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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

Expected but not Quantified

Creation Date

2009-02-03 10:14:16 UTC

Update Date

2022-03-07 02:51:12 UTC

HMDB ID

HMDB0011653

Secondary Accession Numbers

HMDB0003851
HMDB03851
HMDB11653

Metabolite Identification

Common Name

17alpha,20alpha-Dihydroxypregn-4-en-3-one

Description

17 alpha,20alpha-Dihydroxypregn-4-en-3-one, also known as 17,20 alpha-OHP or 20alpha-dihydroxyprogesterone, is a steroid hormone that is elevated in late pregnancy. In particular, the concentration of plasma 17,20 alpha-OHP is significantly increased during the third trimester of pregnancy, and the increment continues to increase through labour and delivery (PMID:6874891 ). 17,20 alpha-OHP is known to be a substrate for the enzyme 20alpha-hydroxysteroid dehydrogenase or 20alpha-HSD (EC 1.1.1.149). This enzyme catalyzes the following chemical reaction: 17alpha,20alpha-dihydroxypregn-4-en-3-one + NAD(P)+ = 17alpha-hydroxyprogesterone + NAD(P)H + H+. This enzyme is actively involved in the control of progesterone homeostasis in the pregnancy of mammals. While 20alpha-HSD expression and activity is downregulated in the corpus luteum of pregnancy, 24 hours prior to parturition, ovarian 20alpha-HSD activity is acutely stimulated. 17,20 alpha-OHP is a biologically weaker progestin. Progestin facilitates estrogen induction of the preovulatory luteinizing hormone (LH) surge. It is known that 17,20 alpha-OHP is increased at midcycle but its importance in regulating LH has not been studied. However, periovulatory levels of 17,20 alpha-OHP do not play a role in modulating the estrogen-induced bioactive LH surge (PMID:2245841 ).

Structure

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

      
  Mrv1652305261923532D          

 27 30  0  0  1  0            999 V2000
   11.6103   -5.0194    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1544   -5.8797    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8685   -5.4667    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1544   -6.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5827   -5.8797    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5827   -4.2189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4402   -7.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4402   -5.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8685   -4.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8685   -7.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5827   -6.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7175   -6.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7175   -5.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1544   -5.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3055   -3.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9947   -7.1272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9037   -6.2435    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3267   -6.3331    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5751   -5.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3055   -4.6368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3055   -5.4618    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0901   -5.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0901   -4.3819    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0901   -3.5569    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3768   -3.1359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8065   -3.1479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8747   -4.1269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  8  2  1  0  0  0  0
  2 14  1  1  0  0  0
  5  3  1  0  0  0  0
  9  3  1  0  0  0  0
  7  4  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
  9  6  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 11 10  1  0  0  0  0
 13 12  1  0  0  0  0
 12 16  2  0  0  0  0
  3 17  1  6  0  0  0
  5  1  1  1  0  0  0
 19 22  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  1  0  0  0
 26 24  1  0  0  0  0
 19 23  1  0  0  0  0
 23 20  1  0  0  0  0
 21 18  1  6  0  0  0
  5 21  1  0  0  0  0
 20 15  1  1  0  0  0
  6 20  1  0  0  0  0
 23 27  1  6  0  0  0
M  END

HMDB0011653
     RDKit          3D
17alpha,20alpha-Dihydroxypregn-4-en-3-one
 56 59  0  0  0  0  0  0  0  0999 V2000
   -5.3887   -0.6106   -0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1153   -0.8094    0.1883 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2896   -0.5084    1.5213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0255   -0.0593   -0.4891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9534   -0.4467   -1.8055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1613    1.4329   -0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7310    2.0003   -0.4367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9135    0.7889   -0.7112 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5259    0.8785   -0.4056 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2013    1.6094   -1.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6543    1.3770   -1.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2910    0.6026   -0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5972    0.6886   -0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1991   -0.0833    0.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1758    0.3826    1.2892 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6440   -1.4152    0.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2492   -1.5954    0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5224   -0.2770    0.3250 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4610    0.4197    1.6617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1703   -0.4753   -0.2886 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3714   -1.4818    0.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0417   -1.5647   -0.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6667   -0.2471    0.1334 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6084    0.2145    1.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9711    0.2607   -0.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0878   -0.4787   -1.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0306   -1.5208   -0.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8767   -1.8910    0.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9669   -1.1413    1.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9173   -1.4161   -1.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7078    1.7765    0.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7060    1.8306   -1.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358    2.7943   -1.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999    2.3711    0.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0392    0.5424   -1.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7672    1.4637    0.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9554    2.7030   -1.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7046    1.2368   -2.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9460    0.8795   -2.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1812    2.3720   -1.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2151    1.3295   -1.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328   -2.1960    0.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6034   -1.5330    2.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6812   -2.2799    1.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339   -2.0126   -0.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576    0.1278    2.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5120    1.5233    1.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5856    0.1575    2.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3382   -0.8723   -1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3137   -1.3218    1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8231   -2.4801    0.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9795   -1.7340   -1.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6340   -2.3497    0.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6792    0.7743    1.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6421   -0.6291    2.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4448    0.8924    1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  6
  4  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  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23  4  1  0
 23  8  1  0
 20  9  1  0
 18 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  1
  3 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  6
  9 36  1  1
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 13 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 17 45  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  6
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
M  END

      
  Mrv1652305261923532D          

 27 30  0  0  1  0            999 V2000
   11.6103   -5.0194    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1544   -5.8797    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8685   -5.4667    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.1544   -6.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5827   -5.8797    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.5827   -4.2189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4402   -7.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4402   -5.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8685   -4.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8685   -7.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5827   -6.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7175   -6.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7175   -5.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1544   -5.0449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3055   -3.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9947   -7.1272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9037   -6.2435    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3267   -6.3331    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5751   -5.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3055   -4.6368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3055   -5.4618    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0901   -5.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0901   -4.3819    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0901   -3.5569    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.3768   -3.1359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8065   -3.1479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8747   -4.1269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  8  2  1  0  0  0  0
  2 14  1  1  0  0  0
  5  3  1  0  0  0  0
  9  3  1  0  0  0  0
  7  4  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
  9  6  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 11 10  1  0  0  0  0
 13 12  1  0  0  0  0
 12 16  2  0  0  0  0
  3 17  1  6  0  0  0
  5  1  1  1  0  0  0
 19 22  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  1  0  0  0
 26 24  1  0  0  0  0
 19 23  1  0  0  0  0
 23 20  1  0  0  0  0
 21 18  1  6  0  0  0
  5 21  1  0  0  0  0
 20 15  1  1  0  0  0
  6 20  1  0  0  0  0
 23 27  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0011653

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@](O)([C@H](C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12-13,16-18,22,24H,4-11H2,1-3H3/t13-,16+,17-,18-,19-,20-,21-/m0/s1

> <INCHI_KEY>
MASCESDECGBIBB-HNXXTFFGSA-N

> <FORMULA>
C21H32O3

> <MOLECULAR_WEIGHT>
332.477

> <EXACT_MASS>
332.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.63240111514087

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

> <ALOGPS_LOGP>
2.84

> <JCHEM_LOGP>
3.0156650240000014

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.109278210716084

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.417379542655251

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1313712193039143

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
95.03049999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0011653
     RDKit          3D
17alpha,20alpha-Dihydroxypregn-4-en-3-one
 56 59  0  0  0  0  0  0  0  0999 V2000
   -5.3887   -0.6106   -0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1153   -0.8094    0.1883 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2896   -0.5084    1.5213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0255   -0.0593   -0.4891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9534   -0.4467   -1.8055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1613    1.4329   -0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7310    2.0003   -0.4367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9135    0.7889   -0.7112 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5259    0.8785   -0.4056 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2013    1.6094   -1.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6543    1.3770   -1.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2910    0.6026   -0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5972    0.6886   -0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1991   -0.0833    0.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1758    0.3826    1.2892 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6440   -1.4152    0.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2492   -1.5954    0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5224   -0.2770    0.3250 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4610    0.4197    1.6617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1703   -0.4753   -0.2886 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3714   -1.4818    0.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0417   -1.5647   -0.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6667   -0.2471    0.1334 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6084    0.2145    1.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9711    0.2607   -0.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0878   -0.4787   -1.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0306   -1.5208   -0.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8767   -1.8910    0.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9669   -1.1413    1.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9173   -1.4161   -1.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7078    1.7765    0.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7060    1.8306   -1.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358    2.7943   -1.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999    2.3711    0.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0392    0.5424   -1.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7672    1.4637    0.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9554    2.7030   -1.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7046    1.2368   -2.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9460    0.8795   -2.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1812    2.3720   -1.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2151    1.3295   -1.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328   -2.1960    0.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6034   -1.5330    2.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6812   -2.2799    1.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339   -2.0126   -0.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576    0.1278    2.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5120    1.5233    1.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5856    0.1575    2.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3382   -0.8723   -1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3137   -1.3218    1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8231   -2.4801    0.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9795   -1.7340   -1.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6340   -2.3497    0.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6792    0.7743    1.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6421   -0.6291    2.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4448    0.8924    1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  6
  4  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  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23  4  1  0
 23  8  1  0
 20  9  1  0
 18 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  1
  3 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  6
  9 36  1  1
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 13 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 17 45  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  6
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
M  END

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  H   UNK     0      21.673  -9.370   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      18.955 -10.975   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.288 -10.205   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.955 -12.517   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.621 -10.975   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.621  -7.875   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.622 -13.288   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.622 -10.205   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.288  -8.646   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.288 -13.288   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.621 -12.517   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.273 -12.517   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.273 -10.975   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.955  -9.417   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.970  -7.104   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.923 -13.304   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0      20.354 -11.655   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0      23.010 -11.822   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0      25.340  -9.425   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      22.970  -8.655   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      22.970 -10.195   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.435 -10.671   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      24.435  -8.180   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      24.435  -6.640   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      23.103  -5.854   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      25.772  -5.876   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      25.899  -7.704   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    3    4    8   14                                             
CONECT    3    2    5    9   17                                             
CONECT    4    2    7   10                                                  
CONECT    5    3   11    1   21                                             
CONECT    6    9   20                                                       
CONECT    7    4   12                                                       
CONECT    8    2   13                                                       
CONECT    9    3    6                                                       
CONECT   10    4   11                                                       
CONECT   11    5   10                                                       
CONECT   12    7   13   16                                                  
CONECT   13    8   12                                                       
CONECT   14    2                                                            
CONECT   15   20                                                            
CONECT   16   12                                                            
CONECT   17    3                                                            
CONECT   18   21                                                            
CONECT   19   22   23                                                       
CONECT   20   21   23   15    6                                             
CONECT   21   20   22   18    5                                             
CONECT   22   19   21                                                       
CONECT   23   24   19   20   27                                             
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   23                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0011653
HETATM    1  C1  UNL     1      -5.389  -0.611  -0.617  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.115  -0.809   0.188  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.290  -0.508   1.521  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.026  -0.059  -0.489  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.953  -0.447  -1.806  1.00  0.00           O  
HETATM    6  C4  UNL     1      -3.161   1.433  -0.418  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.731   2.000  -0.437  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.913   0.789  -0.711  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.526   0.878  -0.406  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.201   1.609  -1.548  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.654   1.377  -1.682  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.291   0.603  -0.593  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.597   0.689  -0.418  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.199  -0.083   0.660  1.00  0.00           C  
HETATM   15  O3  UNL     1       6.176   0.383   1.289  1.00  0.00           O  
HETATM   16  C13 UNL     1       4.644  -1.415   0.996  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.249  -1.595   0.428  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.522  -0.277   0.325  1.00  0.00           C  
HETATM   19  C16 UNL     1       2.461   0.420   1.662  1.00  0.00           C  
HETATM   20  C17 UNL     1       1.170  -0.475  -0.289  1.00  0.00           C  
HETATM   21  C18 UNL     1       0.371  -1.482   0.457  1.00  0.00           C  
HETATM   22  C19 UNL     1      -1.042  -1.565  -0.125  1.00  0.00           C  
HETATM   23  C20 UNL     1      -1.667  -0.247   0.133  1.00  0.00           C  
HETATM   24  C21 UNL     1      -1.608   0.215   1.556  1.00  0.00           C  
HETATM   25  H1  UNL     1      -5.971   0.261  -0.286  1.00  0.00           H  
HETATM   26  H2  UNL     1      -5.088  -0.479  -1.688  1.00  0.00           H  
HETATM   27  H3  UNL     1      -6.031  -1.521  -0.566  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.877  -1.891   0.122  1.00  0.00           H  
HETATM   29  H5  UNL     1      -4.967  -1.141   1.878  1.00  0.00           H  
HETATM   30  H6  UNL     1      -2.917  -1.416  -1.878  1.00  0.00           H  
HETATM   31  H7  UNL     1      -3.708   1.776   0.486  1.00  0.00           H  
HETATM   32  H8  UNL     1      -3.706   1.831  -1.285  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.636   2.794  -1.208  1.00  0.00           H  
HETATM   34  H10 UNL     1      -1.500   2.371   0.579  1.00  0.00           H  
HETATM   35  H11 UNL     1      -1.039   0.542  -1.803  1.00  0.00           H  
HETATM   36  H12 UNL     1       0.767   1.464   0.512  1.00  0.00           H  
HETATM   37  H13 UNL     1       0.955   2.703  -1.528  1.00  0.00           H  
HETATM   38  H14 UNL     1       0.705   1.237  -2.491  1.00  0.00           H  
HETATM   39  H15 UNL     1       2.946   0.879  -2.649  1.00  0.00           H  
HETATM   40  H16 UNL     1       3.181   2.372  -1.705  1.00  0.00           H  
HETATM   41  H17 UNL     1       5.215   1.329  -1.069  1.00  0.00           H  
HETATM   42  H18 UNL     1       5.333  -2.196   0.622  1.00  0.00           H  
HETATM   43  H19 UNL     1       4.603  -1.533   2.108  1.00  0.00           H  
HETATM   44  H20 UNL     1       2.681  -2.280   1.095  1.00  0.00           H  
HETATM   45  H21 UNL     1       3.334  -2.013  -0.595  1.00  0.00           H  
HETATM   46  H22 UNL     1       3.358   0.128   2.283  1.00  0.00           H  
HETATM   47  H23 UNL     1       2.512   1.523   1.567  1.00  0.00           H  
HETATM   48  H24 UNL     1       1.586   0.158   2.262  1.00  0.00           H  
HETATM   49  H25 UNL     1       1.338  -0.872  -1.322  1.00  0.00           H  
HETATM   50  H26 UNL     1       0.314  -1.322   1.541  1.00  0.00           H  
HETATM   51  H27 UNL     1       0.823  -2.480   0.283  1.00  0.00           H  
HETATM   52  H28 UNL     1      -0.980  -1.734  -1.207  1.00  0.00           H  
HETATM   53  H29 UNL     1      -1.634  -2.350   0.380  1.00  0.00           H  
HETATM   54  H30 UNL     1      -0.679   0.774   1.770  1.00  0.00           H  
HETATM   55  H31 UNL     1      -1.642  -0.629   2.284  1.00  0.00           H  
HETATM   56  H32 UNL     1      -2.445   0.892   1.829  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4   28
CONECT    3   29
CONECT    4    5    6   23
CONECT    5   30
CONECT    6    7   31   32
CONECT    7    8   33   34
CONECT    8    9   23   35
CONECT    9   10   20   36
CONECT   10   11   37   38
CONECT   11   12   39   40
CONECT   12   13   13   18
CONECT   13   14   41
CONECT   14   15   15   16
CONECT   16   17   42   43
CONECT   17   18   44   45
CONECT   18   19   20
CONECT   19   46   47   48
CONECT   20   21   49
CONECT   21   22   50   51
CONECT   22   23   52   53
CONECT   23   24
CONECT   24   54   55   56
END

HMDB0011653
     RDKit          3D
17alpha,20alpha-Dihydroxypregn-4-en-3-one
 56 59  0  0  0  0  0  0  0  0999 V2000
   -5.3887   -0.6106   -0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1153   -0.8094    0.1883 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2896   -0.5084    1.5213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0255   -0.0593   -0.4891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9534   -0.4467   -1.8055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1613    1.4329   -0.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7310    2.0003   -0.4367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9135    0.7889   -0.7112 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5259    0.8785   -0.4056 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2013    1.6094   -1.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6543    1.3770   -1.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2910    0.6026   -0.5934 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5972    0.6886   -0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1991   -0.0833    0.6597 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1758    0.3826    1.2892 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6440   -1.4152    0.9959 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2492   -1.5954    0.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5224   -0.2770    0.3250 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4610    0.4197    1.6617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1703   -0.4753   -0.2886 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3714   -1.4818    0.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0417   -1.5647   -0.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6667   -0.2471    0.1334 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6084    0.2145    1.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9711    0.2607   -0.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0878   -0.4787   -1.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0306   -1.5208   -0.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8767   -1.8910    0.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9669   -1.1413    1.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9173   -1.4161   -1.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7078    1.7765    0.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7060    1.8306   -1.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358    2.7943   -1.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999    2.3711    0.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0392    0.5424   -1.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7672    1.4637    0.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9554    2.7030   -1.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7046    1.2368   -2.4906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9460    0.8795   -2.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1812    2.3720   -1.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2151    1.3295   -1.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328   -2.1960    0.6223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6034   -1.5330    2.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6812   -2.2799    1.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339   -2.0126   -0.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576    0.1278    2.2826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5120    1.5233    1.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5856    0.1575    2.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3382   -0.8723   -1.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3137   -1.3218    1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8231   -2.4801    0.2829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9795   -1.7340   -1.2068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6340   -2.3497    0.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6792    0.7743    1.7696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6421   -0.6291    2.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4448    0.8924    1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  6
  4  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  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23  4  1  0
 23  8  1  0
 20  9  1  0
 18 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  1
  3 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  6
  9 36  1  1
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 13 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 17 45  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  6
 21 50  1  0
 21 51  1  0
 22 52  1  0
 22 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
17a,20a-Dihydroxypregn-4-en-3-one	Generator
17Α,20α-dihydroxypregn-4-en-3-one	Generator
17alpha,20alpha-Dihydroxypregn-4-en-3-one	ChEBI
17-a,20-a-Dihydroxypregn-4-en-3-one	Generator, HMDB
17-α,20-α-dihydroxypregn-4-en-3-one	Generator, HMDB
(20S)-17,20-Dihydroxypregn-4-en-3-one	HMDB
17 alpha, 20 alpha-OHP	HMDB
17 alpha, 20 alpha-P	HMDB
17,20 alpha-OHP	HMDB
17-alpha,20-alpha-Dihydroxypregn-4-en-3-one	HMDB
4-Pregnen-17a, 20a-diol-3-one	HMDB
4-Pregnen-17α, 20α-diol-3-one	HMDB
4-Pregnen-17alpha, 20alpha-diol-3-one	HMDB
17a-Hydroxy-20a-dihydroprogesterone	HMDB
17α-Hydroxy-20α-dihydroprogesterone	HMDB
17alpha-Hydroxy-20alpha-dihydroprogesterone	HMDB
20a-Dihydroxyprogesterone	HMDB
20α-Dihydroxyprogesterone	HMDB
20alpha-Dihydroxyprogesterone	HMDB
17,20α-Dihydroxy-4-pregnen-3-one	HMDB
17,20a-Dihydroxy-4-pregnen-3-one	HMDB
17,20alpha-Dihydroxy-4-pregnen-3-one	HMDB
17,20α-Dihydroxy-pregn-4-en-3-one	HMDB
17,20a-Dihydroxy-pregn-4-en-3-one	HMDB
17,20alpha-Dihydroxy-pregn-4-en-3-one	HMDB
17α,20α-Dihydroxy-4-pregnen-3-one	HMDB
17a,20a-Dihydroxy-4-pregnen-3-one	HMDB
17alpha,20alpha-Dihydroxy-4-pregnen-3-one	HMDB
17α,20α-Dihydroxypregn-4-ene-3-one	HMDB
17a,20a-Dihydroxypregn-4-ene-3-one	HMDB
17alpha,20alpha-Dihydroxypregn-4-ene-3-one	HMDB
17α,20α-Dihydroxyprogesterone	HMDB
17a,20a-Dihydroxyprogesterone	HMDB
17alpha,20alpha-Dihydroxyprogesterone	HMDB
Pregn-4-ene-17α,20α-diol-3-one	HMDB
Pregn-4-ene-17a,20a-diol-3-one	HMDB
Pregn-4-ene-17alpha,20alpha-diol-3-one	HMDB

Chemical Formula

C₂₁H₃₂O₃

Average Molecular Weight

332.477

Monoisotopic Molecular Weight

332.23514489

IUPAC Name

(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Traditional Name

(1S,2R,10R,11S,14R,15S)-14-hydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

CAS Registry Number

652-69-7

SMILES

[H][C@@]12CC[C@](O)([C@H](C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C21H32O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12-13,16-18,22,24H,4-11H2,1-3H3/t13-,16+,17-,18-,19-,20-,21-/m0/s1

InChI Key

MASCESDECGBIBB-HNXXTFFGSA-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-hydroxysteroid
3-oxo-delta-4-steroid
3-oxosteroid
17-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Cyclic alcohol
Tertiary alcohol
1,2-diol
Cyclic ketone
Secondary alcohol
Ketone
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

17,20-dihydroxypregn-4-en-3-one (CHEBI:16418 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030183 )

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	0.041 g/L	ALOGPS
logP	2.84	ALOGPS
logP	3.02	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.42	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	95.03 m³·mol⁻¹	ChemAxon
Polarizability	38.63 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	180.338	31661259
DarkChem	[M-H]-	177.721	31661259
DeepCCS	[M-2H]-	216.201	30932474
DeepCCS	[M+Na]+	191.613	30932474
AllCCS	[M+H]+	185.1	32859911
AllCCS	[M+H-H2O]+	182.3	32859911
AllCCS	[M+NH4]+	187.7	32859911
AllCCS	[M+Na]+	188.5	32859911
AllCCS	[M-H]-	188.9	32859911
AllCCS	[M+Na-2H]-	189.4	32859911
AllCCS	[M+HCOO]-	190.1	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.	6.64 minutes	32390414
Predicted by Siyang on May 30, 2022	14.5713 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.0 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2609.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	282.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	195.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	173.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	412.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	654.2 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	647.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	93.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1204.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	460.0 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	1427.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	405.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	426.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	253.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	412.0 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	10.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
17alpha,20alpha-Dihydroxypregn-4-en-3-one	[H][C@@]12CC[C@](O)([C@H](C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	4042.3	Standard polar	33892256
17alpha,20alpha-Dihydroxypregn-4-en-3-one	[H][C@@]12CC[C@](O)([C@H](C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	2878.7	Standard non polar	33892256
17alpha,20alpha-Dihydroxypregn-4-en-3-one	[H][C@@]12CC[C@](O)([C@H](C)O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	3063.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
17alpha,20alpha-Dihydroxypregn-4-en-3-one,1TMS,isomer #1	C[C@H](O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3078.8	Semi standard non polar	33892256
17alpha,20alpha-Dihydroxypregn-4-en-3-one,1TMS,isomer #2	C[C@H](O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3058.4	Semi standard non polar	33892256
17alpha,20alpha-Dihydroxypregn-4-en-3-one,1TMS,isomer #3	C[C@H](O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	2942.2	Semi standard non polar	33892256
17alpha,20alpha-Dihydroxypregn-4-en-3-one,2TMS,isomer #1	C[C@H](O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3153.8	Semi standard non polar	33892256
17alpha,20alpha-Dihydroxypregn-4-en-3-one,2TMS,isomer #2	C[C@H](O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3002.7	Semi standard non polar	33892256
17alpha,20alpha-Dihydroxypregn-4-en-3-one,2TMS,isomer #3	C[C@H](O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	2970.8	Semi standard non polar	33892256
17alpha,20alpha-Dihydroxypregn-4-en-3-one,3TMS,isomer #1	C[C@H](O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3063.1	Semi standard non polar	33892256
17alpha,20alpha-Dihydroxypregn-4-en-3-one,3TMS,isomer #1	C[C@H](O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3043.1	Standard non polar	33892256
17alpha,20alpha-Dihydroxypregn-4-en-3-one,3TMS,isomer #1	C[C@H](O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3181.3	Standard polar	33892256
17alpha,20alpha-Dihydroxypregn-4-en-3-one,1TBDMS,isomer #1	C[C@H](O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3326.4	Semi standard non polar	33892256
17alpha,20alpha-Dihydroxypregn-4-en-3-one,1TBDMS,isomer #2	C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3293.5	Semi standard non polar	33892256
17alpha,20alpha-Dihydroxypregn-4-en-3-one,1TBDMS,isomer #3	C[C@H](O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3223.5	Semi standard non polar	33892256
17alpha,20alpha-Dihydroxypregn-4-en-3-one,2TBDMS,isomer #1	C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C	3616.7	Semi standard non polar	33892256
17alpha,20alpha-Dihydroxypregn-4-en-3-one,2TBDMS,isomer #2	C[C@H](O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3511.8	Semi standard non polar	33892256
17alpha,20alpha-Dihydroxypregn-4-en-3-one,2TBDMS,isomer #3	C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3489.0	Semi standard non polar	33892256
17alpha,20alpha-Dihydroxypregn-4-en-3-one,3TBDMS,isomer #1	C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3802.9	Semi standard non polar	33892256
17alpha,20alpha-Dihydroxypregn-4-en-3-one,3TBDMS,isomer #1	C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3720.1	Standard non polar	33892256
17alpha,20alpha-Dihydroxypregn-4-en-3-one,3TBDMS,isomer #1	C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3CC[C@@]21C	3452.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 17alpha,20alpha-Dihydroxypregn-4-en-3-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-1009-3389000000-cb7be02bfc7f8d750db9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17alpha,20alpha-Dihydroxypregn-4-en-3-one GC-MS (2 TMS) - 70eV, Positive	splash10-03di-2221900000-4d8859515388ae586c48	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17alpha,20alpha-Dihydroxypregn-4-en-3-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17alpha,20alpha-Dihydroxypregn-4-en-3-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 - 17alpha,20alpha-Dihydroxypregn-4-en-3-one 10V, Positive-QTOF	splash10-00lr-0029000000-4a1c28efa846463a0725	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,20alpha-Dihydroxypregn-4-en-3-one 20V, Positive-QTOF	splash10-05nb-0296000000-5f113d14e04b9e53fe21	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,20alpha-Dihydroxypregn-4-en-3-one 40V, Positive-QTOF	splash10-00r5-2591000000-c29c05785ba6023d6c32	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,20alpha-Dihydroxypregn-4-en-3-one 10V, Negative-QTOF	splash10-001i-0019000000-9163bb555789226a64c8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,20alpha-Dihydroxypregn-4-en-3-one 20V, Negative-QTOF	splash10-001r-0097000000-6fd6b47c5cef917bc228	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,20alpha-Dihydroxypregn-4-en-3-one 40V, Negative-QTOF	splash10-05tr-0091000000-a0583d76ae6c45c3876f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,20alpha-Dihydroxypregn-4-en-3-one 10V, Positive-QTOF	splash10-001i-0019000000-dc49633d891cfa3ca389	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,20alpha-Dihydroxypregn-4-en-3-one 20V, Positive-QTOF	splash10-0400-0900000000-0bdc7df8e969edc68b24	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,20alpha-Dihydroxypregn-4-en-3-one 40V, Positive-QTOF	splash10-072a-2920000000-c955f907f75e91d61e53	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,20alpha-Dihydroxypregn-4-en-3-one 10V, Negative-QTOF	splash10-001i-0019000000-3d48d03153e0762a8c96	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,20alpha-Dihydroxypregn-4-en-3-one 20V, Negative-QTOF	splash10-001r-0098000000-2ed26b3a398241f5362e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17alpha,20alpha-Dihydroxypregn-4-en-3-one 40V, Negative-QTOF	splash10-014r-0090000000-926949293e5e1b71b18e	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB028344

KNApSAcK ID

Not Available

Chemspider ID

389326

KEGG Compound ID

C04518

BioCyc ID

17-ALPHA20-ALPHA-DIHYDROXYPREGN-4-EN-3-

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440368

PDB ID

Not Available

ChEBI ID

16418

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)

Download (PDF)

General References

Mahajan DK, Anderson G, Poole WK, Billiar RB, Little B: Changes in the concentration of 17 alpha,20 alpha-dihydroxypregn-4-en-3-one during pregnancy, labor, and delivery and the effect of dexamethasone treatment during the third trimester of pregnancy. J Clin Endocrinol Metab. 1983 Sep;57(3):585-91. [PubMed:6874891 ]
Schenken RS, Williams RF, Hodgen GD: Effect of 20 alpha-dihydroxyprogesterone on the estrogen-induced bioactive luteinizing hormone surge in ovariectomized monkeys. Fertil Steril. 1990 Dec;54(6):1146-9. [PubMed:2245841 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Aldo-keto reductase family 1 member C1

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

Reactions

17alpha,20alpha-Dihydroxypregn-4-en-3-one + NAD(P)(+) → 17-Hydroxyprogesterone + NAD(P)H	details

Showing metabocard for 17alpha,20alpha-Dihydroxypregn-4-en-3-one (HMDB0011653)

MOL for HMDB0011653 (17alpha,20alpha-Dihydroxypregn-4-en-3-one)

3D MOL for HMDB0011653 (17alpha,20alpha-Dihydroxypregn-4-en-3-one)

3D SDF for HMDB0011653 (17alpha,20alpha-Dihydroxypregn-4-en-3-one)

3D-SDF for HMDB0011653 (17alpha,20alpha-Dihydroxypregn-4-en-3-one)

PDB for HMDB0011653 (17alpha,20alpha-Dihydroxypregn-4-en-3-one)

3D PDB for HMDB0011653 (17alpha,20alpha-Dihydroxypregn-4-en-3-one)

SMILES for HMDB0011653 (17alpha,20alpha-Dihydroxypregn-4-en-3-one)

INCHI for HMDB0011653 (17alpha,20alpha-Dihydroxypregn-4-en-3-one)

Structure for HMDB0011653 (17alpha,20alpha-Dihydroxypregn-4-en-3-one)

3D Structure for HMDB0011653 (17alpha,20alpha-Dihydroxypregn-4-en-3-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions