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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2008-08-06 14:56:15 UTC

Update Date

2022-03-07 02:49:33 UTC

HMDB ID

HMDB0006759

Secondary Accession Numbers

HMDB06759

Metabolite Identification

Common Name

3a-Hydroxy-5b-pregnane-20-one

Description

3alpha-Hydroxy-5beta-pregnane-20-one is an intermediate in C21-Steroid hormone metabolism. 3alpha-Hydroxy-5beta-pregnane-20-one is converted from 5beta-Pregnane-3,20-dione via the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC 1.1.1.50). It is then converted to Pregnanediol via the enzyme 3alpha(or 20beta)-hydroxysteroid dehydrogenase (EC 1.1.1.53).

Structure

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

HMDB0006759
     RDKit          3D
3a-Hydroxy-5b-pregnane-20-one
 57 60  0  0  0  0  0  0  0  0999 V2000
   -5.8025    0.1881   -1.5211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3753   -0.1889   -1.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9488   -1.0477   -2.1781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4912    0.4639   -0.4825 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9062    0.3014    0.9646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6226    0.2963    1.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5721    0.5403    0.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1859    0.1638    1.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4504    1.3106    1.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8023    1.6946    1.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6729    0.5304    1.0003 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9091    1.0616    0.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7976   -0.0534   -0.1904 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8120    0.5369   -0.9429 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0753   -1.0283   -1.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6659   -0.4830   -1.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0182   -0.4528    0.0965 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2828   -1.8454    0.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5512   -0.2994   -0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1413    0.5719   -1.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2760    0.1287   -1.6221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1045   -0.2002   -0.4357 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3345   -1.6554   -0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0790    0.4646   -2.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0732    1.0351   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4098   -0.7198   -1.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2976    1.5287   -0.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4864    1.2093    1.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4915   -0.6127    1.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6596    1.0752    2.5933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5193   -0.6733    2.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5874    1.6230    0.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2782   -0.6918    1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4926    1.1196    2.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1957    2.2350    1.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7988    2.4316    0.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3266    2.2188    2.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0277    0.0718    1.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5037    1.5830    1.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7023    1.8132   -0.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2937   -0.5563    0.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3126   -0.1580   -1.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0500   -2.0079   -0.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5285   -1.1149   -2.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1264   -1.2096   -1.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667    0.5201   -1.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1766   -2.6327   -0.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4273   -2.0036    1.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2029   -1.8690    1.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409   -1.3254   -0.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1659    1.6397   -1.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7749    0.3050   -2.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7329    1.0404   -2.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2598   -0.6521   -2.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9938   -2.2987   -1.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4282   -1.9188   -0.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8848   -2.0035    0.7802 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  0
  8 33  1  0
  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  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  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
M  END


  Mrv0541 02231220502D          

 24 27  0  0  1  0            999 V2000
   18.5818  -10.9276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5818  -11.7525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.2963  -12.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0108  -11.7525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.0108  -10.9276    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.2963  -10.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7253  -12.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4398  -11.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4398  -10.9276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7253  -10.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1542  -10.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1542   -9.6900    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.4398   -9.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7253   -9.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9389  -10.7700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4238  -10.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9389   -9.4351    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.1938   -8.6505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6418   -8.0374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0008   -8.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0108  -10.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2987   -8.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0027  -12.3370    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.8681  -12.1647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
  5 21  1  1  0  0  0
 12 22  1  1  0  0  0
  4 23  1  1  0  0  0
  2 24  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0006759

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12CCC3C4CC[C@H](C(C)=O)[C@@]4(C)CCC3[C@@]1(C)CC[C@@H](O)C2

> <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-KCZNCWLVSA-N

> <FORMULA>
C21H34O2

> <MOLECULAR_WEIGHT>
318.4935

> <EXACT_MASS>
318.255880332

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
38.3647338042203

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.28

> <JCHEM_LOGP>
3.9869379340000006

> <ALOGPS_LOGS>
-5.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.403041090785273

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.296396321121705

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569558150513044

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
92.90669999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pregnanolone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0006759
     RDKit          3D
3a-Hydroxy-5b-pregnane-20-one
 57 60  0  0  0  0  0  0  0  0999 V2000
   -5.8025    0.1881   -1.5211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3753   -0.1889   -1.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9488   -1.0477   -2.1781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4912    0.4639   -0.4825 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9062    0.3014    0.9646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6226    0.2963    1.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5721    0.5403    0.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1859    0.1638    1.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4504    1.3106    1.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8023    1.6946    1.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6729    0.5304    1.0003 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9091    1.0616    0.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7976   -0.0534   -0.1904 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8120    0.5369   -0.9429 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0753   -1.0283   -1.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6659   -0.4830   -1.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0182   -0.4528    0.0965 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2828   -1.8454    0.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5512   -0.2994   -0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1413    0.5719   -1.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2760    0.1287   -1.6221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1045   -0.2002   -0.4357 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3345   -1.6554   -0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0790    0.4646   -2.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0732    1.0351   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4098   -0.7198   -1.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2976    1.5287   -0.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4864    1.2093    1.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4915   -0.6127    1.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6596    1.0752    2.5933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5193   -0.6733    2.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5874    1.6230    0.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2782   -0.6918    1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4926    1.1196    2.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1957    2.2350    1.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7988    2.4316    0.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3266    2.2188    2.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0277    0.0718    1.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5037    1.5830    1.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7023    1.8132   -0.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2937   -0.5563    0.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3126   -0.1580   -1.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0500   -2.0079   -0.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5285   -1.1149   -2.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1264   -1.2096   -1.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667    0.5201   -1.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1766   -2.6327   -0.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4273   -2.0036    1.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2029   -1.8690    1.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409   -1.3254   -0.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1659    1.6397   -1.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7749    0.3050   -2.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7329    1.0404   -2.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2598   -0.6521   -2.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9938   -2.2987   -1.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4282   -1.9188   -0.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8848   -2.0035    0.7802 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  0
  8 33  1  0
  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  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  0
 20 51  1  0
 20 52  1  0
 21 53  1  0
 21 54  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      34.686 -20.398   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      34.686 -21.938   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      36.020 -22.708   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      37.353 -21.938   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      37.353 -20.398   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      36.020 -19.628   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      38.687 -22.708   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      40.021 -21.938   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      40.021 -20.398   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      38.687 -19.628   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      41.355 -19.628   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      41.355 -18.088   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      40.021 -17.318   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      38.687 -18.088   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      42.819 -20.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      43.724 -18.858   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      42.819 -17.612   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      43.295 -16.148   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      42.265 -15.003   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      44.801 -15.827   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      37.353 -18.858   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      41.624 -16.572   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      37.338 -23.029   0.000  0.00  0.00           H+0
HETATM   24  O   UNK     0      33.354 -22.707   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   23                                             
CONECT    5    4    6   10   21                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    5   14                                                  
CONECT   11    9   12   15                                                  
CONECT   12   11   13   17   22                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    5                                                            
CONECT   22   12                                                            
CONECT   23    4                                                            
CONECT   24    2                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0006759
HETATM    1  C1  UNL     1      -5.803   0.188  -1.521  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.375  -0.189  -1.439  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.949  -1.048  -2.178  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.491   0.464  -0.483  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.906   0.301   0.965  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.623   0.296   1.782  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.572   0.540   0.763  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.186   0.164   1.156  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.450   1.311   1.869  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.802   1.695   1.373  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.673   0.530   1.000  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.909   1.062   0.316  1.00  0.00           C  
HETATM   13  C12 UNL     1       4.798  -0.053  -0.190  1.00  0.00           C  
HETATM   14  O2  UNL     1       5.812   0.537  -0.943  1.00  0.00           O  
HETATM   15  C13 UNL     1       4.075  -1.028  -1.069  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.666  -0.483  -1.289  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.018  -0.453   0.096  1.00  0.00           C  
HETATM   18  C16 UNL     1       2.283  -1.845   0.689  1.00  0.00           C  
HETATM   19  C17 UNL     1       0.551  -0.299  -0.068  1.00  0.00           C  
HETATM   20  C18 UNL     1       0.141   0.572  -1.232  1.00  0.00           C  
HETATM   21  C19 UNL     1      -1.276   0.129  -1.622  1.00  0.00           C  
HETATM   22  C20 UNL     1      -2.105  -0.200  -0.436  1.00  0.00           C  
HETATM   23  C21 UNL     1      -2.334  -1.655  -0.197  1.00  0.00           C  
HETATM   24  H1  UNL     1      -6.079   0.465  -2.569  1.00  0.00           H  
HETATM   25  H2  UNL     1      -6.073   1.035  -0.890  1.00  0.00           H  
HETATM   26  H3  UNL     1      -6.410  -0.720  -1.292  1.00  0.00           H  
HETATM   27  H4  UNL     1      -3.298   1.529  -0.690  1.00  0.00           H  
HETATM   28  H5  UNL     1      -4.486   1.209   1.267  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.492  -0.613   1.075  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.660   1.075   2.593  1.00  0.00           H  
HETATM   31  H8  UNL     1      -2.519  -0.673   2.311  1.00  0.00           H  
HETATM   32  H9  UNL     1      -1.587   1.623   0.501  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.278  -0.692   1.889  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.493   1.120   2.982  1.00  0.00           H  
HETATM   35  H12 UNL     1      -0.196   2.235   1.793  1.00  0.00           H  
HETATM   36  H13 UNL     1       1.799   2.432   0.548  1.00  0.00           H  
HETATM   37  H14 UNL     1       2.327   2.219   2.226  1.00  0.00           H  
HETATM   38  H15 UNL     1       3.028   0.072   1.969  1.00  0.00           H  
HETATM   39  H16 UNL     1       4.504   1.583   1.119  1.00  0.00           H  
HETATM   40  H17 UNL     1       3.702   1.813  -0.453  1.00  0.00           H  
HETATM   41  H18 UNL     1       5.294  -0.556   0.673  1.00  0.00           H  
HETATM   42  H19 UNL     1       6.313  -0.158  -1.463  1.00  0.00           H  
HETATM   43  H20 UNL     1       4.050  -2.008  -0.578  1.00  0.00           H  
HETATM   44  H21 UNL     1       4.529  -1.115  -2.084  1.00  0.00           H  
HETATM   45  H22 UNL     1       2.126  -1.210  -1.900  1.00  0.00           H  
HETATM   46  H23 UNL     1       2.767   0.520  -1.724  1.00  0.00           H  
HETATM   47  H24 UNL     1       2.177  -2.633  -0.067  1.00  0.00           H  
HETATM   48  H25 UNL     1       1.427  -2.004   1.410  1.00  0.00           H  
HETATM   49  H26 UNL     1       3.203  -1.869   1.272  1.00  0.00           H  
HETATM   50  H27 UNL     1       0.141  -1.325  -0.307  1.00  0.00           H  
HETATM   51  H28 UNL     1       0.166   1.640  -1.022  1.00  0.00           H  
HETATM   52  H29 UNL     1       0.775   0.305  -2.103  1.00  0.00           H  
HETATM   53  H30 UNL     1      -1.733   1.040  -2.108  1.00  0.00           H  
HETATM   54  H31 UNL     1      -1.260  -0.652  -2.391  1.00  0.00           H  
HETATM   55  H32 UNL     1      -1.994  -2.299  -1.036  1.00  0.00           H  
HETATM   56  H33 UNL     1      -3.428  -1.919  -0.076  1.00  0.00           H  
HETATM   57  H34 UNL     1      -1.885  -2.003   0.780  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

HMDB0006759
     RDKit          3D
3a-Hydroxy-5b-pregnane-20-one
 57 60  0  0  0  0  0  0  0  0999 V2000
   -5.8025    0.1881   -1.5211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3753   -0.1889   -1.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9488   -1.0477   -2.1781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4912    0.4639   -0.4825 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9062    0.3014    0.9646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6226    0.2963    1.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5721    0.5403    0.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1859    0.1638    1.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4504    1.3106    1.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8023    1.6946    1.3726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6729    0.5304    1.0003 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9091    1.0616    0.3164 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7976   -0.0534   -0.1904 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8120    0.5369   -0.9429 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0753   -1.0283   -1.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6659   -0.4830   -1.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0182   -0.4528    0.0965 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2828   -1.8454    0.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5512   -0.2994   -0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1413    0.5719   -1.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2760    0.1287   -1.6221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1045   -0.2002   -0.4357 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3345   -1.6554   -0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0790    0.4646   -2.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0732    1.0351   -0.8900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4098   -0.7198   -1.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2976    1.5287   -0.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4864    1.2093    1.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4915   -0.6127    1.0747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6596    1.0752    2.5933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5193   -0.6733    2.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5874    1.6230    0.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2782   -0.6918    1.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4926    1.1196    2.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1957    2.2350    1.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7988    2.4316    0.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3266    2.2188    2.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0277    0.0718    1.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5037    1.5830    1.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7023    1.8132   -0.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2937   -0.5563    0.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3126   -0.1580   -1.4629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0500   -2.0079   -0.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5285   -1.1149   -2.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1264   -1.2096   -1.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667    0.5201   -1.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1766   -2.6327   -0.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4273   -2.0036    1.4101 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2029   -1.8690    1.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409   -1.3254   -0.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1659    1.6397   -1.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7749    0.3050   -2.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7329    1.0404   -2.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2598   -0.6521   -2.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9938   -2.2987   -1.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4282   -1.9188   -0.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8848   -2.0035    0.7802 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  0
  8 33  1  0
  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  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  0
 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-Hydroxy-5beta-pregnane-20-one	HMDB

Chemical Formula

C₂₁H₃₄O₂

Average Molecular Weight

318.4935

Monoisotopic Molecular Weight

318.255880332

IUPAC Name

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

Traditional Name

pregnanolone

CAS Registry Number

Not Available

SMILES

[H][C@]12CCC3C4CC[C@H](C(C)=O)[C@@]4(C)CCC3[C@@]1(C)CC[C@@H](O)C2

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-KCZNCWLVSA-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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16720657)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006759)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0006759)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006759)

Source

Endogenous

Endogenous (HMDB: HMDB0006759)

Animal

Animal (HMDB: HMDB0006759)

Exogenous

Food

Food (HMDB: HMDB0006759)

Animal origin

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)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0006759)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0006759)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0006759)
Steroidogenesis (PathBank: SMP0063672)

Disease pathway

Apparent Mineralocorticoid Excess Syndrome (PathBank: SMP0120649)
3-beta-Hydroxysteroid Dehydrogenase Deficiency (PathBank: SMP0120650)
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia Due to 17 alpha-Hydroxylase Deficiency (PathBank: SMP0120672)
11-beta-Hydroxylase Deficiency (CYP11B1) (PathBank: SMP0120858)
Corticosterone Methyl Oxidase I Deficiency (CMO I) (PathBank: SMP0120860)
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH (HMDB: HMDB0006759)
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH (PathBank: SMP0120470)
21-Hydroxylase Deficiency (CYP21) (PathBank: SMP0120640)
17-alpha-Hydroxylase Deficiency (CYP17) (PathBank: SMP0120849)
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia Due to 21-Hydroxylase Deficiency (PathBank: SMP0120450)
Corticosterone Methyl Oxidase II Deficiency (CMO II) (PathBank: SMP0120642)

Lipid metabolism pathway (HMDB: HMDB0006759)

Cellular process

Cell signaling (HMDB: HMDB0006759)

Biochemical process

Lipid transport (HMDB: HMDB0006759)

System process

Reproduction (HMDB: HMDB0006759)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0006759)

Molecular messenger

Signaling molecule (HMDB: HMDB0006759)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006759)

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	38.36 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]+	173.031	31661259
DarkChem	[M-H]-	172.863	31661259
DeepCCS	[M-2H]-	223.391	30932474
DeepCCS	[M+Na]+	198.618	30932474
AllCCS	[M+H]+	183.3	32859911
AllCCS	[M+H-H2O]+	180.4	32859911
AllCCS	[M+NH4]+	185.9	32859911
AllCCS	[M+Na]+	186.6	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.	7.47 minutes	32390414
Predicted by Siyang on May 30, 2022	17.457 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.39 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
3a-Hydroxy-5b-pregnane-20-one	[H][C@]12CCC3C4CC[C@H](C(C)=O)[C@@]4(C)CCC3[C@@]1(C)CC[C@@H](O)C2	2278.9	Standard polar	33892256
3a-Hydroxy-5b-pregnane-20-one	[H][C@]12CCC3C4CC[C@H](C(C)=O)[C@@]4(C)CCC3[C@@]1(C)CC[C@@H](O)C2	2660.8	Standard non polar	33892256
3a-Hydroxy-5b-pregnane-20-one	[H][C@]12CCC3C4CC[C@H](C(C)=O)[C@@]4(C)CCC3[C@@]1(C)CC[C@@H](O)C2	2834.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3a-Hydroxy-5b-pregnane-20-one,1TMS,isomer #1	CC(=O)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@@]21C	2742.2	Semi standard non polar	33892256
3a-Hydroxy-5b-pregnane-20-one,1TMS,isomer #2	CC(O[Si](C)(C)C)=C1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3CC[C@]12C	2764.7	Semi standard non polar	33892256
3a-Hydroxy-5b-pregnane-20-one,1TMS,isomer #3	C=C(O[Si](C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3CC[C@@]21C	2743.4	Semi standard non polar	33892256
3a-Hydroxy-5b-pregnane-20-one,2TMS,isomer #1	CC(O[Si](C)(C)C)=C1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@]12C	2754.3	Semi standard non polar	33892256
3a-Hydroxy-5b-pregnane-20-one,2TMS,isomer #1	CC(O[Si](C)(C)C)=C1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@]12C	2748.8	Standard non polar	33892256
3a-Hydroxy-5b-pregnane-20-one,2TMS,isomer #1	CC(O[Si](C)(C)C)=C1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@]12C	3115.8	Standard polar	33892256
3a-Hydroxy-5b-pregnane-20-one,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@@]21C	2718.9	Semi standard non polar	33892256
3a-Hydroxy-5b-pregnane-20-one,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@@]21C	2736.5	Standard non polar	33892256
3a-Hydroxy-5b-pregnane-20-one,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C)CC[C@]4(C)C3CC[C@@]21C	3208.2	Standard polar	33892256
3a-Hydroxy-5b-pregnane-20-one,1TBDMS,isomer #1	CC(=O)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@@]21C	2989.8	Semi standard non polar	33892256
3a-Hydroxy-5b-pregnane-20-one,1TBDMS,isomer #2	CC(O[Si](C)(C)C(C)(C)C)=C1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3CC[C@]12C	3021.5	Semi standard non polar	33892256
3a-Hydroxy-5b-pregnane-20-one,1TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O)CC[C@]4(C)C3CC[C@@]21C	3010.0	Semi standard non polar	33892256
3a-Hydroxy-5b-pregnane-20-one,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]12C	3226.2	Semi standard non polar	33892256
3a-Hydroxy-5b-pregnane-20-one,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]12C	3256.6	Standard non polar	33892256
3a-Hydroxy-5b-pregnane-20-one,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@]12C	3358.5	Standard polar	33892256
3a-Hydroxy-5b-pregnane-20-one,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@@]21C	3211.9	Semi standard non polar	33892256
3a-Hydroxy-5b-pregnane-20-one,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@@]21C	3240.8	Standard non polar	33892256
3a-Hydroxy-5b-pregnane-20-one,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CCC2C3CC[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)C3CC[C@@]21C	3424.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-11du-0292000000-d5c96280786507060adf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one GC-MS (1 TMS) - 70eV, Positive	splash10-01t9-1109000000-2c47b5bb98f082161201	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 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 - 3a-Hydroxy-5b-pregnane-20-one 10V, Positive-QTOF	splash10-0uxr-0019000000-82b5328b4643c0421b0d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 20V, Positive-QTOF	splash10-0uxr-1496000000-6fd25d5861771fb104b7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 40V, Positive-QTOF	splash10-002o-2490000000-ba6e2bc4d584ea3d3a4b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 10V, Negative-QTOF	splash10-014i-0029000000-826f869c8c8e3739b52e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 20V, Negative-QTOF	splash10-014i-0059000000-699658e7c96cdaee62e8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 40V, Negative-QTOF	splash10-0zmr-1092000000-9cb4a247b808ab6f5c27	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 10V, Negative-QTOF	splash10-014i-0009000000-bbaa566ea695ae62f84e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 20V, Negative-QTOF	splash10-014i-0019000000-b27ed891ac6811eab39d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 40V, Negative-QTOF	splash10-014i-0039000000-ee44f8ffc9f4d431f1b9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 10V, Positive-QTOF	splash10-0uxr-0039000000-5b11ff3658bc22f27d0a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 20V, Positive-QTOF	splash10-0j6v-0984000000-16637ba86fccb8e48e17	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3a-Hydroxy-5b-pregnane-20-one 40V, Positive-QTOF	splash10-0a4m-6950000000-17eb447f04784923dcfe	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Steroidogenesis
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency		Not Available
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH		Not Available
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase Deficiency		Not Available
17-alpha-hydroxylase deficiency (CYP17)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00016 +/- 0.00018 uM	Adult (>18 years old)	Female	Normal	16720657	details
Blood	Detected and Quantified	0.00052 +/- 0.00042 uM	Adult (>18 years old)	Female	Normal	16720657	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024063

KNApSAcK ID

Not Available

Chemspider ID

23141070

KEGG Compound ID

C05480

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24779614

PDB ID

Not Available

ChEBI ID

88767

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Aldo-keto reductase family 1 member C4

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:: AKR1C4
Uniprot ID:: P17516
Molecular weight:: 37094.57

Reactions

3a-Hydroxy-5b-pregnane-20-one + NAD → 5a-Pregnane-3,20-dione + NADH + Hydrogen Ion	details
3a-Hydroxy-5b-pregnane-20-one + NADP → 5a-Pregnane-3,20-dione + NADPH + Hydrogen Ion	details

Showing metabocard for 3a-Hydroxy-5b-pregnane-20-one (HMDB0006759)

MOL for HMDB0006759 (3a-Hydroxy-5b-pregnane-20-one)

3D MOL for HMDB0006759 (3a-Hydroxy-5b-pregnane-20-one)

3D SDF for HMDB0006759 (3a-Hydroxy-5b-pregnane-20-one)

3D-SDF for HMDB0006759 (3a-Hydroxy-5b-pregnane-20-one)

PDB for HMDB0006759 (3a-Hydroxy-5b-pregnane-20-one)

3D PDB for HMDB0006759 (3a-Hydroxy-5b-pregnane-20-one)

SMILES for HMDB0006759 (3a-Hydroxy-5b-pregnane-20-one)

INCHI for HMDB0006759 (3a-Hydroxy-5b-pregnane-20-one)

Structure for HMDB0006759 (3a-Hydroxy-5b-pregnane-20-one)

3D Structure for HMDB0006759 (3a-Hydroxy-5b-pregnane-20-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions