NP-MRD: Showing NP-Card for Androstanedione (NP0001267)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-06-29 00:46:37 UTC

NP-MRD ID

NP0001267

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Androstanedione

Description

Androstanedione belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Thus, androstanedione is considered to be a steroid lipid molecule. Androstanedione is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.

Structure

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

1561
  Mrv1652305271900032D          

 25 28  0  0  1  0            999 V2000
    7.1353    1.7956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -1.7578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697   -0.0648    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3842   -0.4772    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9191   -0.4829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0985   -0.0648    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0985    0.7601    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9125   -1.3421    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6697    0.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3974   -1.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3842    1.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6566   -1.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8790   -0.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1546   -0.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8790    1.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9254    0.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1409   -1.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3604    0.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0985    1.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3726   -0.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3657   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2413    0.2652    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9581   -0.8028    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1683   -0.7210    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9150   -2.0020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  2  0  0  0  0
  2 21  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  9  1  0  0  0  0
  3 22  1  6  0  0  0
  4  6  1  0  0  0  0
  4 10  1  0  0  0  0
  4 23  1  1  0  0  0
  5  8  1  0  0  0  0
  5 14  1  0  0  0  0
  5 16  1  1  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
  6 24  1  6  0  0  0
  7 11  1  0  0  0  0
  7 15  1  0  0  0  0
  7 19  1  1  0  0  0
  8 12  1  0  0  0  0
  8 17  1  0  0  0  0
  8 25  1  6  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 13 18  1  0  0  0  0
 14 20  1  0  0  0  0
 15 18  1  0  0  0  0
 17 21  1  0  0  0  0
 20 21  1  0  0  0  0
M  END

HMDB0000899
     RDKit          3D
Androstanedione
 49 52  0  0  0  0  0  0  0  0999 V2000
    2.7485   -0.6092   -1.5586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6175   -0.7646   -0.0668 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8505   -1.9608    0.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3948   -1.8210    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2109   -0.5271    0.5011 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6336    0.6518    0.0142 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0828    1.9601    0.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3825    2.1096    0.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1835    0.8741    0.6083 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5922    1.1470    0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3946   -0.0747   -0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6152    0.0396    0.0333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8391   -1.4166   -0.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4475   -1.5325    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819   -0.3500   -0.0637 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5924   -0.0836   -1.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9857    0.4525    0.5870 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9781    1.5149    0.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3135    0.7971    0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9804   -0.6707    0.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7003   -1.5294    0.9692 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1704   -1.4367   -2.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4899    0.3844   -1.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8153   -0.7905   -1.8847 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2212   -2.8340   -0.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0972   -2.2317    1.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2250   -1.9557   -1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1283   -2.6407    0.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2922   -0.4706    1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6402    0.5712   -1.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5496    2.7551   -0.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4819    2.1930    1.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6985    2.8542    1.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7367    2.5841   -0.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2806    0.6187    1.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0954    1.7988    0.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5936    1.7037   -0.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8460   -1.7244   -1.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4520   -2.2067    0.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0254   -2.4899   -0.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5329   -1.5368    1.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6807   -0.0903   -1.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2618    0.9631   -1.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0372   -0.8160   -2.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9108    0.2299    1.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9737    2.2925    1.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8505    2.0202   -0.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9021    1.1338    1.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8877    0.9148   -0.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  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  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 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  1
  6 30  1  6
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  1
 10 36  1  0
 10 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  1
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
M  END

1561
  Mrv1652305271900032D          

 25 28  0  0  1  0            999 V2000
    7.1353    1.7956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498   -1.7578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6697   -0.0648    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3842   -0.4772    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9191   -0.4829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0985   -0.0648    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0985    0.7601    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9125   -1.3421    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6697    0.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3974   -1.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3842    1.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6566   -1.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8790   -0.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1546   -0.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8790    1.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9254    0.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1409   -1.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3604    0.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0985    1.5850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3726   -0.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3657   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2413    0.2652    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9581   -0.8028    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1683   -0.7210    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9150   -2.0020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  2  0  0  0  0
  2 21  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  9  1  0  0  0  0
  3 22  1  6  0  0  0
  4  6  1  0  0  0  0
  4 10  1  0  0  0  0
  4 23  1  1  0  0  0
  5  8  1  0  0  0  0
  5 14  1  0  0  0  0
  5 16  1  1  0  0  0
  6  7  1  0  0  0  0
  6 13  1  0  0  0  0
  6 24  1  6  0  0  0
  7 11  1  0  0  0  0
  7 15  1  0  0  0  0
  7 19  1  1  0  0  0
  8 12  1  0  0  0  0
  8 17  1  0  0  0  0
  8 25  1  6  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 13 18  1  0  0  0  0
 14 20  1  0  0  0  0
 15 18  1  0  0  0  0
 17 21  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001267

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O2/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/h12,14-16H,3-11H2,1-2H3/t12-,14-,15-,16-,18-,19-/m0/s1

> <INCHI_KEY>
RAJWOBJTTGJROA-WZNAKSSCSA-N

> <FORMULA>
C19H28O2

> <MOLECULAR_WEIGHT>
288.4244

> <EXACT_MASS>
288.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
33.826012044347785

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
3.9747853383333336

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.776207883092308

> <JCHEM_PKA_STRONGEST_BASIC>
-7.108868634299542

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
82.7808

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.39e-03 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0000899
     RDKit          3D
Androstanedione
 49 52  0  0  0  0  0  0  0  0999 V2000
    2.7485   -0.6092   -1.5586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6175   -0.7646   -0.0668 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8505   -1.9608    0.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3948   -1.8210    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2109   -0.5271    0.5011 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6336    0.6518    0.0142 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0828    1.9601    0.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3825    2.1096    0.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1835    0.8741    0.6083 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5922    1.1470    0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3946   -0.0747   -0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6152    0.0396    0.0333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8391   -1.4166   -0.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4475   -1.5325    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819   -0.3500   -0.0637 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5924   -0.0836   -1.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9857    0.4525    0.5870 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9781    1.5149    0.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3135    0.7971    0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9804   -0.6707    0.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7003   -1.5294    0.9692 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1704   -1.4367   -2.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4899    0.3844   -1.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8153   -0.7905   -1.8847 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2212   -2.8340   -0.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0972   -2.2317    1.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2250   -1.9557   -1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1283   -2.6407    0.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2922   -0.4706    1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6402    0.5712   -1.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5496    2.7551   -0.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4819    2.1930    1.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6985    2.8542    1.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7367    2.5841   -0.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2806    0.6187    1.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0954    1.7988    0.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5936    1.7037   -0.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8460   -1.7244   -1.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4520   -2.2067    0.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0254   -2.4899   -0.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5329   -1.5368    1.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6807   -0.0903   -1.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2618    0.9631   -1.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0372   -0.8160   -2.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9108    0.2299    1.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9737    2.2925    1.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8505    2.0202   -0.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9021    1.1338    1.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8877    0.9148   -0.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  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  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 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  1
  6 30  1  6
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  1
 10 36  1  0
 10 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  1
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1561                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      13.319   3.352   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.080  -3.281   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.717  -0.121   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.051  -0.891   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.316  -0.901   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.384  -0.121   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.384   1.419   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.303  -2.505   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.717   1.419   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.075  -2.494   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.051   2.189   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.692  -3.307   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.841  -0.590   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.889  -0.033   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.841   1.888   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.327   0.638   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.863  -3.352   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.739   0.649   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.384   2.959   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.429  -0.846   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.416  -2.516   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       9.784   0.495   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      11.122  -1.499   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      11.514  -1.346   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       7.308  -3.737   0.000  0.00  0.00           H+0
CONECT    1   15                                                            
CONECT    2   21                                                            
CONECT    3    4    5    9   22                                             
CONECT    4    3    6   10   23                                             
CONECT    5    3    8   14   16                                             
CONECT    6    4    7   13   24                                             
CONECT    7    6   11   15   19                                             
CONECT    8    5   12   17   25                                             
CONECT    9    3   11                                                       
CONECT   10    4   12                                                       
CONECT   11    7    9                                                       
CONECT   12    8   10                                                       
CONECT   13    6   18                                                       
CONECT   14    5   20                                                       
CONECT   15    1    7   18                                                  
CONECT   16    5                                                            
CONECT   17    8   21                                                       
CONECT   18   13   15                                                       
CONECT   19    7                                                            
CONECT   20   14   21                                                       
CONECT   21    2   17   20                                                  
CONECT   22    3                                                            
CONECT   23    4                                                            
CONECT   24    6                                                            
CONECT   25    8                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0000899
HETATM    1  C1  UNL     1       2.749  -0.609  -1.559  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.618  -0.765  -0.067  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.850  -1.961   0.353  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.395  -1.821   0.084  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.211  -0.527   0.501  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.634   0.652   0.014  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.083   1.960   0.462  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.383   2.110   0.382  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.183   0.874   0.608  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.592   1.147   0.117  1.00  0.00           C  
HETATM   11  C11 UNL     1      -4.395  -0.075  -0.032  1.00  0.00           C  
HETATM   12  O1  UNL     1      -5.615   0.040   0.033  1.00  0.00           O  
HETATM   13  C12 UNL     1      -3.839  -1.417  -0.253  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.448  -1.532   0.298  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.582  -0.350  -0.064  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.592  -0.084  -1.550  1.00  0.00           C  
HETATM   17  C16 UNL     1       1.986   0.453   0.587  1.00  0.00           C  
HETATM   18  C17 UNL     1       2.978   1.515   0.330  1.00  0.00           C  
HETATM   19  C18 UNL     1       4.313   0.797   0.422  1.00  0.00           C  
HETATM   20  C19 UNL     1       3.980  -0.671   0.515  1.00  0.00           C  
HETATM   21  O2  UNL     1       4.700  -1.529   0.969  1.00  0.00           O  
HETATM   22  H1  UNL     1       2.170  -1.437  -2.039  1.00  0.00           H  
HETATM   23  H2  UNL     1       2.490   0.384  -1.933  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.815  -0.791  -1.885  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.221  -2.834  -0.260  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.097  -2.232   1.402  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.225  -1.956  -1.011  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.128  -2.641   0.659  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.292  -0.471   1.610  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.640   0.571  -1.093  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.550   2.755  -0.189  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.482   2.193   1.490  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.699   2.854   1.172  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.737   2.584  -0.579  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.281   0.619   1.702  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.095   1.799   0.865  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.594   1.704  -0.854  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.846  -1.724  -1.322  1.00  0.00           H  
HETATM   39  H18 UNL     1      -4.452  -2.207   0.272  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.025  -2.490  -0.075  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.533  -1.537   1.413  1.00  0.00           H  
HETATM   42  H21 UNL     1      -2.681  -0.090  -1.852  1.00  0.00           H  
HETATM   43  H22 UNL     1      -1.262   0.963  -1.723  1.00  0.00           H  
HETATM   44  H23 UNL     1      -1.037  -0.816  -2.138  1.00  0.00           H  
HETATM   45  H24 UNL     1       1.911   0.230   1.661  1.00  0.00           H  
HETATM   46  H25 UNL     1       2.974   2.293   1.134  1.00  0.00           H  
HETATM   47  H26 UNL     1       2.850   2.020  -0.648  1.00  0.00           H  
HETATM   48  H27 UNL     1       4.902   1.134   1.296  1.00  0.00           H  
HETATM   49  H28 UNL     1       4.888   0.915  -0.514  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   15   35
CONECT   10   11   36   37
CONECT   11   12   12   13
CONECT   13   14   38   39
CONECT   14   15   40   41
CONECT   15   16
CONECT   16   42   43   44
CONECT   17   18   45
CONECT   18   19   46   47
CONECT   19   20   48   49
CONECT   20   21   21
END

HMDB0000899
     RDKit          3D
Androstanedione
 49 52  0  0  0  0  0  0  0  0999 V2000
    2.7485   -0.6092   -1.5586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6175   -0.7646   -0.0668 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8505   -1.9608    0.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3948   -1.8210    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2109   -0.5271    0.5011 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6336    0.6518    0.0142 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0828    1.9601    0.4624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3825    2.1096    0.3822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1835    0.8741    0.6083 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5922    1.1470    0.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3946   -0.0747   -0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6152    0.0396    0.0333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8391   -1.4166   -0.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4475   -1.5325    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819   -0.3500   -0.0637 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5924   -0.0836   -1.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9857    0.4525    0.5870 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9781    1.5149    0.3298 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3135    0.7971    0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9804   -0.6707    0.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7003   -1.5294    0.9692 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1704   -1.4367   -2.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4899    0.3844   -1.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8153   -0.7905   -1.8847 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2212   -2.8340   -0.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0972   -2.2317    1.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2250   -1.9557   -1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1283   -2.6407    0.6594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2922   -0.4706    1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6402    0.5712   -1.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5496    2.7551   -0.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4819    2.1930    1.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6985    2.8542    1.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7367    2.5841   -0.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2806    0.6187    1.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0954    1.7988    0.8648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5936    1.7037   -0.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8460   -1.7244   -1.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4520   -2.2067    0.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0254   -2.4899   -0.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5329   -1.5368    1.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6807   -0.0903   -1.8520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2618    0.9631   -1.7229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0372   -0.8160   -2.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9108    0.2299    1.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9737    2.2925    1.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8505    2.0202   -0.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9021    1.1338    1.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8877    0.9148   -0.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  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  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
  6 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 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  1
  6 30  1  6
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  1
 10 36  1  0
 10 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  1
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
M  END

View in JSmol

Synonyms

Value	Source
5alpha-Androstan-3,17-dione	ChEBI
5a-Androstan-3,17-dione	Generator
5Α-androstan-3,17-dione	Generator
(5a)-Androstane-3,17-dione	HMDB
5-alpha-Androstane-3,17-dione	HMDB
5a-Androsta-3,17-dione	HMDB
5a-Androstane-3, 17-dione	HMDB
5a-Androstane-3,17-dione	HMDB
5a-Androstanedione	HMDB
5alpha-Androstane-3,17-dione	HMDB
Androstane-3,17-dione	HMDB
Androstane-3,7-dione	HMDB
Androstane-3,17-dione, (2-3(H)-labeled, (2beta,5beta))-isomer	HMDB
Androstane-3,17-dione, (4-(3)H-labeled, (4alpha,5beta))-isomer	HMDB
Androstane-3,17-dione, (2-3(H)-labeled, (2alpha,5beta))-isomer	HMDB
Androstane-3,17-dione, (4-(3)H-labeled, (4beta,5beta))-isomer	HMDB
Androstane-3,17-dione, (5beta)-isomer	HMDB
3,17-Dioxy-5 alpha-androstane	HMDB
5 alpha-Androstanedione	HMDB
5 beta-Androstane-3,17-dione	HMDB
5 alpha-Androstane-3,17-dione	HMDB
Androstane-3,17-dione, (5alpha)-isomer	HMDB

Chemical Formula

C₁₉H₂₈O₂

Average Mass

288.4244 Da

Monoisotopic Mass

288.20893 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

846-46-8

SMILES

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

InChI Identifier

InChI=1S/C19H28O2/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/h12,14-16H,3-11H2,1-2H3/t12-,14-,15-,16-,18-,19-/m0/s1

InChI Key

RAJWOBJTTGJROA-WZNAKSSCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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
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
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
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
3-oxo-5-alpha-steroid
Oxosteroid
17-oxosteroid
3-oxosteroid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

androstane-3,17-dione (CHEBI:15994 )
C19 steroids (androgens) and derivatives (LMST02020085 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	133.5 - 134.0 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0074 g/L	ALOGPS
logP	3.4	ALOGPS
logP	3.97	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	19.78	ChemAxon
pKa (Strongest Basic)	-7.1	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	82.78 m³·mol⁻¹	ChemAxon
Polarizability	33.83 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

HMDB0000899

DrugBank ID

DB01561

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022307

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15994

Good Scents ID

Not Available

References

General References

Karlsson T, Vahlquist A, Kedishvili N, Torma H: 13-cis-retinoic acid competitively inhibits 3 alpha-hydroxysteroid oxidation by retinol dehydrogenase RoDH-4: a mechanism for its anti-androgenic effects in sebaceous glands? Biochem Biophys Res Commun. 2003 Mar 28;303(1):273-8. [PubMed:12646198 ]
Gonzalez-Santos MR, Gaja-Rodriguez OV, Alonso-Uriarte R, Sojo-Aranda I, Cortes-Gallegos V: Sleep deprivation and adaptive hormonal responses of healthy men. Arch Androl. 1989;22(3):203-7. [PubMed:2757458 ]
Sharifi N: The 5alpha-androstanedione pathway to dihydrotestosterone in castration-resistant prostate cancer. J Investig Med. 2012 Feb;60(2):504-7. doi: 10.2310/JIM.0b013e31823874a4. [PubMed:22064602 ]
Milewich L, Kaimal V, Shaw CB, Johnson AR: Androstenedione metabolism in human lung fibroblasts. J Steroid Biochem. 1986 Apr;24(4):893-7. doi: 10.1016/0022-4731(86)90451-6. [PubMed:3702464 ]
Howell S, Song W, Pastuszak A, Khera M: Differential Gene Expression in Post-Finasteride Syndrome Patients. J Sex Med. 2021 Sep;18(9):1479-1490. doi: 10.1016/j.jsxm.2021.05.009. Epub 2021 Jul 8. [PubMed:34247957 ]

Showing NP-Card for Androstanedione (NP0001267)

MOL for NP0001267 (Androstanedione)

3D MOL for NP0001267 (Androstanedione)

3D SDF for NP0001267 (Androstanedione)

3D-SDF for NP0001267 (Androstanedione)

PDB for NP0001267 (Androstanedione)

3D PDB for NP0001267 (Androstanedione)

SMILES for NP0001267 (Androstanedione)

INCHI for NP0001267 (Androstanedione)

Structure for NP0001267 (Androstanedione)

3D Structure for NP0001267 (Androstanedione)