NP-MRD: Showing NP-Card for 17alpha,20alpha-Dihydroxypregn-4-en-3-one (NP0000610)

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Record Information

Version

2.0

Created at

2009-02-03 10:14:16 UTC

Updated at

2024-09-17 15:42:24 UTC

NP-MRD ID

NP0000610

Secondary Accession Numbers

None

Natural Product 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>
NP0000610

> <DATABASE_NAME>
NP-MRD

> <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 NMR Assignments

Synonyms

Value	Source
17a,20a-Dihydroxypregn-4-en-3-one	Generator
17Α,20α-dihydroxypregn-4-en-3-one	Generator
17-a,20-a-Dihydroxypregn-4-en-3-one	HMDB
17-Α,20-α-dihydroxypregn-4-en-3-one	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
17alpha,20alpha-Dihydroxypregn-4-en-3-one	ChEBI

Chemical Formula

C₂₁H₃₂O₃

Average Mass

332.4770 Da

Monoisotopic Mass

332.23514 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

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

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-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 )

Physical Properties

State

Solid

Experimental Properties

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

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0011653

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing NP-Card for 17alpha,20alpha-Dihydroxypregn-4-en-3-one (NP0000610)

MOL for NP0000610 (17alpha,20alpha-Dihydroxypregn-4-en-3-one)

3D MOL for NP0000610 (17alpha,20alpha-Dihydroxypregn-4-en-3-one)

3D SDF for NP0000610 (17alpha,20alpha-Dihydroxypregn-4-en-3-one)

3D-SDF for NP0000610 (17alpha,20alpha-Dihydroxypregn-4-en-3-one)

PDB for NP0000610 (17alpha,20alpha-Dihydroxypregn-4-en-3-one)

3D PDB for NP0000610 (17alpha,20alpha-Dihydroxypregn-4-en-3-one)

SMILES for NP0000610 (17alpha,20alpha-Dihydroxypregn-4-en-3-one)

INCHI for NP0000610 (17alpha,20alpha-Dihydroxypregn-4-en-3-one)

Structure for NP0000610 (17alpha,20alpha-Dihydroxypregn-4-en-3-one)

3D Structure for NP0000610 (17alpha,20alpha-Dihydroxypregn-4-en-3-one)