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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:48:59 UTC

HMDB ID

HMDB0000053

Secondary Accession Numbers

HMDB00053

Metabolite Identification

Common Name

Androstenedione

Description

Androstenedione is a delta-4 19-carbon steroid that is produced not only in the testis, but also in the ovary and the adrenal cortex. Depending on the tissue type, androstenedione can serve as a precursor to testosterone as well as estrone and estradiol. It is the common precursor of male and female sex hormones. Some androstenedione is also secreted into the plasma and may be converted in peripheral tissues to testosterone and estrogens. Androstenedione originates either from the conversion of dehydroepiandrosterone or from 17-hydroxyprogesterone. It is further converted to either testosterone or estrone. The production of adrenal androstenedione is governed by ACTH, while the production of gonadal androstenedione is under control by gonadotropins.

Structure

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

HMDB0000053
     RDKit          3D
Androstenedione
 47 50  0  0  0  0  0  0  0  0999 V2000
    2.9375   -0.8455    0.6588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5725    0.3198   -0.2015 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0079    1.4762    0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7619    1.0068    1.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2567    0.5805    0.2593 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2569   -0.5038   -0.6725 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7193   -0.7802   -1.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0099   -0.0478   -1.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5264    0.0854   -0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8278    0.1809   -0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3261    0.3110    1.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5119    0.0001    1.4749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4756    0.7981    2.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0387    0.9417    1.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5440    0.1071    0.8461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4277   -1.3291    1.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335   -0.0502   -1.2701 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2966   -1.0636   -2.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6708   -0.3908   -2.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7118    0.6353   -1.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5428    1.4969   -1.0168 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3968   -1.7678    0.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0335   -1.0979    0.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8281   -0.5294    1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7250    1.9739    1.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6645    2.2301   -0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9692    0.2502    2.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3589    1.8951    1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4868    1.4725   -0.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4607   -1.4327   -0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2923   -0.5666   -2.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9393   -1.8859   -1.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7663   -0.6126   -2.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9858    0.9723   -2.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4786    0.1570   -1.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6369    0.1103    3.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9222    1.7744    2.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4493    0.6227    2.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8097    2.0230    1.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6224   -2.0563    0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4318   -1.5216    1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2451   -1.5115    2.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4170    0.8540   -1.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8682   -1.1750   -3.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4146   -2.0348   -1.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4807   -1.1139   -1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8213    0.0416   -3.1623 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  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  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
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  6
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
M  END

  Mrv1652303182019402D          

 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
 9997.1658 9998.1238    0.0000 O   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
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
10001.4479 9998.9596    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5937 9999.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8792 9999.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8792 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5937 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3067 9999.3661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.3067 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0212 9998.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7357 9998.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.734610001.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.020110000.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0201 9999.7870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7346 9999.3746    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.233810000.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.449210000.6121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.4491 9999.7871    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.2337 9999.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.718610000.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.488710001.6517    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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9  2  2  0  0  0  0
 10 12  2  0  0  0  0
  7 11  1  0  0  0  0
 11  1  1  1  0  0  0
 17 11  1  0  0  0  0
 17  5  1  6  0  0  0
 14 18  1  0  0  0  0
 18  4  1  1  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  2  0  0  0  0
 18 21  1  0  0  0  0
 21  6  1  6  0  0  0
 15 20  1  0  0  0  0
 20  3  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0000053

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O2/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/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1

> <INCHI_KEY>
AEMFNILZOJDQLW-QAGGRKNESA-N

> <FORMULA>
C19H26O2

> <MOLECULAR_WEIGHT>
286.4085

> <EXACT_MASS>
286.193280076

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
33.2052257389703

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
3.9289510033333337

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.028996560003517

> <JCHEM_PKA_STRONGEST_BASIC>
-4.816491550715536

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
83.60749999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.70e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000053
     RDKit          3D
Androstenedione
 47 50  0  0  0  0  0  0  0  0999 V2000
    2.9375   -0.8455    0.6588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5725    0.3198   -0.2015 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0079    1.4762    0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7619    1.0068    1.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2567    0.5805    0.2593 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2569   -0.5038   -0.6725 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7193   -0.7802   -1.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0099   -0.0478   -1.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5264    0.0854   -0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8278    0.1809   -0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3261    0.3110    1.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5119    0.0001    1.4749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4756    0.7981    2.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0387    0.9417    1.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5440    0.1071    0.8461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4277   -1.3291    1.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335   -0.0502   -1.2701 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2966   -1.0636   -2.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6708   -0.3908   -2.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7118    0.6353   -1.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5428    1.4969   -1.0168 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3968   -1.7678    0.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0335   -1.0979    0.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8281   -0.5294    1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7250    1.9739    1.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6645    2.2301   -0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9692    0.2502    2.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3589    1.8951    1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4868    1.4725   -0.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4607   -1.4327   -0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2923   -0.5666   -2.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9393   -1.8859   -1.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7663   -0.6126   -2.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9858    0.9723   -2.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4786    0.1570   -1.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6369    0.1103    3.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9222    1.7744    2.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4493    0.6227    2.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8097    2.0230    1.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6224   -2.0563    0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4318   -1.5216    1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2451   -1.5115    2.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4170    0.8540   -1.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8682   -1.1750   -3.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4146   -2.0348   -1.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4807   -1.1139   -1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8213    0.0416   -3.1623 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  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  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
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  6
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
M  END

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  C   UNK     0    8665.3728667.030   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8661.3768663.164   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8669.3698669.361   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0    8668.0368667.030   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8666.7078664.725   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8669.3698664.725   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0    8664.0428666.253   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.7088665.483   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.7088663.943   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8664.0428663.173   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8665.3738665.483   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8665.3738663.943   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.7068663.173   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8668.0408663.943   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8668.0388668.579   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8666.7048667.809   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8666.7048666.269   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8668.0388665.499   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    8669.3728667.809   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8669.3728666.269   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   11                                                            
CONECT    2    9                                                            
CONECT    3   20                                                            
CONECT    4   18                                                            
CONECT    5   17                                                            
CONECT    6   21                                                            
CONECT    7    8   11                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10    2                                                  
CONECT   10    9   12                                                       
CONECT   11   12    7    1   17                                             
CONECT   12   11   13   10                                                  
CONECT   13   12   14                                                       
CONECT   14   13   18                                                       
CONECT   15   16   20                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   11    5                                             
CONECT   18   17   14    4   21                                             
CONECT   19   20   23   24                                                  
CONECT   20   19   21   15    3                                             
CONECT   21   20   22   18    6                                             
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    HMDB0000053
HETATM    1  C1  UNL     1       2.937  -0.846   0.659  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.573   0.320  -0.201  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.008   1.476   0.544  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.762   1.007   1.266  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.257   0.581   0.259  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.257  -0.504  -0.673  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.719  -0.780  -1.763  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.010  -0.048  -1.667  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.526   0.085  -0.297  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.828   0.181  -0.116  1.00  0.00           C  
HETATM   11  C11 UNL     1      -4.326   0.311   1.227  1.00  0.00           C  
HETATM   12  O1  UNL     1      -5.512   0.000   1.475  1.00  0.00           O  
HETATM   13  C12 UNL     1      -3.476   0.798   2.304  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.039   0.942   1.986  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.544   0.107   0.846  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.428  -1.329   1.316  1.00  0.00           C  
HETATM   17  C16 UNL     1       1.533  -0.050  -1.270  1.00  0.00           C  
HETATM   18  C17 UNL     1       2.297  -1.064  -2.045  1.00  0.00           C  
HETATM   19  C18 UNL     1       3.671  -0.391  -2.173  1.00  0.00           C  
HETATM   20  C19 UNL     1       3.712   0.635  -1.078  1.00  0.00           C  
HETATM   21  O2  UNL     1       4.543   1.497  -1.017  1.00  0.00           O  
HETATM   22  H1  UNL     1       2.397  -1.768   0.459  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.033  -1.098   0.562  1.00  0.00           H  
HETATM   24  H3  UNL     1       2.828  -0.529   1.729  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.725   1.974   1.222  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.665   2.230  -0.205  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.969   0.250   2.040  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.359   1.895   1.794  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.487   1.472  -0.377  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.461  -1.433  -0.085  1.00  0.00           H  
HETATM   31  H10 UNL     1      -0.292  -0.567  -2.787  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.939  -1.886  -1.797  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.766  -0.613  -2.281  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.986   0.972  -2.131  1.00  0.00           H  
HETATM   35  H14 UNL     1      -4.479   0.157  -1.001  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.637   0.110   3.187  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.922   1.774   2.660  1.00  0.00           H  
HETATM   38  H17 UNL     1      -1.449   0.623   2.896  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.810   2.023   1.866  1.00  0.00           H  
HETATM   40  H19 UNL     1      -1.622  -2.056   0.501  1.00  0.00           H  
HETATM   41  H20 UNL     1      -0.432  -1.522   1.791  1.00  0.00           H  
HETATM   42  H21 UNL     1      -2.245  -1.511   2.074  1.00  0.00           H  
HETATM   43  H22 UNL     1       1.417   0.854  -1.910  1.00  0.00           H  
HETATM   44  H23 UNL     1       1.868  -1.175  -3.081  1.00  0.00           H  
HETATM   45  H24 UNL     1       2.415  -2.035  -1.563  1.00  0.00           H  
HETATM   46  H25 UNL     1       4.481  -1.114  -1.979  1.00  0.00           H  
HETATM   47  H26 UNL     1       3.821   0.042  -3.162  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   12   13
CONECT   13   14   36   37
CONECT   14   15   38   39
CONECT   15   16
CONECT   16   40   41   42
CONECT   17   18   43
CONECT   18   19   44   45
CONECT   19   20   46   47
CONECT   20   21   21
END

HMDB0000053
     RDKit          3D
Androstenedione
 47 50  0  0  0  0  0  0  0  0999 V2000
    2.9375   -0.8455    0.6588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5725    0.3198   -0.2015 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0079    1.4762    0.5441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7619    1.0068    1.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2567    0.5805    0.2593 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2569   -0.5038   -0.6725 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7193   -0.7802   -1.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0099   -0.0478   -1.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5264    0.0854   -0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8278    0.1809   -0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3261    0.3110    1.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5119    0.0001    1.4749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4756    0.7981    2.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0387    0.9417    1.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5440    0.1071    0.8461 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4277   -1.3291    1.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5335   -0.0502   -1.2701 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2966   -1.0636   -2.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6708   -0.3908   -2.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7118    0.6353   -1.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5428    1.4969   -1.0168 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3968   -1.7678    0.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0335   -1.0979    0.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8281   -0.5294    1.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7250    1.9739    1.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6645    2.2301   -0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9692    0.2502    2.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3589    1.8951    1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4868    1.4725   -0.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4607   -1.4327   -0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2923   -0.5666   -2.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9393   -1.8859   -1.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7663   -0.6126   -2.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9858    0.9723   -2.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4786    0.1570   -1.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6369    0.1103    3.1870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9222    1.7744    2.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4493    0.6227    2.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8097    2.0230    1.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6224   -2.0563    0.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4318   -1.5216    1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2451   -1.5115    2.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4170    0.8540   -1.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8682   -1.1750   -3.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4146   -2.0348   -1.5631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4807   -1.1139   -1.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8213    0.0416   -3.1623 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  1
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  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
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  6
 18 44  1  0
 18 45  1  0
 19 46  1  0
 19 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Androstene-3,17-dione	ChEBI
4-ANDROSTENE-3-17-dione	ChEBI
delta(4)-Androsten-3,17-dione	ChEBI
delta(4)-Androstene-3,17-dione	ChEBI
Δ(4)-Androsten-3,17-dione	Generator
Δ(4)-Androstene-3,17-dione	Generator
(4)-Androsten-3,17-dione	HMDB
17-Ketotestosterone	HMDB
3,17-Dioxoandrost-4-ene	HMDB
4-Androsten-3,17-dione	HMDB
4-Androstenedione	HMDB
Androst-4-ene-3,17-dione	HMDB, KEGG
Androstendione	HMDB
D4-Androstene-3,17-dione	HMDB
delta4-Androstenedione	HMDB
Fecundin	HMDB
delta 4 Androstenedione	MeSH, HMDB
delta-4-Androstenedione	MeSH, HMDB
4 Androstene 3,17 dione	MeSH, HMDB
Androstenedione	HMDB
delta4-Androstene-3,17-dione	HMDB
Δ4-Androstene-3,17-dione	HMDB

Chemical Formula

C₁₉H₂₆O₂

Average Molecular Weight

286.4085

Monoisotopic Molecular Weight

286.193280076

IUPAC Name

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

Traditional Name

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

CAS Registry Number

63-05-8

SMILES

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

InChI Identifier

InChI=1S/C19H26O2/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/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1

InChI Key

AEMFNILZOJDQLW-QAGGRKNESA-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
Oxosteroid
17-oxosteroid
3-oxosteroid
3-oxo-delta-4-steroid
Delta-4-steroid
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo Delta(4)-steroid (CHEBI:16422 )
17-oxo steroid (CHEBI:16422 )
androstanoid (CHEBI:16422 )
androstane (C00280 )
C19 steroids (androgens) and derivatives (C00280 )
Androstane and derivatives (C00280 )
Androgens (C00280 )
C19 steroids (androgens) and derivatives (LMST02020007 )

Ontology

Not Available

Adipose tissue (HMDB: HMDB0000053)

Muscle tissue

Skeletal muscle (HMDB: HMDB0000053)

Epithelium

Epidermis (HMDB: HMDB0000053)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16890572)
Cerebrospinal Fluid (CSF) (PMID: 1620285)

Organ substructure

Adrenal cortex (HMDB: HMDB0000053)

Organ

Gland

Adrenal Gland (HMDB: HMDB0000053)

Cell

Fibroblasts (HMDB: HMDB0000053)

Excreta

Biofluid or Excreta

Urine (PMID: 15249323)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0000053)

Tissue substructure

Muscle (HMDB: HMDB0000053)

Source

Exogenous

Exogenous (HMDB: HMDB0000053)

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Endogenous

Endogenous (HMDB: HMDB0000053)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Androgen and Estrogen Metabolism (HMDB: HMDB0000053)
Androstenedione Metabolism (PathBank: SMP0087421)

Disease pathway

Role

Biological role

Human metabolite (HMDB: HMDB0000053)
Androgen (HMDB: HMDB0000053)

Industrial application

Pharmaceutical industry

Biomarker

Rheumatoid arthritis (MarkerDB: MDB00000026)
11-beta-hydroxylase deficiency (MarkerDB: MDB00000026)
Congenital Adrenal Insufficiency with 46,XY Sex Reversal (MarkerDB: MDB00000026)
Polycystic ovary syndrome (MarkerDB: MDB00000026)
Lipoid Congenital Adrenal Hyperplasia (MarkerDB: MDB00000026)
Congenital Adrenal Hyperplasia (MarkerDB: MDB00000026)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	170 - 173 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.058 mg/mL	Not Available
LogP	2.75	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	172.766	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000176
[M+H]+	Not Available	178.8	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000176

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.027 g/L	ALOGPS
logP	2.93	ALOGPS
logP	3.93	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	19.03	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	83.61 m³·mol⁻¹	ChemAxon
Polarizability	33.21 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	170.797	31661259
DarkChem	[M-H]-	166.657	31661259
AllCCS	[M+H]+	172.435	32859911
AllCCS	[M-H]-	178.359	32859911
DeepCCS	[M-2H]-	203.315	30932474
DeepCCS	[M+Na]+	177.56	30932474
AllCCS	[M+H]+	172.4	32859911
AllCCS	[M+H-H2O]+	169.3	32859911
AllCCS	[M+NH4]+	175.3	32859911
AllCCS	[M+Na]+	176.2	32859911
AllCCS	[M-H]-	178.4	32859911
AllCCS	[M+Na-2H]-	178.3	32859911
AllCCS	[M+HCOO]-	178.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Androstenedione	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	3342.5	Standard polar	33892256
Androstenedione	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	2547.8	Standard non polar	33892256
Androstenedione	[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	2706.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Androstenedione,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C	2739.9	Semi standard non polar	33892256
Androstenedione,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C	2460.2	Standard non polar	33892256
Androstenedione,1TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C	2902.2	Standard polar	33892256
Androstenedione,1TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CCC2=O	2630.6	Semi standard non polar	33892256
Androstenedione,1TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CCC2=O	2564.3	Standard non polar	33892256
Androstenedione,1TMS,isomer #2	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CCC2=O	2995.0	Standard polar	33892256
Androstenedione,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C	2694.2	Semi standard non polar	33892256
Androstenedione,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C	2621.7	Standard non polar	33892256
Androstenedione,2TMS,isomer #1	C[C@]12CC[C@H]3[C@@H](CCC4=CC(O[Si](C)(C)C)=CC[C@@]43C)[C@@H]1CC=C2O[Si](C)(C)C	2963.6	Standard polar	33892256
Androstenedione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	2978.8	Semi standard non polar	33892256
Androstenedione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	2622.0	Standard non polar	33892256
Androstenedione,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	3066.2	Standard polar	33892256
Androstenedione,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CCC(=O)[C@@]3(C)CC[C@@H]12	2874.7	Semi standard non polar	33892256
Androstenedione,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CCC(=O)[C@@]3(C)CC[C@@H]12	2806.7	Standard non polar	33892256
Androstenedione,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CCC(=O)[C@@]3(C)CC[C@@H]12	3159.2	Standard polar	33892256
Androstenedione,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC=C(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12	3215.9	Semi standard non polar	33892256
Androstenedione,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC=C(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12	2932.7	Standard non polar	33892256
Androstenedione,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC[C@@]2(C)C(=C1)CC[C@H]1[C@@H]3CC=C(O[Si](C)(C)C(C)(C)C)[C@@]3(C)CC[C@@H]12	3219.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Androstenedione GC-MS (Non-derivatized)	splash10-004l-5910000000-518e1ad38bcc73325b53	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Androstenedione GC-MS (Non-derivatized)	splash10-004l-5910000000-5172e05f9889ee2bfaf4	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Androstenedione EI-B (Non-derivatized)	splash10-000f-8940000000-f2892fe3b281d44164c8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Androstenedione EI-B (Non-derivatized)	splash10-007d-1960000000-167f1765b095da9d603b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Androstenedione GC-MS (Non-derivatized)	splash10-004l-5910000000-518e1ad38bcc73325b53	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Androstenedione GC-MS (Non-derivatized)	splash10-004l-5910000000-5172e05f9889ee2bfaf4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Androstenedione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0590000000-502d6b821317a01a1990	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Androstenedione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-059m-3940000000-9cb32ac21e46afb2829a	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Androstenedione Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-000i-0090000000-36e848ba16b141eef47b	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Androstenedione Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-052b-9600000000-712954fc35a84c8217de	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Androstenedione Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-052b-9300000000-f8e9aa16b4b208b69f7b	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Androstenedione EI-B (HITACHI M-80) , Positive-QTOF	splash10-000f-8940000000-e12025ea2b7808c64b9c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Androstenedione LC-ESI-ITFT , positive-QTOF	splash10-052b-6910000000-b616785c86a92f46158e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Androstenedione LC-ESI-ITFT , positive-QTOF	splash10-052b-9800000000-73e545a1eb2232d55371	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Androstenedione LC-ESI-ITFT , positive-QTOF	splash10-00kb-5790000000-735473bc44dd70e29259	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Androstenedione LC-ESI-ITFT , positive-QTOF	splash10-00kb-5790000000-114675a4457063901f2b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Androstenedione 55V, Positive-QTOF	splash10-052b-7910000000-f0d8591998137c42f717	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Androstenedione 35V, Positive-QTOF	splash10-00kb-5790000000-f47366cff1ef47253455	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Androstenedione 80V, Positive-QTOF	splash10-052b-9800000000-58ced8830fbdd255377e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Androstenedione 55V, Positive-QTOF	splash10-00kb-5790000000-4d32bf4d34aaef92de91	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Androstenedione 60V, Positive-QTOF	splash10-052b-9700000000-5a645018a15e2dd1adeb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Androstenedione 75V, Positive-QTOF	splash10-052b-9500000000-70913f3a4e21abdcf9ee	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Androstenedione 75V, Positive-QTOF	splash10-052b-9500000000-1405c9c7f6ea07c8d1e4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Androstenedione 20V, Positive-QTOF	splash10-000i-0090000000-eec15e6fd9d08b27ef07	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Androstenedione 10V, Positive-QTOF	splash10-000i-0090000000-778071650dcadc3b3069	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Androstenedione 50V, Positive-QTOF	splash10-00c3-0900000000-faf22b1b9717d889edd8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Androstenedione 30V, Positive-QTOF	splash10-00ei-0940000000-930c091a3d1471221653	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstenedione 10V, Positive-QTOF	splash10-000i-0190000000-0347db9e9578e8d5d6f2	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstenedione 20V, Positive-QTOF	splash10-05pc-0490000000-d4049441f1c172450dc3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstenedione 40V, Positive-QTOF	splash10-0uk9-4790000000-355bc0834a6465ecad30	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstenedione 10V, Negative-QTOF	splash10-000i-0090000000-887b6f223b77c683ef99	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstenedione 20V, Negative-QTOF	splash10-000i-0090000000-9dafdd780cca012f1fb3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Androstenedione 40V, Negative-QTOF	splash10-05mo-2190000000-264074b1eefeed0e3103	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Endoplasmic reticulum

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Epidermis
Fibroblasts
Kidney
Liver
Ovary
Placenta
Prostate
Skeletal Muscle
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Androgen and Estrogen Metabolism
17-Beta Hydroxysteroid Dehydrogenase III Deficiency		Not Available
Aromatase deficiency		Not Available
Androstenedione Metabolism		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000698 uM	Newborn (0-30 days old)	Female	Normal	18182448	details
Blood	Detected and Quantified	0.00244-0.00768 uM	Not Specified	Not Specified	Normal	11038205	details
Blood	Detected and Quantified	<0.0140 uM	Infant (0-1 year old)	Not Specified	Normal	19390483	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.00489 +/- 0.00196 uM	Adult (>18 years old)	Female	Normal	11826238	details
Blood	Detected and Quantified	0.0059 (0.0023-0.0094) uM	Adult (>18 years old)	Both	Normal	The Merck Manual,...	details
Blood	Detected and Quantified	0.00315 (0.00000-0.00630) uM	Adult (>18 years old)	Female	Normal	The Merck Manual,...	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22944140	details
Blood	Detected and Quantified	0.00524 +/- 0.00140 uM	Adult (>18 years old)	Female	Normal	7951484	details
Blood	Detected and Quantified	0.000978-0.00803 uM	Adult (>18 years old)	Both	Normal	Vancouver Co...	details
Blood	Detected and Quantified	0.00061 +/- 0.00022 uM	Adult (>18 years old)	Female	Normal	8478958	details
Blood	Detected and Quantified	<0.00100 uM	Not Specified	Both	Normal	8933406	details
Blood	Detected and Quantified	0.0022 (0.0010-0.0034) uM	Children (1-13 years old)	Both	Normal	Mayo Medical Labo...	details
Blood	Detected and Quantified	0.005 (0.0024-0.0070) uM	Adolescent (13-18 years old)	Female	Normal	Mayo Medical Labo...	details
Blood	Detected and Quantified	0.0040 (0.0013-0.0066) uM	Children (1-13 years old)	Female	Normal	Mayo Medical Labo...	details
Blood	Detected and Quantified	0.001 (0.00034-0.00170) uM	Children (1-13 years old)	Female	Normal	Mayo Medical Labo...	details
Blood	Detected and Quantified	0.0057 (0.00069-0.01) uM	Adult (>18 years old)	Female	Normal	Mayo Medical Labo...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00101 (0.00002-0.002) uM	Adult (>18 years old)	Not Specified	Normal	1620285	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	19010317	details
Urine	Detected and Quantified	0.00009 (0.00003-0.00077) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	23159298	details
Urine	Detected and Quantified	0.0007 (0-0.0052) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	23159298	details
Urine	Detected and Quantified	0.090 +/- 0.058 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	14643447	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.0068 +/- 0.0013 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15249323	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.000698-0.0583 uM	Newborn (0-30 days old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	27476613	details
Blood	Detected and Quantified	0.0066 +/- 0.0038 uM	Adult (>18 years old)	Female	Polycystic ovary syndrome (PCOS)	16890572	details
Blood	Detected and Quantified	0.00663 uM	Adolescent (13-18 years old)	Female	21-hydroxylase deficiency	11038205	details
Blood	Detected and Quantified	0-0.00244 uM	Adult (>18 years old)	Female	21-hydroxylase deficiency	11038205	details
Blood	Detected and Quantified	0.517 uM	Infant (0-1 year old)	Both	Congenital Adrenal Hyperplasia, due to 21-Hydroxylase-Deficiency (CAH)	19390483	details
Blood	Detected and Quantified	0.00154-0.0174 uM	Adult (>18 years old)	Female	21-hydroxylase deficiency	11826238	details
Blood	Detected and Quantified	0.00137 +/- 0.000800 uM	Newborn (0-30 days old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.000810 +/- 0.00140 uM	Children (1-13 years old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.000900-0.00420 uM	Adult (>18 years old)	Male	X-linked ichthyosis	3864567	details
Blood	Detected and Quantified	0.0017 uM	Adult (>18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.0041 uM	Adolescent (13-18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.00175-0.0770 uM	Newborn (0-30 days old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.000270-0.0480 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.000570 +/- 0.000200 uM	Children (1-13 years old)	Both	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.00103 +/- 0.00100 uM	Infant (0-1 year old)	Not Specified	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.00380 +/- 0.00100 uM	Adult (>18 years old)	Male	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected and Quantified	0.00430 +/- 0.00180 uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	12050224	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Schizophrenia	22944140	details
Blood	Detected and Quantified	<0.00003 uM	Adult (>18 years old)	Female	Lipoid Adrenal Hyperplasia	9077535	details
Blood	Detected and Quantified	<0.00003 uM	Adolescent (13-18 years old)	Female	Lipoid Adrenal Hyperplasia	9077535	details
Blood	Detected and Quantified	0.00279-0.00454 uM	Adult (>18 years old)	Female	Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency	7951484	details
Blood	Detected and Quantified	0.12 uM	Newborn (0-30 days old)	Female	11-beta-hydroxylase deficiency	8933406	details
Blood	Detected and Quantified	0.00360-0.0227 uM	Children (1-13 years old)	Both	11-beta-hydroxylase deficiency	8933406	details
Blood	Detected and Quantified	0.0090 +/- 0.0046 uM	Adult (>18 years old)	Female	Polycystic ovary syndrome (PCOS)	16890572	details
Blood	Detected and Quantified	0.0090 +/- 0.0065 uM	Adult (>18 years old)	Both	Cushing's syndrome	8384536	details
Blood	Detected and Quantified	0.0031 +/- 0.0030 uM	Adult (>18 years old)	Both	Cushing's syndrome	8384536	details
Blood	Detected and Quantified	0.000873 uM	Newborn (0-30 days old)	Female	Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete	18182448	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Ovarian cancer	19010317	details
Urine	Detected and Quantified	0.090 +/- 0.073 umol/mmol creatinine	Adult (>18 years old)	Female	Thyroid cancer	14643447	details
Urine	Detected and Quantified	0.0017 +/- 0.00034 umol/mmol creatinine	Adult (>18 years old)	Both	Rheumatoid arthritis	15249323	details
Urine	Detected and Quantified	0.0025 +/- 0.00071 umol/mmol creatinine	Adult (>18 years old)	Both	Rheumatoid arthritis	15249323	details
Urine	Detected and Quantified	0.0025 +/- 0.00042 umol/mmol creatinine	Adult (>18 years old)	Both	Systemic lupus erythematosus (SLE)	15249323	details
Urine	Detected and Quantified	0.0047 +/- 0.0005 umol/mmol creatinine	Adult (>18 years old)	Both	Systemic lupus erythematosus (SLE)	15249323	details

Associated Disorders and Diseases

Disease References

Polycystic ovary syndrome
Berria R, Gastaldelli A, Lucidi S, Belfort R, De Filippis E, Easton C, Brytzki R, Cusi K, Jovanovic L, DeFronzo R: Reduction in hematocrit level after pioglitazone treatment is correlated with decreased plasma free testosterone level, not hemodilution, in women with polycystic ovary syndrome. Clin Pharmacol Ther. 2006 Aug;80(2):105-14. Epub 2006 Jun 30. [PubMed:16890572 ]
Cushing's Syndrome
Mune T, Morita H, Yasuda K, Murayama M, Yamakita N, Miura K: Elevated plasma 19-hydroxyandrostenedione levels in Cushing's disease: stimulation with ACTH and inhibition with metyrapone. Clin Endocrinol (Oxf). 1993 Mar;38(3):265-72. [PubMed:8384536 ]
Schizophrenia
Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24. [PubMed:22944140 ]
Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency
Hattori N, Ishihara T, Moridera K, Hino M, Ikekubo K, Kurahachi H: A case of late-onset congenital adrenal hyperplasia due to partial 3 beta-hydroxysteroid dehydrogenase deficiency. Endocr J. 1993 Feb;40(1):107-9. [PubMed:7951484 ] Lutfallah C, Wang W, Mason JI, Chang YT, Haider A, Rich B, Castro-Magana M, Copeland KC, David R, Pang S: Newly proposed hormonal criteria via genotypic proof for type II 3beta-hydroxysteroid dehydrogenase deficiency. J Clin Endocrinol Metab. 2002 Jun;87(6):2611-22. doi: 10.1210/jcem.87.6.8615. [PubMed:12050224 ] Guven A, Polat S: Testicular Adrenal Rest Tumor in Two Brothers with a Novel Mutation in the 3-Beta-Hydroxysteroid Dehydrogenase-2 Gene. J Clin Res Pediatr Endocrinol. 2017 Mar 1;9(1):85-90. doi: 10.4274/jcrpe.3306. Epub 2016 Jul 29. [PubMed:27476613 ]
11-beta-Hydroxylase deficiency
Burren CP, Montalto J, Yong AB, Batch JA: CYP11 beta 1 (11-beta-hydroxylase) deficiency in congenital adrenal hyperplasia. J Paediatr Child Health. 1996 Oct;32(5):433-8. [PubMed:8933406 ]
21-Hydroxylase deficiency
Warinner SA, Zimmerman D, Thompson GB, Grant CS: Study of three patients with congenital adrenal hyperplasia treated by bilateral adrenalectomy. World J Surg. 2000 Nov;24(11):1347-52. [PubMed:11038205 ] Gmyrek GA, New MI, Sosa RE, Poppas DP: Bilateral laparoscopic adrenalectomy as a treatment for classic congenital adrenal hyperplasia attributable to 21-hydroxylase deficiency. Pediatrics. 2002 Feb;109(2):E28. [PubMed:11826238 ]
Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete
Kim CJ, Lin L, Huang N, Quigley CA, AvRuskin TW, Achermann JC, Miller WL: Severe combined adrenal and gonadal deficiency caused by novel mutations in the cholesterol side chain cleavage enzyme, P450scc. J Clin Endocrinol Metab. 2008 Mar;93(3):696-702. doi: 10.1210/jc.2007-2330. Epub 2008 Jan 8. [PubMed:18182448 ]
Congenital Adrenal Hyperplasia, due to 21-Hydroxylase-Deficiency
Schwarz E, Liu A, Randall H, Haslip C, Keune F, Murray M, Longo N, Pasquali M: Use of steroid profiling by UPLC-MS/MS as a second tier test in newborn screening for congenital adrenal hyperplasia: the Utah experience. Pediatr Res. 2009 Aug;66(2):230-5. doi: 10.1203/PDR.0b013e3181aa3777. [PubMed:19390483 ]
X-linked ichthyosis
Lykkesfeldt G, Bennett P, Lykkesfeldt AE, Micic S, Moller S, Svenstrup B: Abnormal androgen and oestrogen metabolism in men with steroid sulphatase deficiency and recessive X-linked ichthyosis. Clin Endocrinol (Oxf). 1985 Oct;23(4):385-93. [PubMed:3864567 ]
Lipoid Congenital Adrenal Hyperplasia
Fujieda K, Tajima T, Nakae J, Sageshima S, Tachibana K, Suwa S, Sugawara T, Strauss JF 3rd: Spontaneous puberty in 46,XX subjects with congenital lipoid adrenal hyperplasia. Ovarian steroidogenesis is spared to some extent despite inactivating mutations in the steroidogenic acute regulatory protein (StAR) gene. J Clin Invest. 1997 Mar 15;99(6):1265-71. doi: 10.1172/JCI119284. [PubMed:9077535 ]
Rheumatoid arthritis
Straub RH, Weidler C, Demmel B, Herrmann M, Kees F, Schmidt M, Scholmerich J, Schedel J: Renal clearance and daily excretion of cortisol and adrenal androgens in patients with rheumatoid arthritis and systemic lupus erythematosus. Ann Rheum Dis. 2004 Aug;63(8):961-8. [PubMed:15249323 ]
Thyroid cancer
Kim KM, Jung BH, Lho DS, Chung WY, Paeng KJ, Chung BC: Alteration of urinary profiles of endogenous steroids and polyunsaturated fatty acids in thyroid cancer. Cancer Lett. 2003 Dec 30;202(2):173-9. [PubMed:14643447 ]
Ovarian cancer
Woo HM, Kim KM, Choi MH, Jung BH, Lee J, Kong G, Nam SJ, Kim S, Bai SW, Chung BC: Mass spectrometry based metabolomic approaches in urinary biomarker study of women's cancers. Clin Chim Acta. 2009 Feb;400(1-2):63-9. doi: 10.1016/j.cca.2008.10.014. Epub 2008 Oct 30. [PubMed:19010317 ]

Associated OMIM IDs

184700 (Polycystic ovary syndrome)
181500 (Schizophrenia)
201810 (Adrenal hyperplasia, congenital, due to 3-beta-hydroxysteroid dehydrogenase 2 deficiency)
202010 (11-beta-Hydroxylase deficiency)
201910 (21-Hydroxylase deficiency)
613743 (Adrenal insufficiency, congenital, with 46,XY sex reversal, partial or complete)
201910 (Congenital Adrenal Hyperplasia, due to 21-Hydroxylase-Deficiency)
308100 (X-linked ichthyosis)
201710 (Lipoid Congenital Adrenal Hyperplasia)
180300 (Rheumatoid arthritis)
167000 (Ovarian cancer)

External Links

DrugBank ID

DB01536

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16422

Food Biomarker Ontology

Not Available

VMH ID

ANDRSTNDN

MarkerDB ID

MDB00000026

Good Scents ID

Not Available

References

Synthesis Reference

Egorova, Olga V.; Gulevskaya, Seraphima A.; Puntus, Irina F.; Filonov, Andrey E.; Donova, Marina V. Production of androstenedione using mutants of Mycobacterium sp. Journal of Chemical Technology and Biotechnology (2002), 77(2), 141-147.

Material Safety Data Sheet (MSDS)

Not Available

General References

Berkovitz GD, Guerami A, Brown TR, MacDonald PC, Migeon CJ: Familial gynecomastia with increased extraglandular aromatization of plasma carbon19-steroids. J Clin Invest. 1985 Jun;75(6):1763-9. [PubMed:3924954 ]
Cutolo M, Sulli A, Capellino S, Villaggio B, Montagna P, Pizzorni C, Paolino S, Seriolo B, Felli L, Straub RH: Anti-TNF and sex hormones. Ann N Y Acad Sci. 2006 Jun;1069:391-400. [PubMed:16855166 ]
Schwarz S, Pohl P: Steroid hormones and steroid hormone binding globulins in cerebrospinal fluid studied in individuals with intact and with disturbed blood-cerebrospinal fluid barrier. Neuroendocrinology. 1992 Feb;55(2):174-82. [PubMed:1620285 ]
van Vloten WA, van Haselen CW, van Zuuren EJ, Gerlinger C, Heithecker R: The effect of 2 combined oral Contraceptives containing either drospirenone or cyproterone acetate on acne and seborrhea. Cutis. 2002 Apr;69(4 Suppl):2-15. [PubMed:12096825 ]
Jasuja R, Ramaraj P, Mac RP, Singh AB, Storer TW, Artaza J, Miller A, Singh R, Taylor WE, Lee ML, Davidson T, Sinha-Hikim I, Gonzalez-Cadavid N, Bhasin S: Delta-4-androstene-3,17-dione binds androgen receptor, promotes myogenesis in vitro, and increases serum testosterone levels, fat-free mass, and muscle strength in hypogonadal men. J Clin Endocrinol Metab. 2005 Feb;90(2):855-63. Epub 2004 Nov 2. [PubMed:15522925 ]
Egloff M, Savoure N, Tardivel-Lacombe J, Massart C, Nicol M, Degrelle H: Influence of sex hormone binding globulin and serum albumin on the conversion of androstenedione to testosterone by human erythrocytes. Acta Endocrinol (Copenh). 1981 Jan;96(1):136-40. [PubMed:7192922 ]
Zarrilli S, Lombardi G, Paesano L, Di Somma C, Colao A, Mirone V, De Rosa M: Hormonal and seminal evaluation of Leydig cell tumour patients before and after orchiectomy. Andrologia. 2000 May;32(3):147-54. [PubMed:10863969 ]
Heikkila R, Aho K, Heliovaara M, Hakama M, Marniemi J, Reunanen A, Knekt P: Serum testosterone and sex hormone-binding globulin concentrations and the risk of prostate carcinoma: a longitudinal study. Cancer. 1999 Jul 15;86(2):312-5. [PubMed:10421267 ]
Schlaghecke R, Kley HK, Kruskemper HL: The measurement of 4-androstene-3, 11, 17-trione (11-oxo-androstenedione) by radioimmunoassay in human plasma. Steroids. 1984 Jul;44(1):23-33. [PubMed:6100340 ]
King DS, Sharp RL, Vukovich MD, Brown GA, Reifenrath TA, Uhl NL, Parsons KA: Effect of oral androstenedione on serum testosterone and adaptations to resistance training in young men: a randomized controlled trial. JAMA. 1999 Jun 2;281(21):2020-8. [PubMed:10359391 ]
Johansson A, Henriksson A, Olofsson BO, Olsson T: Adrenal steroid dysregulation in dystrophia myotonica. J Intern Med. 1999 Apr;245(4):345-51. [PubMed:10356596 ]
Atkinson G, Campbell DJ, Cawood ML, Oakey RE: Steroids in human intrauterine fluids of early pregnancy. Clin Endocrinol (Oxf). 1996 Apr;44(4):435-40. [PubMed:8706310 ]
Zarrilli S, Paesano L, Mirone V, Finelli L, De Rosa M: [Evaluation of seminal and hormonal parameters in idiopathic varicocele before and after surgical intervention]. Chir Ital. 1998 Mar-Aug;50(2-4):21-8. [PubMed:11762080 ]
Berria R, Gastaldelli A, Lucidi S, Belfort R, De Filippis E, Easton C, Brytzki R, Cusi K, Jovanovic L, DeFronzo R: Reduction in hematocrit level after pioglitazone treatment is correlated with decreased plasma free testosterone level, not hemodilution, in women with polycystic ovary syndrome. Clin Pharmacol Ther. 2006 Aug;80(2):105-14. Epub 2006 Jun 30. [PubMed:16890572 ]
Thomson S, Wallace AM, Cook B: A 125I-radioimmunoassay for measuring androstenedione in serum and in blood-spot samples from neonates. Clin Chem. 1989 Aug;35(8):1706-12. [PubMed:2758640 ]
Riikonen RS: How do cryptogenic and symptomatic infantile spasms differ? Review of biochemical studies in Finnish patients. J Child Neurol. 1996 Sep;11(5):383-8. [PubMed:8877606 ]
Azurmendi A, Braza F, Sorozabal A, Garcia A, Braza P, Carreras MR, Munoz JM, Cardas J, Sanchez-Martin JR: Cognitive abilities, androgen levels, and body mass index in 5-year-old children. Horm Behav. 2005 Aug;48(2):187-95. [PubMed:15878571 ]
Schairer C, Hill D, Sturgeon SR, Fears T, Mies C, Ziegler RG, Hoover RN, Sherman ME: Serum concentrations of estrogens, sex hormone binding globulin, and androgens and risk of breast hyperplasia in postmenopausal women. Cancer Epidemiol Biomarkers Prev. 2005 Jul;14(7):1660-5. [PubMed:16030098 ]
Feldman PS, Kovacs K, Horvath E, Adelson GL: Malignant Leydig cell tumor: clinical, histologic and electron microscopic features. Cancer. 1982 Feb 15;49(4):714-21. [PubMed:7055782 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Only showing the first 10 proteins. There are 43 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Aldo-keto reductase family 1 member C3

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone.
Gene Name:: AKR1C3
Uniprot ID:: P42330
Molecular weight:: 36866.91

Reactions

Testosterone + NAD → Androstenedione + NADH	details
Testosterone + NADP → Androstenedione + NADPH	details

References

Amin SA, Huang CC, Reierstad S, Lin Z, Arbieva Z, Wiley E, Saborian H, Haynes B, Cotterill H, Dowsett M, Bulun SE: Paracrine-stimulated gene expression profile favors estradiol production in breast tumors. Mol Cell Endocrinol. 2006 Jul 11;253(1-2):44-55. Epub 2006 Jun 2. [PubMed:16735089 ]

Enzyme Details

2. Cytochrome P450 11B1, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
Gene Name:: CYP11B1
Uniprot ID:: P15538
Molecular weight:: 57572.44

Reactions

Reduced adrenal ferredoxin + Androstenedione + Oxygen → 11b-Hydroxyandrost-4-ene-3,17-dione + Oxidized adrenal ferredoxin + Water	details

Enzyme Details

3. Estradiol 17-beta-dehydrogenase 2

General function:: Involved in oxidoreductase activity
Specific function:: Capable of catalyzing the interconversion of testosterone and androstenedione, as well as estradiol and estrone. Also has 20-alpha-HSD activity. Uses NADH while EDH17B3 uses NADPH.
Gene Name:: HSD17B2
Uniprot ID:: P37059
Molecular weight:: 42784.75

Reactions

Testosterone + NAD → Androstenedione + NADH	details
Testosterone + NAD → Androstenedione + NADH + Hydrogen Ion	details

References

Su EJ, Cheng YH, Chatterton RT, Lin ZH, Yin P, Reierstad S, Innes J, Bulun SE: Regulation of 17-beta hydroxysteroid dehydrogenase type 2 in human placental endothelial cells. Biol Reprod. 2007 Sep;77(3):517-25. Epub 2007 May 30. [PubMed:17538076 ]

Enzyme Details

4. Estradiol 17-beta-dehydrogenase 8

General function:: Involved in oxidoreductase activity
Specific function:: NAD-dependent 17-beta-hydroxysteroid dehydrogenase with highest activity towards estradiol. Has very low activity towards testosterone. The heteroteramer with CBR4 has NADH-dependent 3-ketoacyl-acyl carrier protein reductase activity. May play a role in biosynthesis of fatty acids in mitochondria.
Gene Name:: HSD17B8
Uniprot ID:: Q92506
Molecular weight:: 26973.56

Reactions

Testosterone + NAD → Androstenedione + NADH	details
Testosterone + NAD → Androstenedione + NADH + Hydrogen Ion	details

Enzyme Details

5. 3-oxo-5-beta-steroid 4-dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:: AKR1D1
Uniprot ID:: P51857
Molecular weight:: 32889.38

Reactions

Etiocholanedione + NADP → Hydrogen Ion + NADPH + Androstenedione	details

Enzyme Details

6. 3-oxo-5-alpha-steroid 4-dehydrogenase 2

General function:: Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase activity
Specific function:: Converts testosterone (T) into 5-alpha-dihydrotestosterone (DHT) and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:: SRD5A2
Uniprot ID:: P31213
Molecular weight:: 28407.035

Reactions

Androstanedione + Acceptor → Androstenedione + Reduced acceptor	details

Enzyme Details

7. 3-oxo-5-alpha-steroid 4-dehydrogenase 1

General function:: Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase activity
Specific function:: Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:: SRD5A1
Uniprot ID:: P18405
Molecular weight:: 29458.18

Reactions

Androstanedione + Acceptor → Androstenedione + Reduced acceptor	details

Enzyme Details

8. Testosterone 17-beta-dehydrogenase 3

General function:: Involved in oxidoreductase activity
Specific function:: Favors the reduction of androstenedione to testosterone. Uses NADPH while the two other EDH17B enzymes use NADH.
Gene Name:: HSD17B3
Uniprot ID:: P37058
Molecular weight:: 34515.345

Reactions

Testosterone + NADP → Androstenedione + NADPH	details
Testosterone + NADP → Androstenedione + NADPH + Hydrogen Ion	details

References

Lindqvist A, Hughes IA, Andersson S: Substitution mutation C268Y causes 17 beta-hydroxysteroid dehydrogenase 3 deficiency. J Clin Endocrinol Metab. 2001 Feb;86(2):921-3. [PubMed:11158067 ]

Enzyme Details

9. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Enzyme Details

10. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

Only showing the first 10 proteins. There are 43 proteins in total.

Show all enzymes and transporters

Showing metabocard for Androstenedione (HMDB0000053)

MOL for HMDB0000053 (Androstenedione)

3D MOL for HMDB0000053 (Androstenedione)

3D SDF for HMDB0000053 (Androstenedione)

3D-SDF for HMDB0000053 (Androstenedione)

PDB for HMDB0000053 (Androstenedione)

3D PDB for HMDB0000053 (Androstenedione)

SMILES for HMDB0000053 (Androstenedione)

INCHI for HMDB0000053 (Androstenedione)

Structure for HMDB0000053 (Androstenedione)

3D Structure for HMDB0000053 (Androstenedione)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

References

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References

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