NP-MRD: Showing NP-Card for (3R,4S,5S,17R,20R)-3,17,20-trihydroxy-4-methylpregn-8-en-7-one (NP0009323)

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Record Information

Version

2.0

Created at

2020-12-09 06:44:14 UTC

Updated at

2021-07-15 17:02:56 UTC

NP-MRD ID

NP0009323

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3R,4S,5S,17R,20R)-3,17,20-trihydroxy-4-methylpregn-8-en-7-one

Provided By

NPAtlas

Description

(3R,4S,5S,17R,20R)-3,17,20-trihydroxy-4-methylpregn-8-en-7-one 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. (3R,4S,5S,17R,20R)-3,17,20-trihydroxy-4-methylpregn-8-en-7-one is found in Phellinus igniarius. Based on a literature review very few articles have been published on (3R,4S,5S,17R,20R)-3,17,20-trihydroxy-4-methylpregn-8-en-7-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106343D          

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M  END

     RDKit          3D

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  Mrv1652306242106343D          

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    3.6314    1.8180    0.1231 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7213    0.7655   -0.0284 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4000    0.5703    1.1748 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6550   -1.8945    1.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750   -1.4706    0.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0744   -0.6578   -1.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7625   -0.1243    1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6881   -2.4355    1.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3357   -2.5821   -0.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1889    1.9328    1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1542    2.5816   -0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8195    1.9128   -1.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414    2.3496    0.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2951   -0.6920   -1.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7866    0.1714   -2.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9438   -1.4064   -1.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4889   -0.0063    1.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0447   -2.4877    0.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9432   -2.3881    1.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0556   -1.4807    2.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1935   -1.8151    0.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5263    0.3456    2.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6713    0.2383    0.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3805    2.3633   -1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0160    2.1908   -0.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6830    2.5185    0.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5643   -0.9526   -1.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4376   -0.4809   -2.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7727    0.0980   -2.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1762   -1.4635   -1.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9795    2.4470   -1.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1767    1.3600   -1.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2117    1.8646    1.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0983    2.7921   -0.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4204    1.0575   -0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7890    1.4072    1.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25  2  1  0  0  0  0
 21  3  1  0  0  0  0
 13  7  1  0  0  0  0
 16 11  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  2 30  1  6  0  0  0
  3 31  1  1  0  0  0
  4 32  1  0  0  0  0
  4 33  1  0  0  0  0
  9 34  1  0  0  0  0
  9 35  1  0  0  0  0
 10 36  1  0  0  0  0
 10 37  1  0  0  0  0
 12 38  1  0  0  0  0
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 15 44  1  0  0  0  0
 15 45  1  0  0  0  0
 17 46  1  0  0  0  0
 18 47  1  1  0  0  0
 19 48  1  0  0  0  0
 19 49  1  0  0  0  0
 19 50  1  0  0  0  0
 20 51  1  0  0  0  0
 22 52  1  0  0  0  0
 22 53  1  0  0  0  0
 22 54  1  0  0  0  0
 23 55  1  0  0  0  0
 23 56  1  0  0  0  0
 24 57  1  0  0  0  0
 24 58  1  0  0  0  0
 25 59  1  6  0  0  0
 26 60  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0009323

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]([H])(C([H])([H])[H])[C@@]1(O[H])C([H])([H])C([H])([H])[C@@]2([H])C3=C(C([H])([H])C([H])([H])[C@]12C([H])([H])[H])[C@@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]([H])(O[H])[C@@]([H])(C([H])([H])[H])[C@]1([H])C([H])([H])C3=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O4/c1-12-16-11-18(25)19-14(20(16,3)8-7-17(12)24)5-9-21(4)15(19)6-10-22(21,26)13(2)23/h12-13,15-17,23-24,26H,5-11H2,1-4H3/t12-,13+,15-,16-,17+,20+,21-,22-/m0/s1

> <INCHI_KEY>
MHAYDOHKEQXCEG-GLVQIBCTSA-N

> <FORMULA>
C22H34O4

> <MOLECULAR_WEIGHT>
362.51

> <EXACT_MASS>
362.245709575

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
41.46514689346161

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,5R,6S,7S,11R,14R,15S)-5,14-dihydroxy-14-[(1R)-1-hydroxyethyl]-2,6,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-9-one

> <ALOGPS_LOGP>
2.28

> <JCHEM_LOGP>
2.1024507163333324

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.107095436762904

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.407428865178826

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0393214118153975

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
100.98010000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5R,6S,7S,11R,14R,15S)-5,14-dihydroxy-14-[(1R)-1-hydroxyethyl]-2,6,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
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    0.5279    0.4595   -0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2328    1.6993    0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.2784    0.2380   -0.0035 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -4.9353    2.0059   -0.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9418   -0.2097   -1.1912 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5729   -0.4517   -1.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5680    1.5634   -0.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6314    1.8180    0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7213    0.7655   -0.0284 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4000    0.5703    1.1748 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9750   -1.4706    0.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7625   -0.1243    1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3357   -2.5821   -0.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1889    1.9328    1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1542    2.5816   -0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8195    1.9128   -1.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414    2.3496    0.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0447   -2.4877    0.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9432   -2.3881    1.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0556   -1.4807    2.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1935   -1.8151    0.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5263    0.3456    2.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3805    2.3633   -1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0160    2.1908   -0.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6830    2.5185    0.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5643   -0.9526   -1.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4376   -0.4809   -2.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7727    0.0980   -2.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1762   -1.4635   -1.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9795    2.4470   -1.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1767    1.3600   -1.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2117    1.8646    1.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0983    2.7921   -0.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4204    1.0575   -0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7890    1.4072    1.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 18 20  1  0
  8 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25  2  1  0
 21  3  1  0
 13  7  1  0
 16 11  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  6
  3 31  1  1
  4 32  1  0
  4 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  1
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 17 46  1  0
 18 47  1  1
 19 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  6
 26 60  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       4.910  -1.721   0.189  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.080  -0.586  -0.373  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.697  -0.552   0.209  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.166  -1.962   0.335  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.675  -1.934   0.548  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.129  -3.038   0.770  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.030  -0.656   0.488  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.528   0.460  -0.004  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.233   1.699   0.193  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.694   1.588  -0.139  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.278   0.238  -0.004  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.335  -0.478  -1.325  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.399  -0.552   0.981  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.181  -1.820   1.060  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.630  -1.306   1.121  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.572   0.162   0.752  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.467   0.913   1.900  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.783   0.519  -0.018  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.935   2.006  -0.258  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.942  -0.210  -1.191  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.816   0.304  -0.667  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.573  -0.452  -1.972  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.568   1.563  -0.951  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.631   1.818   0.123  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.721   0.766  -0.028  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.400   0.570   1.175  0.00  0.00           O+0
HETATM   27  H   UNK     0       4.655  -1.895   1.248  0.00  0.00           H+0
HETATM   28  H   UNK     0       5.975  -1.471   0.048  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.721  -2.633  -0.414  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.074  -0.658  -1.457  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.763  -0.124   1.240  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.688  -2.436   1.191  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.336  -2.582  -0.549  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.189   1.933   1.299  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.154   2.582  -0.308  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.819   1.913  -1.213  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.241   2.350   0.456  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.295  -0.692  -1.648  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.787   0.171  -2.083  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.944  -1.406  -1.281  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.489  -0.006   1.943  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.045  -2.488   0.194  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.943  -2.388   1.976  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.056  -1.481   2.124  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.194  -1.815   0.308  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.526   0.346   2.716  0.00  0.00           H+0
HETATM   47  H   UNK     0      -5.671   0.238   0.625  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.380   2.363  -1.136  0.00  0.00           H+0
HETATM   49  H   UNK     0      -6.016   2.191  -0.457  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.683   2.519   0.682  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.564  -0.953  -1.109  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.438  -0.481  -2.633  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.773   0.098  -2.549  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.176  -1.464  -1.813  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.980   2.447  -1.176  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.177   1.360  -1.885  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.212   1.865   1.126  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.098   2.792  -0.136  0.00  0.00           H+0
HETATM   59  H   UNK     0       5.420   1.058  -0.814  0.00  0.00           H+0
HETATM   60  H   UNK     0       5.789   1.407   1.516  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    1    3   25   30                                             
CONECT    3    2    4   21   31                                             
CONECT    4    3    5   32   33                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   13                                                  
CONECT    8    7    9   21                                                  
CONECT    9    8   10   34   35                                             
CONECT   10    9   11   36   37                                             
CONECT   11   10   12   13   16                                             
CONECT   12   11   38   39   40                                             
CONECT   13   11   14    7   41                                             
CONECT   14   13   15   42   43                                             
CONECT   15   14   16   44   45                                             
CONECT   16   15   17   18   11                                             
CONECT   17   16   46                                                       
CONECT   18   16   19   20   47                                             
CONECT   19   18   48   49   50                                             
CONECT   20   18   51                                                       
CONECT   21    8   22   23    3                                             
CONECT   22   21   52   53   54                                             
CONECT   23   21   24   55   56                                             
CONECT   24   23   25   57   58                                             
CONECT   25   24   26    2   59                                             
CONECT   26   25   60                                                       
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    2                                                            
CONECT   31    3                                                            
CONECT   32    4                                                            
CONECT   33    4                                                            
CONECT   34    9                                                            
CONECT   35    9                                                            
CONECT   36   10                                                            
CONECT   37   10                                                            
CONECT   38   12                                                            
CONECT   39   12                                                            
CONECT   40   12                                                            
CONECT   41   13                                                            
CONECT   42   14                                                            
CONECT   43   14                                                            
CONECT   44   15                                                            
CONECT   45   15                                                            
CONECT   46   17                                                            
CONECT   47   18                                                            
CONECT   48   19                                                            
CONECT   49   19                                                            
CONECT   50   19                                                            
CONECT   51   20                                                            
CONECT   52   22                                                            
CONECT   53   22                                                            
CONECT   54   22                                                            
CONECT   55   23                                                            
CONECT   56   23                                                            
CONECT   57   24                                                            
CONECT   58   24                                                            
CONECT   59   25                                                            
CONECT   60   26                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  126    0
END

RDKit          3D

60 63  0  0  0  0  0  0  0  0999 V2000
    4.9100   -1.7208    0.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0803   -0.5855   -0.3725 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6971   -0.5523    0.2087 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1663   -1.9616    0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6747   -1.9335    0.5484 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1294   -3.0380    0.7695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0301   -0.6561    0.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5279    0.4595   -0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2328    1.6993    0.1931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6941    1.5876   -0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2784    0.2380   -0.0035 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3347   -0.4784   -1.3245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3992   -0.5517    0.9810 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1812   -1.8199    1.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6301   -1.3062    1.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5725    0.1618    0.7516 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4668    0.9127    1.9004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7830    0.5192   -0.0178 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9353    2.0059   -0.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9418   -0.2097   -1.1912 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8161    0.3038   -0.6672 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5729   -0.4517   -1.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5680    1.5634   -0.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6314    1.8180    0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7213    0.7655   -0.0284 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4000    0.5703    1.1748 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6550   -1.8945    1.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750   -1.4706    0.0481 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7205   -2.6326   -0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0744   -0.6578   -1.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7625   -0.1243    1.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6881   -2.4355    1.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3357   -2.5821   -0.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1889    1.9328    1.2993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1542    2.5816   -0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8195    1.9128   -1.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414    2.3496    0.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2951   -0.6920   -1.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7866    0.1714   -2.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9438   -1.4064   -1.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4889   -0.0063    1.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0447   -2.4877    0.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9432   -2.3881    1.9761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0556   -1.4807    2.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1935   -1.8151    0.3084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5263    0.3456    2.7161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6713    0.2383    0.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3805    2.3633   -1.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0160    2.1908   -0.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6830    2.5185    0.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5643   -0.9526   -1.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4376   -0.4809   -2.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7727    0.0980   -2.5485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1762   -1.4635   -1.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9795    2.4470   -1.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1767    1.3600   -1.8848 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2117    1.8646    1.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0983    2.7921   -0.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4204    1.0575   -0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7890    1.4072    1.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
 16 18  1  0
 18 19  1  0
 18 20  1  0
  8 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25  2  1  0
 21  3  1  0
 13  7  1  0
 16 11  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  6
  3 31  1  1
  4 32  1  0
  4 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 12 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  1
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 17 46  1  0
 18 47  1  1
 19 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  6
 26 60  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₂H₃₄O₄

Average Mass

362.5100 Da

Monoisotopic Mass

362.24571 Da

IUPAC Name

(2S,5R,6S,7S,11R,14R,15S)-5,14-dihydroxy-14-[(1R)-1-hydroxyethyl]-2,6,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-9-one

Traditional Name

(2S,5R,6S,7S,11R,14R,15S)-5,14-dihydroxy-14-[(1R)-1-hydroxyethyl]-2,6,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-9-one

CAS Registry Number

Not Available

SMILES

C[C@@H](O)[C@@]1(O)CC[C@H]2C3=C(CC[C@]12C)[C@@]1(C)CC[C@@H](O)[C@@H](C)[C@@H]1CC3=O

InChI Identifier

InChI=1S/C22H34O4/c1-12-16-11-18(25)19-14(20(16,3)8-7-17(12)24)5-9-21(4)15(19)6-10-22(21,26)13(2)23/h12-13,15-17,23-24,26H,5-11H2,1-4H3/t12-,13+,15-,16-,17+,20+,21-,22-/m0/s1

InChI Key

MHAYDOHKEQXCEG-GLVQIBCTSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Phellinus igniarius	NPAtlas	20583752

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

20-hydroxysteroid
Androgen-skeleton
3-hydroxysteroid
Hydroxysteroid
Oxosteroid
3-alpha-hydroxysteroid
17-hydroxysteroid
7-oxosteroid
Cyclohexenone
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Organooxygen compound
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic homopolycyclic compound

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	2.28	ALOGPS
logP	2.1	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	13.41	ChemAxon
pKa (Strongest Basic)	-1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	100.98 m³·mol⁻¹	ChemAxon
Polarizability	41.47 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

NPAtlas ID

NPA003779

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28287922

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46872462

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (3R,4S,5S,17R,20R)-3,17,20-trihydroxy-4-methylpregn-8-en-7-one (NP0009323)

MOL for NP0009323 ((3R,4S,5S,17R,20R)-3,17,20-trihydroxy-4-methylpregn-8-en-7-one)

3D MOL for NP0009323 ((3R,4S,5S,17R,20R)-3,17,20-trihydroxy-4-methylpregn-8-en-7-one)

3D SDF for NP0009323 ((3R,4S,5S,17R,20R)-3,17,20-trihydroxy-4-methylpregn-8-en-7-one)

3D-SDF for NP0009323 ((3R,4S,5S,17R,20R)-3,17,20-trihydroxy-4-methylpregn-8-en-7-one)

PDB for NP0009323 ((3R,4S,5S,17R,20R)-3,17,20-trihydroxy-4-methylpregn-8-en-7-one)

3D PDB for NP0009323 ((3R,4S,5S,17R,20R)-3,17,20-trihydroxy-4-methylpregn-8-en-7-one)

SMILES for NP0009323 ((3R,4S,5S,17R,20R)-3,17,20-trihydroxy-4-methylpregn-8-en-7-one)

INCHI for NP0009323 ((3R,4S,5S,17R,20R)-3,17,20-trihydroxy-4-methylpregn-8-en-7-one)

Structure for NP0009323 ((3R,4S,5S,17R,20R)-3,17,20-trihydroxy-4-methylpregn-8-en-7-one)

3D Structure for NP0009323 ((3R,4S,5S,17R,20R)-3,17,20-trihydroxy-4-methylpregn-8-en-7-one)