9999.3661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.233610000.8671    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.449010000.6121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.4490 9999.7871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.2336 9999.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.718510000.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.488510001.6517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  9  6  1  6  0  0  0
 12 10  1  0  0  0  0
 10  5  1  1  0  0  0
 15  4  1  1  0  0  0
 18  1  1  1  0  0  0
  9 18  1  0  0  0  0
 17 11  1  0  0  0  0
 19 20  1  0  0  0  0
 19 23  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 19 24  1  1  0  0  0
 10 21  1  0  0  0  0
 21  3  1  6  0  0  0
  7 20  1  0  0  0  0
 20  2  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0005849

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,13-17,20-21H,3-10H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1

> <INCHI_KEY>
BTTWKVFKBPAFDK-LOVVWNRFSA-N

> <FORMULA>
C19H30O2

> <MOLECULAR_WEIGHT>
290.4403

> <EXACT_MASS>
290.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
34.37828684998394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-diol

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
2.954084809666667

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.37770520810813

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.504415926529536

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8227000810590906

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
85.3272

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005849
     RDKit          3D
4-Androstenediol
 51 54  0  0  0  0  0  0  0  0999 V2000
    3.0176    1.2686   -0.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4900   -0.1266   -0.7488 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5677   -0.3260   -1.9261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3122    0.5098   -1.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3654   -0.1062   -0.3948 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5613    0.1510    0.7702 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0661   -0.2184    2.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1809    0.7897    2.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1968    0.4674    1.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4751    0.3709    1.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5193    0.0586    0.5105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9112    1.1155   -0.2652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9280   -1.1050   -0.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6309   -0.7622   -0.8744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7900    0.2815   -0.1932 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0513    1.6096   -0.9255 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8019   -0.6229    0.4737 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8603   -0.6429    1.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0672   -1.1763    0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6965   -1.0505   -0.7738 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7665   -0.3902   -1.3768 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0293    1.2823   -0.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3982    1.9773   -0.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1557    1.6537   -1.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273    0.1686   -2.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3321   -1.3788   -2.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7728    1.4834   -1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3237    0.6181   -2.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2930   -1.2228   -0.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7288    1.2525    0.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4501   -1.2385    2.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7167   -0.1291    2.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5992    0.6302    3.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7504    1.7868    2.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8003    0.5211    2.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4270   -0.3836    1.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7585    0.9022   -0.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7428   -1.8963    0.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6251   -1.4775   -1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0504   -1.7398   -0.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8172   -0.5049   -1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6847    1.4312   -1.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1318    2.0759   -1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4918    2.3731   -0.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4870   -1.6809    0.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0847    0.3206    1.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6223   -1.3809    2.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2006   -2.2618    0.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9321   -0.5690    0.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4809   -2.0152   -1.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9515   -0.6933   -2.2904 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  1  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
 20 21  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  6
  6 30  1  1
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 11 36  1  1
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  6
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  6
 21 51  1  0
M  END

HEADER    PROTEIN                                 04-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-OCT-19         0                                  
HETATM    1  C   UNK     0    8665.3728667.030   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8669.3698669.361   0.000  0.00  0.00           C+0
HETATM    3  H   UNK     0    8669.3698664.725   0.000  0.00  0.00           H+0
HETATM    4  O   UNK     0    8661.3768663.164   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0    8668.0368667.030   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8666.7078664.725   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0    8668.0388668.579   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8666.7048667.809   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8666.7048666.269   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8668.0388665.499   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8666.7058663.173   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8668.0398663.943   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8664.0418666.253   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8662.7078665.483   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8662.7078663.943   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8664.0418663.173   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8665.3758663.943   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8665.3758665.483   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8670.8368668.285   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8669.3718667.809   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8669.3718666.269   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8670.8368665.793   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8671.7418667.039   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0    8671.3128669.750   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4   15                                                            
CONECT    5   10                                                            
CONECT    6    9                                                            
CONECT    7    8   20                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10    6   18                                             
CONECT   10    9   12    5   21                                             
CONECT   11   12   17                                                       
CONECT   12   11   10                                                       
CONECT   13   14   18                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16    4                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   11                                                  
CONECT   18   13   17    1    9                                             
CONECT   19   20   23   24                                                  
CONECT   20   19   21    7    2                                             
CONECT   21   20   22   10    3                                             
CONECT   22   21   23                                                       
CONECT   23   19   22                                                       
CONECT   24   19                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0005849
HETATM    1  C1  UNL     1       3.018   1.269  -0.651  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.490  -0.127  -0.749  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.568  -0.326  -1.926  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.312   0.510  -1.598  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.365  -0.106  -0.395  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.561   0.151   0.770  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.066  -0.218   2.091  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.181   0.790   2.289  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.197   0.467   1.196  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.475   0.371   1.522  1.00  0.00           C  
HETATM   11  C11 UNL     1      -4.519   0.059   0.511  1.00  0.00           C  
HETATM   12  O1  UNL     1      -4.911   1.115  -0.265  1.00  0.00           O  
HETATM   13  C12 UNL     1      -3.928  -1.105  -0.265  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.631  -0.762  -0.874  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.790   0.282  -0.193  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.051   1.610  -0.925  1.00  0.00           C  
HETATM   17  C16 UNL     1       1.802  -0.623   0.474  1.00  0.00           C  
HETATM   18  C17 UNL     1       2.860  -0.643   1.489  1.00  0.00           C  
HETATM   19  C18 UNL     1       4.067  -1.176   0.710  1.00  0.00           C  
HETATM   20  C19 UNL     1       3.697  -1.051  -0.774  1.00  0.00           C  
HETATM   21  O2  UNL     1       4.767  -0.390  -1.377  1.00  0.00           O  
HETATM   22  H1  UNL     1       4.029   1.282  -0.188  1.00  0.00           H  
HETATM   23  H2  UNL     1       2.398   1.977  -0.117  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.156   1.654  -1.686  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.027   0.169  -2.800  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.332  -1.379  -2.058  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.773   1.483  -1.246  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.324   0.618  -2.472  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.293  -1.223  -0.572  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.729   1.253   0.799  1.00  0.00           H  
HETATM   31  H10 UNL     1      -0.450  -1.238   2.028  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.717  -0.129   2.865  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.599   0.630   3.278  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.750   1.787   2.118  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.800   0.521   2.561  1.00  0.00           H  
HETATM   36  H15 UNL     1      -5.427  -0.384   1.036  1.00  0.00           H  
HETATM   37  H16 UNL     1      -5.758   0.902  -0.691  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.743  -1.896   0.521  1.00  0.00           H  
HETATM   39  H18 UNL     1      -4.625  -1.477  -1.040  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.050  -1.740  -0.953  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.817  -0.505  -1.949  1.00  0.00           H  
HETATM   42  H21 UNL     1      -2.685   1.431  -1.817  1.00  0.00           H  
HETATM   43  H22 UNL     1      -1.132   2.076  -1.299  1.00  0.00           H  
HETATM   44  H23 UNL     1      -2.492   2.373  -0.229  1.00  0.00           H  
HETATM   45  H24 UNL     1       1.487  -1.681   0.263  1.00  0.00           H  
HETATM   46  H25 UNL     1       3.085   0.321   1.966  1.00  0.00           H  
HETATM   47  H26 UNL     1       2.622  -1.381   2.271  1.00  0.00           H  
HETATM   48  H27 UNL     1       4.201  -2.262   0.898  1.00  0.00           H  
HETATM   49  H28 UNL     1       4.932  -0.569   0.975  1.00  0.00           H  
HETATM   50  H29 UNL     1       3.481  -2.015  -1.230  1.00  0.00           H  
HETATM   51  H30 UNL     1       4.951  -0.693  -2.290  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   17   20
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6   15   29
CONECT    6    7   17   30
CONECT    7    8   31   32
CONECT    8    9   33   34
CONECT    9   10   10   15
CONECT   10   11   35
CONECT   11   12   13   36
CONECT   12   37
CONECT   13   14   38   39
CONECT   14   15   40   41
CONECT   15   16
CONECT   16   42   43   44
CONECT   17   18   45
CONECT   18   19   46   47
CONECT   19   20   48   49
CONECT   20   21   50
CONECT   21   51
END

HMDB0005849
     RDKit          3D
4-Androstenediol
 51 54  0  0  0  0  0  0  0  0999 V2000
    3.0176    1.2686   -0.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4900   -0.1266   -0.7488 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5677   -0.3260   -1.9261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3122    0.5098   -1.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3654   -0.1062   -0.3948 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5613    0.1510    0.7702 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0661   -0.2184    2.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1809    0.7897    2.2891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1968    0.4674    1.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4751    0.3709    1.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5193    0.0586    0.5105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9112    1.1155   -0.2652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9280   -1.1050   -0.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6309   -0.7622   -0.8744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7900    0.2815   -0.1932 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0513    1.6096   -0.9255 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8019   -0.6229    0.4737 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8603   -0.6429    1.4888 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0672   -1.1763    0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6965   -1.0505   -0.7738 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7665   -0.3902   -1.3768 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0293    1.2823   -0.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3982    1.9773   -0.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1557    1.6537   -1.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273    0.1686   -2.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3321   -1.3788   -2.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7728    1.4834   -1.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3237    0.6181   -2.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2930   -1.2228   -0.5720 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7288    1.2525    0.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4501   -1.2385    2.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7167   -0.1291    2.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5992    0.6302    3.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7504    1.7868    2.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8003    0.5211    2.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4270   -0.3836    1.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7585    0.9022   -0.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7428   -1.8963    0.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6251   -1.4775   -1.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0504   -1.7398   -0.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8172   -0.5049   -1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6847    1.4312   -1.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1318    2.0759   -1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4918    2.3731   -0.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4870   -1.6809    0.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0847    0.3206    1.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6223   -1.3809    2.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2006   -2.2618    0.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9321   -0.5690    0.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4809   -2.0152   -1.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9515   -0.6933   -2.2904 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  1  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
 20 21  1  0
 17  2  1  0
 20  2  1  0
 15  5  1  0
 15  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  6
  6 30  1  1
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 11 36  1  1
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  6
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  6
 21 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Androst-4-ene-3beta,17beta-diol	Kegg
Androst-4-ene-3b,17b-diol	Generator
Androst-4-ene-3β,17β-diol	Generator
(3b,17b)-Androst-4-ene-3,17-diol	HMDB
3b,17b-Dihydroxy-4-androstene	HMDB
4-Androstene-3b,17b-diol	HMDB
Androst-4-en-3b,17b-diol	HMDB
D4-Androstene-3b,17b-diol	HMDB
(3beta,17beta)-Androst-4-ene-3,17-diol	HMDB
(3β,17β)-Androst-4-ene-3,17-diol	HMDB
3beta,17beta-Dihydroxy-4-androstene	HMDB
3β,17β-Dihydroxy-4-androstene	HMDB
4-Androstenediol	HMDB

Chemical Formula

C₁₉H₃₀O₂

Average Molecular Weight

290.4403

Monoisotopic Molecular Weight

290.224580204

IUPAC Name

(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-diol

Traditional Name

(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-diol

CAS Registry Number

1156-92-9

SMILES

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

InChI Identifier

InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,13-17,20-21H,3-10H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1

InChI Key

BTTWKVFKBPAFDK-LOVVWNRFSA-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
17-hydroxysteroid
3-beta-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-4-steroid
Delta-4-steroid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-hydroxy steroid (CHEBI:34386 )
Androstane and derivatives (C14210 )
C19 steroids (androgens) and derivatives (LMST02020105 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 24816252)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0005849)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0005849)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0005849)

Source

Exogenous

Exogenous (HMDB: HMDB0005849)

Food

Food (HMDB: HMDB0005849)

Animal origin

Poultry

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0005849)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0005849)

Molecular messenger

Hormone (HMDB: HMDB0005849)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0005849)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0005849)

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	0.048 g/L	ALOGPS
logP	3.1	ALOGPS
logP	2.95	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	17.5	ChemAxon
pKa (Strongest Basic)	-0.82	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.33 m³·mol⁻¹	ChemAxon
Polarizability	34.38 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]+	168.466	31661259
DarkChem	[M-H]-	163.958	31661259
DeepCCS	[M-2H]-	208.499	30932474
DeepCCS	[M+Na]+	182.845	30932474
AllCCS	[M+H]+	176.6	32859911
AllCCS	[M+H-H2O]+	173.5	32859911
AllCCS	[M+NH4]+	179.5	32859911
AllCCS	[M+Na]+	180.3	32859911
AllCCS	[M-H]-	178.7	32859911
AllCCS	[M+Na-2H]-	178.9	32859911
AllCCS	[M+HCOO]-	179.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.08 minutes	32390414
Predicted by Siyang on May 30, 2022	14.5513 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.89 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2526.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	314.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	191.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	437.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	603.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	604.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	103.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1178.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	443.9 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	1428.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	400.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	415.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	322.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	410.1 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	31.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Androstenediol	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C[C@@H](O)CC[C@]12C	2430.7	Standard polar	33892256
4-Androstenediol	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C[C@@H](O)CC[C@]12C	2530.1	Standard non polar	33892256
4-Androstenediol	[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C[C@@H](O)CC[C@]12C	2547.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Androstenediol,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@@H]2O[Si](C)(C)C	2607.0	Semi standard non polar	33892256
4-Androstenediol,1TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2O	2591.2	Semi standard non polar	33892256
4-Androstenediol,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](O[Si](C)(C)C)CC[C@@]43C)[C@@H]1CC[C@@H]2O[Si](C)(C)C	2639.6	Semi standard non polar	33892256
4-Androstenediol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CC[C@H]2[C@@H]3CCC4=C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	2867.9	Semi standard non polar	33892256
4-Androstenediol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1C=C2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1	2851.4	Semi standard non polar	33892256
4-Androstenediol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C=C2CC[C@H]3[C@@H]4CC[C@H](O[Si](C)(C)C(C)(C)C)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1	3164.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Androstenediol GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-0290000000-7d52fa98e687764c22a2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Androstenediol GC-MS (2 TMS) - 70eV, Positive	splash10-066r-3236900000-b524811a4353b5996ed1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Androstenediol 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 - 4-Androstenediol 10V, Positive-QTOF	splash10-00dl-0090000000-f4b512d07e8fa29cf8be	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Androstenediol 20V, Positive-QTOF	splash10-05fr-0290000000-7a460a768fecd3e1cea3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Androstenediol 40V, Positive-QTOF	splash10-01oy-3890000000-8177324a0ce9fde3f678	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Androstenediol 10V, Negative-QTOF	splash10-000i-0090000000-7318adfbaee2ca1f4eef	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Androstenediol 20V, Negative-QTOF	splash10-0079-0090000000-ea1dd5bd96f621180cc7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Androstenediol 40V, Negative-QTOF	splash10-0abc-1190000000-355691f711b0faad45c2	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Androstenediol 10V, Negative-QTOF	splash10-000i-0090000000-c8c452fd99c6bb4f3631	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Androstenediol 20V, Negative-QTOF	splash10-000i-0090000000-1ce9bb01eb35f26908c4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Androstenediol 40V, Negative-QTOF	splash10-000i-0090000000-f2f475ae4c62e877a9ba	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Androstenediol 10V, Positive-QTOF	splash10-0006-0090000000-9de0edc3a8b815dd7071	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Androstenediol 20V, Positive-QTOF	splash10-0abd-0940000000-d28d8b5f304b6ca1a699	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Androstenediol 40V, Positive-QTOF	splash10-0aos-2900000000-0737f10b02bfa62847f5	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24816252	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01526

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023781

KNApSAcK ID

Not Available

Chemspider ID

120071

KEGG Compound ID

C14210

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

4-Androstenediol

METLIN ID

Not Available

PubChem Compound

136297

PDB ID

Not Available

ChEBI ID

34386

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

Thuyne WV, Delbeke FT: Validation of a GC-MS screening method for anabolizing agents in aqueous nutritional supplements. J Chromatogr Sci. 2005 Jan;43(1):2-6. [PubMed:15808000 ]
Van Thuyne W, Delbeke FT: Validation of a GC-MS screening method for anabolizing agents in solid nutritional supplements. Biomed Chromatogr. 2004 Apr;18(3):155-9. [PubMed:15103700 ]
Earnest CP, Olson MA, Broeder CE, Breuel KF, Beckham SG: In vivo 4-androstene-3,17-dione and 4-androstene-3 beta,17 beta-diol supplementation in young men. Eur J Appl Physiol. 2000 Feb;81(3):229-32. [PubMed:10638382 ]
Parr MK, Geyer H, Reinhart U, Schanzer W: Analytical strategies for the detection of non-labelled anabolic androgenic steroids in nutritional supplements. Food Addit Contam. 2004 Jul;21(7):632-40. [PubMed:15370836 ]

Showing metabocard for 4-Androstenediol (HMDB0005849)

MOL for HMDB0005849 (4-Androstenediol)

3D MOL for HMDB0005849 (4-Androstenediol)

3D SDF for HMDB0005849 (4-Androstenediol)

3D-SDF for HMDB0005849 (4-Androstenediol)

PDB for HMDB0005849 (4-Androstenediol)

3D PDB for HMDB0005849 (4-Androstenediol)

SMILES for HMDB0005849 (4-Androstenediol)

INCHI for HMDB0005849 (4-Androstenediol)

Structure for HMDB0005849 (4-Androstenediol)

3D Structure for HMDB0005849 (4-Androstenediol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra