NP-MRD: Showing NP-Card for 1-[(5as,7r,9as,11as)-7-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethanone (NP0256561)

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Record Information

Version

2.0

Created at

2022-09-07 21:26:16 UTC

Updated at

2022-09-07 21:26:17 UTC

NP-MRD ID

NP0256561

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-[(5as,7r,9as,11as)-7-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethanone

Description

Allopregnanolone 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. 1-[(5as,7r,9as,11as)-7-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethanone is found in Homo sapiens. 1-[(5as,7r,9as,11as)-7-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethanone was first documented in 2022 (PMID: 35931327). Based on a literature review a significant number of articles have been published on Allopregnanolone (PMID: 36084357) (PMID: 36044784) (PMID: 36029538) (PMID: 35974667) (PMID: 35967446) (PMID: 35963123).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    5.3510    1.1889    1.4709 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9780    0.6123    1.4832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3132    0.7038    2.4786 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4998   -0.0431    0.2743 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5021    0.9637   -0.8683 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4874    0.4534   -1.8501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5922   -0.5111   -1.1006 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1629   -0.0847   -1.1206 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0714    1.3736   -0.9155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1717    1.7478   -0.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2644    0.7840    0.1894 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6110    1.2824   -0.3555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6858    0.3401    0.0829 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5832    1.0924    0.8803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2357   -0.8132    0.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0042   -1.5136    0.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0684   -0.5827   -0.3480 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4026   -0.7103   -1.8226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6165   -0.9681   -0.1915 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1201   -0.9323    1.2049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2577   -0.3137    1.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1806   -0.7000    0.2781 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4547   -2.2037    0.4929 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2988    2.3146    1.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9783    0.7708    0.6553 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9008    0.9916    2.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3335   -0.7687   -0.0228 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2934    1.9952   -0.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4878    1.0157   -1.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9892   -0.0116   -2.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9150    1.3221   -2.2577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6564   -1.4745   -1.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2196   -0.3308   -2.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2057    1.9027   -1.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9065    1.8027   -0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6370    2.7128   -0.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7237    2.0637    0.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4617    0.6761    1.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5836    1.4124   -1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7253    2.3138    0.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3066    0.0579   -0.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4587    0.8663    1.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1378   -0.5204    1.9646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0594   -1.5809    0.8834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2242   -2.4191   -0.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4429   -1.8697    1.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4839   -1.0079   -1.9585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1783    0.1839   -2.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8272   -1.5853   -2.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5397   -2.0130   -0.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1437   -1.9674    1.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7945   -0.3435    1.8828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6346   -0.8059    2.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1915    0.7616    1.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3508   -2.4184   -0.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417   -2.4266    1.5468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6304   -2.7860    0.0481 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  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 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  6
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  1
 12 39  1  0
 12 40  1  0
 13 41  1  6
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 18 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  6
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
M  END


  Mrv1652309072223262D          

 23 26  0  0  1  0            999 V2000
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  4 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0256561

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1CCC2C3CC[C@H]4C[C@H](O)CC[C@]4(C)C3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C21H34O2/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/h14-19,23H,4-12H2,1-3H3/t14-,15+,16?,17?,18?,19?,20-,21+/m0/s1

> <INCHI_KEY>
AURFZBICLPNKBZ-SUZPBREPSA-N

> <FORMULA>
C21H34O2

> <MOLECULAR_WEIGHT>
318.501

> <EXACT_MASS>
318.255880335

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
38.38699484529886

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(2S,5R,7S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one

> <JCHEM_LOGP>
3.9869379340000006

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.403041090785273

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.296396321121705

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569558150513044

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
92.90669999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-[(2S,5R,7S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethanone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.363  -7.289   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   22                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   22                                                  
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   11   18   19                                             
CONECT   18   17                                                            
CONECT   19   17    8   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    4    7   23                                             
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₄O₂

Average Mass

318.5010 Da

Monoisotopic Mass

318.25588 Da

IUPAC Name

1-[(2S,5R,7S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one

Traditional Name

1-[(2S,5R,7S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethanone

CAS Registry Number

Not Available

SMILES

CC(=O)C1CCC2C3CC[C@H]4C[C@H](O)CC[C@]4(C)C3CC[C@]12C

InChI Identifier

InChI=1S/C21H34O2/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/h14-19,23H,4-12H2,1-3H3/t14-,15+,16?,17?,18?,19?,20-,21+/m0/s1

InChI Key

AURFZBICLPNKBZ-SUZPBREPSA-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
Homo sapiens	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-alpha-hydroxysteroid
Oxosteroid
Hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	3.99	ChemAxon
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.91 m³·mol⁻¹	ChemAxon
Polarizability	38.39 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21396097

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Allopregnanolone

METLIN ID

Not Available

PubChem Compound

16760287

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bukanova JV, Kondratenko RV, Solntseva EI: Positive allosteric modulators of GABA(A) receptor restore chloride current from blockade by competitive antagonists in a ligand-dependent manner. J Steroid Biochem Mol Biol. 2022 Aug 2;224:106158. doi: 10.1016/j.jsbmb.2022.106158. [PubMed:35931327 ]
Potter NA, Arita Y, Peltier MR, Zelikoff JT: Ex vivo toxicity of E-cigarette constituents on human placental tissues. J Reprod Immunol. 2022 Dec;154:103737. doi: 10.1016/j.jri.2022.103737. Epub 2022 Aug 30. [PubMed:36084357 ]
Kim JL, Kim SS, Hwang KS, Park HC, Cho SH, Bae MA, Kim KT: Chronic exposure to butyl-paraben causes photosensitivity disruption and memory impairment in adult zebrafish. Aquat Toxicol. 2022 Oct;251:106279. doi: 10.1016/j.aquatox.2022.106279. Epub 2022 Aug 24. [PubMed:36044784 ]
Garcia-Baos A, Gallego-Landin I, Ferreres-Alvarez I, Puig-Reyne X, Castro-Zavala A, Valverde O, Martin-Sanchez A: Effects of fast-acting antidepressant drugs on a postpartum depression mice model. Biomed Pharmacother. 2022 Oct;154:113598. doi: 10.1016/j.biopha.2022.113598. Epub 2022 Aug 25. [PubMed:36029538 ]
Ciccone N, Kovacheff MB, Frey BN: The pharmacotherapeutic management of premenstrual dysphoric disorder. Expert Opin Pharmacother. 2023 Jan;24(1):145-151. doi: 10.1080/14656566.2022.2114345. Epub 2022 Aug 22. [PubMed:35974667 ]
Balan I, Aurelian L, Williams KS, Campbell B, Meeker RB, Morrow AL: Inhibition of human macrophage activation via pregnane neurosteroid interactions with toll-like receptors: Sex differences and structural requirements. Front Immunol. 2022 Jul 29;13:940095. doi: 10.3389/fimmu.2022.940095. eCollection 2022. [PubMed:35967446 ]
Marciniak E, Mlotkowska P, Roszkowicz-Ostrowska K, Ciska E, Misztal T: Involvement of neurosteroids in the control of prolactin secretion in sheep under basal, stressful and pregnancy conditions. Theriogenology. 2022 Sep 15;190:73-80. doi: 10.1016/j.theriogenology.2022.08.013. Epub 2022 Aug 6. [PubMed:35963123 ]
Hatipoglu E, Hacioglu Y, Polat Y, Arslan HF, Oner S, Ekmekci OB, Niyazoglu M: Do neurosteroids have impact on depression and cognitive functions in cases with acromegaly? Growth Horm IGF Res. 2022 Oct;66:101496. doi: 10.1016/j.ghir.2022.101496. Epub 2022 Jul 27. [PubMed:35952406 ]
Cai H, Zeng C, Zhang X, Liu Y, Wu R, Guo W, Wang J, Wu H, Tang H, Ge X, Yu Y, Zhang S, Cao T, Li N, Liang X, Yang P, Zhang B: Diminished treatment response in relapsed versus first-episode schizophrenia as revealed by a panel of blood-based biomarkers: A combined cross-sectional and longitudinal study. Psychiatry Res. 2022 Oct;316:114762. doi: 10.1016/j.psychres.2022.114762. Epub 2022 Aug 3. [PubMed:35940088 ]
Germann AL, Burbridge AB, Pierce SR, Akk G: Activation of the Rat alpha1beta2epsilon GABA(A) Receptor by Orthosteric and Allosteric Agonists. Biomolecules. 2022 Jun 21;12(7):868. doi: 10.3390/biom12070868. [PubMed:35883422 ]
Mincheva G, Gimenez-Garzo C, Izquierdo-Altarejos P, Martinez-Garcia M, Doverskog M, Blackburn TP, Hallgren A, Backstrom T, Llansola M, Felipo V: Golexanolone, a GABA(A) receptor modulating steroid antagonist, restores motor coordination and cognitive function in hyperammonemic rats by dual effects on peripheral inflammation and neuroinflammation. CNS Neurosci Ther. 2022 Nov;28(11):1861-1874. doi: 10.1111/cns.13926. Epub 2022 Jul 26. [PubMed:35880480 ]
Wald J, Henningsson A, Hanze E, Hoffmann E, Li H, Colquhoun H, Deligiannidis KM: Allopregnanolone Concentrations in Breast Milk and Plasma from Healthy Volunteers Receiving Brexanolone Injection, With Population Pharmacokinetic Modeling of Potential Relative Infant Dose. Clin Pharmacokinet. 2022 Sep;61(9):1307-1319. doi: 10.1007/s40262-022-01155-w. Epub 2022 Jul 23. [PubMed:35869362 ]
Qrareya AN, Mahdi F, Kaufman MJ, Ashpole NM, Paris JJ: Age-related neuroendocrine, cognitive, and behavioral co-morbidities are promoted by HIV-1 Tat expression in male mice. Aging (Albany NY). 2022 Jul 12;14(13):5345-5365. doi: 10.18632/aging.204166. Epub 2022 Jul 12. [PubMed:35830469 ]
Moncayo JA, Ayala IN, Argudo JM, Aguirre AS, Parwani J, Pachano A, Ojeda D, Cordova S, Mora MG, Tapia CM, Ortiz JF: Understanding Protein Protocadherin-19 (PCDH19) Syndrome: A Literature Review of the Pathophysiology. Cureus. 2022 Jun 10;14(6):e25808. doi: 10.7759/cureus.25808. eCollection 2022 Jun. [PubMed:35822151 ]
Boi L, Petralla S, Monti B, Talani G, Sanna E, Pisu MG, Calderisi G, Maciocco E, Serra M, Concas A, Porcu P: Chronic treatment with hormonal contraceptives alters hippocampal BDNF and histone H3 post-translational modifications but not learning and memory in female rats. Horm Behav. 2022 Aug;144:105218. doi: 10.1016/j.yhbeh.2022.105218. Epub 2022 Jul 1. [PubMed:35785712 ]
Gilfarb RA, Leuner B: GABA System Modifications During Periods of Hormonal Flux Across the Female Lifespan. Front Behav Neurosci. 2022 Jun 16;16:802530. doi: 10.3389/fnbeh.2022.802530. eCollection 2022. [PubMed:35783228 ]
Vasiliu O: Investigational Drugs for the Treatment of Depression (Part 1): Monoaminergic, Orexinergic, GABA-Ergic, and Anti-Inflammatory Agents. Front Pharmacol. 2022 Jun 14;13:884143. doi: 10.3389/fphar.2022.884143. eCollection 2022. [PubMed:35774601 ]
Bassani TB, Bartolomeo CS, Oliveira RB, Ureshino RP: Progestogen-Mediated Neuroprotection in Central Nervous System Disorders. Neuroendocrinology. 2023;113(1):14-35. doi: 10.1159/000525677. Epub 2022 Jun 27. [PubMed:35760047 ]
LOTUS database [Link]

Showing NP-Card for 1-[(5as,7r,9as,11as)-7-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethanone (NP0256561)

MOL for NP0256561 (1-[(5as,7r,9as,11as)-7-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethanone)

3D MOL for NP0256561 (1-[(5as,7r,9as,11as)-7-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethanone)

3D SDF for NP0256561 (1-[(5as,7r,9as,11as)-7-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethanone)

3D-SDF for NP0256561 (1-[(5as,7r,9as,11as)-7-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethanone)

PDB for NP0256561 (1-[(5as,7r,9as,11as)-7-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethanone)

3D PDB for NP0256561 (1-[(5as,7r,9as,11as)-7-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethanone)

SMILES for NP0256561 (1-[(5as,7r,9as,11as)-7-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethanone)

INCHI for NP0256561 (1-[(5as,7r,9as,11as)-7-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethanone)

Structure for NP0256561 (1-[(5as,7r,9as,11as)-7-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethanone)

3D Structure for NP0256561 (1-[(5as,7r,9as,11as)-7-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]ethanone)