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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-16 15:13:08 UTC

Update Date

2022-03-07 02:49:10 UTC

HMDB ID

HMDB0001455

Secondary Accession Numbers

HMDB01455

Metabolite Identification

Common Name

Alloepipregnanolone

Description

Alloepipregnanolone, also known as 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. Based on a literature review very few articles have been published on Alloepipregnanolone.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D 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

HMDB0001455
     RDKit          3D
Alloepipregnanolone
 57 60  0  0  0  0  0  0  0  0999 V2000
    6.0004    0.1265    0.6505 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5777   -0.2423    0.8116 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2759   -1.0696    1.6537 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5242    0.3601   -0.0130 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7391    0.0886   -1.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3491   -0.1719   -2.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4673    0.2929   -1.0202 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0773   -0.1464   -0.9646 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7096   -0.0837   -2.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0929   -0.6679   -1.8983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7548    0.1625   -0.8615 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1576   -0.3186   -0.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8778    0.4923    0.4212 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9147   -0.3288    0.9213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0316    0.8871    1.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6667    1.4094    1.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9593    0.3117    0.4205 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9855   -0.9303    1.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5920    0.7857    0.0609 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3152    1.0867    1.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477    0.1265    1.3985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1867   -0.2943    0.2069 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3871   -1.7746    0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3776   -0.3711   -0.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0540    1.2306    0.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6219   -0.1542    1.5082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4075    1.4527    0.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4136   -0.7617   -1.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0943    1.0360   -1.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2329   -1.2620   -2.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2296    0.3404   -3.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5685    1.4054   -0.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0293   -1.1671   -0.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356    0.9677   -2.5182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2511   -0.7087   -3.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6670   -0.6171   -2.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9645   -1.7124   -1.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8487    1.2068   -1.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7153   -0.1521   -1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2156   -1.4127   -0.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3792    1.3909    0.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4736   -1.1874    1.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9030    0.1234    2.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5509    1.7509    2.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8012    2.2840    0.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1633    1.7242    2.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0392   -1.3350    1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3432   -1.7400    0.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7346   -0.6935    2.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7394    1.7459   -0.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135    1.1534    2.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7911    2.1084    1.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0000   -0.7891    1.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0911    0.5689    2.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4051   -2.0318   -0.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2974   -2.2173    1.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784   -2.2778   -0.5890 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  1
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 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  1
  8 33  1  1
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  6
 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


  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>
HMDB0001455

> <DATABASE_NAME>
hmdb

> <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

$$$$

HMDB0001455
     RDKit          3D
Alloepipregnanolone
 57 60  0  0  0  0  0  0  0  0999 V2000
    6.0004    0.1265    0.6505 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5777   -0.2423    0.8116 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2759   -1.0696    1.6537 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5242    0.3601   -0.0130 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7391    0.0886   -1.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3491   -0.1719   -2.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4673    0.2929   -1.0202 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0773   -0.1464   -0.9646 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7096   -0.0837   -2.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0929   -0.6679   -1.8983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7548    0.1625   -0.8615 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1576   -0.3186   -0.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8778    0.4923    0.4212 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9147   -0.3288    0.9213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0316    0.8871    1.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6667    1.4094    1.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9593    0.3117    0.4205 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9855   -0.9303    1.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5920    0.7857    0.0609 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3152    1.0867    1.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477    0.1265    1.3985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1867   -0.2943    0.2069 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3871   -1.7746    0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3776   -0.3711   -0.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0540    1.2306    0.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6219   -0.1542    1.5082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4075    1.4527    0.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4136   -0.7617   -1.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0943    1.0360   -1.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2329   -1.2620   -2.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2296    0.3404   -3.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5685    1.4054   -0.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0293   -1.1671   -0.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356    0.9677   -2.5182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2511   -0.7087   -3.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6670   -0.6171   -2.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9645   -1.7124   -1.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8487    1.2068   -1.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7153   -0.1521   -1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2156   -1.4127   -0.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3792    1.3909    0.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4736   -1.1874    1.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9030    0.1234    2.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5509    1.7509    2.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8012    2.2840    0.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1633    1.7242    2.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0392   -1.3350    1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3432   -1.7400    0.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7346   -0.6935    2.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7394    1.7459   -0.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135    1.1534    2.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7911    2.1084    1.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0000   -0.7891    1.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0911    0.5689    2.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4051   -2.0318   -0.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2974   -2.2173    1.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784   -2.2778   -0.5890 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  1
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 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  1
  8 33  1  1
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  6
 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

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

COMPND    HMDB0001455
HETATM    1  C1  UNL     1       6.000   0.126   0.651  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.578  -0.242   0.812  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.276  -1.070   1.654  1.00  0.00           O  
HETATM    4  C3  UNL     1       3.524   0.360  -0.013  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.739   0.089  -1.509  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.349  -0.172  -2.090  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.467   0.293  -1.020  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.077  -0.146  -0.965  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.710  -0.084  -2.225  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.093  -0.668  -1.898  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.755   0.162  -0.861  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.158  -0.319  -0.619  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.878   0.492   0.421  1.00  0.00           C  
HETATM   14  O2  UNL     1      -5.915  -0.329   0.921  1.00  0.00           O  
HETATM   15  C13 UNL     1      -4.032   0.887   1.579  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.667   1.409   1.191  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.959   0.312   0.421  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.986  -0.930   1.246  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.592   0.786   0.061  1.00  0.00           C  
HETATM   20  C18 UNL     1       0.315   1.087   1.190  1.00  0.00           C  
HETATM   21  C19 UNL     1       1.448   0.127   1.398  1.00  0.00           C  
HETATM   22  C20 UNL     1       2.187  -0.294   0.207  1.00  0.00           C  
HETATM   23  C21 UNL     1       2.387  -1.775   0.066  1.00  0.00           C  
HETATM   24  H1  UNL     1       6.378  -0.371  -0.274  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.054   1.231   0.551  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.622  -0.154   1.508  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.407   1.453   0.151  1.00  0.00           H  
HETATM   28  H5  UNL     1       4.414  -0.762  -1.668  1.00  0.00           H  
HETATM   29  H6  UNL     1       4.094   1.036  -1.961  1.00  0.00           H  
HETATM   30  H7  UNL     1       2.233  -1.262  -2.269  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.230   0.340  -3.072  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.568   1.405  -0.891  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.029  -1.167  -0.545  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.836   0.968  -2.518  1.00  0.00           H  
HETATM   35  H12 UNL     1      -0.251  -0.709  -3.016  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.667  -0.617  -2.821  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.964  -1.712  -1.549  1.00  0.00           H  
HETATM   38  H15 UNL     1      -2.849   1.207  -1.277  1.00  0.00           H  
HETATM   39  H16 UNL     1      -4.715  -0.152  -1.586  1.00  0.00           H  
HETATM   40  H17 UNL     1      -4.216  -1.413  -0.446  1.00  0.00           H  
HETATM   41  H18 UNL     1      -5.379   1.391   0.004  1.00  0.00           H  
HETATM   42  H19 UNL     1      -5.474  -1.187   1.139  1.00  0.00           H  
HETATM   43  H20 UNL     1      -3.903   0.123   2.353  1.00  0.00           H  
HETATM   44  H21 UNL     1      -4.551   1.751   2.089  1.00  0.00           H  
HETATM   45  H22 UNL     1      -2.801   2.284   0.515  1.00  0.00           H  
HETATM   46  H23 UNL     1      -2.163   1.724   2.098  1.00  0.00           H  
HETATM   47  H24 UNL     1      -3.039  -1.335   1.219  1.00  0.00           H  
HETATM   48  H25 UNL     1      -1.343  -1.740   0.906  1.00  0.00           H  
HETATM   49  H26 UNL     1      -1.735  -0.693   2.298  1.00  0.00           H  
HETATM   50  H27 UNL     1      -0.739   1.746  -0.521  1.00  0.00           H  
HETATM   51  H28 UNL     1      -0.214   1.153   2.187  1.00  0.00           H  
HETATM   52  H29 UNL     1       0.791   2.108   1.089  1.00  0.00           H  
HETATM   53  H30 UNL     1       1.000  -0.789   1.886  1.00  0.00           H  
HETATM   54  H31 UNL     1       2.091   0.569   2.208  1.00  0.00           H  
HETATM   55  H32 UNL     1       3.405  -2.032  -0.290  1.00  0.00           H  
HETATM   56  H33 UNL     1       2.297  -2.217   1.080  1.00  0.00           H  
HETATM   57  H34 UNL     1       1.678  -2.278  -0.589  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3    4
CONECT    4    5   22   27
CONECT    5    6   28   29
CONECT    6    7   30   31
CONECT    7    8   22   32
CONECT    8    9   19   33
CONECT    9   10   34   35
CONECT   10   11   36   37
CONECT   11   12   17   38
CONECT   12   13   39   40
CONECT   13   14   15   41
CONECT   14   42
CONECT   15   16   43   44
CONECT   16   17   45   46
CONECT   17   18   19
CONECT   18   47   48   49
CONECT   19   20   50
CONECT   20   21   51   52
CONECT   21   22   53   54
CONECT   22   23
CONECT   23   55   56   57
END

HMDB0001455
     RDKit          3D
Alloepipregnanolone
 57 60  0  0  0  0  0  0  0  0999 V2000
    6.0004    0.1265    0.6505 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5777   -0.2423    0.8116 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2759   -1.0696    1.6537 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5242    0.3601   -0.0130 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7391    0.0886   -1.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3491   -0.1719   -2.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4673    0.2929   -1.0202 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0773   -0.1464   -0.9646 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7096   -0.0837   -2.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0929   -0.6679   -1.8983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7548    0.1625   -0.8615 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1576   -0.3186   -0.6192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8778    0.4923    0.4212 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9147   -0.3288    0.9213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0316    0.8871    1.5786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6667    1.4094    1.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9593    0.3117    0.4205 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9855   -0.9303    1.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5920    0.7857    0.0609 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3152    1.0867    1.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477    0.1265    1.3985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1867   -0.2943    0.2069 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3871   -1.7746    0.0665 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3776   -0.3711   -0.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0540    1.2306    0.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6219   -0.1542    1.5082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4075    1.4527    0.1512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4136   -0.7617   -1.6681 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0943    1.0360   -1.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2329   -1.2620   -2.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2296    0.3404   -3.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5685    1.4054   -0.8913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0293   -1.1671   -0.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8356    0.9677   -2.5182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2511   -0.7087   -3.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6670   -0.6171   -2.8208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9645   -1.7124   -1.5493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8487    1.2068   -1.2765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7153   -0.1521   -1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2156   -1.4127   -0.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3792    1.3909    0.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4736   -1.1874    1.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9030    0.1234    2.3534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5509    1.7509    2.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8012    2.2840    0.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1633    1.7242    2.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0392   -1.3350    1.2188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3432   -1.7400    0.9056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7346   -0.6935    2.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7394    1.7459   -0.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2135    1.1534    2.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7911    2.1084    1.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0000   -0.7891    1.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0911    0.5689    2.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4051   -2.0318   -0.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2974   -2.2173    1.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784   -2.2778   -0.5890 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  1
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
 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  1
  8 33  1  1
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  6
 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

View in JSmol View Stereo Labels

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 Hydroxypregnan 20 one	MeSH
3 alpha Hydroxy 5 alpha pregnan 20 one	MeSH
3 alpha Hydroxy 5 beta pregnan 20 one	MeSH
3 alpha, 5 beta Tetrahydroprogesterone	MeSH
3 alpha, 5 beta-Tetrahydroprogesterone	MeSH
3 alpha-Hydroxy-5 alpha-pregnan-20-one	MeSH
3 alpha-Hydroxy-5 beta-pregnan-20-one	MeSH
3-Hydroxypregnan-20-one	MeSH
3beta Hydroxy 5alpha pregnan 20 one	MeSH
Allopregnan 3 beta ol 20 one	MeSH
Allopregnan-3 beta-ol-20-one	MeSH
Eltanolone	MeSH
Epipregnanolone	MeSH
Pregnan 3alpha ol 20 one	MeSH
Pregnan-3alpha-ol-20-one	MeSH
Pregnanolone	MeSH
Pregnanolone, (3alpha)-isomer	MeSH
Pregnanolone, (3alpha, 5beta, 17-alpha)-isomer	MeSH
Pregnanolone, (3alpha,5alpha)-isomer	MeSH
Pregnanolone, (3alpha,5beta)-isomer	MeSH
Pregnanolone, (3beta)-isomer	MeSH
Pregnanolone, (3beta, 5alpha)-isomer	MeSH
Pregnanolone, (3beta, 5alpha, 17alpha)-isomer	MeSH
Pregnanolone, (3beta, 5alpha, 8alpha, 17beta)-isomer	MeSH
Pregnanolone, (3beta, 5beta)-isomer	MeSH
Pregnanolone, (3beta, 5beta, 17alpha)-isomer	MeSH
Pregnanolone, (3beta, 5beta,14beta)-isomer	MeSH
Pregnanolone, (5alpha)-isomer	MeSH
Sepranolone	MeSH
alpha-Hydroxy-5 alpha-pregnan-20-one, 3	MeSH
alpha-Hydroxy-5 beta-pregnan-20-one, 3	MeSH
alpha-Pregnan-20-one, 3 alpha-hydroxy-5	MeSH
beta-Ol-20-one, allopregnan-3	MeSH
beta-Pregnan-20-one, 3 alpha-hydroxy-5	MeSH
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, MeSH
Isopregnanolone	HMDB

Chemical Formula

C₂₁H₃₄O₂

Average Molecular Weight

318.4935

Monoisotopic Molecular Weight

318.255880332

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

516-55-2

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

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 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	194.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0014 g/L	ALOGPS
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	175.488	31661259
DarkChem	[M-H]-	171.838	31661259
AllCCS	[M+H]+	183.358	32859911
AllCCS	[M-H]-	187.191	32859911
DeepCCS	[M-2H]-	216.176	30932474
DeepCCS	[M+Na]+	190.611	30932474
AllCCS	[M+H]+	183.4	32859911
AllCCS	[M+H-H2O]+	180.5	32859911
AllCCS	[M+NH4]+	186.0	32859911
AllCCS	[M+Na]+	186.8	32859911
AllCCS	[M-H]-	187.2	32859911
AllCCS	[M+Na-2H]-	187.7	32859911
AllCCS	[M+HCOO]-	188.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.46 minutes	32390414
Predicted by Siyang on May 30, 2022	17.457 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.36 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2755.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	444.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	225.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	194.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	527.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	719.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	706.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	102.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1346.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	495.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1610.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	419.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	466.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	263.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	443.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	12.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Alloepipregnanolone	[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	2222.5	Standard polar	33892256
Alloepipregnanolone	[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	2649.9	Standard non polar	33892256
Alloepipregnanolone	[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	2869.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Alloepipregnanolone,1TMS,isomer #1	CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2738.7	Semi standard non polar	33892256
Alloepipregnanolone,1TMS,isomer #2	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	2783.9	Semi standard non polar	33892256
Alloepipregnanolone,1TMS,isomer #3	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	2734.6	Semi standard non polar	33892256
Alloepipregnanolone,2TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2787.6	Semi standard non polar	33892256
Alloepipregnanolone,2TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2777.0	Standard non polar	33892256
Alloepipregnanolone,2TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3133.8	Standard polar	33892256
Alloepipregnanolone,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2760.9	Semi standard non polar	33892256
Alloepipregnanolone,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2765.2	Standard non polar	33892256
Alloepipregnanolone,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3230.8	Standard polar	33892256
Alloepipregnanolone,1TBDMS,isomer #1	CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	2985.7	Semi standard non polar	33892256
Alloepipregnanolone,1TBDMS,isomer #2	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	3032.5	Semi standard non polar	33892256
Alloepipregnanolone,1TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C	2995.8	Semi standard non polar	33892256
Alloepipregnanolone,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3282.4	Semi standard non polar	33892256
Alloepipregnanolone,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3254.0	Standard non polar	33892256
Alloepipregnanolone,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3369.8	Standard polar	33892256
Alloepipregnanolone,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3288.7	Semi standard non polar	33892256
Alloepipregnanolone,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3256.2	Standard non polar	33892256
Alloepipregnanolone,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@]12C	3436.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Alloepipregnanolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-1174-0292000000-fb2c0f3a1cfddb10cb08	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alloepipregnanolone GC-MS (1 TMS) - 70eV, Positive	splash10-004i-2139000000-ab8a6de8f5a129af086e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alloepipregnanolone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloepipregnanolone 10V, Positive-QTOF	splash10-0uxr-0129000000-90e5fcb36022dd1ba688	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloepipregnanolone 20V, Positive-QTOF	splash10-0uxr-0396000000-4c39fe7ccd8e0c86e179	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloepipregnanolone 40V, Positive-QTOF	splash10-0006-2490000000-7ac55935cc0d4da95860	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloepipregnanolone 10V, Negative-QTOF	splash10-014i-0029000000-fa09e69c9c0b6736d2e7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloepipregnanolone 20V, Negative-QTOF	splash10-014i-0069000000-d1d57e3e1a99da4ed11f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloepipregnanolone 40V, Negative-QTOF	splash10-0zg0-1193000000-44d1597a59ac11f16a41	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloepipregnanolone 10V, Positive-QTOF	splash10-0gb9-0029000000-87d0f95f5dbd34be3481	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloepipregnanolone 20V, Positive-QTOF	splash10-0i0v-1985000000-41959912f77ca2ce0a84	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloepipregnanolone 40V, Positive-QTOF	splash10-052b-6950000000-e08ac95bf48862f7a6a8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloepipregnanolone 10V, Negative-QTOF	splash10-014i-0009000000-bbaa566ea695ae62f84e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloepipregnanolone 20V, Negative-QTOF	splash10-014i-0019000000-2f80b71569ae462f9c19	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alloepipregnanolone 40V, Negative-QTOF	splash10-014i-0039000000-8ffa894a38bb04888d3b	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0015 +/- 0.00062 uM	Adult (>18 years old)	Both	Normal	12215085	details
Blood	Detected and Quantified	0.00034 +/- 0.000075 uM	Adult (>18 years old)	Male	Normal	10625505	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	22944140	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22944140	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.001 +/- 0.00075 uM	Adult (>18 years old)	Female	Premenstrual dysphoric disorder	12215085	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Schizophrenia	22944140	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Schizophrenia	22944140	details

Associated Disorders and Diseases

Disease References

Premenstrual dysphoric disorder
Epperson CN, Haga K, Mason GF, Sellers E, Gueorguieva R, Zhang W, Weiss E, Rothman DL, Krystal JH: Cortical gamma-aminobutyric acid levels across the menstrual cycle in healthy women and those with premenstrual dysphoric disorder: a proton magnetic resonance spectroscopy study. Arch Gen Psychiatry. 2002 Sep;59(9):851-8. [PubMed:12215085 ]
Schizophrenia
Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24. [PubMed:22944140 ]

Associated OMIM IDs

181500 (Schizophrenia)

External Links

DrugBank ID

DB12972

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Kametani, Tetsuji; Suzuki, Koji; Nemoto, Hideo. Efficient synthesis of a pregnane-type steroid. Total synthesis of (+)-5a-dihydropregnenolone [(+)-3b-hydroxy-5a-pregnan-20-one]. Journal of the Chemical Society, Perkin Transactions 1. 1980, p.2805-2807

Material Safety Data Sheet (MSDS)

Not Available

General References

Pearson Murphy BE, Steinberg SI, Hu FY, Allison CM: Neuroactive ring A-reduced metabolites of progesterone in human plasma during pregnancy: elevated levels of 5 alpha-dihydroprogesterone in depressed patients during the latter half of pregnancy. J Clin Endocrinol Metab. 2001 Dec;86(12):5981-7. [PubMed:11739473 ]
Debatin T, Barbosa AD: Effect of isopregnanolone on rapid tolerance to the anxiolytic effect of ethanol. Rev Bras Psiquiatr. 2006 Mar;28(1):18-23. Epub 2006 Mar 24. [PubMed:16612485 ]

Showing metabocard for Alloepipregnanolone (HMDB0001455)

MOL for HMDB0001455 (Alloepipregnanolone)

3D MOL for HMDB0001455 (Alloepipregnanolone)

3D SDF for HMDB0001455 (Alloepipregnanolone)

3D-SDF for HMDB0001455 (Alloepipregnanolone)

PDB for HMDB0001455 (Alloepipregnanolone)

3D PDB for HMDB0001455 (Alloepipregnanolone)

SMILES for HMDB0001455 (Alloepipregnanolone)

INCHI for HMDB0001455 (Alloepipregnanolone)

Structure for HMDB0001455 (Alloepipregnanolone)

3D Structure for HMDB0001455 (Alloepipregnanolone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra