NP-MRD: Showing NP-Card for Alloepipregnanolone (NP0086792)

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Record Information

Version

2.0

Created at

2022-05-11 16:31:08 UTC

Updated at

2022-05-11 16:31:09 UTC

NP-MRD ID

NP0086792

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Alloepipregnanolone

Description

Alloepipregnanolone, also known as 5a-dihydropregnenolone or eltanolone, 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, alloepipregnanolone is considered to be a steroid lipid molecule. Alloepipregnanolone was first documented in 2006 (PMID: 16612485). Alloepipregnanolone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv0541 02231219092D          

 27 30  0  0  1  0            999 V2000
   16.4154  -12.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4154  -12.9355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.1298  -13.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8443  -12.9355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.8443  -12.1105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.1298  -11.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5588  -13.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2733  -12.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2733  -12.1105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.5588  -11.6980    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.9878  -11.6980    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.9878  -10.8730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.2733  -10.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5588  -10.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7724  -11.9530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2573  -11.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7724  -10.6181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.0273   -9.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8343   -9.6619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4752   -9.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0740  -10.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2733  -11.2855    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.8443  -13.7605    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.0740  -12.5185    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.8443  -11.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7009  -13.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5588  -12.5230    0.0000 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  1  0  0  0  0
  6  1  1  0  0  0  0
  4  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
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 12 21  1  1  0  0  0
  9 22  1  1  0  0  0
  4 23  1  6  0  0  0
 11 24  1  6  0  0  0
  5 25  1  1  0  0  0
  2 26  1  1  0  0  0
 10 27  1  6  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
   -5.0253    1.1148    1.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7221   -0.1287    0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5830   -0.5164   -0.3300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4764   -0.8841    0.5599 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5302   -2.0770   -0.3698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1755   -2.1035   -1.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3376   -1.3212   -0.1897 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0923   -0.7281   -0.6706 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7789   -1.5760   -1.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9023   -0.6314   -1.9940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6752   -0.2422   -0.7745 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9409    0.4773   -1.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7515    0.7300    0.0534 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0173    2.0850    0.2499 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1320    0.1173    1.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7250    0.5840    1.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8760    0.5093    0.2508 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5284    1.9047   -0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6690   -0.3261    0.5920 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2308    0.2453    1.6095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5818    0.6585    1.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2518   -0.1288    0.1451 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5810    0.6699   -1.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8606    1.6768    0.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2326    0.9224    2.2613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1542    1.8228    1.1810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3971   -1.2200    1.6352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6199   -2.9983    0.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3625   -2.0330   -1.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2452   -1.7821   -2.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8076   -3.1680   -1.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274   -1.8663    0.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2444    0.2459   -1.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2249   -2.4397   -1.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2001   -1.8586   -2.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4191    0.2300   -2.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5625   -1.1673   -2.6728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0040   -1.1988   -0.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7646    1.3632   -1.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4957   -0.2494   -1.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7655    0.2432   -0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5803    2.4570    1.0411 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2548   -0.9773    1.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7397    0.5048    2.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7944    1.6374    1.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3048   -0.0052    2.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4424    2.5074    0.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3819    2.3674   -0.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5760    2.0258   -0.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0802   -1.3018    0.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2822    1.1525    2.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3435   -0.4374    2.5039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2430    0.6992    2.0926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5314    1.7328    0.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1932    1.7242   -1.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6865    0.7039   -1.2870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1329    0.2539   -2.0125 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 22  1  0
 22 23  1  6
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19  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
 22  7  1  0
 17 19  1  0
  8  7  1  0
 17 11  1  0
  7 32  1  1
  6 30  1  0
  6 31  1  0
  5 28  1  0
  5 29  1  0
  4 27  1  1
  1 24  1  0
  1 25  1  0
  1 26  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
 21 53  1  0
 21 54  1  0
 20 51  1  0
 20 52  1  0
 19 50  1  1
  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
M  END

  Mrv0541 02231219092D          

 27 30  0  0  1  0            999 V2000
   16.4154  -12.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4154  -12.9355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.1298  -13.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8443  -12.9355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.8443  -12.1105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.1298  -11.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5588  -13.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2733  -12.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2733  -12.1105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.5588  -11.6980    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.9878  -11.6980    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.9878  -10.8730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.2733  -10.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5588  -10.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7724  -11.9530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2573  -11.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7724  -10.6181    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.0273   -9.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8343   -9.6619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4752   -9.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0740  -10.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2733  -11.2855    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.8443  -13.7605    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.0740  -12.5185    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.8443  -11.2855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7009  -13.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5588  -12.5230    0.0000 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  1  0  0  0  0
  6  1  1  0  0  0  0
  4  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
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 12 21  1  1  0  0  0
  9 22  1  1  0  0  0
  4 23  1  6  0  0  0
 11 24  1  6  0  0  0
  5 25  1  1  0  0  0
  2 26  1  1  0  0  0
 10 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0086792

> <DATABASE_NAME>
NP-MRD

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

> <FORMULA>
C21H34O2

> <MOLECULAR_WEIGHT>
318.4935

> <EXACT_MASS>
318.255880332

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
38.71874784586384

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.28

> <JCHEM_LOGP>
3.9869379340000006

> <ALOGPS_LOGS>
-5.37

> <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

> <ALOGPS_SOLUBILITY>
1.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isopregnanolone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      30.642 -22.606   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      30.642 -24.146   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.976 -24.916   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      33.309 -24.146   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      33.309 -22.606   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      31.976 -21.836   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      34.643 -24.916   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      35.977 -24.146   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      35.977 -22.606   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.643 -21.836   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      37.311 -21.836   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      37.311 -20.296   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      35.977 -19.526   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      34.643 -20.296   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      38.775 -22.312   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      39.680 -21.066   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      38.775 -19.820   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      39.251 -18.356   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      40.757 -18.036   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      38.220 -17.211   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      37.471 -18.765   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0      35.977 -21.066   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      33.309 -25.686   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      37.471 -23.368   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0      33.309 -21.066   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      29.308 -24.916   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0      34.643 -23.376   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   23                                             
CONECT    5    4    6   10   25                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   22                                             
CONECT   10    9    5   14   27                                             
CONECT   11    9   12   15   24                                             
CONECT   12   11   13   17   21                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   12                                                            
CONECT   22    9                                                            
CONECT   23    4                                                            
CONECT   24   11                                                            
CONECT   25    5                                                            
CONECT   26    2                                                            
CONECT   27   10                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Value	Source
(3beta,5alpha)-3-Hydroxypregnan-20-one	ChEBI
3beta-Hydroxy-5alpha-pregnane-20-one	ChEBI
5alpha-Pregnan-3beta-ol-20-one	ChEBI
Allopregnan-3beta-ol-20-one	ChEBI
Epiallopregnanolone	Kegg
3beta-Hydroxy-5alpha-pregnan-20-one	Kegg
(3b,5a)-3-Hydroxypregnan-20-one	Generator
(3Β,5α)-3-hydroxypregnan-20-one	Generator
3b-Hydroxy-5a-pregnane-20-one	Generator
3Β-hydroxy-5α-pregnane-20-one	Generator
5a-Pregnan-3b-ol-20-one	Generator
5Α-pregnan-3β-ol-20-one	Generator
Allopregnan-3b-ol-20-one	Generator
Allopregnan-3β-ol-20-one	Generator
3b-Hydroxy-5a-pregnan-20-one	Generator
3Β-hydroxy-5α-pregnan-20-one	Generator
3-Deoxo-3b-hydroxy-5a-dihydroprogesterone	HMDB
3b-Allopregnanolone	HMDB
3b-Hydroxy-5a,17b-pregnan-20-one	HMDB
3b-Hydroxy-5a-tetrahydroprogesterone	HMDB
5a-Dihydropregnenolone	HMDB
5a-Pregnane-3b-ol-20-one	HMDB
Allopregnanolone	HMDB
Isopregnanolone	HMDB
3 alpha, 5 beta Tetrahydroprogesterone	HMDB
Allopregnan 3 beta ol 20 one	HMDB
Allopregnan-3 beta-ol-20-one	HMDB
Pregnanolone, (3beta)-isomer	HMDB
Pregnanolone, (3beta, 5alpha)-isomer	HMDB
Pregnanolone, (3beta, 5beta,14beta)-isomer	HMDB
beta-Ol-20-one, allopregnan-3	HMDB
beta-Pregnan-20-one, 3 alpha-hydroxy-5	HMDB
3 alpha Hydroxy 5 beta pregnan 20 one	HMDB
3-Hydroxypregnan-20-one	HMDB
3beta Hydroxy 5alpha pregnan 20 one	HMDB
Eltanolone	HMDB
Epipregnanolone	HMDB
Pregnanolone	HMDB
Pregnanolone, (3alpha)-isomer	HMDB
Pregnanolone, (3alpha,5alpha)-isomer	HMDB
Pregnanolone, (3beta, 5alpha, 8alpha, 17beta)-isomer	HMDB
alpha-Hydroxy-5 alpha-pregnan-20-one, 3	HMDB
3 Hydroxypregnan 20 one	HMDB
3 alpha Hydroxy 5 alpha pregnan 20 one	HMDB
3 alpha, 5 beta-Tetrahydroprogesterone	HMDB
3 alpha-Hydroxy-5 alpha-pregnan-20-one	HMDB
3 alpha-Hydroxy-5 beta-pregnan-20-one	HMDB
Pregnan 3alpha ol 20 one	HMDB
Pregnanolone, (3alpha, 5beta, 17-alpha)-isomer	HMDB
Pregnanolone, (3alpha,5beta)-isomer	HMDB
Pregnanolone, (3beta, 5alpha, 17alpha)-isomer	HMDB
alpha-Hydroxy-5 beta-pregnan-20-one, 3	HMDB
alpha-Pregnan-20-one, 3 alpha-hydroxy-5	HMDB
Pregnan-3alpha-ol-20-one	HMDB
Pregnanolone, (3beta, 5beta)-isomer	HMDB
Pregnanolone, (3beta, 5beta, 17alpha)-isomer	HMDB
Pregnanolone, (5alpha)-isomer	HMDB
Sepranolone	HMDB

Chemical Formula

C₂₁H₃₄O₂

Average Mass

318.4935 Da

Monoisotopic Mass

318.25588 Da

IUPAC Name

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

Traditional Name

isopregnanolone

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](O)CC[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-FZCSVUEKSA-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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
3-hydroxysteroid
Hydroxysteroid
3-beta-hydroxysteroid
Oxosteroid
Cyclic alcohol
Ketone
Secondary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-hydroxy-5alpha-pregnan-20-one (CHEBI:11909 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030173 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.28	ALOGPS
logP	3.99	ChemAxon
logS	-5.4	ALOGPS
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	38.72 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

HMDB0001455

DrugBank ID

DB12972

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022634

KNApSAcK ID

Not Available

Chemspider ID

83761

KEGG Compound ID

C15484

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92787

PDB ID

Not Available

ChEBI ID

11909

Good Scents ID

Not Available

References

General References

Debatin T, Barbosa AD: Effect of isopregnanolone on rapid tolerance to the anxiolytic effect of ethanol. Braz J Psychiatry. 2006 Mar;28(1):18-23. doi: 10.1590/s1516-44462006000100005. Epub 2006 Mar 24. [PubMed:16612485 ]

Showing NP-Card for Alloepipregnanolone (NP0086792)

MOL for NP0086792 (Alloepipregnanolone)

3D MOL for NP0086792 (Alloepipregnanolone)

3D SDF for NP0086792 (Alloepipregnanolone)

3D-SDF for NP0086792 (Alloepipregnanolone)

PDB for NP0086792 (Alloepipregnanolone)

3D PDB for NP0086792 (Alloepipregnanolone)

SMILES for NP0086792 (Alloepipregnanolone)

INCHI for NP0086792 (Alloepipregnanolone)

Structure for NP0086792 (Alloepipregnanolone)

3D Structure for NP0086792 (Alloepipregnanolone)