NP-MRD: Showing NP-Card for Adrenosterone (NP0002772)

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Record Information

Version

2.0

Created at

2020-11-23 19:40:03 UTC

Updated at

2021-08-12 19:52:06 UTC

NP-MRD ID

NP0002772

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Adrenosterone

Provided By

BMRB

Description

Adrenosterone, also known as 11-oxo or NSC 12166, 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. In humans, adrenosterone is involved in the androstenedione metabolism pathway. Adrenosterone is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Adrenosterone is found in Mus musculus. It was first documented in 1953 (PMID: 13061495). Based on a literature review a significant number of articles have been published on Adrenosterone (PMID: 17984079) (PMID: 10469997) (PMID: 12434991) (PMID: 12460593).

Structure

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


     RDKit          2D

 46 49  0  0  0  0  0  0  0  0999 V2000
   -3.1374    2.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4681    0.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5140    1.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0345    1.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7714    2.8438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4907    0.1737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4634   -0.9837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0618   -2.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5413   -2.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4954   -1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9748   -1.7265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9290   -0.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4084   -0.8168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4037    0.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9243    1.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9701   -0.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4449    1.3311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9428   -0.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1168   -1.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3676   -0.8418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9667    0.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5353    1.1623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7949    2.6806    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8888    1.7453    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5001   -3.1316    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5683    2.3251    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0948    2.7897    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7471   -2.2232    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5188   -3.0455    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0709   -2.8272    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0603   -2.1723    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7632   -0.2920    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
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  9 10  1  0
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 20 45  1  6
 20 46  1  0
M  END

NP0002772
     RDKit          3D

 46 49  0  0  0  0  0  0  0  0999 V2000
   -2.6632   -1.6515   -0.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5172   -0.3277   -0.6972 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7173   -0.3942   -1.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2609   -0.2672   -1.7349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4775   -0.7391   -2.5972 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3687    0.3706   -0.5722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5618    0.2453    0.6339 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0138    1.0133    1.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2421    0.2136    2.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1520    0.0448    1.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4706    0.0392    1.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4540   -0.1205    0.3388 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6298   -0.4547    0.6255 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1180    0.1000   -1.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7158    0.6730   -1.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7459   -0.1203   -0.2817 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9264   -1.5867   -0.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8815    0.7287    0.1820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9115    0.9463    1.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1992    0.9821    0.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8682    0.2516   -0.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5627    0.1438   -1.8491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7303   -2.2498   -0.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3957   -2.2505   -0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1315   -1.5181    0.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8968   -1.3912   -2.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0684    0.3502   -2.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4130    1.4756   -0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5344   -0.8262    0.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7680    0.9886    2.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8665   -0.8063    2.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8076    0.1580    2.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2563   -0.7748   -1.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7942    0.9031   -1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3519    0.8174   -2.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7757    1.6876   -0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4205   -1.6691   -1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5926   -2.0861    0.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9254   -2.0636   -0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7722    1.6406   -0.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7336    1.9425    1.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478    2.0641    0.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0469    0.5551    0.9258 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
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 10 11  2  0
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 12 14  1  0
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  7 18  1  0
 18 19  1  0
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 21  2  1  0
 16  6  1  0
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 18 42  1  6
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
M  END


     RDKit          2D

 46 49  0  0  0  0  0  0  0  0999 V2000
   -3.1374    2.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5413   -2.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4954   -1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9748   -1.7265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4084   -0.8168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4037    0.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9701   -0.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0
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  3 26  1  1
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  6 28  1  1
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 20 45  1  6
 20 46  1  0
M  END
> <DATABASE_ID>
NP0002772

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-14,17H,3-8,10H2,1-2H3/t13-,14-,17+,18-,19-/m0/s1

> <INCHI_KEY>
RZRPTBIGEANTGU-IRIMSJTPSA-N

> <FORMULA>
C19H24O3

> <MOLECULAR_WEIGHT>
300.3921

> <EXACT_MASS>
300.172544634

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.27833469742076

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10S,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14,17-trione

> <ALOGPS_LOGP>
2.42

> <JCHEM_LOGP>
3.00570046

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.013159867942825

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.987284876634927

> <JCHEM_PKA_STRONGEST_BASIC>
-4.868723836000967

> <JCHEM_POLAR_SURFACE_AREA>
51.21

> <JCHEM_REFRACTIVITY>
84.27479999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.46e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
adrenosterone

> <JCHEM_VEBER_RULE>
0

$$$$

NP0002772
     RDKit          3D

 46 49  0  0  0  0  0  0  0  0999 V2000
   -2.6632   -1.6515   -0.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5172   -0.3277   -0.6972 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7173   -0.3942   -1.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2609   -0.2672   -1.7349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4775   -0.7391   -2.5972 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3687    0.3706   -0.5722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5618    0.2453    0.6339 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0138    1.0133    1.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2421    0.2136    2.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1520    0.0448    1.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4706    0.0392    1.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4540   -0.1205    0.3388 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6298   -0.4547    0.6255 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1180    0.1000   -1.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7158    0.6730   -1.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7459   -0.1203   -0.2817 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9264   -1.5867   -0.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8815    0.7287    0.1820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9115    0.9463    1.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1992    0.9821    0.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8682    0.2516   -0.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5627    0.1438   -1.8491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7303   -2.2498   -0.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3957   -2.2505   -0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1315   -1.5181    0.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8968   -1.3912   -2.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0684    0.3502   -2.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4130    1.4756   -0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5344   -0.8262    0.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2950    2.0390    1.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7680    0.9886    2.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8665   -0.8063    2.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7198    0.7068    3.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8076    0.1580    2.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2563   -0.7748   -1.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7942    0.9031   -1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3519    0.8174   -2.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7757    1.6876   -0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4205   -1.6691   -1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5926   -2.0861    0.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9254   -2.0636   -0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7722    1.6406   -0.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9639    0.2167    2.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7336    1.9425    1.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478    2.0641    0.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0469    0.5551    0.9258 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
  7 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 18  2  1  0
 21  2  1  0
 16  6  1  0
 16 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  6 28  1  6
  7 29  1  1
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 11 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  6
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  H   UNK     0      27.256 -14.676   0.000  0.00  0.00           H+0
HETATM    2  H   UNK     0      29.112 -16.922   0.000  0.00  0.00           H+0
HETATM    3  H   UNK     0      26.162 -16.940   0.000  0.00  0.00           H+0
HETATM    4  C   UNK     0      24.614 -14.417   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.931 -12.204   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.951 -18.381   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.319 -17.674   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.201 -15.973   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.163 -14.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.063 -15.886   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.431 -15.180   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.287 -18.256   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.536 -13.060   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.655 -17.549   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.990 -17.425   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.391 -16.136   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.760 -15.429   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.167 -13.766   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      30.317 -13.484   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      26.095 -15.305   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.727 -16.011   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      28.832 -13.891   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      20.622 -18.131   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      24.871 -12.935   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      30.861 -12.044   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   17                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5   22                                                            
CONECT    6   14    7                                                       
CONECT    7    6   16                                                       
CONECT    8   17    9                                                       
CONECT    9    8   19                                                       
CONECT   10   11   15                                                       
CONECT   11   10   21                                                       
CONECT   12   15   14                                                       
CONECT   13   22   18                                                       
CONECT   14    6   12   21                                                  
CONECT   15   10   12   23                                                  
CONECT   16    7   17   20    1                                             
CONECT   17    8   16   22    2                                             
CONECT   18   13   24   20                                                  
CONECT   19    9   25   22                                                  
CONECT   20   16   18   21    3                                             
CONECT   21    4   11   14   20                                             
CONECT   22    5   13   17   19                                             
CONECT   23   15                                                            
CONECT   24   18                                                            
CONECT   25   19                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    NP0002772
HETATM    1  C1  UNL     1      -2.663  -1.652  -0.014  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.517  -0.328  -0.697  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.717  -0.394  -1.964  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.261  -0.267  -1.735  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.477  -0.739  -2.597  1.00  0.00           O  
HETATM    6  C5  UNL     1       0.369   0.371  -0.572  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.562   0.245   0.634  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.014   1.013   1.807  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.242   0.214   2.261  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.152   0.045   1.126  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.471   0.039   1.385  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.454  -0.120   0.339  1.00  0.00           C  
HETATM   13  O2  UNL     1       5.630  -0.455   0.625  1.00  0.00           O  
HETATM   14  C12 UNL     1       4.118   0.100  -1.084  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.716   0.673  -1.135  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.746  -0.120  -0.282  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.926  -1.587  -0.694  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.882   0.729   0.182  1.00  0.00           C  
HETATM   19  C17 UNL     1      -2.912   0.946   1.217  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.199   0.982   0.377  1.00  0.00           C  
HETATM   21  C19 UNL     1      -3.868   0.252  -0.871  1.00  0.00           C  
HETATM   22  O3  UNL     1      -4.563   0.144  -1.849  1.00  0.00           O  
HETATM   23  H1  UNL     1      -1.730  -2.250  -0.000  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.396  -2.250  -0.629  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.132  -1.518   0.963  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.897  -1.391  -2.417  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.068   0.350  -2.720  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.413   1.476  -0.786  1.00  0.00           H  
HETATM   29  H7  UNL     1      -0.534  -0.826   0.919  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.295   2.039   1.557  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.768   0.989   2.613  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.867  -0.806   2.538  1.00  0.00           H  
HETATM   33  H11 UNL     1       1.720   0.707   3.107  1.00  0.00           H  
HETATM   34  H12 UNL     1       3.808   0.158   2.409  1.00  0.00           H  
HETATM   35  H13 UNL     1       4.256  -0.775  -1.721  1.00  0.00           H  
HETATM   36  H14 UNL     1       4.794   0.903  -1.482  1.00  0.00           H  
HETATM   37  H15 UNL     1       2.352   0.817  -2.172  1.00  0.00           H  
HETATM   38  H16 UNL     1       2.776   1.688  -0.667  1.00  0.00           H  
HETATM   39  H17 UNL     1       2.420  -1.669  -1.680  1.00  0.00           H  
HETATM   40  H18 UNL     1       2.593  -2.086   0.047  1.00  0.00           H  
HETATM   41  H19 UNL     1       0.925  -2.064  -0.666  1.00  0.00           H  
HETATM   42  H20 UNL     1      -1.772   1.641  -0.429  1.00  0.00           H  
HETATM   43  H21 UNL     1      -2.964   0.217   2.022  1.00  0.00           H  
HETATM   44  H22 UNL     1      -2.734   1.942   1.690  1.00  0.00           H  
HETATM   45  H23 UNL     1      -4.348   2.064   0.118  1.00  0.00           H  
HETATM   46  H24 UNL     1      -5.047   0.555   0.926  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   18   21
CONECT    3    4   26   27
CONECT    4    5    5    6
CONECT    6    7   16   28
CONECT    7    8   18   29
CONECT    8    9   30   31
CONECT    9   10   32   33
CONECT   10   11   11   16
CONECT   11   12   34
CONECT   12   13   13   14
CONECT   14   15   35   36
CONECT   15   16   37   38
CONECT   16   17
CONECT   17   39   40   41
CONECT   18   19   42
CONECT   19   20   43   44
CONECT   20   21   45   46
CONECT   21   22   22
END

NP0002772
     RDKit          3D

46 49  0  0  0  0  0  0  0  0999 V2000
   -2.6632   -1.6515   -0.0144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5172   -0.3277   -0.6972 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7173   -0.3942   -1.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2609   -0.2672   -1.7349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4775   -0.7391   -2.5972 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3687    0.3706   -0.5722 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5618    0.2453    0.6339 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0138    1.0133    1.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2421    0.2136    2.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1520    0.0448    1.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4706    0.0392    1.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4540   -0.1205    0.3388 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6298   -0.4547    0.6255 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1180    0.1000   -1.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7158    0.6730   -1.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7459   -0.1203   -0.2817 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9264   -1.5867   -0.6938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8815    0.7287    0.1820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9115    0.9463    1.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1992    0.9821    0.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8682    0.2516   -0.8708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5627    0.1438   -1.8491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7303   -2.2498   -0.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3957   -2.2505   -0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1315   -1.5181    0.9626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8968   -1.3912   -2.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0684    0.3502   -2.7200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4130    1.4756   -0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5344   -0.8262    0.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2950    2.0390    1.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7680    0.9886    2.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8665   -0.8063    2.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7198    0.7068    3.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8076    0.1580    2.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2563   -0.7748   -1.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7942    0.9031   -1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3519    0.8174   -2.1716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7757    1.6876   -0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4205   -1.6691   -1.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5926   -2.0861    0.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9254   -2.0636   -0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7722    1.6406   -0.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9639    0.2167    2.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7336    1.9425    1.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478    2.0641    0.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0469    0.5551    0.9258 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
  7 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 18  2  1  0
 21  2  1  0
 16  6  1  0
 16 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  6 28  1  6
  7 29  1  1
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 11 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
 18 42  1  6
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
M  END

View in JSmol

Synonyms

Value	Source
11-Keto-androstenedione	ChEBI
11-Ketoandrostenedione	ChEBI
11-oxo	ChEBI
11-Oxoandrost-4-ene-3,17-dione	ChEBI
11-Oxoandrostenedione	ChEBI
11-Oxy-4-androstenedione	ChEBI
4-Androsten-3,11,17-trione	ChEBI
Andrenosterone	ChEBI
Androst-4-ene-3,11,17-trione	ChEBI
NSC 12166	ChEBI
Reichstein's substance g	ChEBI
4-Androstene-3,11,17-trione	MeSH, HMDB
Adrenosterone, 3H-labeled	MeSH, HMDB

Chemical Formula

C₁₉H₂₄O₃

Average Mass

300.3921 Da

Monoisotopic Mass

300.17254 Da

IUPAC Name

(1S,2R,10S,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14,17-trione

Traditional Name

adrenosterone

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C19H24O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-14,17H,3-8,10H2,1-2H3/t13-,14-,17+,18-,19-/m0/s1

InChI Key

RZRPTBIGEANTGU-IRIMSJTPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 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
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

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.42	ALOGPS
logP	3.01	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	17.99	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	51.21 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	84.27 m³·mol⁻¹	ChemAxon
Polarizability	33.28 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0006772

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB024074

KNApSAcK ID

Not Available

Chemspider ID

194597

KEGG Compound ID

C05285

BioCyc ID

CPD-18926

BiGG ID

Not Available

Wikipedia Link

Adrenosterone

METLIN ID

Not Available

PubChem Compound

223997

PDB ID

Not Available

ChEBI ID

2495

Good Scents ID

Not Available

References

General References

Manire CA, Rasmussen LE, Gross TS: Serum steroid hormones including 11-ketotestosterone, 11-ketoandrostenedione, and dihydroprogesterone in juvenile and adult bonnethead sharks, Sphyrna tiburo. J Exp Zool. 1999 Oct 1;284(5):595-603. doi: 10.1002/(sici)1097-010x(19991001)284:5<595::aid-jez15>3.0.co;2-6. [PubMed:10469997 ]
Musharraf SG, Atta-Ur-Rahman, Choudhary MI, Sultan S: Microbial transformation of (+)-adrenosterone. Nat Prod Lett. 2002 Oct;16(5):345-9. doi: 10.1080/10575630290033105. [PubMed:12434991 ]
Pall MK, Mayer I, Borg B: Androgen and behavior in the male three-spined stickleback, Gasterosteus aculeatus. II. Castration and 11-ketoandrostenedione effects on courtship and parental care during the nesting cycle. Horm Behav. 2002 Nov;42(3):337-44. doi: 10.1006/hbeh.2002.1820. [PubMed:12460593 ]
SAVARD K, BURSTEIN S, ROSENKRANTZ H, DORFMAN RI: The metabolism of adrenosterone in vivo. J Biol Chem. 1953 Jun;202(2):717-25. [PubMed:13061495 ]

Showing NP-Card for Adrenosterone (NP0002772)

MOL for NP0002772 (Adrenosterone)

3D MOL for NP0002772 (Adrenosterone)

3D SDF for NP0002772 (Adrenosterone)

3D-SDF for NP0002772 (Adrenosterone)

PDB for NP0002772 (Adrenosterone)

3D PDB for NP0002772 (Adrenosterone)

SMILES for NP0002772 (Adrenosterone)

INCHI for NP0002772 (Adrenosterone)

Structure for NP0002772 (Adrenosterone)

3D Structure for NP0002772 (Adrenosterone)