NP-MRD: Showing NP-Card for 11-alpha-Hydroxyprogesterone (NP0002775)

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Record Information

Version

1.0

Created at

2020-11-23 19:40:07 UTC

Updated at

2021-08-12 19:52:06 UTC

NP-MRD ID

NP0002775

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-alpha-Hydroxyprogesterone

Provided By

BMRB

Description

11Alpha-hydroxyprogesterone is also known as 4-pregnen-11alpha-ol-3,20-dione. It was first documented in 1953 (PMID: 13068348). Based on a literature review a significant number of articles have been published on 11alpha-hydroxyprogesterone (PMID: 17984079) (PMID: 10373218) (PMID: 1245704) (PMID: 13740999).

Structure

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


     RDKit          2D

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M  END

NP0002775
     RDKit          3D

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    4.0899   -0.1703    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8032   -2.2721    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  2  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  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23  4  1  1
 23  7  1  0
 19  8  1  0
 17 11  1  6
  1 25  1  6
  1 26  1  0
  1 27  1  0
  4 28  1  1
  5 29  1  6
  5 30  1  0
  6 31  1  6
  6 32  1  0
  7 33  1  1
  8 34  1  6
  9 35  1  6
  9 36  1  0
 10 37  1  6
 10 38  1  0
 12 39  1  0
 15 40  1  1
 15 41  1  0
 16 42  1  6
 16 43  1  0
 18 44  1  1
 18 45  1  0
 18 46  1  0
 19 47  1  1
 20 48  1  6
 21 49  1  0
 22 50  1  1
 22 51  1  0
 24 52  1  1
 24 53  1  0
 24 54  1  0
M  END
> <DATABASE_ID>
NP0002775

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])[C@]([H])(O)C[C@]12C)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h10,15-19,24H,4-9,11H2,1-3H3/t15-,16+,17-,18+,19+,20-,21+/m0/s1

> <INCHI_KEY>
BFZHCUBIASXHPK-QJSKAATBSA-N

> <FORMULA>
C21H30O3

> <MOLECULAR_WEIGHT>
330.4611

> <EXACT_MASS>
330.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
38.04389526557156

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
2.8398396036666673

> <ALOGPS_LOGS>
-3.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.545038962490786

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.87532633266298

> <JCHEM_PKA_STRONGEST_BASIC>
-0.2594841269974141

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
94.29779999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11α-hydroxyprogesterone

> <JCHEM_VEBER_RULE>
0

$$$$

NP0002775
     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -5.7950   -0.0446   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4278   -0.5451   -0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3038   -1.6441    0.3253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2720    0.2891   -0.4665 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3979    1.5884    0.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0618    1.7583    1.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1568    1.0016    0.1163 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2058    0.7347    0.5818 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9356    2.0859    0.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2296    1.7517    1.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9859    0.6990    0.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2937    0.6366    0.8678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1187   -0.3736    0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2368   -0.7594    0.6158 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5932   -0.9814   -1.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2467   -0.3538   -1.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3552   -0.3152   -0.1913 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4292   -1.6439    0.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9388   -0.0147   -0.5429 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1856   -1.2544   -0.9436 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7328   -1.7217   -2.1357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2663   -0.9961   -1.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9296   -0.2797   -0.0820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9611   -1.1907    1.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1351    0.6230    0.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8694    0.5575   -1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5279   -0.8803   -0.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2803    0.4910   -1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5200    2.4003   -0.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2395    1.5339    1.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1151    1.3039    2.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857    2.8258    1.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1055    1.5385   -0.8514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3438    0.2646    1.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3221    2.7152    1.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0880    2.5553   -0.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9772    1.4181    2.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7925    2.7029    1.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8195    1.3506    1.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2734   -0.7557   -1.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4823   -2.0664   -0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4946    0.6863   -1.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8706   -0.9125   -2.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3257   -1.7420    1.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4058   -2.4717   -0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5680   -1.6713    1.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9336    0.6768   -1.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406   -2.0752   -0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6557   -2.6815   -2.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3946   -0.4404   -2.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7659   -1.9813   -1.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7075   -0.9298    1.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9568   -1.2290    1.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1053   -2.2335    0.6906 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  2  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
 20 22  1  0
 22 23  1  0
 23 24  1  1
 23  4  1  0
 23  7  1  0
 19  8  1  0
 17 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  6
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  6
  8 34  1  1
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  6
 20 48  1  1
 21 49  1  0
 22 50  1  0
 22 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
M  END

HEADER    PROTEIN                                 04-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   12                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4    5   13                                                       
CONECT    5    4   15                                                       
CONECT    6    7   16                                                       
CONECT    7    6   17                                                       
CONECT    8    9   14                                                       
CONECT    9    8   20                                                       
CONECT   10   13   14                                                       
CONECT   11   18   21                                                       
CONECT   12    1   16   22                                                  
CONECT   13    4   10   20                                                  
CONECT   14    8   10   23                                                  
CONECT   15    5   17   19   25                                             
CONECT   16    6   12   21   26                                             
CONECT   17    7   15   21   27                                             
CONECT   18   11   19   24   28                                             
CONECT   19   15   18   20   29                                             
CONECT   20    2    9   13   19                                             
CONECT   21    3   11   16   17                                             
CONECT   22   12                                                            
CONECT   23   14                                                            
CONECT   24   18                                                            
CONECT   25   15                                                            
CONECT   26   16                                                            
CONECT   27   17                                                            
CONECT   28   18                                                            
CONECT   29   19                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

COMPND    NP0002775
HETATM    1  C1  UNL     1      -5.795  -0.045  -0.437  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.428  -0.545  -0.157  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.304  -1.644   0.325  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.272   0.289  -0.466  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.398   1.588   0.339  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.062   1.758   1.036  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.157   1.002   0.116  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.206   0.735   0.582  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.936   2.086   0.695  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.230   1.752   1.419  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.986   0.699   0.710  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.294   0.637   0.868  1.00  0.00           C  
HETATM   13  C12 UNL     1       5.119  -0.374   0.202  1.00  0.00           C  
HETATM   14  O2  UNL     1       6.237  -0.759   0.616  1.00  0.00           O  
HETATM   15  C13 UNL     1       4.593  -0.981  -1.048  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.247  -0.354  -1.412  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.355  -0.315  -0.191  1.00  0.00           C  
HETATM   18  C16 UNL     1       2.429  -1.644   0.546  1.00  0.00           C  
HETATM   19  C17 UNL     1       0.939  -0.015  -0.543  1.00  0.00           C  
HETATM   20  C18 UNL     1       0.186  -1.254  -0.944  1.00  0.00           C  
HETATM   21  O3  UNL     1       0.733  -1.722  -2.136  1.00  0.00           O  
HETATM   22  C19 UNL     1      -1.266  -0.996  -1.234  1.00  0.00           C  
HETATM   23  C20 UNL     1      -1.930  -0.280  -0.082  1.00  0.00           C  
HETATM   24  C21 UNL     1      -1.961  -1.191   1.088  1.00  0.00           C  
HETATM   25  H1  UNL     1      -6.135   0.623   0.408  1.00  0.00           H  
HETATM   26  H2  UNL     1      -5.869   0.557  -1.352  1.00  0.00           H  
HETATM   27  H3  UNL     1      -6.528  -0.880  -0.551  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.280   0.491  -1.565  1.00  0.00           H  
HETATM   29  H5  UNL     1      -3.520   2.400  -0.400  1.00  0.00           H  
HETATM   30  H6  UNL     1      -4.240   1.534   1.057  1.00  0.00           H  
HETATM   31  H7  UNL     1      -2.115   1.304   2.038  1.00  0.00           H  
HETATM   32  H8  UNL     1      -1.786   2.826   1.126  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.106   1.538  -0.851  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.344   0.265   1.556  1.00  0.00           H  
HETATM   35  H11 UNL     1       0.322   2.715   1.363  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.088   2.555  -0.275  1.00  0.00           H  
HETATM   37  H13 UNL     1       1.977   1.418   2.444  1.00  0.00           H  
HETATM   38  H14 UNL     1       2.793   2.703   1.511  1.00  0.00           H  
HETATM   39  H15 UNL     1       4.820   1.351   1.514  1.00  0.00           H  
HETATM   40  H16 UNL     1       5.273  -0.756  -1.895  1.00  0.00           H  
HETATM   41  H17 UNL     1       4.482  -2.066  -0.989  1.00  0.00           H  
HETATM   42  H18 UNL     1       3.495   0.686  -1.743  1.00  0.00           H  
HETATM   43  H19 UNL     1       2.871  -0.912  -2.258  1.00  0.00           H  
HETATM   44  H20 UNL     1       3.326  -1.742   1.166  1.00  0.00           H  
HETATM   45  H21 UNL     1       2.406  -2.472  -0.168  1.00  0.00           H  
HETATM   46  H22 UNL     1       1.568  -1.671   1.269  1.00  0.00           H  
HETATM   47  H23 UNL     1       0.934   0.677  -1.410  1.00  0.00           H  
HETATM   48  H24 UNL     1       0.241  -2.075  -0.219  1.00  0.00           H  
HETATM   49  H25 UNL     1       0.656  -2.681  -2.263  1.00  0.00           H  
HETATM   50  H26 UNL     1      -1.395  -0.440  -2.173  1.00  0.00           H  
HETATM   51  H27 UNL     1      -1.766  -1.981  -1.340  1.00  0.00           H  
HETATM   52  H28 UNL     1      -2.708  -0.930   1.865  1.00  0.00           H  
HETATM   53  H29 UNL     1      -0.957  -1.229   1.555  1.00  0.00           H  
HETATM   54  H30 UNL     1      -2.105  -2.234   0.691  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3    4
CONECT    4    5   23   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8   23   33
CONECT    8    9   19   34
CONECT    9   10   35   36
CONECT   10   11   37   38
CONECT   11   12   12   17
CONECT   12   13   39
CONECT   13   14   14   15
CONECT   15   16   40   41
CONECT   16   17   42   43
CONECT   17   18   19
CONECT   18   44   45   46
CONECT   19   20   47
CONECT   20   21   22   48
CONECT   21   49
CONECT   22   23   50   51
CONECT   23   24
CONECT   24   52   53   54
END

NP0002775
     RDKit          3D

54 57  0  0  0  0  0  0  0  0999 V2000
   -5.7950   -0.0446   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4278   -0.5451   -0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3038   -1.6441    0.3253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2720    0.2891   -0.4665 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3979    1.5884    0.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0618    1.7583    1.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1568    1.0016    0.1163 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2058    0.7347    0.5818 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9356    2.0859    0.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2296    1.7517    1.4194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9859    0.6990    0.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2937    0.6366    0.8678 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1187   -0.3736    0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2368   -0.7594    0.6158 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5932   -0.9814   -1.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2467   -0.3538   -1.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3552   -0.3152   -0.1913 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4292   -1.6439    0.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9388   -0.0147   -0.5429 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1856   -1.2544   -0.9436 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7328   -1.7217   -2.1357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2663   -0.9961   -1.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9296   -0.2797   -0.0820 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9611   -1.1907    1.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1351    0.6230    0.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8694    0.5575   -1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5279   -0.8803   -0.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2803    0.4910   -1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5200    2.4003   -0.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2395    1.5339    1.0565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1151    1.3039    2.0378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857    2.8258    1.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1055    1.5385   -0.8514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3438    0.2646    1.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3221    2.7152    1.3631 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0880    2.5553   -0.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9772    1.4181    2.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7925    2.7029    1.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8195    1.3506    1.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2734   -0.7557   -1.8948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4823   -2.0664   -0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4946    0.6863   -1.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8706   -0.9125   -2.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3257   -1.7420    1.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4058   -2.4717   -0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5680   -1.6713    1.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9336    0.6768   -1.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406   -2.0752   -0.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6557   -2.6815   -2.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3946   -0.4404   -2.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7659   -1.9813   -1.3397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7075   -0.9298    1.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9568   -1.2290    1.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1053   -2.2335    0.6906 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  2  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
 20 22  1  0
 22 23  1  0
 23 24  1  1
 23  4  1  0
 23  7  1  0
 19  8  1  0
 17 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  6
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  6
  8 34  1  1
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  6
 20 48  1  1
 21 49  1  0
 22 50  1  0
 22 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
M  END

View in JSmol

Synonyms

Value	Source
(11alpha)-11-Hydroxypregn-4-ene-3,20-dione	ChEBI
4-Pregnen-11alpha-ol-3,20-dione	ChEBI
(11a)-11-Hydroxypregn-4-ene-3,20-dione	Generator
(11Α)-11-hydroxypregn-4-ene-3,20-dione	Generator
4-Pregnen-11a-ol-3,20-dione	Generator
4-Pregnen-11α-ol-3,20-dione	Generator
11a-Hydroxyprogesterone	Generator
11Α-hydroxyprogesterone	Generator
11 alpha-Hydroxyprogesterone	MeSH
11 beta-Hydroxy-4-pregnen-3,20-dione	MeSH
11-Hydroxyprogesterone	MeSH
11-Hydroxyprogesterone, (11alpha)-(+-)-isomer	MeSH
11-Hydroxyprogesterone, (11alpha)-isomer	MeSH
11-Hydroxyprogesterone, (11alpha,17alpha)-(+-)-isomer	MeSH
11-Hydroxyprogesterone, (11beta)-isomer	MeSH
11-Hydroxyprogesterone, (9beta,10alpha,11alpha)-isomer	MeSH
11ohp Compound	MeSH
11beta-Hydroxyprogesterone	MeSH
Duralutin	MeSH
Gesterol	MeSH
Hy-gestrone	MeSH
Hylutin	MeSH
Hyprogest	MeSH
Pergestron	MeSH
Pro-depo	MeSH
Prodrox	MeSH
Pregn-4-ene-11 beta-ol-3,20-dione	MeSH

Chemical Formula

C₂₁H₃₀O₃

Average Mass

330.4611 Da

Monoisotopic Mass

330.21949 Da

IUPAC Name

(1S,2R,10S,11S,14S,15S,17R)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Traditional Name

11α-hydroxyprogesterone

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])[C@]([H])(O)C[C@]12C)C(C)=O

InChI Identifier

InChI=1S/C21H30O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h10,15-19,24H,4-9,11H2,1-3H3/t15-,16+,17-,18+,19+,20-,21+/m0/s1

InChI Key

BFZHCUBIASXHPK-QJSKAATBSA-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

Not Available

Chemical Taxonomy

Description

This compound 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-delta-4-steroid
3-oxosteroid
11-hydroxysteroid
11-alpha-hydroxysteroid
Hydroxysteroid
Oxosteroid
Delta-4-steroid
Cyclohexenone
Cyclic alcohol
Ketone
Secondary alcohol
Cyclic ketone
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo Delta(4)-steroid (CHEBI:16076 )
20-oxo steroid (CHEBI:16076 )
11alpha-hydroxy steroid (CHEBI:16076 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030184 )

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	2.65	ALOGPS
logP	2.84	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	18.88	ChemAxon
pKa (Strongest Basic)	-0.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.3 m³·mol⁻¹	ChemAxon
Polarizability	38.04 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

83709

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

11α-Hydroxyprogesterone

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

16076

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 ]
Gomez-Sanchez EP, Gomez-Sanchez CE: Maternal hypertension and progeny blood pressure: role of aldosterone and 11beta-HSD. Hypertension. 1999 Jun;33(6):1369-73. doi: 10.1161/01.hyp.33.6.1369. [PubMed:10373218 ]
Johnson WS, Escher S, Metcalf BW: Letter: A stereospecific total synthesis of racemic 11alpha-hydroxyprogesterone via a biomimetic polyene cyclization. J Am Chem Soc. 1976 Feb 18;98(4):1039-4. doi: 10.1021/ja00420a041. [PubMed:1245704 ]
INGLE DJ, BEARY DF, PURMALIS A: Comparison of the effect of 11-ketoprogesterone, 11alpha-hydroxyprogesterone and 11 beta-hydroxyprogesterone upon the glycosuria of the partially depancreatized rat. Endocrinology. 1953 Aug;53(2):221-5. doi: 10.1210/endo-53-2-221. [PubMed:13068348 ]
REUSSER F, KOEPSELL HJ, SAVAGE GM: Continuous microbiological transformation of steroids. Appl Microbiol. 1961 Jul;9:346-8. doi: 10.1128/am.9.4.346-348.1961. [PubMed:13740999 ]

Showing NP-Card for 11-alpha-Hydroxyprogesterone (NP0002775)

MOL for NP0002775 (11-alpha-Hydroxyprogesterone)

3D MOL for NP0002775 (11-alpha-Hydroxyprogesterone)

3D SDF for NP0002775 (11-alpha-Hydroxyprogesterone)

3D-SDF for NP0002775 (11-alpha-Hydroxyprogesterone)

PDB for NP0002775 (11-alpha-Hydroxyprogesterone)

3D PDB for NP0002775 (11-alpha-Hydroxyprogesterone)

SMILES for NP0002775 (11-alpha-Hydroxyprogesterone)

INCHI for NP0002775 (11-alpha-Hydroxyprogesterone)

Structure for NP0002775 (11-alpha-Hydroxyprogesterone)

3D Structure for NP0002775 (11-alpha-Hydroxyprogesterone)