NP-MRD: Showing NP-Card for 11-Dehydrocorticosterone (NP0087118)

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Record Information

Version

2.0

Created at

2022-05-11 16:40:37 UTC

Updated at

2022-05-11 16:40:37 UTC

NP-MRD ID

NP0087118

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-Dehydrocorticosterone

Description

11-Dehydrocorticosterone, also known as 17-deoxycortisone or kendall's compound a, 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, 11-dehydrocorticosterone is considered to be a steroid lipid molecule. 11-Dehydrocorticosterone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 11-Dehydrocorticosterone can be biosynthesized from corticosterone through the action of the enzyme corticosteroid 11-beta-dehydrogenase isozyme 2. In humans, 11-dehydrocorticosterone is involved in the metabolic disorder called the apparent mineralocorticoid excess syndrome pathway. 11-Dehydrocorticosterone is a potentially toxic compound. 11-Dehydrocorticosterone was first documented in 1996 (PMID: 8733012). It is a potent mineralocorticoid, with generally greater such activity than that of corticosterone (PMID: 15708676) (PMID: 10651756) (PMID: 10650936) (PMID: 17584152).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231219512D          

 28 31  0  0  1  0            999 V2000
    8.5756   -4.0893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2901   -4.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0045   -4.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7190   -4.5018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5734   -6.7747    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5734   -7.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8589   -6.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8589   -8.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1444   -6.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1444   -7.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0023   -6.7747    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0023   -7.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2878   -6.3622    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2878   -8.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7169   -5.5372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7169   -6.3622    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0023   -5.1247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2879   -5.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2917   -5.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9444   -5.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9350   -6.3655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7114   -4.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6974   -7.1733    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2851   -7.1453    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9983   -6.0126    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724   -7.9563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5720   -6.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   -5.1597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 12 11  1  0  0  0  0
 14 12  1  0  0  0  0
  5 13  1  0  0  0  0
  6 14  1  0  0  0  0
  6  5  1  0  0  0  0
 17 15  1  0  0  0  0
 11 16  1  0  0  0  0
 18 17  1  0  0  0  0
 13 11  1  0  0  0  0
 13 18  1  0  0  0  0
 19 15  1  0  0  0  0
 16 15  1  0  0  0  0
 20 19  1  0  0  0  0
 21 16  1  0  0  0  0
 21 20  1  0  0  0  0
 10  9  1  0  0  0  0
 15 22  1  1  0  0  0
 16 23  1  6  0  0  0
 13 24  1  6  0  0  0
 11 25  1  1  0  0  0
 10 26  2  0  0  0  0
  5 27  1  1  0  0  0
  2 19  1  0  0  0  0
 18 28  2  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
    2.1228   -0.5450   -1.5049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7571   -0.4906   -0.0704 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9858   -1.6390    0.4571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4727   -1.5376    0.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0850   -2.5563    0.0621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1671   -0.2548    0.3659 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3245    0.7753   -0.3490 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9934    2.1366   -0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1600    2.0171   -1.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0715    0.9829   -0.6830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3720    1.2122   -0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2974    0.2356   -0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4139    0.0407   -0.7269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8654   -0.4969    1.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3998   -0.6446    1.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6009   -0.2608   -0.0722 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8612   -1.3837   -1.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0057    0.7876    0.3171 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9620    1.8185   -0.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3075    1.2266    0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304   -0.2009    0.7216 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1199   -1.1199    0.3779 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9777   -2.1020   -0.3268 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4765   -0.8427    0.9167 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3883   -1.7855    0.5110 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2232   -0.3597   -1.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5981    0.1274   -2.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9527   -1.5863   -1.8972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2146   -1.7892    1.5362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3827   -2.5733   -0.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1011    0.0493    1.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2477    0.4705   -1.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2465    2.8838   -0.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3869    2.3334    0.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6493    2.9915   -1.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7487    1.6945   -2.2456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7509    2.1442   -1.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3158    0.0220    1.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3433   -1.5195    1.0345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0657   -0.0148    2.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1387   -1.6916    1.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0276   -1.5396   -1.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7185   -1.0646   -1.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2686   -2.2958   -0.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9436    0.7674    1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8941    1.9328   -1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8531    2.7992    0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7795    1.8198    1.0693 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0062    1.2531   -0.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8423   -0.1432    1.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4678   -0.7919    2.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8518    0.1558    0.5935 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9506   -1.4480   -0.2244 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  6
  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  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
  2 18  1  0
 16  6  1  0
  7 18  1  0
 16 10  1  0
 18 45  1  1
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  1
 24 51  1  0
 24 52  1  0
 25 53  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  1
  7 32  1  6
  8 33  1  0
  8 34  1  0
  9 35  1  0
  9 36  1  0
 11 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
M  END


  Mrv0541 02231219512D          

 28 31  0  0  1  0            999 V2000
    8.5756   -4.0893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2901   -4.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0045   -4.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7190   -4.5018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5734   -6.7747    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5734   -7.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8589   -6.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8589   -8.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1444   -6.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1444   -7.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0023   -6.7747    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0023   -7.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2878   -6.3622    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2878   -8.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7169   -5.5372    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7169   -6.3622    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0023   -5.1247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2879   -5.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2917   -5.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9444   -5.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9350   -6.3655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7114   -4.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6974   -7.1733    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2851   -7.1453    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9983   -6.0126    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724   -7.9563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5720   -6.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   -5.1597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 12 11  1  0  0  0  0
 14 12  1  0  0  0  0
  5 13  1  0  0  0  0
  6 14  1  0  0  0  0
  6  5  1  0  0  0  0
 17 15  1  0  0  0  0
 11 16  1  0  0  0  0
 18 17  1  0  0  0  0
 13 11  1  0  0  0  0
 13 18  1  0  0  0  0
 19 15  1  0  0  0  0
 16 15  1  0  0  0  0
 20 19  1  0  0  0  0
 21 16  1  0  0  0  0
 21 20  1  0  0  0  0
 10  9  1  0  0  0  0
 15 22  1  1  0  0  0
 16 23  1  6  0  0  0
 13 24  1  6  0  0  0
 11 25  1  1  0  0  0
 10 26  2  0  0  0  0
  5 27  1  1  0  0  0
  2 19  1  0  0  0  0
 18 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0087118

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O4/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/h9,14-16,19,22H,3-8,10-11H2,1-2H3/t14-,15-,16?,19+,20-,21-/m0/s1

> <INCHI_KEY>
FUFLCEKSBBHCMO-IWBQTIMDSA-N

> <FORMULA>
C21H28O4

> <MOLECULAR_WEIGHT>
344.4446

> <EXACT_MASS>
344.198759384

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
37.881793516992246

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10S,11S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,17-dione

> <ALOGPS_LOGP>
2.44

> <JCHEM_LOGP>
2.408105811333334

> <ALOGPS_LOGS>
-3.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.82102388247558

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.864704868727241

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2953240661973906

> <JCHEM_POLAR_SURFACE_AREA>
71.44

> <JCHEM_REFRACTIVITY>
95.07479999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-dehydrocorticosterone

> <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  O   UNK     0      16.008  -7.633   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      17.342  -8.403   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.675  -7.633   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      20.009  -8.403   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      12.270 -12.646   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.270 -14.186   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.937 -11.876   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.937 -14.956   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.603 -12.646   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.603 -14.186   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.938 -12.646   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.938 -14.186   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.604 -11.876   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.604 -14.956   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.272 -10.336   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.272 -11.876   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.938  -9.566   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.604 -10.336   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.345  -9.808   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.563 -10.245   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.545 -11.882   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.261  -9.057   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      16.235 -13.390   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      13.599 -13.338   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      14.930 -11.224   0.000  0.00  0.00           H+0
HETATM   26  O   UNK     0       8.535 -14.852   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      12.268 -11.380   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.320  -9.631   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    7   13    6   27                                             
CONECT    6    8   14    5                                                  
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   10                                                       
CONECT   10    8    9   26                                                  
CONECT   11   12   16   13   25                                             
CONECT   12   11   14                                                       
CONECT   13    5   11   18   24                                             
CONECT   14   12    6                                                       
CONECT   15   17   19   16   22                                             
CONECT   16   11   15   21   23                                             
CONECT   17   15   18                                                       
CONECT   18   17   13   28                                                  
CONECT   19   15   20    2                                                  
CONECT   20   19   21                                                       
CONECT   21   16   20                                                       
CONECT   22   15                                                            
CONECT   23   16                                                            
CONECT   24   13                                                            
CONECT   25   11                                                            
CONECT   26   10                                                            
CONECT   27    5                                                            
CONECT   28   18                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
11-Dehydro-corticosterone	HMDB
11-Dehydrocorticosteron	HMDB
11-oxo-11-Deoxycorticosterone	HMDB
11-Oxocorticosterone	HMDB
17-(1-Keto-2-hydroxyethyl)-D4-androsten-3,11-dione	HMDB
17-Deoxycortisone	HMDB
21-Hydroxypregn-4-ene-3,11,20-trione	HMDB
21-Hydroxypregn-4-ene-3,11-20-trione	HMDB
4-Pregnen-21-ol-3,11,20-trione	HMDB
D4-Pregnen-21-ol-3,11,20-trione	HMDB
D4-Pregnene-21-ol-3,11,20-trione	HMDB
Dehydrocorticosterone	HMDB
Dehydrocortocicosterone	HMDB
Kendall'S compound a	HMDB
11-Dehydrocorticosterone, 4-(14)C labeled	HMDB

Chemical Formula

C₂₁H₂₈O₄

Average Mass

344.4446 Da

Monoisotopic Mass

344.19876 Da

IUPAC Name

(1S,2R,10S,11S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,17-dione

Traditional Name

11-dehydrocorticosterone

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H28O4/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/h9,14-16,19,22H,3-8,10-11H2,1-2H3/t14-,15-,16?,19+,20-,21-/m0/s1

InChI Key

FUFLCEKSBBHCMO-IWBQTIMDSA-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
Pregnane-skeleton
20-oxosteroid
3-oxo-delta-4-steroid
3-oxosteroid
Oxosteroid
11-oxosteroid
Delta-4-steroid
Cyclohexenone
Alpha-hydroxy ketone
Cyclic ketone
Ketone
Organic oxygen compound
Organooxygen compound
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030192 )

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	2.44	ALOGPS
logP	2.41	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.86	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.44 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	95.07 m³·mol⁻¹	ChemAxon
Polarizability	37.88 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

HMDB0004029

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023282

KNApSAcK ID

Not Available

Chemspider ID

24850107

KEGG Compound ID

C05490

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

11-Dehydrocorticosterone

METLIN ID

7003

PubChem Compound

13783449

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ronquist-Nii Y, Edlund PO: Determination of corticosteroids in tissue samples by liquid chromatography-tandem mass spectrometry. J Pharm Biomed Anal. 2005 Feb 23;37(2):341-50. doi: 10.1016/j.jpba.2004.10.044. [PubMed:15708676 ]
Walker BR, Rodin A, Taylor NF, Clayton RN: Endogenous inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 do not explain abnormal cortisol metabolism in polycystic ovary syndrome. Clin Endocrinol (Oxf). 2000 Jan;52(1):77-80. doi: 10.1046/j.1365-2265.2000.00893.x. [PubMed:10651756 ]
Edwards CR, Benediktsson R, Lindsay RS, Seckl JR: 11 beta-Hydroxysteroid dehydrogenases: key enzymes in determining tissue-specific glucocorticoid effects. Steroids. 1996 Apr;61(4):263-9. doi: 10.1016/0039-128x(96)00033-5. [PubMed:8733012 ]
Livingstone DE, Jones GC, Smith K, Jamieson PM, Andrew R, Kenyon CJ, Walker BR: Understanding the role of glucocorticoids in obesity: tissue-specific alterations of corticosterone metabolism in obese Zucker rats. Endocrinology. 2000 Feb;141(2):560-3. doi: 10.1210/endo.141.2.7297. [PubMed:10650936 ]
Atanasov AG, Odermatt A: Readjusting the glucocorticoid balance: an opportunity for modulators of 11beta-hydroxysteroid dehydrogenase type 1 activity? Endocr Metab Immune Disord Drug Targets. 2007 Jun;7(2):125-40. doi: 10.2174/187153007780832082. [PubMed:17584152 ]

Showing NP-Card for 11-Dehydrocorticosterone (NP0087118)

MOL for NP0087118 (11-Dehydrocorticosterone)

3D MOL for NP0087118 (11-Dehydrocorticosterone)

3D SDF for NP0087118 (11-Dehydrocorticosterone)

3D-SDF for NP0087118 (11-Dehydrocorticosterone)

PDB for NP0087118 (11-Dehydrocorticosterone)

3D PDB for NP0087118 (11-Dehydrocorticosterone)

SMILES for NP0087118 (11-Dehydrocorticosterone)

INCHI for NP0087118 (11-Dehydrocorticosterone)

Structure for NP0087118 (11-Dehydrocorticosterone)

3D Structure for NP0087118 (11-Dehydrocorticosterone)