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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:11 UTC

Update Date

2021-09-14 15:40:03 UTC

HMDB ID

HMDB0002802

Secondary Accession Numbers

HMDB02802

Metabolite Identification

Common Name

Cortisone

Description

Cortisone is a naturally occurring glucocorticoid. It has been used in replacement therapy for adrenal insufficiency and as an anti-inflammatory agent. Cortisone itself is inactive. It is converted in the liver into the active metabolite cortisol. Cortisone is a corticosteroid hormone released by the adrenal gland in response to stress. One of cortisone's effects on the body, and a potentially harmful side effect when administered clinically, is the suppression of the immune system. This is an explanation for the apparent correlation between high stress and sickness.

Structure

MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652305271900062D          

 29 32  0  0  1  0            999 V2000
    0.7146   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7146    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6986    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4290   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7146    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2136    1.0800    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136    1.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4992    2.3175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282    2.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6427    1.9050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282    1.4925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15  1  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  7  1  0  0  0  0
  4 19  1  0  0  0  0
 19  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7 11  1  0  0  0  0
 11 21  1  0  0  0  0
 21  8  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 13  1  0  0  0  0
 18  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  6  0  0  0
 13 14  1  6  0  0  0
 15 16  1  1  0  0  0
 18 27  1  6  0  0  0
 18 23  1  0  0  0  0
 23 25  1  0  0  0  0
 19 20  2  0  0  0  0
 21 22  2  0  0  0  0
 23 24  2  0  0  0  0
 25 26  1  0  0  0  0
  7 28  1  1  0  0  0
 17 29  1  1  0  0  0
M  END


  Mrv1652305271900062D          

 29 32  0  0  1  0            999 V2000
    0.7146   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7146    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6986    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4290   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7146    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2136    1.0800    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136    1.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4992    2.3175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282    2.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6427    1.9050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9282    1.4925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15  1  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  7  1  0  0  0  0
  4 19  1  0  0  0  0
 19  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7 11  1  0  0  0  0
 11 21  1  0  0  0  0
 21  8  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 13  1  0  0  0  0
 18  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
 11 12  1  6  0  0  0
 13 14  1  6  0  0  0
 15 16  1  1  0  0  0
 18 27  1  6  0  0  0
 18 23  1  0  0  0  0
 23 25  1  0  0  0  0
 19 20  2  0  0  0  0
 21 22  2  0  0  0  0
 23 24  2  0  0  0  0
 25 26  1  0  0  0  0
  7 28  1  1  0  0  0
 17 29  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0002802

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-15,18,22,26H,3-8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1

> <INCHI_KEY>
MFYSYFVPBJMHGN-ZPOLXVRWSA-N

> <FORMULA>
C21H28O5

> <MOLECULAR_WEIGHT>
360.444

> <EXACT_MASS>
360.193674006

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.95004409634094

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,17-dione

> <ALOGPS_LOGP>
1.98

> <JCHEM_LOGP>
1.6606806883333327

> <ALOGPS_LOGS>
-3.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.90448417023887

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.576200785155365

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3299891188847104

> <JCHEM_POLAR_SURFACE_AREA>
91.67

> <JCHEM_REFRACTIVITY>
96.47479999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D12CC%5BC@%5D(O)...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:53})
 54 57  0  0  0  0  0  0  0  0999 V2000
   -0.7090    1.4140   -1.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8562    1.3155   -0.5367 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7277    2.4626   -0.0089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1554    2.0560   -0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1353    0.5190   -0.6443 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3673    0.1805   -2.0130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1768   -0.1240    0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5541    0.4386    1.2346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7475   -1.4692   -0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7085   -1.8639    0.8477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7368    0.0761   -0.2202 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7143   -0.2091    1.2828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1619   -1.1029   -0.9891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2753   -1.2662   -0.5151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839   -2.3492   -0.1707 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1839   -0.0645   -0.4800 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4666    0.2024   -1.4983 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4763    1.1398    0.1637 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2916    0.9356    1.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3735    2.3689    0.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6464    2.1535    0.8390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2969    0.8474    0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6060    0.8605    0.1707 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2923   -0.3746   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3512   -0.3561   -0.8151 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6085   -1.6756    0.1492 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1539   -1.5736   -0.3080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4460   -0.3748    0.3297 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0268   -0.7662    1.7481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6704    2.5212    1.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4346    3.4093   -0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8829    2.3326    0.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4007    2.5416   -1.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2259    0.4712   -2.3500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2298   -1.4045   -1.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9452   -2.2059   -0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1179   -2.7227    0.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4191   -1.0085    1.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7107   -0.5135    1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9971    0.6915    1.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7325   -2.0056   -0.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1816   -0.8968   -2.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6362    2.5042   -1.0346 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8476    3.2515    0.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3379    2.9774    0.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3915    2.1109    1.8979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1623    1.7821    0.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0978   -2.5090   -0.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6484   -1.8195    1.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1289   -1.4680   -1.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6289   -2.4872   -0.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9108   -1.0312    2.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5197    0.0742    2.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3513   -1.6205    1.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2 11  1  0  0  0  0
  2 18  1  0  0  0  0
  3  4  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
  4  5  1  0  0  0  0
  4 32  1  0  0  0  0
  4 33  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  5 11  1  0  0  0  0
  6 34  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 35  1  0  0  0  0
  9 36  1  0  0  0  0
 10 37  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 12 38  1  0  0  0  0
 12 39  1  0  0  0  0
 12 40  1  0  0  0  0
 13 14  1  0  0  0  0
 13 41  1  0  0  0  0
 13 42  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 16 28  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 43  1  0  0  0  0
 20 44  1  0  0  0  0
 21 22  1  0  0  0  0
 21 45  1  0  0  0  0
 21 46  1  0  0  0  0
 22 23  2  0  0  0  0
 22 28  1  0  0  0  0
 23 24  1  0  0  0  0
 23 47  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 48  1  0  0  0  0
 26 49  1  0  0  0  0
 27 28  1  0  0  0  0
 27 50  1  0  0  0  0
 27 51  1  0  0  0  0
 28 29  1  1  0  0  0
 29 52  1  0  0  0  0
 29 53  1  0  0  0  0
 29 54  1  0  0  0  0
M  END
$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.037   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.132  -0.476   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       0.000  -1.540   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.132   2.016   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.132   3.556   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.799   4.326   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.466   4.326   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.800   3.556   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.466   2.786   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
CONECT    1   15    2                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3   19                                                       
CONECT    5   19    6                                                       
CONECT    6    5    7                                                       
CONECT    7    3    6   11   28                                             
CONECT    8   21   17                                                       
CONECT    9   18   10                                                       
CONECT   10    9   13                                                       
CONECT   11   15    7   21   12                                             
CONECT   12   11                                                            
CONECT   13   15   17   10   14                                             
CONECT   14   13                                                            
CONECT   15    1   11   13   16                                             
CONECT   16   15                                                            
CONECT   17    8   18   13   29                                             
CONECT   18   17    9   27   23                                             
CONECT   19    4    5   20                                                  
CONECT   20   19                                                            
CONECT   21   11    8   22                                                  
CONECT   22   21                                                            
CONECT   23   18   25   24                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27   18                                                            
CONECT   28    7                                                            
CONECT   29   17                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D12CC%5BC@%5D(O)... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  H   UNL     1      -0.709   1.414  -1.612  1.00  0.00           H  
HETATM    2  C   UNL     1      -0.856   1.315  -0.537  1.00  0.00           C  
HETATM    3  C   UNL     1      -1.728   2.463  -0.009  1.00  0.00           C  
HETATM    4  C   UNL     1      -3.155   2.056  -0.462  1.00  0.00           C  
HETATM    5  C   UNL     1      -3.135   0.519  -0.644  1.00  0.00           C  
HETATM    6  O   UNL     1      -3.367   0.180  -2.013  1.00  0.00           O  
HETATM    7  C   UNL     1      -4.177  -0.124   0.235  1.00  0.00           C  
HETATM    8  O   UNL     1      -4.554   0.439   1.235  1.00  0.00           O  
HETATM    9  C   UNL     1      -4.747  -1.469  -0.134  1.00  0.00           C  
HETATM   10  O   UNL     1      -5.708  -1.864   0.848  1.00  0.00           O  
HETATM   11  C   UNL     1      -1.737   0.076  -0.220  1.00  0.00           C  
HETATM   12  C   UNL     1      -1.714  -0.209   1.283  1.00  0.00           C  
HETATM   13  C   UNL     1      -1.162  -1.103  -0.989  1.00  0.00           C  
HETATM   14  C   UNL     1       0.275  -1.266  -0.515  1.00  0.00           C  
HETATM   15  O   UNL     1       0.684  -2.349  -0.171  1.00  0.00           O  
HETATM   16  C   UNL     1       1.184  -0.065  -0.480  1.00  0.00           C  
HETATM   17  H   UNL     1       1.467   0.202  -1.498  1.00  0.00           H  
HETATM   18  C   UNL     1       0.476   1.140   0.164  1.00  0.00           C  
HETATM   19  H   UNL     1       0.292   0.936   1.218  1.00  0.00           H  
HETATM   20  C   UNL     1       1.373   2.369   0.015  1.00  0.00           C  
HETATM   21  C   UNL     1       2.646   2.154   0.839  1.00  0.00           C  
HETATM   22  C   UNL     1       3.297   0.847   0.421  1.00  0.00           C  
HETATM   23  C   UNL     1       4.606   0.861   0.171  1.00  0.00           C  
HETATM   24  C   UNL     1       5.292  -0.375  -0.223  1.00  0.00           C  
HETATM   25  O   UNL     1       6.351  -0.356  -0.815  1.00  0.00           O  
HETATM   26  C   UNL     1       4.609  -1.676   0.149  1.00  0.00           C  
HETATM   27  C   UNL     1       3.154  -1.574  -0.308  1.00  0.00           C  
HETATM   28  C   UNL     1       2.446  -0.375   0.330  1.00  0.00           C  
HETATM   29  C   UNL     1       2.027  -0.766   1.748  1.00  0.00           C  
HETATM   30  H   UNL     1      -1.670   2.521   1.078  1.00  0.00           H  
HETATM   31  H   UNL     1      -1.435   3.409  -0.463  1.00  0.00           H  
HETATM   32  H   UNL     1      -3.883   2.333   0.301  1.00  0.00           H  
HETATM   33  H   UNL     1      -3.401   2.542  -1.406  1.00  0.00           H  
HETATM   34  H   UNL     1      -4.226   0.471  -2.350  1.00  0.00           H  
HETATM   35  H   UNL     1      -5.230  -1.405  -1.109  1.00  0.00           H  
HETATM   36  H   UNL     1      -3.945  -2.206  -0.173  1.00  0.00           H  
HETATM   37  H   UNL     1      -6.118  -2.723   0.674  1.00  0.00           H  
HETATM   38  H   UNL     1      -2.419  -1.008   1.512  1.00  0.00           H  
HETATM   39  H   UNL     1      -0.711  -0.513   1.580  1.00  0.00           H  
HETATM   40  H   UNL     1      -1.997   0.692   1.828  1.00  0.00           H  
HETATM   41  H   UNL     1      -1.732  -2.006  -0.770  1.00  0.00           H  
HETATM   42  H   UNL     1      -1.182  -0.897  -2.059  1.00  0.00           H  
HETATM   43  H   UNL     1       1.636   2.504  -1.035  1.00  0.00           H  
HETATM   44  H   UNL     1       0.848   3.252   0.378  1.00  0.00           H  
HETATM   45  H   UNL     1       3.338   2.977   0.663  1.00  0.00           H  
HETATM   46  H   UNL     1       2.392   2.111   1.898  1.00  0.00           H  
HETATM   47  H   UNL     1       5.162   1.782   0.258  1.00  0.00           H  
HETATM   48  H   UNL     1       5.098  -2.509  -0.355  1.00  0.00           H  
HETATM   49  H   UNL     1       4.648  -1.819   1.229  1.00  0.00           H  
HETATM   50  H   UNL     1       3.129  -1.468  -1.393  1.00  0.00           H  
HETATM   51  H   UNL     1       2.629  -2.487  -0.029  1.00  0.00           H  
HETATM   52  H   UNL     1       2.911  -1.031   2.328  1.00  0.00           H  
HETATM   53  H   UNL     1       1.520   0.074   2.222  1.00  0.00           H  
HETATM   54  H   UNL     1       1.351  -1.621   1.705  1.00  0.00           H  
CONECT    1    2                                                      
CONECT    2    1    3   11   18                                       
CONECT    3    2    4   30   31                                       
CONECT    4    3    5   32   33                                       
CONECT    5    4    6    7   11                                       
CONECT    6    5   34                                                 
CONECT    7    5    8    8    9                                       
CONECT    8    7    7                                                 
CONECT    9    7   10   35   36                                       
CONECT   10    9   37                                                 
CONECT   11    5    2   12   13                                       
CONECT   12   11   38   39   40                                       
CONECT   13   11   14   41   42                                       
CONECT   14   13   15   15   16                                       
CONECT   15   14   14                                                 
CONECT   16   14   17   18   28                                       
CONECT   17   16                                                      
CONECT   18   16    2   19   20                                       
CONECT   19   18                                                      
CONECT   20   18   21   43   44                                       
CONECT   21   20   22   45   46                                       
CONECT   22   21   23   23   28                                       
CONECT   23   22   22   24   47                                       
CONECT   24   23   25   25   26                                       
CONECT   25   24   24                                                 
CONECT   26   24   27   48   49                                       
CONECT   27   26   28   50   51                                       
CONECT   28   27   16   22   29                                       
CONECT   29   28   52   53   54                                       
CONECT   30    3                                                      
CONECT   31    3                                                      
CONECT   32    4                                                      
CONECT   33    4                                                      
CONECT   34    6                                                      
CONECT   35    9                                                      
CONECT   36    9                                                      
CONECT   37   10                                                      
CONECT   38   12                                                      
CONECT   39   12                                                      
CONECT   40   12                                                      
CONECT   41   13                                                      
CONECT   42   13                                                      
CONECT   43   20                                                      
CONECT   44   20                                                      
CONECT   45   21                                                      
CONECT   46   21                                                      
CONECT   47   23                                                      
CONECT   48   26                                                      
CONECT   49   26                                                      
CONECT   50   27                                                      
CONECT   51   27                                                      
CONECT   52   29                                                      
CONECT   53   29                                                      
CONECT   54   29                                                      
MASTER        0    0    0    0    0    0    0    0   54    0   54    0
END

https://cactus.nci.nih.gov/chemical/structure/%5BH%5D%5BC@@%5D12CC%5BC@%5D(O)...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:53})
 54 57  0  0  0  0  0  0  0  0999 V2000
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  2 18  1  0  0  0  0
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  3 30  1  0  0  0  0
  3 31  1  0  0  0  0
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  4 33  1  0  0  0  0
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  5  7  1  0  0  0  0
  5 11  1  0  0  0  0
  6 34  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 35  1  0  0  0  0
  9 36  1  0  0  0  0
 10 37  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 12 38  1  0  0  0  0
 12 39  1  0  0  0  0
 12 40  1  0  0  0  0
 13 14  1  0  0  0  0
 13 41  1  0  0  0  0
 13 42  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 16 28  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 43  1  0  0  0  0
 20 44  1  0  0  0  0
 21 22  1  0  0  0  0
 21 45  1  0  0  0  0
 21 46  1  0  0  0  0
 22 23  2  0  0  0  0
 22 28  1  0  0  0  0
 23 24  1  0  0  0  0
 23 47  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 48  1  0  0  0  0
 26 49  1  0  0  0  0
 27 28  1  0  0  0  0
 27 50  1  0  0  0  0
 27 51  1  0  0  0  0
 28 29  1  1  0  0  0
 29 52  1  0  0  0  0
 29 53  1  0  0  0  0
 29 54  1  0  0  0  0
M  END
$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
11-Dehydro-17-hydroxycorticosterone	ChEBI
17-Hydroxy-11-dehydrocorticosterone	ChEBI
17alpha,21-Dihydroxy-4-pregnene-3,11,20-trione	ChEBI
4-Pregnene-17alpha,21-diol-3,11,20-trione	ChEBI
Cortison	ChEBI
Delta(4)-Pregnene-17alpha,21-diol-3,11,20-trione	ChEBI
Kendall's compound e	ChEBI
Kortison	ChEBI
Pregn-4-en-17alpha,21-diol-3,11,20-trione	ChEBI
Reichstein's substance fa	ChEBI
Wintersteiner's compound F	ChEBI
17a,21-Dihydroxy-4-pregnene-3,11,20-trione	Generator
17Α,21-dihydroxy-4-pregnene-3,11,20-trione	Generator
4-Pregnene-17a,21-diol-3,11,20-trione	Generator
4-Pregnene-17α,21-diol-3,11,20-trione	Generator
delta(4)-Pregnene-17a,21-diol-3,11,20-trione	Generator
Δ(4)-pregnene-17α,21-diol-3,11,20-trione	Generator
Pregn-4-en-17a,21-diol-3,11,20-trione	Generator
Pregn-4-en-17α,21-diol-3,11,20-trione	Generator
Δ(4)-pregnene-17a,21-diol-3,11,20-trione	HMDB
Andreson	HMDB
Anusol HC	HMDB
Balneol-HC	HMDB
beta-HC	HMDB
Colocort	HMDB
Compound e	HMDB
Corlin	HMDB
Cortadren	HMDB
Cortandren	HMDB
Cortef	HMDB
Cortef acetate	HMDB
Cortisal	HMDB
Cortisate	HMDB
Cortisone acetate	HMDB
Cortistal	HMDB
Cortivite	HMDB
Cortogen	HMDB
Cortone	HMDB
Cortril	HMDB
Dermacort	HMDB
Dricort	HMDB
Flexicort	HMDB
Florinef	HMDB
Fludrocortisone acetate	HMDB
Glycort	HMDB
Hemsol-HC	HMDB
Hi-cor	HMDB
Incortin	HMDB
Kendall'S compound	HMDB
Locoid	HMDB
Locoid lipocream	HMDB
Micort-HC	HMDB
Nogenic HC	HMDB
Orabase hca	HMDB
Pandel	HMDB
Prestwick_132	HMDB
Reichstein fa	HMDB
Scheroson	HMDB
Solu-cortef	HMDB
Stie-cort	HMDB
Texacort	HMDB
Westcort	HMDB
Adreson	HMDB
Cortone acetate	HMDB
17-Hydroxy-3,11,20-trioxopregn-4-en-21-yl acetate	HMDB

Chemical Formula

C₂₁H₂₈O₅

Average Molecular Weight

360.444

Monoisotopic Molecular Weight

360.193674006

IUPAC Name

(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,17-dione

Traditional Name

(1S,2R,10S,11S,14R,15S)-14-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,17-dione

CAS Registry Number

53-06-5

SMILES

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

InChI Identifier

InChI=1S/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-15,18,22,26H,3-8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1

InChI Key

MFYSYFVPBJMHGN-ZPOLXVRWSA-N

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
17-hydroxysteroid
Oxosteroid
11-oxosteroid
Delta-4-steroid
Cyclohexenone
Alpha-hydroxy ketone
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Ketone
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Primary alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo steroid (CHEBI:16962 )
17alpha-hydroxy steroid (CHEBI:16962 )
glucocorticoid (CHEBI:16962 )
20-oxo steroid (CHEBI:16962 )
11-oxo steroid (CHEBI:16962 )
21-hydroxy steroid (CHEBI:16962 )
C21-steroid (CHEBI:16962 )
Pregnane and derivatives [Fig] (C00762 )
Glucocorticoids (C00762 )
C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C00762 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030090 )

Ontology

Physiological effect

Health effect:

Observation:

Tooth Decay

Health condition:

Depersonalization disorder

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Cellular process:

Cell signaling

Industrial application:

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	222 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.28 mg/mL at 25 °C	Not Available
LogP	1.47	HANSCH,C ET AL. (1995)

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	1.98	ALOGPS
logP	1.66	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	12.58	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	96.47 m³·mol⁻¹	ChemAxon
Polarizability	38.95 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Spectral Properties

Collision Cross Sections

Name	Adduct	Type	Data Source	Value	Reference
DeepCCS	[M+H]+	Experimental	MetCCS_train_pos	188.603	30932474
AllCCS	[M-H]-	Experimental	Not Available	191.4	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000266
AllCCS	[M+H]+	Experimental	Not Available	188.7	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000266
DarkChem	[M+H]+	Predicted	Not Available	186.411	31661259
DarkChem	[M-H]-	Predicted	Not Available	181.444	31661259

Retention Indices

Underivatized

Not Available

Derivatized

Derivative	Value	Reference
Cortisone,1TMS,#1	3372.4668	https://arxiv.org/abs/1905.12712
Cortisone,1TMS,#2	3351.181	https://arxiv.org/abs/1905.12712
Cortisone,1TMS,#3	3197.3552	https://arxiv.org/abs/1905.12712
Cortisone,1TMS,#4	3311.7703	https://arxiv.org/abs/1905.12712
Cortisone,1TMS,#5	3251.6511	https://arxiv.org/abs/1905.12712
Cortisone,1TMS,#6	3302.1929	https://arxiv.org/abs/1905.12712
Cortisone,2TMS,#1	3406.504	https://arxiv.org/abs/1905.12712
Cortisone,2TMS,#2	3183.712	https://arxiv.org/abs/1905.12712
Cortisone,2TMS,#3	3241.2412	https://arxiv.org/abs/1905.12712
Cortisone,2TMS,#4	3296.2874	https://arxiv.org/abs/1905.12712
Cortisone,2TMS,#5	3321.8499	https://arxiv.org/abs/1905.12712
Cortisone,2TMS,#6	3181.9219	https://arxiv.org/abs/1905.12712
Cortisone,2TMS,#7	3214.3682	https://arxiv.org/abs/1905.12712
Cortisone,2TMS,#8	3270.6243	https://arxiv.org/abs/1905.12712
Cortisone,2TMS,#9	3347.5327	https://arxiv.org/abs/1905.12712
Cortisone,2TMS,#10	3084.8193	https://arxiv.org/abs/1905.12712
Cortisone,2TMS,#11	3111.2034	https://arxiv.org/abs/1905.12712
Cortisone,2TMS,#12	3133.4346	https://arxiv.org/abs/1905.12712
Cortisone,2TMS,#13	3234.8318	https://arxiv.org/abs/1905.12712
Cortisone,2TMS,#14	3102.433	https://arxiv.org/abs/1905.12712
Cortisone,1TBDMS,#1	3617.2498	https://arxiv.org/abs/1905.12712
Cortisone,1TBDMS,#2	3631.1855	https://arxiv.org/abs/1905.12712
Cortisone,1TBDMS,#3	3437.4988	https://arxiv.org/abs/1905.12712
Cortisone,1TBDMS,#4	3558.2295	https://arxiv.org/abs/1905.12712
Cortisone,1TBDMS,#5	3483.4084	https://arxiv.org/abs/1905.12712
Cortisone,1TBDMS,#6	3555.9824	https://arxiv.org/abs/1905.12712
Cortisone,2TBDMS,#1	3900.8665	https://arxiv.org/abs/1905.12712
Cortisone,2TBDMS,#2	3629.204	https://arxiv.org/abs/1905.12712
Cortisone,2TBDMS,#3	3838.8179	https://arxiv.org/abs/1905.12712
Cortisone,2TBDMS,#4	3774.7322	https://arxiv.org/abs/1905.12712
Cortisone,2TBDMS,#5	3701.8	https://arxiv.org/abs/1905.12712
Cortisone,2TBDMS,#6	3653.1235	https://arxiv.org/abs/1905.12712
Cortisone,2TBDMS,#7	3824.8699	https://arxiv.org/abs/1905.12712
Cortisone,2TBDMS,#8	3767.1482	https://arxiv.org/abs/1905.12712
Cortisone,2TBDMS,#9	3689.0989	https://arxiv.org/abs/1905.12712
Cortisone,2TBDMS,#10	3542.8586	https://arxiv.org/abs/1905.12712
Cortisone,2TBDMS,#11	3566.4497	https://arxiv.org/abs/1905.12712
Cortisone,2TBDMS,#12	3704.1294	https://arxiv.org/abs/1905.12712
Cortisone,2TBDMS,#13	3589.3518	https://arxiv.org/abs/1905.12712
Cortisone,2TBDMS,#14	3570.442	https://arxiv.org/abs/1905.12712

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kf-2910000000-da435cee921dd7b9f8e6	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00kf-2910000000-da435cee921dd7b9f8e6	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05ai-5879000000-d8ce750671bf51b487e2	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0f79-2918800000-ab308a6a5023c34bc22f	2017-10-06	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-0009000000-5d34de066e82cc9f0a41	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03di-0900000000-24ec04976da03c3f9c77	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0fdo-4900000000-d0880bfc6f3d80e4aa72	2012-07-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-03di-3940000000-16be8720b1c49cea9b06	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-0009000000-6c22c083c2dfab97a299	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-0109000000-48c96b3d1471c5cd6171	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-002r-0914000000-2466a9146383b4265e42	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-0900000000-214430a00501054cc774	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-059j-1900000000-0e23516e07f0baf74c79	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0abj-1900000000-ad0282ab7188d9ec3dc1	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0aba-3900000000-e36e464b157b3e6159f1	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0a4j-5900000000-fe9092d76099e1e70a4e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0aou-6900000000-1b218b97a890ac7e8f45	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-03fr-0049000000-3bd424d473bdadd2b9b4	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-03di-0039000000-fd181dfb87e1cbb8ab6f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-03di-0049000000-7633496a1a53bda21707	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004i-0009000000-59db5e627634e4be3907	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004i-0009000000-9781e204df305d722d2d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004i-0009000000-0b5e40226163a1a334db	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-0009000000-946472abc72d41b1633c	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-003u-0149000000-efb3f94efcbdfc468859	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a5j-2392000000-d014016e46f2ae8b1bd1	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0009000000-1c4a8c3698ff1bfa2bd9	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-2029000000-82b546174619108311f8	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-8093000000-47f7996c84edb1324aad	2017-09-01	View Spectrum

NMR

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

Biological Properties

Cellular Locations

Extracellular
Membrane
Endoplasmic reticulum

Biospecimen Locations

Blood
Saliva
Urine

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Epidermis
Fibroblasts
Intestine
Kidney
Neuron
Placenta
Skeletal Muscle
Testis
Thyroid Gland

Pathways

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

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0411 (0.0222 - 0.0750) uM	Adult (>18 years old)	Male	Normal	15087250	details
Blood	Detected and Quantified	0.0380 (0.0222 - 0.0750) uM	Adult (>18 years old)	Female	Normal	15087250	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.0624 +/- 0.009 uM	Adult (>18 years old)	Both	Normal	11448093	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.011 +/- 0.001 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15249323	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	ovarian cancer	26573008	details
Blood	Detected and Quantified	0.0466 +/- 0.0071 uM	Adult (>18 years old)	Both	Depersonalization syndrome	11448093	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Tooth Decay	31026179	details
Urine	Detected and Quantified	0.0042 +/- 0.0011 umol/mmol creatinine	Adult (>18 years old)	Both	Systemic lupus erythematosus (SLE)	15249323	details
Urine	Detected and Quantified	0.014 +/- 0.0013 umol/mmol creatinine	Adult (>18 years old)	Both	Systemic lupus erythematosus (SLE)	15249323	details
Urine	Detected and Quantified	0.0039 +/- 0.0012 umol/mmol creatinine	Adult (>18 years old)	Both	Rheumatoid arthritis	15249323	details
Urine	Detected and Quantified	0.0070 +/- 0.0014 umol/mmol creatinine	Adult (>18 years old)	Both	Rheumatoid arthritis	15249323	details

Associated Disorders and Diseases

Disease References

Depersonalization disorder
Nuller YL, Morozova MG, Kushnir ON, Hamper N: Effect of naloxone therapy on depersonalization: a pilot study. J Psychopharmacol. 2001 Jun;15(2):93-5. [PubMed:11448093 ]
Ovarian cancer
Gaul DA, Mezencev R, Long TQ, Jones CM, Benigno BB, Gray A, Fernandez FM, McDonald JF: Highly-accurate metabolomic detection of early-stage ovarian cancer. Sci Rep. 2015 Nov 17;5:16351. doi: 10.1038/srep16351. [PubMed:26573008 ]
Tooth Decay
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Rheumatoid arthritis
Straub RH, Weidler C, Demmel B, Herrmann M, Kees F, Schmidt M, Scholmerich J, Schedel J: Renal clearance and daily excretion of cortisol and adrenal androgens in patients with rheumatoid arthritis and systemic lupus erythematosus. Ann Rheum Dis. 2004 Aug;63(8):961-8. [PubMed:15249323 ]

Associated OMIM IDs

167000 (Ovarian cancer)
180300 (Rheumatoid arthritis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023065

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16962

Food Biomarker Ontology

Not Available

VMH ID

CORTSN

MarkerDB ID

MDB00030004

References

Synthesis Reference

Ganis, Frank M.; Axelrod, Leonard R.; Miller, Leon L. The metabolism of hydrocortisone by kidney tissue in vitro. Journal of Biological Chemistry (1956), 218 841-8.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Zuber M, Miesel R, Brandl B: A patient with a high titer of antinuclear antibody and a functioning adrenal tumour. Clin Rheumatol. 1995 Jan;14(1):100-3. [PubMed:7743733 ]
Edwin B, Raeder I, Trondsen E, Kaaresen R, Buanes T: Outpatient laparoscopic adrenalectomy in patients with Conn's syndrome. Surg Endosc. 2001 Jun;15(6):589-91. Epub 2001 Mar 13. [PubMed:11591947 ]
Onyimba CU, Vijapurapu N, Curnow SJ, Khosla P, Stewart PM, Murray PI, Walker EA, Rauz S: Characterisation of the prereceptor regulation of glucocorticoids in the anterior segment of the rabbit eye. J Endocrinol. 2006 Aug;190(2):483-93. [PubMed:16899581 ]
Weigand A, Hinzpeter B, Schicha H: [Deterioration of endocrine ophthalmology after radioiodine therapy in Graves' disease?]. Nuklearmedizin. 1998;37(7):234-8. [PubMed:9830613 ]
Mark PJ, Waddell BJ: P-glycoprotein restricts access of cortisol and dexamethasone to the glucocorticoid receptor in placental BeWo cells. Endocrinology. 2006 Nov;147(11):5147-52. Epub 2006 Jul 27. [PubMed:16873536 ]
Sandeep TC, Andrew R, Homer NZ, Andrews RC, Smith K, Walker BR: Increased in vivo regeneration of cortisol in adipose tissue in human obesity and effects of the 11beta-hydroxysteroid dehydrogenase type 1 inhibitor carbenoxolone. Diabetes. 2005 Mar;54(3):872-9. [PubMed:15734867 ]
Pepe GJ, Albrecht ED: Regulation of the primate fetal adrenal cortex. Endocr Rev. 1990 Feb;11(1):151-76. [PubMed:2180686 ]
Boman HG: Innate immunity and the normal microflora. Immunol Rev. 2000 Feb;173:5-16. [PubMed:10719663 ]
Andrew R, Westerbacka J, Wahren J, Yki-Jarvinen H, Walker BR: The contribution of visceral adipose tissue to splanchnic cortisol production in healthy humans. Diabetes. 2005 May;54(5):1364-70. [PubMed:15855321 ]
Sharma KK, Lindqvist A, Zhou XJ, Auchus RJ, Penning TM, Andersson S: Deoxycorticosterone inactivation by AKR1C3 in human mineralocorticoid target tissues. Mol Cell Endocrinol. 2006 Mar 27;248(1-2):79-86. Epub 2005 Dec 5. [PubMed:16337083 ]
Draper N, Stewart PM: 11beta-hydroxysteroid dehydrogenase and the pre-receptor regulation of corticosteroid hormone action. J Endocrinol. 2005 Aug;186(2):251-71. [PubMed:16079253 ]
AvRuskin TW, Krishnan N, Juan CS: Congenital adrenal hypoplasia and male pseudohermaphroditism due to DAX1 mutation, SF1 mutation or neither: a patient report. J Pediatr Endocrinol Metab. 2004 Aug;17(8):1125-32. [PubMed:15379426 ]
Ferrari P, Bianchetti M, Frey FJ: Juvenile hypertension, the role of genetically altered steroid metabolism. Horm Res. 2001;55(5):213-23. [PubMed:11740142 ]
Stormer FC, Reistad R, Alexander J: Glycyrrhizic acid in liquorice--evaluation of health hazard. Food Chem Toxicol. 1993 Apr;31(4):303-12. [PubMed:8386690 ]
Bolt RJ, Van Weissenbruch MM, Popp-Snijders C, Sweep FG, Lafeber HN, Delemarre-van de Waal HA: Maturity of the adrenal cortex in very preterm infants is related to gestational age. Pediatr Res. 2002 Sep;52(3):405-10. [PubMed:12193676 ]
Jiang JQ, Wang DS, Senthilkumaran B, Kobayashi T, Kobayashi HK, Yamaguchi A, Ge W, Young G, Nagahama Y: Isolation, characterization and expression of 11beta-hydroxysteroid dehydrogenase type 2 cDNAs from the testes of Japanese eel (Anguilla japonica) and Nile tilapia (Oreochromis niloticus). J Mol Endocrinol. 2003 Oct;31(2):305-15. [PubMed:14519098 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details

1. 3-oxo-5-beta-steroid 4-dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4-cholesten-3-one can also act as substrates.
Gene Name:: AKR1D1
Uniprot ID:: P51857
Molecular weight:: 32889.38

Reactions

17a,21-Dihydroxy-5b-pregnane-3,11,20-trione + NADP → Cortisone	details
17a,21-Dihydroxy-5b-pregnane-3,11,20-trione + NADP → Cortisone + NADPH + Hydrogen Ion	details

Enzyme Details

2. Corticosteroid 11-beta-dehydrogenase isozyme 2

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the conversion of cortisol to the inactive metabolite cortisone. Modulates intracellular glucocorticoid levels, thus protecting the nonselective mineralocorticoid receptor from occupation by glucocorticoids.
Gene Name:: HSD11B2
Uniprot ID:: P80365
Molecular weight:: 44126.06

Enzyme Details

3. Corticosteroid 11-beta-dehydrogenase isozyme 1

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes reversibly the conversion of cortisol to the inactive metabolite cortisone. Catalyzes reversibly the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol. In intact cells, the reaction runs only in one direction, from 7-ketocholesterol to 7-beta-hydroxycholesterol (By similarity).
Gene Name:: HSD11B1
Uniprot ID:: P28845
Molecular weight:: 32400.665

Reactions

Cortisol + NADP → Cortisone + NADPH + Hydrogen Ion	details

Enzyme Details

4. Dehydrogenase/reductase SDR family member 2

General function:: Involved in oxidoreductase activity
Specific function:: Displays NADPH-dependent dicarbonyl reductase activity in vitro with 3,4-Hexanedione, 2,3-Heptanedione and 1-Phenyl-1,2- propanedione as substrates. No reductase activity is displayed in vitro with steroids, retinoids and sugars as substrates. May inhibit cell replication
Gene Name:: DHRS2
Uniprot ID:: Q13268
Molecular weight:: 27438.4

Showing metabocard for Cortisone (HMDB0002802)

MOL for HMDB0002802 (Cortisone)

3D MOL for HMDB0002802 (Cortisone)

3D SDF for HMDB0002802 (Cortisone)

3D-SDF for HMDB0002802 (Cortisone)

PDB for HMDB0002802 (Cortisone)

3D PDB for HMDB0002802 (Cortisone)

SMILES for HMDB0002802 (Cortisone)

INCHI for HMDB0002802 (Cortisone)

Structure for HMDB0002802 (Cortisone)

3D Structure for HMDB0002802 (Cortisone)

Collision Cross Sections

Retention Indices

Underivatized

Derivatized

GC-MS

LC-MS/MS

NMR

Enzymes

Reactions

Reactions