NP-MRD: Showing NP-Card for 5-alpha-Pregnane-3,20-dione(allo) (NP0002756)

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Record Information

Version

1.0

Created at

2020-11-23 19:39:37 UTC

Updated at

2021-08-12 19:52:03 UTC

NP-MRD ID

NP0002756

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-alpha-Pregnane-3,20-dione(allo)

Provided By

BMRB

Description

5A-Pregnane-3,20-dione, also known as 5-a-dihydroprogesterone or 3,20-allopregnanedione, belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Thus, 5a-pregnane-3,20-dione is considered to be a steroid. 5A-Pregnane-3,20-dione exists in all living organisms, ranging from bacteria to humans. In humans, 5a-pregnane-3,20-dione is involved in the metabolic disorder called the 11-beta-hydroxylase deficiency (cyp11b1) pathway. 5A-Pregnane-3,20-dione is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 5-alpha-Pregnane-3,20-dione(allo) is found in Holarrhena pubescens and Homo sapiens. It was first documented in 1986 (PMID: 3010006). Based on a literature review a significant number of articles have been published on 5a-Pregnane-3,20-dione (PMID: 17984079) (PMID: 9182868) (PMID: 10622400) (PMID: 3595731).

Structure

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


     RDKit          2D

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NP0002756
     RDKit          3D

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   -2.3329   -2.7400    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0154   -1.2974    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6340   -2.7132    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1544   -1.6011    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3888   -2.7954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9038   -2.5536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7033   -2.0814    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3635   -2.7033    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8624   -1.8168    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2253    0.0226    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0921   -2.0945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  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  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  1
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22  4  1  1
 22  7  1  0
 19  8  1  0
 17 11  1  0
  1 24  1  1
  1 25  1  0
  1 26  1  0
  4 27  1  1
  5 28  1  1
  5 29  1  0
  6 30  1  1
  6 31  1  0
  7 32  1  1
  8 33  1  6
  9 34  1  6
  9 35  1  0
 10 36  1  1
 10 37  1  0
 11 38  1  1
 12 39  1  1
 12 40  1  0
 15 41  1  1
 15 42  1  0
 16 43  1  6
 16 44  1  0
 18 45  1  1
 18 46  1  0
 18 47  1  0
 19 48  1  1
 20 49  1  6
 20 50  1  0
 21 51  1  6
 21 52  1  0
 23 53  1  6
 23 54  1  0
 23 55  1  0
M  END
> <DATABASE_ID>
NP0002756

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14,16-19H,4-12H2,1-3H3/t14-,16-,17+,18-,19-,20-,21+/m0/s1

> <INCHI_KEY>
XMRPGKVKISIQBV-BJMCWZGWSA-N

> <FORMULA>
C21H32O2

> <MOLECULAR_WEIGHT>
316.4776

> <EXACT_MASS>
316.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
37.861887083896086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,7S,10R,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

> <ALOGPS_LOGP>
4.06

> <JCHEM_LOGP>
4.194438735666669

> <ALOGPS_LOGS>
-5.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.343395658319462

> <JCHEM_PKA_STRONGEST_BASIC>
-7.053949180108259

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
91.87859999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5a-pregnane-3,20-dione

> <JCHEM_VEBER_RULE>
1

$$$$

NP0002756
     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -4.8200   -1.5071    0.5132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6150   -0.0444    0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4673    0.6895    0.8081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4385    0.4077   -0.3805 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3688    1.9326   -0.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8993    2.2712   -0.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2498    0.9376   -0.6976 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1941    0.8921   -0.4275 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9650    1.5735   -1.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2902    1.0642   -1.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7117   -0.2424   -1.2514 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2304   -0.3103   -1.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7162   -1.0496   -0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7912   -0.7288    0.4898 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9285   -2.1622    0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4566   -1.9004    0.5615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0691   -0.5446    0.0779 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4048    0.4836    1.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5726   -0.5815   -0.2256 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2049   -1.1771    0.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6792   -1.2132    0.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1139    0.1952    0.3298 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0947    0.8721    1.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6554   -1.8479    1.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8604   -1.7902    0.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1560   -2.1109   -0.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3231    0.0107   -1.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9058    2.2327   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8427    2.4523    0.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409    2.8527    0.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7162    2.8825   -1.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4858    0.4371   -1.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3955    1.3696    0.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301    1.5943   -2.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0308    2.6697   -1.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0847    1.8164   -1.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4287    0.9781   -2.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4136   -1.0833   -1.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6366   -0.6839   -2.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5664    0.7554   -1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3254   -2.3821    1.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1659   -3.0701   -0.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9271   -2.7262    0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1078   -1.9767    1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4642    1.4773    0.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6375    0.4432    1.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3680    0.2575    1.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4115   -1.1653   -1.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1646   -2.2090    1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938   -0.6293    1.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2906   -1.6770    1.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7310   -1.8146   -0.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9719    1.4887    1.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2006    1.5058    1.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0631    0.0844    2.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  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  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22  4  1  0
 22  7  1  0
 19  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  6
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  6
  8 33  1  1
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  6
 12 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  6
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HMDB03759.mol                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.391  -1.130   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.391  -2.670   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.057  -3.440   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.723  -2.670   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.723  -1.130   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.057  -0.360   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.390  -3.440   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.944  -2.670   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.944  -1.130   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.390  -0.360   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.278  -0.360   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.278   1.180   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.944   1.950   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.390   1.180   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.742  -0.836   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.647   0.410   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.742   1.656   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.725  -3.440   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.218   3.121   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.439   2.712   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       0.944   0.410   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      -1.689   0.376   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      -1.723  -4.210   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.390  -1.900   0.000  0.00  0.00           H+0
HETATM   25  O   UNK     0       3.129   4.210   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.725   3.441   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       2.278  -1.900   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   23                                             
CONECT    5    4    6   10   22                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   21                                             
CONECT   10    9    5   14   24                                             
CONECT   11    9   12   15   27                                             
CONECT   12   11   13   17   20                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   19                                                  
CONECT   18    2                                                            
CONECT   19   17   25   26                                                  
CONECT   20   12                                                            
CONECT   21    9                                                            
CONECT   22    5                                                            
CONECT   23    4                                                            
CONECT   24   10                                                            
CONECT   25   19                                                            
CONECT   26   19                                                            
CONECT   27   11                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    NP0002756
HETATM    1  C1  UNL     1      -4.820  -1.507   0.513  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.615  -0.044   0.333  1.00  0.00           C  
HETATM    3  O1  UNL     1      -5.467   0.690   0.808  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.438   0.408  -0.381  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.369   1.933  -0.523  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.899   2.271  -0.695  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.250   0.938  -0.698  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.194   0.892  -0.428  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.965   1.574  -1.474  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.290   1.064  -1.833  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.712  -0.242  -1.251  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.230  -0.310  -1.175  1.00  0.00           C  
HETATM   13  C12 UNL     1       4.716  -1.050  -0.004  1.00  0.00           C  
HETATM   14  O2  UNL     1       5.791  -0.729   0.490  1.00  0.00           O  
HETATM   15  C13 UNL     1       3.928  -2.162   0.576  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.457  -1.900   0.562  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.069  -0.545   0.078  1.00  0.00           C  
HETATM   18  C16 UNL     1       2.405   0.484   1.127  1.00  0.00           C  
HETATM   19  C17 UNL     1       0.573  -0.581  -0.226  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.205  -1.177   0.891  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.679  -1.213   0.460  1.00  0.00           C  
HETATM   22  C20 UNL     1      -2.114   0.195   0.330  1.00  0.00           C  
HETATM   23  C21 UNL     1      -2.095   0.872   1.663  1.00  0.00           C  
HETATM   24  H1  UNL     1      -4.655  -1.848   1.553  1.00  0.00           H  
HETATM   25  H2  UNL     1      -5.860  -1.790   0.165  1.00  0.00           H  
HETATM   26  H3  UNL     1      -4.156  -2.111  -0.139  1.00  0.00           H  
HETATM   27  H4  UNL     1      -3.323   0.011  -1.413  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.906   2.233  -1.458  1.00  0.00           H  
HETATM   29  H6  UNL     1      -3.843   2.452   0.308  1.00  0.00           H  
HETATM   30  H7  UNL     1      -1.541   2.853   0.199  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.716   2.882  -1.593  1.00  0.00           H  
HETATM   32  H9  UNL     1      -1.486   0.437  -1.675  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.395   1.370   0.572  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.330   1.594  -2.412  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.031   2.670  -1.197  1.00  0.00           H  
HETATM   36  H13 UNL     1       3.085   1.816  -1.544  1.00  0.00           H  
HETATM   37  H14 UNL     1       2.429   0.978  -2.953  1.00  0.00           H  
HETATM   38  H15 UNL     1       2.414  -1.083  -1.930  1.00  0.00           H  
HETATM   39  H16 UNL     1       4.637  -0.684  -2.140  1.00  0.00           H  
HETATM   40  H17 UNL     1       4.566   0.755  -1.057  1.00  0.00           H  
HETATM   41  H18 UNL     1       4.325  -2.382   1.591  1.00  0.00           H  
HETATM   42  H19 UNL     1       4.166  -3.070  -0.039  1.00  0.00           H  
HETATM   43  H20 UNL     1       1.927  -2.726   0.032  1.00  0.00           H  
HETATM   44  H21 UNL     1       2.108  -1.977   1.633  1.00  0.00           H  
HETATM   45  H22 UNL     1       2.464   1.477   0.644  1.00  0.00           H  
HETATM   46  H23 UNL     1       1.638   0.443   1.926  1.00  0.00           H  
HETATM   47  H24 UNL     1       3.368   0.258   1.593  1.00  0.00           H  
HETATM   48  H25 UNL     1       0.411  -1.165  -1.136  1.00  0.00           H  
HETATM   49  H26 UNL     1       0.165  -2.209   1.061  1.00  0.00           H  
HETATM   50  H27 UNL     1      -0.094  -0.629   1.826  1.00  0.00           H  
HETATM   51  H28 UNL     1      -2.291  -1.677   1.284  1.00  0.00           H  
HETATM   52  H29 UNL     1      -1.731  -1.815  -0.446  1.00  0.00           H  
HETATM   53  H30 UNL     1      -2.972   1.489   1.882  1.00  0.00           H  
HETATM   54  H31 UNL     1      -1.201   1.506   1.835  1.00  0.00           H  
HETATM   55  H32 UNL     1      -2.063   0.084   2.467  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3    4
CONECT    4    5   22   27
CONECT    5    6   28   29
CONECT    6    7   30   31
CONECT    7    8   22   32
CONECT    8    9   19   33
CONECT    9   10   34   35
CONECT   10   11   36   37
CONECT   11   12   17   38
CONECT   12   13   39   40
CONECT   13   14   14   15
CONECT   15   16   41   42
CONECT   16   17   43   44
CONECT   17   18   19
CONECT   18   45   46   47
CONECT   19   20   48
CONECT   20   21   49   50
CONECT   21   22   51   52
CONECT   22   23
CONECT   23   53   54   55
END

NP0002756
     RDKit          3D

55 58  0  0  0  0  0  0  0  0999 V2000
   -4.8200   -1.5071    0.5132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6150   -0.0444    0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4673    0.6895    0.8081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4385    0.4077   -0.3805 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3688    1.9326   -0.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8993    2.2712   -0.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2498    0.9376   -0.6976 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1941    0.8921   -0.4275 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9650    1.5735   -1.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2902    1.0642   -1.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7117   -0.2424   -1.2514 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2304   -0.3103   -1.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7162   -1.0496   -0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7912   -0.7288    0.4898 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9285   -2.1622    0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4566   -1.9004    0.5615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0691   -0.5446    0.0779 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4048    0.4836    1.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5726   -0.5815   -0.2256 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2049   -1.1771    0.8914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6792   -1.2132    0.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1139    0.1952    0.3298 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0947    0.8721    1.6630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6554   -1.8479    1.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8604   -1.7902    0.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1560   -2.1109   -0.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3231    0.0107   -1.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9058    2.2327   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8427    2.4523    0.3085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5409    2.8527    0.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7162    2.8825   -1.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4858    0.4371   -1.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3955    1.3696    0.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301    1.5943   -2.4119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0308    2.6697   -1.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0847    1.8164   -1.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4287    0.9781   -2.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4136   -1.0833   -1.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6366   -0.6839   -2.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5664    0.7554   -1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3254   -2.3821    1.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1659   -3.0701   -0.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9271   -2.7262    0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1078   -1.9767    1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4642    1.4773    0.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6375    0.4432    1.9257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3680    0.2575    1.5932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4115   -1.1653   -1.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1646   -2.2090    1.0610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0938   -0.6293    1.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2906   -1.6770    1.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7310   -1.8146   -0.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9719    1.4887    1.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2006    1.5058    1.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0631    0.0844    2.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  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  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22  4  1  0
 22  7  1  0
 19  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  6
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  6
  8 33  1  1
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  6
 12 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  6
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
M  END

View in JSmol

Synonyms

Value	Source
3,20-Allopregnanedione	ChEBI
3,20-Dioxo-5alpha-pregnane	ChEBI
5-alpha-Dihydroprogesterone	ChEBI
5alpha-Dihydroprogesterone	ChEBI
3,20-Dioxo-5a-pregnane	Generator
3,20-Dioxo-5α-pregnane	Generator
5-a-Dihydroprogesterone	Generator
5-Α-dihydroprogesterone	Generator
5a-Dihydroprogesterone	Generator
5Α-dihydroprogesterone	Generator
5-alpha-Pregnane-3,20-dione	HMDB, MeSH
5a-Pregnan-3,20-dione	HMDB
5alpha-Pregnan-3,20-dione	HMDB
5alpha-Pregnane-3,20-dione	HMDB, MeSH
5b-Pregnane-3,20-dione	HMDB
5beta-Pregnane-3,20-dione	HMDB
Allopregnan-3,20-dione	HMDB
Pregnane-3,20-dione	HMDB
5 alpha Dihydroprogesterone	MeSH, HMDB
5 beta Pregnane 3,20 dione	MeSH, HMDB
5 beta-Pregnane-3,20-dione	MeSH, HMDB
5-beta-Dihydroprogesterone	MeSH, HMDB
5alpha-DHP	MeSH, HMDB
3,20-Allopregnanedione, (5beta,13alpha,17alpha)-isomer	MeSH, HMDB
5 alpha Pregnanedione	MeSH, HMDB
5alpha DHP	MeSH, HMDB
5alpha Pregnane 3,20 dione	MeSH, HMDB
5beta DHP	MeSH, HMDB
5beta-DHP	MeSH, HMDB
3,20 Allopregnanedione	MeSH, HMDB
3,20-Allopregnanedione, (5alpha)-isomer	MeSH, HMDB
5 alpha Pregnane 3,20 dione	MeSH, HMDB
5 alpha-Dihydroprogesterone	MeSH, HMDB
5 alpha-Pregnane-3,20-dione	MeSH, HMDB
5 beta Dihydroprogesterone	MeSH, HMDB
5-alpha-Pregnanedione	MeSH, HMDB

Chemical Formula

C₂₁H₃₂O₂

Average Mass

316.4776 Da

Monoisotopic Mass

316.24023 Da

IUPAC Name

(1S,2S,7S,10R,11S,14S,15S)-14-acetyl-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

Traditional Name

5a-pregnane-3,20-dione

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14,16-19H,4-12H2,1-3H3/t14-,16-,17+,18-,19-,20-,21+/m0/s1

InChI Key

XMRPGKVKISIQBV-BJMCWZGWSA-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
Holarrhena pubescens	LOTUS Database	35616633
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
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 gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
3-oxo-5-alpha-steroid
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

3-oxo steroid (CHEBI:28952 )
20-oxo steroid (CHEBI:28952 )
C21-steroid hormone (CHEBI:28952 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030170 )

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	4.06	ALOGPS
logP	4.19	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	19.34	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	1	ChemAxon
Refractivity	91.88 m³·mol⁻¹	ChemAxon
Polarizability	37.86 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

HMDB0003759

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023222

KNApSAcK ID

Not Available

Chemspider ID

83782

KEGG Compound ID

C03681

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

5%CE%B1-Dihydroprogesterone

METLIN ID

Not Available

PubChem Compound

92810

PDB ID

Not Available

ChEBI ID

28952

Good Scents ID

Not Available

References

General References

Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
Kwan TK, Kraevskaya MA, Makin HL, Trafford DJ, Gower DB: Use of gas chromatographic-mass spectrometric techniques in studies of androst-16-ene and androgen biosynthesis in human testis; cytosolic specific binding of 5alpha-androst-16-en-3-one. J Steroid Biochem Mol Biol. 1997 Jan;60(1-2):137-46. doi: 10.1016/s0960-0760(96)00162-8. [PubMed:9182868 ]
Zhang J, Ming LJ, Sjovall J, Cook HW, Ridgway ND, Byers DM: Progesterone metabolism in human fibroblasts is independent of P-glycoprotein levels and Niemann-Pick type C disease. J Steroid Biochem Mol Biol. 1999 Sep-Oct;70(4-6):123-31. doi: 10.1016/s0960-0760(99)00107-7. [PubMed:10622400 ]
Sandow J, Engelbart K, von Rechenberg W: The different mechanisms for suppression of pituitary and testicular function. Med Biol. 1986;63(5-6):192-200. [PubMed:3010006 ]
Jarczok T, Zwirner M, Schindler AE: Progesterone and 5 alpha-pregnane-3,20-dione in human amniotic fluid. Exp Clin Endocrinol. 1987 Mar;89(1):39-47. doi: 10.1055/s-0029-1210625. [PubMed:3595731 ]

Showing NP-Card for 5-alpha-Pregnane-3,20-dione(allo) (NP0002756)

MOL for NP0002756 (5-alpha-Pregnane-3,20-dione(allo))

3D MOL for NP0002756 (5-alpha-Pregnane-3,20-dione(allo))

3D SDF for NP0002756 (5-alpha-Pregnane-3,20-dione(allo))

3D-SDF for NP0002756 (5-alpha-Pregnane-3,20-dione(allo))

PDB for NP0002756 (5-alpha-Pregnane-3,20-dione(allo))

3D PDB for NP0002756 (5-alpha-Pregnane-3,20-dione(allo))

SMILES for NP0002756 (5-alpha-Pregnane-3,20-dione(allo))

INCHI for NP0002756 (5-alpha-Pregnane-3,20-dione(allo))

Structure for NP0002756 (5-alpha-Pregnane-3,20-dione(allo))

3D Structure for NP0002756 (5-alpha-Pregnane-3,20-dione(allo))