NP-MRD: Showing NP-Card for 3a,21-Dihydroxy-5b-pregnane-11,20-dione (NP0087618)

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Record Information

Version

2.0

Created at

2022-05-11 16:54:57 UTC

Updated at

2022-05-11 16:54:57 UTC

NP-MRD ID

NP0087618

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3a,21-Dihydroxy-5b-pregnane-11,20-dione

Description

3A,21-Dihydroxy-5b-pregnane-11,20-dione, also known as 5beta-pregnane-3alpha,21-diol-11,20-dione, belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Thus, 3a,21-dihydroxy-5b-pregnane-11,20-dione is considered to be a steroid lipid molecule. 3A,21-Dihydroxy-5b-pregnane-11,20-dione is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, 3a,21-dihydroxy-5b-pregnane-11,20-dione participates in a number of enzymatic reactions. In particular, 3a,21-dihydroxy-5b-pregnane-11,20-dione can be biosynthesized from tetrahydrocorticosterone; which is mediated by the enzyme corticosteroid 11-beta-dehydrogenase isozyme 1. In addition, 3a,21-dihydroxy-5b-pregnane-11,20-dione can be converted into 21-hydroxy-5b-pregnane-3,11,20-trione; which is catalyzed by the enzyme aldo-keto reductase family 1 member C4. In humans, 3a,21-dihydroxy-5b-pregnane-11,20-dione is involved in the metabolic disorder called the apparent mineralocorticoid excess syndrome pathway.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv0541 02231220502D          

 29 32  0  0  1  0            999 V2000
   16.0925   -9.2539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5717   -9.4428    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.0687   -8.1705    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8859  -10.5958    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6967   -8.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9042   -6.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5376  -10.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2252   -9.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6604   -8.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1031   -8.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3216   -9.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0091   -8.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1114  -10.3286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0717   -7.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5783   -6.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7989   -9.8726    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3728   -9.9612    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1740   -8.9606    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.8615   -8.5046    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.5777   -7.3781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3842   -7.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7835   -6.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4353   -8.5932    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.7478   -9.0492    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.8104   -7.6812    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.1672   -6.9356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6852  -10.4172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6455   -7.4024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1945   -6.0015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 24  5  1  1  0  0  0
 25  6  1  1  0  0  0
  7 16  1  0  0  0  0
  7  8  1  0  0  0  0
  8 18  1  0  0  0  0
  9 19  1  0  0  0  0
  9 10  1  0  0  0  0
 10 20  1  0  0  0  0
 11 12  1  0  0  0  0
 11 17  1  0  0  0  0
 12 24  1  0  0  0  0
 13 17  1  0  0  0  0
 13 16  1  0  0  0  0
 14 25  1  0  0  0  0
 14 21  1  0  0  0  0
 15 22  1  0  0  0  0
 15 26  1  0  0  0  0
 16 24  1  0  0  0  0
 17 27  1  6  0  0  0
 18 19  1  0  0  0  0
 18 23  1  0  0  0  0
 19 25  1  0  0  0  0
 20 22  1  0  0  0  0
 20 25  1  0  0  0  0
 21 28  2  0  0  0  0
 21 23  1  0  0  0  0
 22 29  2  0  0  0  0
 23 24  1  0  0  0  0
 16  4  1  1  0  0  0
 18  3  1  1  0  0  0
 23  2  1  6  0  0  0
 19  1  1  6  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    2.6778   -0.6361    1.1335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2148    0.0300   -0.1428 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6447    1.3900    0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1544    1.4718    0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2910    2.5977    0.2566 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7851    0.3744   -0.1132 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0160   -0.9109    0.1666 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8142   -2.1273    0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1761   -1.8742   -0.4427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9323   -0.7400    0.1774 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9742   -0.3751   -0.8519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8587    0.7557   -0.4504 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1798    1.4648   -1.6212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2507    1.6857    0.5356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7345    1.7402    0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0696    0.4110    0.6067 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8519    0.3262    2.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1350   -0.7934   -0.8044 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8712   -2.0100   -1.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0612   -1.3826   -1.8675 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3146   -0.0593   -1.1348 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6815   -0.1738   -0.5473 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3496   -1.2195   -0.6645 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3604    0.9025    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5862    2.0383    0.2801 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5634    0.0750    1.9909 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7619   -0.8724    1.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1745   -1.6009    1.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0780    2.0630   -0.7128 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9816    1.7768    1.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0159    0.3127   -1.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3293   -0.7757    1.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3164   -2.8417   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9042   -2.6895    1.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7890   -2.8067   -0.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1444   -1.7761   -1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4767   -1.1253    1.0631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6008   -1.2790   -1.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4646   -0.2011   -1.8249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8387    0.3552   -0.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5073    2.1904   -1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6037    2.7266    0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5236    1.4455    1.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5229    2.1026   -0.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4213    2.4858    1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1695   -0.6735    2.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4689    1.0706    2.6601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7980    0.5302    2.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8580   -0.2662   -1.7541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1602   -2.6895   -0.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2969   -2.5373   -1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9071   -2.0693   -1.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8197   -1.1337   -2.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3368    0.7873   -1.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3172    1.2163   -0.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6853    0.5384    1.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1469    2.7753    0.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 21  2  1  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  2  0
  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  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  1
  2 18  1  0
 16  6  1  0
  7 18  1  0
 16 10  1  0
 18 49  1  6
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  6
 24 55  1  0
 24 56  1  0
 25 57  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  6 31  1  6
  7 32  1  1
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  1
 11 38  1  0
 11 39  1  0
 12 40  1  1
 13 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
M  END

  Mrv0541 02231220502D          

 29 32  0  0  1  0            999 V2000
   16.0925   -9.2539    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5717   -9.4428    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.0687   -8.1705    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8859  -10.5958    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6967   -8.2258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9042   -6.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5376  -10.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2252   -9.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6604   -8.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1031   -8.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3216   -9.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0091   -8.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1114  -10.3286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0717   -7.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5783   -6.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7989   -9.8726    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3728   -9.9612    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1740   -8.9606    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.8615   -8.5046    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.5777   -7.3781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3842   -7.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7835   -6.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4353   -8.5932    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.7478   -9.0492    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.8104   -7.6812    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.1672   -6.9356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6852  -10.4172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6455   -7.4024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1945   -6.0015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 24  5  1  1  0  0  0
 25  6  1  1  0  0  0
  7 16  1  0  0  0  0
  7  8  1  0  0  0  0
  8 18  1  0  0  0  0
  9 19  1  0  0  0  0
  9 10  1  0  0  0  0
 10 20  1  0  0  0  0
 11 12  1  0  0  0  0
 11 17  1  0  0  0  0
 12 24  1  0  0  0  0
 13 17  1  0  0  0  0
 13 16  1  0  0  0  0
 14 25  1  0  0  0  0
 14 21  1  0  0  0  0
 15 22  1  0  0  0  0
 15 26  1  0  0  0  0
 16 24  1  0  0  0  0
 17 27  1  6  0  0  0
 18 19  1  0  0  0  0
 18 23  1  0  0  0  0
 19 25  1  0  0  0  0
 20 22  1  0  0  0  0
 20 25  1  0  0  0  0
 21 28  2  0  0  0  0
 21 23  1  0  0  0  0
 22 29  2  0  0  0  0
 23 24  1  0  0  0  0
 16  4  1  1  0  0  0
 18  3  1  1  0  0  0
 23  2  1  6  0  0  0
 19  1  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0087618

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12-16,19,22-23H,3-11H2,1-2H3/t12-,13-,14+,15+,16?,19-,20+,21+/m1/s1

> <INCHI_KEY>
XWYBFXIUISNTQG-XPYNSANSSA-N

> <FORMULA>
C21H32O4

> <MOLECULAR_WEIGHT>
348.4764

> <EXACT_MASS>
348.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
39.15085783198822

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5R,7R,10S,11S,15S)-5-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
2.2464393446666664

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.29638219625436

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.864708713462385

> <JCHEM_PKA_STRONGEST_BASIC>
-1.356961956512448

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
95.27619999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,7R,10S,11S,15S)-5-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  H   UNK     0      30.039 -17.274   0.000  0.00  0.00           H+0
HETATM    2  H   UNK     0      27.201 -17.627   0.000  0.00  0.00           H+0
HETATM    3  H   UNK     0      28.128 -15.252   0.000  0.00  0.00           H+0
HETATM    4  H   UNK     0      25.920 -19.779   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0      25.567 -15.355   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.688 -12.808   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.137 -19.115   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      28.420 -18.263   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      31.099 -16.259   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      31.926 -14.960   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.000 -17.057   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.284 -16.206   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.475 -19.280   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.134 -13.652   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.813 -11.868   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.758 -18.429   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.096 -18.594   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.325 -16.726   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      29.608 -15.875   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.945 -13.772   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      26.851 -14.504   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      31.329 -12.281   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.946 -16.041   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      25.663 -16.892   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      29.513 -14.338   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      33.912 -12.946   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      21.812 -19.445   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      25.472 -13.818   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      30.230 -11.203   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   23                                                            
CONECT    3   18                                                            
CONECT    4   16                                                            
CONECT    5   24                                                            
CONECT    6   25                                                            
CONECT    7   16    8                                                       
CONECT    8    7   18                                                       
CONECT    9   19   10                                                       
CONECT   10    9   20                                                       
CONECT   11   12   17                                                       
CONECT   12   11   24                                                       
CONECT   13   17   16                                                       
CONECT   14   25   21                                                       
CONECT   15   22   26                                                       
CONECT   16    7   13   24    4                                             
CONECT   17   11   13   27                                                  
CONECT   18    8   19   23    3                                             
CONECT   19    9   18   25    1                                             
CONECT   20   10   22   25                                                  
CONECT   21   14   28   23                                                  
CONECT   22   15   20   29                                                  
CONECT   23   18   21   24    2                                             
CONECT   24    5   12   16   23                                             
CONECT   25    6   14   19   20                                             
CONECT   26   15                                                            
CONECT   27   17                                                            
CONECT   28   21                                                            
CONECT   29   22                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
3alpha,21-Dihydroxy-5beta-pregnane-11,20-dione	HMDB
5beta-Pregnane-3alpha,21-diol-11,20-dione	HMDB

Chemical Formula

C₂₁H₃₂O₄

Average Mass

348.4764 Da

Monoisotopic Mass

348.23006 Da

IUPAC Name

(1S,2S,5R,7R,10S,11S,15S)-5-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one

Traditional Name

(1S,2S,5R,7R,10S,11S,15S)-5-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-17-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H32O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12-16,19,22-23H,3-11H2,1-2H3/t12-,13-,14+,15+,16?,19-,20+,21+/m1/s1

InChI Key

XWYBFXIUISNTQG-XPYNSANSSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
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 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

21-hydroxysteroids

Alternative Parents

Substituents

Progestogin-skeleton
21-hydroxysteroid
20-oxosteroid
Pregnane-skeleton
3-hydroxysteroid
11-oxosteroid
Oxosteroid
3-alpha-hydroxysteroid
Cyclic alcohol
Alpha-hydroxy ketone
Ketone
Secondary alcohol
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Primary alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030199 )

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.56	ALOGPS
logP	2.25	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	13.86	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	95.28 m³·mol⁻¹	ChemAxon
Polarizability	39.15 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

HMDB0006755

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB024059

KNApSAcK ID

Not Available

Chemspider ID

24850110

KEGG Compound ID

C05478

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44263347

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3a,21-Dihydroxy-5b-pregnane-11,20-dione (NP0087618)

MOL for NP0087618 (3a,21-Dihydroxy-5b-pregnane-11,20-dione)

3D MOL for NP0087618 (3a,21-Dihydroxy-5b-pregnane-11,20-dione)

3D SDF for NP0087618 (3a,21-Dihydroxy-5b-pregnane-11,20-dione)

3D-SDF for NP0087618 (3a,21-Dihydroxy-5b-pregnane-11,20-dione)

PDB for NP0087618 (3a,21-Dihydroxy-5b-pregnane-11,20-dione)

3D PDB for NP0087618 (3a,21-Dihydroxy-5b-pregnane-11,20-dione)

SMILES for NP0087618 (3a,21-Dihydroxy-5b-pregnane-11,20-dione)

INCHI for NP0087618 (3a,21-Dihydroxy-5b-pregnane-11,20-dione)

Structure for NP0087618 (3a,21-Dihydroxy-5b-pregnane-11,20-dione)

3D Structure for NP0087618 (3a,21-Dihydroxy-5b-pregnane-11,20-dione)