NP-MRD: Showing NP-Card for Allopregnanolone (NP0086789)

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Record Information

Version

2.0

Created at

2022-05-11 16:31:03 UTC

Updated at

2022-05-11 16:31:03 UTC

NP-MRD ID

NP0086789

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Allopregnanolone

Description

Allopregnanolone, also known as 3alpha-OH DHP or 3alpha,5alpha-THP, 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, allopregnanolone is considered to be a steroid lipid molecule. Allopregnanolone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Allopregnanolone is found in Homo sapiens. Allopregnanolone was first documented in 1998 (PMID: 9501247). Allopregnanolone exists in all living organisms, ranging from bacteria to humans (PMID: 10625505) (PMID: 19290593) (PMID: 28370307).

Structure

MOL 3D MOL SDF 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

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
   -4.8449    1.9343    1.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7419    0.6089    0.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6407    0.2509   -0.3457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6166   -0.3302    0.6014 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8192   -1.6099   -0.1829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4469   -2.0297   -0.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5358   -1.1680    0.0486 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2315   -0.8213   -0.5343 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5143   -1.9030   -1.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8017   -1.2591   -1.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5930   -0.8444   -0.5337 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0165   -0.5844   -0.8784 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7855    0.2971   -0.0005 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7906   -0.4240    0.6895 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0448    1.0935    1.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7483    0.5001    1.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9087    0.2673    0.2019 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8402    1.5489   -0.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5671   -0.2520    0.6459 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2433    0.6746    1.4534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5507    1.1016    0.9174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3135    0.1582    0.1023 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5267    0.6743   -1.3261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9106    2.2348    1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5303    1.8662    2.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2306    2.7114    0.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4990   -0.6153    1.6737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3183   -2.3960    0.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4299   -1.3684   -1.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3781   -2.0419   -1.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3092   -3.0958   -0.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4809   -1.5063    1.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3135    0.0420   -1.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0897   -2.3044   -2.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8338   -2.7197   -0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4717   -0.3212   -2.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3583   -1.9278   -2.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5439   -1.7428    0.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5307   -1.5890   -0.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0323   -0.2279   -1.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3701    1.0248   -0.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6465   -0.4060    0.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6588    1.2734    1.9328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166    2.1284    0.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9835   -0.4747    1.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2840    1.1682    2.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7235    1.6813   -1.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9491    1.6557   -1.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7704    2.3830    0.2047 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -1.1675    1.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3719    1.6063    1.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124    0.2815    2.5004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919    1.4522    1.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3972    2.0462    0.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1835   -0.0336   -2.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9602    1.6202   -1.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6014    0.8790   -1.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  6
  4  2  1  0
  2  1  1  0
  2  3  2  0
 22  4  1  0
 22  7  1  0
 19  8  1  0
 17 11  1  0
  4 27  1  1
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  1
  8 33  1  6
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  1
 12 39  1  0
 12 40  1  0
 13 41  1  6
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 18 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  1
 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
  1 24  1  0
  1 25  1  0
  1 26  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>
NP0086789

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

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 Mass

318.4935 Da

Monoisotopic Mass

318.25588 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
3-hydroxysteroid
Hydroxysteroid
3-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 )

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.28	ALOGPS
logP	3.99	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	18.3	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.91 m³·mol⁻¹	ChemAxon
Polarizability	38.52 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

External Links

HMDB ID

HMDB0001449

DrugBank ID

DB11859

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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 ]
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. doi: 10.1073/pnas.95.6.3239. [PubMed:9501247 ]
Slavikova B, Kristofikova Z, Chodounska H, Budesinsky M, Duran FJ, Veleiro AS, Burton G, Kasal A: Allopregnanolone (3alpha-hydroxy-5alpha-pregnan-20-one) derivatives with a polar chain in position 16alpha: synthesis and activity. J Med Chem. 2009 Apr 9;52(7):2119-25. doi: 10.1021/jm801454a. [PubMed:19290593 ]
Kanes SJ, Colquhoun H, Doherty J, Raines S, Hoffmann E, Rubinow DR, Meltzer-Brody S: Open-label, proof-of-concept study of brexanolone in the treatment of severe postpartum depression. Hum Psychopharmacol. 2017 Mar;32(2). doi: 10.1002/hup.2576. [PubMed:28370307 ]

Showing NP-Card for Allopregnanolone (NP0086789)

MOL for NP0086789 (Allopregnanolone)

3D MOL for NP0086789 (Allopregnanolone)

3D SDF for NP0086789 (Allopregnanolone)

3D-SDF for NP0086789 (Allopregnanolone)

PDB for NP0086789 (Allopregnanolone)

3D PDB for NP0086789 (Allopregnanolone)

SMILES for NP0086789 (Allopregnanolone)

INCHI for NP0086789 (Allopregnanolone)

Structure for NP0086789 (Allopregnanolone)

3D Structure for NP0086789 (Allopregnanolone)