NP-MRD: Showing NP-Card for Androstenedione (NP0000425)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-10-07 20:39:01 UTC

NP-MRD ID

NP0000425

Secondary Accession Numbers

None

Natural Product 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 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>
NP0000425

> <DATABASE_NAME>
NP-MRD

> <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

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
Androst-4-ene-3,17-dione	Kegg
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
Androstendione	HMDB
D4-Androstene-3,17-dione	HMDB
delta4-Androstenedione	HMDB
Fecundin	HMDB
delta 4 Androstenedione	HMDB
delta-4-Androstenedione	HMDB
4 Androstene 3,17 dione	HMDB
delta4-Androstene-3,17-dione	HMDB
Δ4-androstene-3,17-dione	HMDB
Androstenedione	HMDB

Chemical Formula

C₁₉H₂₆O₂

Average Mass

286.4085 Da

Monoisotopic Mass

286.19328 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Varshavi.d26			2021-10-08	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Curvularia lunata	LOTUS Database	35616633
Daphnia magna	LOTUS Database	35616633
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Locusta migratoria	LOTUS Database	35616633
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Pinus sylvestris	Plant	KNApSAcK
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Vitex agnus-castus	LOTUS Database	35616633

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 )

Physical Properties

State

Solid

Experimental 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 CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted 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

External Links

HMDB ID

HMDB0000053

DrugBank ID

DB01536

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing NP-Card for Androstenedione (NP0000425)

MOL for NP0000425 (Androstenedione)

3D MOL for NP0000425 (Androstenedione)

3D SDF for NP0000425 (Androstenedione)

3D-SDF for NP0000425 (Androstenedione)

PDB for NP0000425 (Androstenedione)

3D PDB for NP0000425 (Androstenedione)

SMILES for NP0000425 (Androstenedione)

INCHI for NP0000425 (Androstenedione)

Structure for NP0000425 (Androstenedione)

3D Structure for NP0000425 (Androstenedione)