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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-16 15:10:22 UTC

Update Date

2022-03-07 02:49:10 UTC

HMDB ID

HMDB0001449

Secondary Accession Numbers

HMDB01449

Metabolite Identification

Common Name

Allopregnanolone

Description

Allopregnanolone is a neuroactive metabolite of progesterone and a barbiturate-like modulator of central gamma-aminobutyric acid receptors that modify a range of behaviors, including the stress response. is a steroid created in the body when progesterone, the female sex hormone, is metabolized. Typically, THP (allopregnanolone) is released in the brain in response to stress, and quiets the neural system within 30 minutes of escalation. This steroid hormone has recently been found to be responsible for the extreme mood swings found in teenagers. In adults and pre-pubescent chlidren THP normally helps soothe the activity of brain cells by binding to GABA receptors that inhibit accelerating electrical activity. However, in pubescent teenagers THP actually becomes a GABA receptor antagonist. GABA (gamma-aminobutyric acid) is the primary inhibitory neurotransmitter in the brain with most sedatives (tranquilizers, anesthetics and alcohol) acting on the GABA receptor.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652311181917402D          

 28 31  0  0  0  0            999 V2000
10000.696110000.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.834910001.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8349 9999.1494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5576 9998.3162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.6961 9997.9027    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10002.121210000.3838    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.4097 9999.1494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9842 9999.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2697 9999.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2697 9998.7307    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.9842 9998.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6954 9999.5558    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.6954 9998.7307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.4099 9998.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1244 9998.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.122510001.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.408010000.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4080 9999.9766    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.1225 9999.5642    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.837010000.8016    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.8370 9999.9767    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.6216 9999.7217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.106510000.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.621610001.0567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10003.621610001.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.335210002.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.905910002.2921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.335210001.4671    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 10  4  1  6  0  0  0
 11 13  1  0  0  0  0
 13  5  1  6  0  0  0
  8 12  1  0  0  0  0
 12  1  1  1  0  0  0
 18 12  1  0  0  0  0
 18  7  1  6  0  0  0
 15 19  1  0  0  0  0
 19  6  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 24 28  1  6  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 24 20  1  0  0  0  0
 24 23  1  0  0  0  0
 19 21  1  0  0  0  0
 21  3  1  6  0  0  0
 16 20  1  0  0  0  0
 20  2  1  1  0  0  0
M  END

HMDB0001449
     RDKit          3D
Allopregnanolone
 57 60  0  0  0  0  0  0  0  0999 V2000
   -6.0152   -1.0465   -0.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7004   -0.7948    0.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6453   -0.6823    1.7375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4993   -0.6880   -0.2899 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7084    0.4688   -1.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4299    1.2838   -1.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4600    0.2905   -0.6891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1454    0.7811   -0.2608 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6520    1.4450   -1.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7843    0.6485   -1.8896 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7059    0.0798   -0.8669 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0300    0.7573   -0.7392 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247    0.0517    0.3184 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0774   -0.2696   -0.2594 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2350   -1.2275    0.7965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7990   -1.1816    1.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0282   -0.0769    0.4980 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1679    1.1562    1.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -0.4496    0.2202 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0812   -1.1233    1.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5042   -1.4567    1.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2440   -0.2710    0.4689 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5433    0.6672    1.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4040   -0.0592   -0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7561   -1.4603    0.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9356   -1.6973   -0.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2432   -1.6171   -0.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5895    1.0732   -0.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9300    0.0611   -2.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1535    1.6710   -2.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5642    2.1304   -0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3419   -0.5478   -1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2465    1.5346    0.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0130    2.4535   -1.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0689    1.6134   -2.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3737    1.3060   -2.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3503   -0.1385   -2.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282   -0.9785   -1.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9458    1.8527   -0.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5196    0.6872   -1.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0966    0.7601    1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4882    0.5307   -0.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8203   -1.5395    1.7036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4495   -2.0249    0.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3352   -2.1429    0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6229   -1.1646    2.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273    1.3927    1.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9393    1.0311    2.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4406    2.0613    0.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6131   -1.1612   -0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4362   -2.0842    1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0142   -0.5089    2.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5520   -2.3501    0.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0054   -1.7482    1.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7128    1.3625    1.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4509    1.2845    1.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118    0.0549    2.5286 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  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  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  1
 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


  Mrv1652311181917402D          

 28 31  0  0  0  0            999 V2000
10000.696110000.3838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.834910001.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8349 9999.1494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5576 9998.3162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.6961 9997.9027    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10002.121210000.3838    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.4097 9999.1494    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9842 9999.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2697 9999.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2697 9998.7307    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.9842 9998.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6954 9999.5558    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.6954 9998.7307    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10001.4099 9998.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1244 9998.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.122510001.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.408010000.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4080 9999.9766    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.1225 9999.5642    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.837010000.8016    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.8370 9999.9767    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.6216 9999.7217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.106510000.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.621610001.0567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10003.621610001.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.335210002.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.905910002.2921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.335210001.4671    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 10  4  1  6  0  0  0
 11 13  1  0  0  0  0
 13  5  1  6  0  0  0
  8 12  1  0  0  0  0
 12  1  1  1  0  0  0
 18 12  1  0  0  0  0
 18  7  1  6  0  0  0
 15 19  1  0  0  0  0
 19  6  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 24 28  1  6  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 24 20  1  0  0  0  0
 24 23  1  0  0  0  0
 19 21  1  0  0  0  0
 21  3  1  6  0  0  0
 16 20  1  0  0  0  0
 20  2  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0001449

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)=O

> <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-SYBPFIFISA-N

> <FORMULA>
C21H34O2

> <MOLECULAR_WEIGHT>
318.4935

> <EXACT_MASS>
318.255880332

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
38.51514782441207

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]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>
1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethanone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0001449
     RDKit          3D
Allopregnanolone
 57 60  0  0  0  0  0  0  0  0999 V2000
   -6.0152   -1.0465   -0.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7004   -0.7948    0.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6453   -0.6823    1.7375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4993   -0.6880   -0.2899 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7084    0.4688   -1.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4299    1.2838   -1.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4600    0.2905   -0.6891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1454    0.7811   -0.2608 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6520    1.4450   -1.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7843    0.6485   -1.8896 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7059    0.0798   -0.8669 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0300    0.7573   -0.7392 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247    0.0517    0.3184 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0774   -0.2696   -0.2594 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2350   -1.2275    0.7965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7990   -1.1816    1.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0282   -0.0769    0.4980 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1679    1.1562    1.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -0.4496    0.2202 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0812   -1.1233    1.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5042   -1.4567    1.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2440   -0.2710    0.4689 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5433    0.6672    1.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4040   -0.0592   -0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7561   -1.4603    0.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9356   -1.6973   -0.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2432   -1.6171   -0.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5895    1.0732   -0.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9300    0.0611   -2.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1535    1.6710   -2.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5642    2.1304   -0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3419   -0.5478   -1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2465    1.5346    0.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0130    2.4535   -1.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0689    1.6134   -2.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3737    1.3060   -2.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3503   -0.1385   -2.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282   -0.9785   -1.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9458    1.8527   -0.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5196    0.6872   -1.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0966    0.7601    1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4882    0.5307   -0.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8203   -1.5395    1.7036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4495   -2.0249    0.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3352   -2.1429    0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6229   -1.1646    2.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273    1.3927    1.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9393    1.0311    2.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4406    2.0613    0.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6131   -1.1612   -0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4362   -2.0842    1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0142   -0.5089    2.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5520   -2.3501    0.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0054   -1.7482    1.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7128    1.3625    1.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4509    1.2845    1.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118    0.0549    2.5286 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  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  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  1
 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                                 18-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-NOV-19         0                                  
HETATM    1  C   UNK     0    8667.9668667.383   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8671.9588669.713   0.000  0.00  0.00           C+0
HETATM    3  H   UNK     0    8671.9588665.079   0.000  0.00  0.00           H+0
HETATM    4  O   UNK     0    8663.9748663.524   0.000  0.00  0.00           O+0
HETATM    5  H   UNK     0    8667.9668662.752   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8670.6268667.383   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8669.2988665.079   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0    8666.6378666.607   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8665.3038665.837   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8665.3038664.297   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8666.6378663.527   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8667.9658665.837   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8667.9658664.297   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8669.2988663.527   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8670.6328664.297   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8670.6298668.933   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8669.2958668.163   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8669.2958666.623   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8670.6298665.853   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8671.9628668.163   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8671.9628666.623   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8673.4278666.147   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8674.3328667.393   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8673.4278668.639   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8673.4278670.179   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8674.7598670.945   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0    8672.0918670.945   0.000  0.00  0.00           O+0
HETATM   28  H   UNK     0    8674.7598669.405   0.000  0.00  0.00           H+0
CONECT    1   12                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4   10                                                            
CONECT    5   13                                                            
CONECT    6   19                                                            
CONECT    7   18                                                            
CONECT    8    9   12                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11    4                                                  
CONECT   11   10   13                                                       
CONECT   12   13    8    1   18                                             
CONECT   13   12   14   11    5                                             
CONECT   14   13   15                                                       
CONECT   15   14   19                                                       
CONECT   16   17   20                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   12    7                                             
CONECT   19   18   15    6   21                                             
CONECT   20   21   24   16    2                                             
CONECT   21   20   22   19    3                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   25   28   20   23                                             
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   24                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0001449
HETATM    1  C1  UNL     1      -6.015  -1.047  -0.089  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.700  -0.795   0.541  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.645  -0.682   1.737  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.499  -0.688  -0.290  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.708   0.469  -1.280  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.430   1.284  -1.252  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.460   0.291  -0.689  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.145   0.781  -0.261  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.652   1.445  -1.363  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.784   0.649  -1.890  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.706   0.080  -0.867  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.030   0.757  -0.739  1.00  0.00           C  
HETATM   13  C12 UNL     1       4.825   0.052   0.318  1.00  0.00           C  
HETATM   14  O2  UNL     1       6.077  -0.270  -0.259  1.00  0.00           O  
HETATM   15  C13 UNL     1       4.235  -1.228   0.796  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.799  -1.182   1.198  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.028  -0.077   0.498  1.00  0.00           C  
HETATM   18  C16 UNL     1       2.168   1.156   1.346  1.00  0.00           C  
HETATM   19  C17 UNL     1       0.625  -0.450   0.220  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.081  -1.123   1.358  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.504  -1.457   1.007  1.00  0.00           C  
HETATM   22  C20 UNL     1      -2.244  -0.271   0.469  1.00  0.00           C  
HETATM   23  C21 UNL     1      -2.543   0.667   1.576  1.00  0.00           C  
HETATM   24  H1  UNL     1      -6.404  -0.059  -0.442  1.00  0.00           H  
HETATM   25  H2  UNL     1      -6.756  -1.460   0.643  1.00  0.00           H  
HETATM   26  H3  UNL     1      -5.936  -1.697  -0.984  1.00  0.00           H  
HETATM   27  H4  UNL     1      -3.243  -1.617  -0.833  1.00  0.00           H  
HETATM   28  H5  UNL     1      -4.590   1.073  -0.991  1.00  0.00           H  
HETATM   29  H6  UNL     1      -3.930   0.061  -2.288  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.153   1.671  -2.243  1.00  0.00           H  
HETATM   31  H8  UNL     1      -2.564   2.130  -0.576  1.00  0.00           H  
HETATM   32  H9  UNL     1      -1.342  -0.548  -1.414  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.246   1.535   0.525  1.00  0.00           H  
HETATM   34  H11 UNL     1       1.013   2.454  -1.079  1.00  0.00           H  
HETATM   35  H12 UNL     1      -0.069   1.613  -2.202  1.00  0.00           H  
HETATM   36  H13 UNL     1       2.374   1.306  -2.564  1.00  0.00           H  
HETATM   37  H14 UNL     1       1.350  -0.139  -2.575  1.00  0.00           H  
HETATM   38  H15 UNL     1       2.928  -0.979  -1.203  1.00  0.00           H  
HETATM   39  H16 UNL     1       3.946   1.853  -0.552  1.00  0.00           H  
HETATM   40  H17 UNL     1       4.520   0.687  -1.755  1.00  0.00           H  
HETATM   41  H18 UNL     1       5.097   0.760   1.156  1.00  0.00           H  
HETATM   42  H19 UNL     1       6.488   0.531  -0.675  1.00  0.00           H  
HETATM   43  H20 UNL     1       4.820  -1.539   1.704  1.00  0.00           H  
HETATM   44  H21 UNL     1       4.449  -2.025   0.041  1.00  0.00           H  
HETATM   45  H22 UNL     1       2.335  -2.143   0.827  1.00  0.00           H  
HETATM   46  H23 UNL     1       2.623  -1.165   2.285  1.00  0.00           H  
HETATM   47  H24 UNL     1       1.227   1.393   1.922  1.00  0.00           H  
HETATM   48  H25 UNL     1       2.939   1.031   2.163  1.00  0.00           H  
HETATM   49  H26 UNL     1       2.441   2.061   0.807  1.00  0.00           H  
HETATM   50  H27 UNL     1       0.613  -1.161  -0.650  1.00  0.00           H  
HETATM   51  H28 UNL     1       0.436  -2.084   1.558  1.00  0.00           H  
HETATM   52  H29 UNL     1       0.014  -0.509   2.263  1.00  0.00           H  
HETATM   53  H30 UNL     1      -1.552  -2.350   0.361  1.00  0.00           H  
HETATM   54  H31 UNL     1      -2.005  -1.748   1.973  1.00  0.00           H  
HETATM   55  H32 UNL     1      -1.713   1.363   1.789  1.00  0.00           H  
HETATM   56  H33 UNL     1      -3.451   1.284   1.420  1.00  0.00           H  
HETATM   57  H34 UNL     1      -2.612   0.055   2.529  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

HMDB0001449
     RDKit          3D
Allopregnanolone
 57 60  0  0  0  0  0  0  0  0999 V2000
   -6.0152   -1.0465   -0.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7004   -0.7948    0.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6453   -0.6823    1.7375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4993   -0.6880   -0.2899 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7084    0.4688   -1.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4299    1.2838   -1.2516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4600    0.2905   -0.6891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1454    0.7811   -0.2608 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6520    1.4450   -1.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7843    0.6485   -1.8896 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7059    0.0798   -0.8669 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0300    0.7573   -0.7392 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247    0.0517    0.3184 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0774   -0.2696   -0.2594 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2350   -1.2275    0.7965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7990   -1.1816    1.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0282   -0.0769    0.4980 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1679    1.1562    1.3460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -0.4496    0.2202 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0812   -1.1233    1.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5042   -1.4567    1.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2440   -0.2710    0.4689 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5433    0.6672    1.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4040   -0.0592   -0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7561   -1.4603    0.6430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9356   -1.6973   -0.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2432   -1.6171   -0.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5895    1.0732   -0.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9300    0.0611   -2.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1535    1.6710   -2.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5642    2.1304   -0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3419   -0.5478   -1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2465    1.5346    0.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0130    2.4535   -1.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0689    1.6134   -2.2021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3737    1.3060   -2.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3503   -0.1385   -2.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282   -0.9785   -1.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9458    1.8527   -0.5523 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5196    0.6872   -1.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0966    0.7601    1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4882    0.5307   -0.6753 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8203   -1.5395    1.7036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4495   -2.0249    0.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3352   -2.1429    0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6229   -1.1646    2.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273    1.3927    1.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9393    1.0311    2.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4406    2.0613    0.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6131   -1.1612   -0.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4362   -2.0842    1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0142   -0.5089    2.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5520   -2.3501    0.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0054   -1.7482    1.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7128    1.3625    1.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4509    1.2845    1.4202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118    0.0549    2.5286 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  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  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  1
 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
(3alpha,5alpha)-3-Hydroxypregnan-20-one	ChEBI
3alpha,5alpha-Tetrahydroprogesterone	ChEBI
3alpha,5alpha-THP	ChEBI
3alpha-Hydroxy-5alpha-dihydroprogesterone	ChEBI
3alpha-Hydroxy-5alpha-pregnan-20-one	ChEBI
3alpha-OH DHP	ChEBI
5alpha-Pregnan-3alpha-ol-20-one	ChEBI
Allopregnan-3alpha-ol-20-one	ChEBI
Allotetrahydroprogesterone	ChEBI
Brexanolona	ChEBI
Brexanolonum	ChEBI
SAGE-547	ChEBI
SGE-102	ChEBI
Zulresso	ChEBI
(3a,5a)-3-Hydroxypregnan-20-one	Generator
(3Α,5α)-3-hydroxypregnan-20-one	Generator
3a,5a-Tetrahydroprogesterone	Generator
3Α,5α-tetrahydroprogesterone	Generator
3a,5a-THP	Generator
3Α,5α-THP	Generator
3a-Hydroxy-5a-dihydroprogesterone	Generator
3Α-hydroxy-5α-dihydroprogesterone	Generator
3a-Hydroxy-5a-pregnan-20-one	Generator
3Α-hydroxy-5α-pregnan-20-one	Generator
3a-OH DHP	Generator
3Α-OH DHP	Generator
5a-Pregnan-3a-ol-20-one	Generator
5Α-pregnan-3α-ol-20-one	Generator
Allopregnan-3a-ol-20-one	Generator
Allopregnan-3α-ol-20-one	Generator
(+)-3a-Hydroxy-5a-pregnan-20-one	HMDB
(3a)-Allopregnanolone	HMDB
3-a-Tetrahydroprogesterone	HMDB
3-alpha-Tetrahydroprogesterone	HMDB
3a,5a-Pregnanolone	HMDB
3a-Hydroxy-5a-pregnane-20-one	HMDB
5a-Pregnane-3a-ol-20-one	HMDB
3-Hydroxypregnan-20-one	HMDB
alpha-Hydroxy-5 alpha-pregnan-20-one, 3	HMDB
Pregnan-3alpha-ol-20-one	HMDB
Pregnanolone, (3alpha)-isomer	HMDB
3 Hydroxypregnan 20 one	HMDB
3 alpha Hydroxy 5 alpha pregnan 20 one	HMDB
3 alpha-Hydroxy-5 alpha-pregnan-20-one	HMDB
Pregnan 3alpha ol 20 one	HMDB
alpha-Pregnan-20-one, 3 alpha-hydroxy-5	HMDB
(+)-3alpha-Hydroxy-5alpha-pregnan-20-one	HMDB
(+)-3Α-hydroxy-5α-pregnan-20-one	HMDB
(3alpha)-Allopregnanolone	HMDB
(3Α)-allopregnanolone	HMDB
3alpha,5alpha-Pregnanolone	HMDB
3alpha-Hydroxy-5alpha-pregnane-20-one	HMDB
3Α,5α-pregnanolone	HMDB
3Α-hydroxy-5α-pregnane-20-one	HMDB
5alpha-Pregnane-3alpha-ol-20-one	HMDB
5Α-pregnane-3α-ol-20-one	HMDB
Allopregnanolone	MeSH, ChEBI

Chemical Formula

C₂₁H₃₄O₂

Average Molecular Weight

318.4935

Monoisotopic Molecular Weight

318.255880332

IUPAC Name

1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one

Traditional Name

1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethanone

CAS Registry Number

516-54-1

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)=O

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-SYBPFIFISA-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-alpha-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:50169 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030156 )

Ontology

Physiological effect

Health effect

Major depressive disorder (HMDB: HMDB0001449)
Prepartum depression (HMDB: HMDB0001449)

Disposition

Biological location

Biofluid or Excreta

Urine (HMDB: HMDB0001449)
Cerebrospinal fluid (HMDB: HMDB0001449)

Non-excretory biofluid

Blood (PMID: 16959481)
Cerebrospinal Fluid (CSF) (PMID: 9501247)

Cytoplasm (HMDB: HMDB0001449)
Cell membrane (HMDB: HMDB0001449)

Tissue substructure

Hepatic tissue (HMDB: HMDB0001449)

Cellular substructure

Extracellular (HMDB: HMDB0001449)
Membrane (HMDB: HMDB0001449)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001449)

Source

Endogenous

Endogenous (HMDB: HMDB0001449)

Exogenous

Food

Food (HMDB: HMDB0001449)

Animal origin

Lagomorph

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Velvet duck (FooDB: FOOD00427)
Ostrich (FooDB: FOOD00422)

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Elk (FooDB: FOOD00359)
Mule deer (FooDB: FOOD00348)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Alcoholism (HMDB: HMDB0001449)

Chemical reaction

Lipid peroxidation (HMDB: HMDB0001449)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0001449)

Cellular process

Cell signaling (HMDB: HMDB0001449)

System process

Reproduction (HMDB: HMDB0001449)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	177 °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	38.52 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]+	176.529	31661259
DarkChem	[M-H]-	174.188	31661259
AllCCS	[M+H]+	183.358	32859911
AllCCS	[M-H]-	187.191	32859911
DeepCCS	[M-2H]-	206.435	30932474
DeepCCS	[M+Na]+	180.687	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 Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Allopregnanolone	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)=O	2222.5	Standard polar	33892256
Allopregnanolone	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)=O	2649.9	Standard non polar	33892256
Allopregnanolone	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)=O	2869.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Allopregnanolone,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
Allopregnanolone,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
Allopregnanolone,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
Allopregnanolone,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
Allopregnanolone,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
Allopregnanolone,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
Allopregnanolone,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
Allopregnanolone,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
Allopregnanolone,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
Allopregnanolone,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
Allopregnanolone,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
Allopregnanolone,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
Allopregnanolone,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
Allopregnanolone,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
Allopregnanolone,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
Allopregnanolone,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
Allopregnanolone,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
Allopregnanolone,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
Experimental GC-MS	GC-MS Spectrum - Allopregnanolone GC-MS (1 MEOX; 1 TMS)	splash10-0udi-6910000000-837b37f206729753b640	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Allopregnanolone GC-MS (Non-derivatized)	splash10-0udi-6910000000-837b37f206729753b640	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopregnanolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-1174-0292000000-fb2c0f3a1cfddb10cb08	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopregnanolone GC-MS (1 TMS) - 70eV, Positive	splash10-004i-2139000000-ab8a6de8f5a129af086e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Allopregnanolone 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 - Allopregnanolone 10V, Positive-QTOF	splash10-0uxr-0129000000-90e5fcb36022dd1ba688	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopregnanolone 20V, Positive-QTOF	splash10-0uxr-0396000000-4c39fe7ccd8e0c86e179	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopregnanolone 40V, Positive-QTOF	splash10-0006-2490000000-7ac55935cc0d4da95860	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopregnanolone 10V, Negative-QTOF	splash10-014i-0029000000-fa09e69c9c0b6736d2e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopregnanolone 20V, Negative-QTOF	splash10-014i-0069000000-d1d57e3e1a99da4ed11f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopregnanolone 40V, Negative-QTOF	splash10-0zg0-1193000000-44d1597a59ac11f16a41	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopregnanolone 10V, Positive-QTOF	splash10-0gb9-0019000000-5b53b3ba37ccafca449f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopregnanolone 20V, Positive-QTOF	splash10-0lgi-1797000000-c11629ffa10cac4be118	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopregnanolone 40V, Positive-QTOF	splash10-0a4m-8910000000-2813a600e98ff5997275	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopregnanolone 10V, Negative-QTOF	splash10-014i-0009000000-bbaa566ea695ae62f84e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopregnanolone 20V, Negative-QTOF	splash10-014i-0029000000-ac1c6a15538469151b6c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Allopregnanolone 40V, Negative-QTOF	splash10-00ks-0093000000-db70f670eb2440b743f9	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)

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	0.01 +/- 0.003 uM	Adult (>18 years old)	Female	Normal	11739473	details
Blood	Detected and Quantified	0.001 +/- 0.00025 uM	Adult (>18 years old)	Both	Normal	16959481	details
Blood	Detected and Quantified	0.0002 +/- 0.000062 uM	Adult (>18 years old)	Male	Normal	10625505	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00016 +/- 0.00011 uM	Adult (>18 years old)	Male	Normal	10625505	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.011 +/- 0.002 uM	Adult (>18 years old)	Female	Prepartum depression	11739473	details
Blood	Detected and Quantified	0.001 +/- 0.00028 uM	Adult (>18 years old)	Both	Psychiatric disorder	16959481	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0000150 +/- 0.0000015 uM	Adult (>18 years old)	Both	Major depression	9501247	details

Associated Disorders and Diseases

Disease References

Alcoholism
Nieminen LR, Makino KK, Mehta N, Virkkunen M, Kim HY, Hibbeln JR: Relationship between omega-3 fatty acids and plasma neuroactive steroids in alcoholism, depression and controls. Prostaglandins Leukot Essent Fatty Acids. 2006 Oct-Nov;75(4-5):309-14. Epub 2006 Sep 7. [PubMed:16959481 ]
Prepartum depression
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 ]
Major depressive disorder
Uzunova V, Sheline Y, Davis JM, Rasmusson A, Uzunov DP, Costa E, Guidotti A: Increase in the cerebrospinal fluid content of neurosteroids in patients with unipolar major depression who are receiving fluoxetine or fluvoxamine. Proc Natl Acad Sci U S A. 1998 Mar 17;95(6):3239-44. [PubMed:9501247 ] Nieminen LR, Makino KK, Mehta N, Virkkunen M, Kim HY, Hibbeln JR: Relationship between omega-3 fatty acids and plasma neuroactive steroids in alcoholism, depression and controls. Prostaglandins Leukot Essent Fatty Acids. 2006 Oct-Nov;75(4-5):309-14. Epub 2006 Sep 7. [PubMed:16959481 ]

Associated OMIM IDs

608516 (Major depressive disorder)

External Links

DrugBank ID

DB11859

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022630

KNApSAcK ID

Not Available

Chemspider ID

83760

KEGG Compound ID

C13712

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Allopregnanolone

METLIN ID

Not Available

PubChem Compound

92786

PDB ID

Not Available

ChEBI ID

50169

Food Biomarker Ontology

Not Available

VMH ID

CE2211

MarkerDB ID

MDB00000326

Good Scents ID

Not Available

References

Synthesis Reference

Wiebe, J. P.; Deline, C.; Buckingham, K. D.; Dave, Vinod; Stothers, J. B. Synthesis of the allylic gonadal steroids, 3a-hydroxy-4-pregnen-20-one and 3a-hydroxy-4-androsten-17-one, and of 3a-hydroxy-5a-pregnan-20-one. Steroids (1985), 45(1), 39-51.

Material Safety Data Sheet (MSDS)

Not Available

General References

Kim YS, Zhang H, Kim HY: Profiling neurosteroids in cerebrospinal fluids and plasma by gas chromatography/electron capture negative chemical ionization mass spectrometry. Anal Biochem. 2000 Jan 15;277(2):187-95. [PubMed:10625505 ]
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 ]
Uzunova V, Sheline Y, Davis JM, Rasmusson A, Uzunov DP, Costa E, Guidotti A: Increase in the cerebrospinal fluid content of neurosteroids in patients with unipolar major depression who are receiving fluoxetine or fluvoxamine. Proc Natl Acad Sci U S A. 1998 Mar 17;95(6):3239-44. [PubMed:9501247 ]

Enzymes

Enzyme Details

1. Aldo-keto reductase family 1 member C3

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2. Functions as a bi-directional 3-alpha-, 17-beta- and 20-alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone.
Gene Name:: AKR1C3
Uniprot ID:: P42330
Molecular weight:: 36866.91

Reactions

5a-Pregnane-3,20-dione + NADPH + Hydrogen Ion → Allopregnanolone + NADP	details

Enzyme Details

2. Aldo-keto reductase family 1 member C1

General function:: Involved in oxidoreductase activity
Specific function:: Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:: AKR1C1
Uniprot ID:: Q04828
Molecular weight:: 36788.02

Reactions

5a-Pregnane-3,20-dione + NADPH + Hydrogen Ion → Allopregnanolone + NADP	details

Enzyme Details

3. Aldo-keto reductase family 1 member C2

General function:: Involved in oxidoreductase activity
Specific function:: Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent androgen 5-alpha-dihydrotestosterone (5-alpha-DHT) to 5-alpha-androstane-3-alpha,17-beta-diol (3-alpha-diol). Has a high bile-binding ability.
Gene Name:: AKR1C2
Uniprot ID:: P52895
Molecular weight:: 15747.91

Reactions

5a-Pregnane-3,20-dione + NADPH + Hydrogen Ion → Allopregnanolone + NADP	details

Showing metabocard for Allopregnanolone (HMDB0001449)

MOL for HMDB0001449 (Allopregnanolone)

3D MOL for HMDB0001449 (Allopregnanolone)

3D SDF for HMDB0001449 (Allopregnanolone)

3D-SDF for HMDB0001449 (Allopregnanolone)

PDB for HMDB0001449 (Allopregnanolone)

3D PDB for HMDB0001449 (Allopregnanolone)

SMILES for HMDB0001449 (Allopregnanolone)

INCHI for HMDB0001449 (Allopregnanolone)

Structure for HMDB0001449 (Allopregnanolone)

3D Structure for HMDB0001449 (Allopregnanolone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions

Reactions