NP-MRD: Showing NP-Card for 11-β-hydroxyprogesterone (NP0315556)

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Record Information

Version

2.0

Created at

2022-09-11 14:14:56 UTC

Updated at

2022-09-11 14:14:56 UTC

NP-MRD ID

NP0315556

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-β-hydroxyprogesterone

Description

11Beta-Hydroxyprogesterone, also known as 21-deoxycorticosterone or hylutin, 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, 11beta-hydroxyprogesterone is considered to be a steroid lipid molecule. 11-β-hydroxyprogesterone is found in Mus musculus. 11-β-hydroxyprogesterone was first documented in 1955 (PMID: 13252188). 11Beta-Hydroxyprogesterone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 1022526) (PMID: 3546944).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652308132018492D          

 27 30  0  0  0  0            999 V2000
 9999.287510000.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.285510000.8428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1482 9997.9399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.424810001.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.713410000.0077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9999 9998.7732    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.4248 9998.7732    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.0003 9997.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7148 9998.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.713010000.8386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.998510000.4261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.9985 9999.6010    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7130 9999.1886    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.5745 9999.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8600 9999.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8600 9998.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5745 9997.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2890 9998.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2890 9999.1796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.427510000.4261    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.4275 9999.6011    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.2121 9999.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.697010000.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.212110000.6811    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.467110001.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.915010002.0788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.274010001.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 11  2  1  1  0  0  0
 12  6  1  6  0  0  0
  9 13  1  0  0  0  0
 13  5  1  1  0  0  0
 16  3  2  0  0  0  0
 19  1  1  1  0  0  0
 12 19  1  0  0  0  0
 18  8  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 20  1  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  1  0  0  0
 25 27  1  0  0  0  0
 25 26  2  0  0  0  0
 13 21  1  0  0  0  0
 21  7  1  6  0  0  0
 10 20  1  0  0  0  0
 20  4  1  1  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    5.6804   -0.4491    0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2481   -0.7940    0.5743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9190   -1.9571    0.6762 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2091    0.2247    0.3177 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4346    0.9958   -0.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0459    1.2236   -1.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1583    0.8224   -0.4730 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2853    0.6104   -0.7863 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8771    1.8190   -1.3892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1062    2.3792   -0.7672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9011    1.4421    0.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0510    1.8384    0.5043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9350    0.9928    1.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9109    1.4793    1.9435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6235   -0.4571    1.3217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1292   -0.6536    1.3503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4139    0.0683    0.2575 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6933   -0.7011   -1.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9484    0.2134    0.4949 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3234   -0.9801    1.1497 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7868   -2.1960    0.6511 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1600   -0.9141    1.2280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8601   -0.4385    0.0165 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0775   -1.4340   -1.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9704    0.3489    0.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8177   -0.0254    1.7324 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3185   -1.3489    0.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0994    0.9294    1.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8896    1.9839   -0.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0604    0.4498   -1.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9002    2.2815   -1.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9390    0.5726   -2.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2690    1.5698    0.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3294   -0.2594   -1.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0498    1.6292   -2.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1080    2.6483   -1.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7601    2.7718   -1.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8610    3.3006   -0.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4302    2.8649    0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0019   -0.8772    2.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0983   -0.9952    0.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9959   -1.7671    1.2124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7378   -0.3287    2.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7833    0.0084   -1.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6800   -1.1972   -0.9707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9494   -1.4701   -1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8244    1.0700    1.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6971   -0.9631    2.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2369   -2.6156   -0.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4143   -0.1960    2.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5217   -1.8994    1.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3766   -1.3351   -1.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0954   -1.3347   -1.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0632   -2.4562   -0.6259 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  4 23  1  0
 23 24  1  6
 23 22  1  0
 22 20  1  0
 20 21  1  0
 20 19  1  0
 19  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  6
 23  7  1  0
 17 19  1  0
  8  7  1  0
 17 11  1  0
  7 33  1  1
  6 31  1  0
  6 32  1  0
  5 29  1  0
  5 30  1  0
  4 28  1  1
  1 25  1  0
  1 26  1  0
  1 27  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
 22 50  1  0
 22 51  1  0
 20 48  1  1
 21 49  1  0
 19 47  1  1
  8 34  1  6
  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
M  END


  Mrv1652308132018492D          

 27 30  0  0  0  0            999 V2000
 9999.287510000.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.285510000.8428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1482 9997.9399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.424810001.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.713410000.0077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9999 9998.7732    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.4248 9998.7732    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.0003 9997.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7148 9998.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.713010000.8386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.998510000.4261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.9985 9999.6010    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7130 9999.1886    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.5745 9999.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8600 9999.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8600 9998.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5745 9997.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2890 9998.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2890 9999.1796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.427510000.4261    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.4275 9999.6011    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.2121 9999.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.697010000.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.212110000.6811    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.467110001.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.915010002.0788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.274010001.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 11  2  1  1  0  0  0
 12  6  1  6  0  0  0
  9 13  1  0  0  0  0
 13  5  1  1  0  0  0
 16  3  2  0  0  0  0
 19  1  1  1  0  0  0
 12 19  1  0  0  0  0
 18  8  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 20  1  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  1  0  0  0
 25 27  1  0  0  0  0
 25 26  2  0  0  0  0
 13 21  1  0  0  0  0
 21  7  1  6  0  0  0
 10 20  1  0  0  0  0
 20  4  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0315556

> <DATABASE_NAME>
NP-MRD

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

> <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-ATWVFEABSA-N

> <FORMULA>
C21H30O3

> <MOLECULAR_WEIGHT>
330.4611

> <EXACT_MASS>
330.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.11860709950443

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10S,11S,14S,15S,17S)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]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>
54.37

> <JCHEM_REFRACTIVITY>
94.2978

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,10S,11S,14S,15S,17S)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-AUG-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-AUG-20         0                                  
HETATM    1  C   UNK     0    8665.3378666.681   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8665.3338668.240   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8661.3438662.821   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8669.3268669.013   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0    8667.9988666.681   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8666.6668664.377   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8669.3268664.377   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0    8666.6678662.825   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8668.0018663.595   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8667.9988668.232   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8666.6648667.462   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8666.6648665.922   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8667.9988665.152   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8664.0068665.905   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8662.6728665.135   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8662.6728663.595   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8664.0068662.825   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8665.3398663.595   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8665.3398665.135   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8669.3318667.462   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8669.3318665.922   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8670.7968665.446   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8671.7018666.692   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8670.7968667.938   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8671.2728669.403   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0    8670.2418670.547   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0    8672.7788669.723   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2   11                                                            
CONECT    3   16                                                            
CONECT    4   20                                                            
CONECT    5   13                                                            
CONECT    6   12                                                            
CONECT    7   21                                                            
CONECT    8    9   18                                                       
CONECT    9    8   13                                                       
CONECT   10   11   20                                                       
CONECT   11   10   12    2                                                  
CONECT   12   11   13    6   19                                             
CONECT   13   12    9    5   21                                             
CONECT   14   15   19                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17    3                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19    8                                                  
CONECT   19   14   18    1   12                                             
CONECT   20   21   24   10    4                                             
CONECT   21   20   22   13    7                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   20   23   25                                                  
CONECT   25   24   27   26                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Value	Source
(11beta)-11-Hydroxypregn-4-ene-3,20-dione	ChEBI
21-Deoxycorticosterone	ChEBI
(11b)-11-Hydroxypregn-4-ene-3,20-dione	Generator
(11Β)-11-hydroxypregn-4-ene-3,20-dione	Generator
11b-Hydroxyprogesterone	Generator
11Β-hydroxyprogesterone	Generator
Pregn-4-ene-11 beta-ol-3,20-dione	MeSH
Hylutin	MeSH
Hyprogest	MeSH
11-Hydroxyprogesterone, (11alpha,17alpha)-(+-)-isomer	MeSH
11-Hydroxyprogesterone	MeSH
Duralutin	MeSH
Prodrox	MeSH
11 beta-Hydroxy-4-pregnen-3,20-dione	MeSH
11-Hydroxyprogesterone, (11beta)-isomer	MeSH
11-Hydroxyprogesterone, (11alpha)-(+-)-isomer	MeSH
11-Hydroxyprogesterone, (9beta,10alpha,11alpha)-isomer	MeSH
11 alpha-Hydroxyprogesterone	MeSH
11ohp Compound	MeSH
Hy-gestrone	MeSH
Pergestron	MeSH
Pro-depo	MeSH
Gesterol	MeSH
11-Hydroxyprogesterone, (11alpha)-isomer	MeSH
11beta-Hydroxy-4-pregnene-3,20-dione	HMDB
11beta-Hydroxy-P4	HMDB
11beta-Hydroxyprogesterone	HMDB
11β-Hydroxy-4-pregnene-3,20-dione	HMDB
11β-Hydroxy-P4	HMDB
Pregn-4-en-11beta-ol-3,20-dione	HMDB
Pregn-4-en-11β-ol-3,20-dione	HMDB
Pregn-4-ene-11beta-ol-3,20-dione	HMDB
Pregn-4-ene-11β-ol-3,20-dione	HMDB
delta4-Pregnene-11beta-ol-3,20-dione	HMDB
Δ4-Pregnene-11β-ol-3,20-dione	HMDB

Chemical Formula

C₂₁H₃₀O₃

Average Mass

330.4611 Da

Monoisotopic Mass

330.21949 Da

IUPAC Name

(1S,2R,10S,11S,14S,15S,17S)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Traditional Name

(1S,2R,10S,11S,14S,15S,17S)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

CAS Registry Number

Not Available

SMILES

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

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-ATWVFEABSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Mus musculus	LOTUS Database	35616633

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-delta-4-steroid
3-oxosteroid
11-hydroxysteroid
11-beta-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

11beta-hydroxy steroid (CHEBI:28247 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030168 )

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	38.12 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

HMDB0041822

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023284

KNApSAcK ID

Not Available

Chemspider ID

91968

KEGG Compound ID

C05498

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

11β-Hydroxyprogesterone

METLIN ID

Not Available

PubChem Compound

101788

PDB ID

Not Available

ChEBI ID

28247

Good Scents ID

Not Available

References

General References

Milkovic S, Klepac R, Milkovic K: Fetal rat adrenal steroidogenesis and steroid transfer to adrenalectomized mother. Endocrinol Jpn. 1976 Dec;23(6):527-30. doi: 10.1507/endocrj1954.23.527. [PubMed:1022526 ]
HUGGINS C, JENSEN EV: The depression of growth of the uterus, adrenals, and ovaries by fluorinated steroids in the pregnane series. J Exp Med. 1955 Sep 1;102(3):347-60. doi: 10.1084/jem.102.3.347. [PubMed:13252188 ]
Gueux B, Fiet J, Galons H, Bonete R, Villette JM, Vexiau P, Pham-Huu-Trung MT, Raux-Eurin MC, Gourmelen M, Brerault JL, et al.: The measurement of 11 beta-hydroxy-4-pregnene-3,20-dione (21-deoxycorticosterone) by radioimmunoassay in human plasma. J Steroid Biochem. 1987 Jan;26(1):145-50. doi: 10.1016/0022-4731(87)90043-4. [PubMed:3546944 ]
LOTUS database [Link]

Showing NP-Card for 11-β-hydroxyprogesterone (NP0315556)

MOL for NP0315556 (11-β-hydroxyprogesterone)

3D MOL for NP0315556 (11-β-hydroxyprogesterone)

3D SDF for NP0315556 (11-β-hydroxyprogesterone)

3D-SDF for NP0315556 (11-β-hydroxyprogesterone)

PDB for NP0315556 (11-β-hydroxyprogesterone)

3D PDB for NP0315556 (11-β-hydroxyprogesterone)

SMILES for NP0315556 (11-β-hydroxyprogesterone)

INCHI for NP0315556 (11-β-hydroxyprogesterone)

Structure for NP0315556 (11-β-hydroxyprogesterone)

3D Structure for NP0315556 (11-β-hydroxyprogesterone)