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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-16 15:25:22 UTC

Update Date

2022-03-07 02:49:10 UTC

HMDB ID

HMDB0001471

Secondary Accession Numbers

HMDB01471

Metabolite Identification

Common Name

Epipregnanolone

Description

Epipregnanolone, also known as 3beta-hydroxy-5beta-pregnan-20-one, belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogens, and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Thus, epipregnanolone is considered to be a steroid lipid molecule. Epipregnanolone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Epipregnanolone is a pregnane found in the urine of pregnant women and sows. It has anesthetic, hypnotic, and sedative properties. It is a substrate of the enzyme 3beta-hydroxy-5beta-steroid dehydrogenase (EC 1.1.1.277).

Structure

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


  Mrv1652311181917452D          

 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  1  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  2  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  1  0  0  0
 11 13  1  0  0  0  0
 13  5  1  1  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

HMDB0001471
     RDKit          3D
Epipregnanolone
 57 60  0  0  0  0  0  0  0  0999 V2000
   -5.3639   -0.6884    0.3289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6775   -0.3046   -0.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1574   -0.6786   -1.9783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4649    0.4950   -0.9184 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6061    1.8377   -0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2268    2.1531    0.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3458    1.1418   -0.2872 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0952    0.7920    0.4213 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7424    2.0786    0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1706    1.7946    0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6586    0.5501    0.8619 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1382    0.3896    0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6034   -0.2511   -0.5397 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5499   -1.2560   -0.2256 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5347   -0.9388   -1.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6502   -1.6387   -0.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8604   -0.6661    0.4846 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4622   -1.4260    1.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6664   -0.2362   -0.3263 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1424   -1.3710   -0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5253   -1.0391   -1.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2389   -0.1026   -0.3260 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3879   -0.7205    1.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9519   -0.2465    1.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3384   -1.8123    0.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4573   -0.4567    0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1590    0.7883   -1.9832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3195    1.7948    0.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9636    2.6006   -0.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9248    3.1660   -0.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1790    2.1609    1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1006    1.3629   -1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2532    0.5320    1.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3755    2.7837   -0.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993    2.6125    1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7689    2.6394    0.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4306    1.8193   -0.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4724    0.7429    1.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5783   -0.1222    1.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5733    1.4320    0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1933    0.4670   -1.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6689   -1.8865   -0.9741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750   -0.2456   -2.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0251   -1.7365   -1.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3435   -2.1861    0.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0562   -2.3885   -0.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0057   -0.7072    2.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7365   -2.2196    1.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3825   -1.7914    2.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1107    0.3017   -1.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1818   -2.2707   -0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3782   -1.7388   -1.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0880   -1.9973   -1.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5024   -0.5305   -2.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3776   -1.1392    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0284   -1.6213    0.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6537   -0.0223    1.8175 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  1
 12 39  1  0
 12 40  1  0
 13 41  1  6
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 18 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  6
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
M  END


  Mrv1652311181917452D          

 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  1  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  2  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  1  0  0  0
 11 13  1  0  0  0  0
 13  5  1  1  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>
HMDB0001471

> <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-/m1/s1

> <INCHI_KEY>
AURFZBICLPNKBZ-GRWISUQFSA-N

> <FORMULA>
C21H34O2

> <MOLECULAR_WEIGHT>
318.4935

> <EXACT_MASS>
318.255880332

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
38.26436963503062

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(1S,2S,5S,7R,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,5S,7R,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

$$$$

HMDB0001471
     RDKit          3D
Epipregnanolone
 57 60  0  0  0  0  0  0  0  0999 V2000
   -5.3639   -0.6884    0.3289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6775   -0.3046   -0.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1574   -0.6786   -1.9783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4649    0.4950   -0.9184 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6061    1.8377   -0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2268    2.1531    0.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3458    1.1418   -0.2872 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0952    0.7920    0.4213 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7424    2.0786    0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1706    1.7946    0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6586    0.5501    0.8619 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1382    0.3896    0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6034   -0.2511   -0.5397 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5499   -1.2560   -0.2256 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5347   -0.9388   -1.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6502   -1.6387   -0.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8604   -0.6661    0.4846 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4622   -1.4260    1.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6664   -0.2362   -0.3263 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1424   -1.3710   -0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5253   -1.0391   -1.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2389   -0.1026   -0.3260 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3879   -0.7205    1.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9519   -0.2465    1.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3384   -1.8123    0.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4573   -0.4567    0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1590    0.7883   -1.9832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3195    1.7948    0.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9636    2.6006   -0.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9248    3.1660   -0.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1790    2.1609    1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1006    1.3629   -1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2532    0.5320    1.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3755    2.7837   -0.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993    2.6125    1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7689    2.6394    0.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4306    1.8193   -0.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4724    0.7429    1.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5783   -0.1222    1.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5733    1.4320    0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1933    0.4670   -1.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6689   -1.8865   -0.9741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750   -0.2456   -2.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0251   -1.7365   -1.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3435   -2.1861    0.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0562   -2.3885   -0.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0057   -0.7072    2.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7365   -2.2196    1.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3825   -1.7914    2.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1107    0.3017   -1.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1818   -2.2707   -0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3782   -1.7388   -1.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0880   -1.9973   -1.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5024   -0.5305   -2.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3776   -1.1392    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0284   -1.6213    0.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6537   -0.0223    1.8175 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  1
 12 39  1  0
 12 40  1  0
 13 41  1  6
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 18 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  6
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
M  END

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    HMDB0001471
HETATM    1  C1  UNL     1      -5.364  -0.688   0.329  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.678  -0.305  -0.924  1.00  0.00           C  
HETATM    3  O1  UNL     1      -5.157  -0.679  -1.978  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.465   0.495  -0.918  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.606   1.838  -0.214  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.227   2.153   0.337  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.346   1.142  -0.287  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.095   0.792   0.421  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.742   2.079   0.460  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.171   1.795   0.148  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.659   0.550   0.862  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.138   0.390   0.704  1.00  0.00           C  
HETATM   13  C12 UNL     1       4.603  -0.251  -0.540  1.00  0.00           C  
HETATM   14  O2  UNL     1       5.550  -1.256  -0.226  1.00  0.00           O  
HETATM   15  C13 UNL     1       3.535  -0.939  -1.355  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.650  -1.639  -0.357  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.860  -0.666   0.485  1.00  0.00           C  
HETATM   18  C16 UNL     1       1.462  -1.426   1.731  1.00  0.00           C  
HETATM   19  C17 UNL     1       0.666  -0.236  -0.326  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.142  -1.371  -0.867  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.525  -1.039  -1.275  1.00  0.00           C  
HETATM   22  C20 UNL     1      -2.239  -0.103  -0.326  1.00  0.00           C  
HETATM   23  C21 UNL     1      -2.388  -0.720   1.019  1.00  0.00           C  
HETATM   24  H1  UNL     1      -4.952  -0.246   1.239  1.00  0.00           H  
HETATM   25  H2  UNL     1      -5.338  -1.812   0.448  1.00  0.00           H  
HETATM   26  H3  UNL     1      -6.457  -0.457   0.283  1.00  0.00           H  
HETATM   27  H4  UNL     1      -3.159   0.788  -1.983  1.00  0.00           H  
HETATM   28  H5  UNL     1      -4.320   1.795   0.615  1.00  0.00           H  
HETATM   29  H6  UNL     1      -3.964   2.601  -0.933  1.00  0.00           H  
HETATM   30  H7  UNL     1      -1.925   3.166  -0.056  1.00  0.00           H  
HETATM   31  H8  UNL     1      -2.179   2.161   1.423  1.00  0.00           H  
HETATM   32  H9  UNL     1      -1.101   1.363  -1.346  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.253   0.532   1.488  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.376   2.784  -0.315  1.00  0.00           H  
HETATM   35  H12 UNL     1       0.599   2.612   1.425  1.00  0.00           H  
HETATM   36  H13 UNL     1       2.769   2.639   0.605  1.00  0.00           H  
HETATM   37  H14 UNL     1       2.431   1.819  -0.919  1.00  0.00           H  
HETATM   38  H15 UNL     1       2.472   0.743   1.941  1.00  0.00           H  
HETATM   39  H16 UNL     1       4.578  -0.122   1.593  1.00  0.00           H  
HETATM   40  H17 UNL     1       4.573   1.432   0.749  1.00  0.00           H  
HETATM   41  H18 UNL     1       5.193   0.467  -1.184  1.00  0.00           H  
HETATM   42  H19 UNL     1       5.669  -1.887  -0.974  1.00  0.00           H  
HETATM   43  H20 UNL     1       2.975  -0.246  -2.012  1.00  0.00           H  
HETATM   44  H21 UNL     1       4.025  -1.736  -1.964  1.00  0.00           H  
HETATM   45  H22 UNL     1       3.344  -2.186   0.343  1.00  0.00           H  
HETATM   46  H23 UNL     1       2.056  -2.389  -0.863  1.00  0.00           H  
HETATM   47  H24 UNL     1       1.006  -0.707   2.472  1.00  0.00           H  
HETATM   48  H25 UNL     1       0.736  -2.220   1.576  1.00  0.00           H  
HETATM   49  H26 UNL     1       2.383  -1.791   2.277  1.00  0.00           H  
HETATM   50  H27 UNL     1       1.111   0.302  -1.224  1.00  0.00           H  
HETATM   51  H28 UNL     1      -0.182  -2.271  -0.220  1.00  0.00           H  
HETATM   52  H29 UNL     1       0.378  -1.739  -1.804  1.00  0.00           H  
HETATM   53  H30 UNL     1      -2.088  -1.997  -1.402  1.00  0.00           H  
HETATM   54  H31 UNL     1      -1.502  -0.531  -2.263  1.00  0.00           H  
HETATM   55  H32 UNL     1      -1.378  -1.139   1.314  1.00  0.00           H  
HETATM   56  H33 UNL     1      -3.028  -1.621   0.953  1.00  0.00           H  
HETATM   57  H34 UNL     1      -2.654  -0.022   1.818  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

HMDB0001471
     RDKit          3D
Epipregnanolone
 57 60  0  0  0  0  0  0  0  0999 V2000
   -5.3639   -0.6884    0.3289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6775   -0.3046   -0.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1574   -0.6786   -1.9783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4649    0.4950   -0.9184 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6061    1.8377   -0.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2268    2.1531    0.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3458    1.1418   -0.2872 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0952    0.7920    0.4213 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7424    2.0786    0.4602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1706    1.7946    0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6586    0.5501    0.8619 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1382    0.3896    0.7040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6034   -0.2511   -0.5397 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5499   -1.2560   -0.2256 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5347   -0.9388   -1.3549 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6502   -1.6387   -0.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8604   -0.6661    0.4846 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4622   -1.4260    1.7307 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6664   -0.2362   -0.3263 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1424   -1.3710   -0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5253   -1.0391   -1.2754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2389   -0.1026   -0.3260 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3879   -0.7205    1.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9519   -0.2465    1.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3384   -1.8123    0.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4573   -0.4567    0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1590    0.7883   -1.9832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3195    1.7948    0.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9636    2.6006   -0.9331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9248    3.1660   -0.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1790    2.1609    1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1006    1.3629   -1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2532    0.5320    1.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3755    2.7837   -0.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5993    2.6125    1.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7689    2.6394    0.6046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4306    1.8193   -0.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4724    0.7429    1.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5783   -0.1222    1.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5733    1.4320    0.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1933    0.4670   -1.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6689   -1.8865   -0.9741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750   -0.2456   -2.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0251   -1.7365   -1.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3435   -2.1861    0.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0562   -2.3885   -0.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0057   -0.7072    2.4718 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7365   -2.2196    1.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3825   -1.7914    2.2767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1107    0.3017   -1.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1818   -2.2707   -0.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3782   -1.7388   -1.8041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0880   -1.9973   -1.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5024   -0.5305   -2.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3776   -1.1392    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0284   -1.6213    0.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6537   -0.0223    1.8175 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  1
 12 39  1  0
 12 40  1  0
 13 41  1  6
 14 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 18 47  1  0
 18 48  1  0
 18 49  1  0
 19 50  1  6
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3beta,5beta)-3-Hydroxypregnan-20-one	ChEBI
3beta-Hydroxy-5beta-pregnane-20-one	ChEBI
3beta-Hydroxy-5beta-tetrahydroprogesterone	ChEBI
(3b,5b)-3-Hydroxypregnan-20-one	Generator
(3Β,5β)-3-hydroxypregnan-20-one	Generator
3b-Hydroxy-5b-pregnane-20-one	Generator
3Β-hydroxy-5β-pregnane-20-one	Generator
3b-Hydroxy-5b-tetrahydroprogesterone	Generator
3Β-hydroxy-5β-tetrahydroprogesterone	Generator
3-deoxo-3b-Hydroxy-5b-dihydroprogesterone	HMDB
3b,5b-Pregnanolone	HMDB
3b-Hydroxy-5b-pregnan-20-one	HMDB, Generator
5b-Pregnan-3b-ol-20-one	HMDB
5b-Pregnane-3b-hydroxy-20-one	HMDB
5b-Pregnane-3b-ol-20-one	HMDB
Pregnanolone I	HMDB
3-Hydroxypregnan-20-one	MeSH, HMDB
Pregnanolone, (3beta)-isomer	MeSH, HMDB
3 Hydroxypregnan 20 one	MeSH, HMDB
Epipregnanolone	ChEBI
3Β-hydroxy-5β-pregnan-20-one	Generator, HMDB
3-Deoxo-3beta-hydroxy-5beta-dihydroprogesterone	HMDB
3-Deoxo-3β-hydroxy-5β-dihydroprogesterone	HMDB
3beta,5beta-Pregnanolone	HMDB
3beta-Hydroxy-5beta-pregnan-20-one	HMDB
3β,5β-Pregnanolone	HMDB
5beta-Pregnan-3beta-ol-20-one	HMDB
5beta-Pregnane-3beta-hydroxy-20-one	HMDB
5beta-Pregnane-3beta-ol-20-one	HMDB
5β-Pregnan-3β-ol-20-one	HMDB
5β-Pregnane-3β-hydroxy-20-one	HMDB
5β-Pregnane-3β-ol-20-one	HMDB

Chemical Formula

C₂₁H₃₄O₂

Average Molecular Weight

318.4935

Monoisotopic Molecular Weight

318.255880332

IUPAC Name

1-[(1S,2S,5S,7R,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,5S,7R,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

128-21-2

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-/m1/s1

InChI Key

AURFZBICLPNKBZ-GRWISUQFSA-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

3beta-hydroxy steroid (CHEBI:16229 )
3-hydroxy-5beta-pregnan-20-one (CHEBI:16229 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030185 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

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	38.26 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]+	177.122	31661259
DarkChem	[M-H]-	173.337	31661259
AllCCS	[M+H]+	183.358	32859911
AllCCS	[M-H]-	187.191	32859911
DeepCCS	[M-2H]-	205.734	30932474
DeepCCS	[M+Na]+	179.938	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.	7.74 minutes	32390414
Predicted by Siyang on May 30, 2022	17.457 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.03 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
Epipregnanolone	[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
Epipregnanolone	[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
Epipregnanolone	[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
Epipregnanolone,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
Epipregnanolone,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
Epipregnanolone,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
Epipregnanolone,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
Epipregnanolone,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
Epipregnanolone,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
Epipregnanolone,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
Epipregnanolone,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
Epipregnanolone,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
Epipregnanolone,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
Epipregnanolone,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
Epipregnanolone,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
Epipregnanolone,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
Epipregnanolone,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
Epipregnanolone,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
Epipregnanolone,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
Epipregnanolone,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
Epipregnanolone,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 - Epipregnanolone GC-EI-TOF (Non-derivatized)	splash10-0udr-4900000000-39156fa655392898752f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Epipregnanolone GC-EI-TOF (Non-derivatized)	splash10-0udr-4900000000-39156fa655392898752f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epipregnanolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-1174-0292000000-fb2c0f3a1cfddb10cb08	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epipregnanolone GC-MS (1 TMS) - 70eV, Positive	splash10-004i-2139000000-ab8a6de8f5a129af086e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epipregnanolone 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 - Epipregnanolone 10V, Positive-QTOF	splash10-0uxr-0019000000-82b5328b4643c0421b0d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epipregnanolone 20V, Positive-QTOF	splash10-0uxr-1496000000-6fd25d5861771fb104b7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epipregnanolone 40V, Positive-QTOF	splash10-002o-2490000000-ba6e2bc4d584ea3d3a4b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epipregnanolone 10V, Negative-QTOF	splash10-014i-0029000000-826f869c8c8e3739b52e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epipregnanolone 20V, Negative-QTOF	splash10-014i-0059000000-699658e7c96cdaee62e8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epipregnanolone 40V, Negative-QTOF	splash10-0zmr-1092000000-19955e9b1f2b26db2425	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epipregnanolone 10V, Negative-QTOF	splash10-014i-0009000000-bbaa566ea695ae62f84e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epipregnanolone 20V, Negative-QTOF	splash10-014i-0029000000-ac1c6a15538469151b6c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epipregnanolone 40V, Negative-QTOF	splash10-00ks-0093000000-db70f670eb2440b743f9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epipregnanolone 10V, Positive-QTOF	splash10-0gb9-0019000000-5b53b3ba37ccafca449f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epipregnanolone 20V, Positive-QTOF	splash10-0lgi-1797000000-c11629ffa10cac4be118	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epipregnanolone 40V, Positive-QTOF	splash10-0a4m-8910000000-2813a600e98ff5997275	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	0.003 +/- 0.0018 uM	Adult (>18 years old)	Both	Normal	11739473	details
Blood	Detected and Quantified	0.00034 +/- 0.00011 uM	Adult (>18 years old)	Male	Normal	10625505	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	0.003 +/- 0.001 uM	Adult (>18 years old)	Female	Prepartum depression	11739473	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Schizophrenia	22944140	details

Associated Disorders and Diseases

Disease References

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 ]
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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022642

KNApSAcK ID

Not Available

Chemspider ID

198867

KEGG Compound ID

C11825

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Epipregnanolone

METLIN ID

Not Available

PubChem Compound

228491

PDB ID

Not Available

ChEBI ID

16229

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Halpern, Otto. Pregnenolones and androstenolones. U.S. (1969), 6 pp.

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 ]

Showing metabocard for Epipregnanolone (HMDB0001471)

MOL for HMDB0001471 (Epipregnanolone)

3D MOL for HMDB0001471 (Epipregnanolone)

3D SDF for HMDB0001471 (Epipregnanolone)

3D-SDF for HMDB0001471 (Epipregnanolone)

PDB for HMDB0001471 (Epipregnanolone)

3D PDB for HMDB0001471 (Epipregnanolone)

SMILES for HMDB0001471 (Epipregnanolone)

INCHI for HMDB0001471 (Epipregnanolone)

Structure for HMDB0001471 (Epipregnanolone)

3D Structure for HMDB0001471 (Epipregnanolone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra