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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:00 UTC

HMDB ID

HMDB0015480

Secondary Accession Numbers

HMDB15480

Metabolite Identification

Common Name

Ciclesonide

Description

Ciclesonide is only found in individuals that have used or taken this drug. It is a glucocorticoid used to treat obstructive airway diseases. It is marketed under the brand name Alvesco.Glucocorticoids such as ciclesonide can inhibit leukocyte infiltration at the site of inflammation, interfere with mediators of inflammatory response, and suppress humoral immune responses. The antiinflammatory actions of glucocorticoids are thought to involve phospholipase A2 inhibitory proteins, lipocortins, which control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes. Ciclesonide reduces inflammatory reaction by limiting the capillary dilatation and permeability of the vascular structures. These compounds restrict the accumulation of polymorphonuclear leukocytes and macrophages and reduce the release of vasoactive kinins. Recent research suggests that corticosteroids may inhibit the release of arachidonic acid from phospholipids, thereby reducing the formation of prostaglandins. Ciclesonide is a glucocorticoid receptor agonist. On binding, the corticoreceptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing an increase or decrease in expression of specific target genes, including suppression of IL2 (interleukin 2) expression.

Structure

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

1410
  Mrv0541 02231215282D          

 43 48  0  0  1  0            999 V2000
    7.4742   -0.4840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9363   -1.6895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3411    2.2169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2956    1.0199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6500    2.7485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6383   -0.4039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0556    0.1544    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.6266    0.1544    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  1 11  1  0  0  0  0
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 33 35  1  0  0  0  0
 34 35  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
M  END

HMDB0015480
     RDKit          3D
Ciclesonide
 83 88  0  0  0  0  0  0  0  0999 V2000
   -6.3438    4.7249    0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4491    4.0151   -0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6875    5.0611   -1.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4981    3.1000   -0.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5632    3.0609    1.0301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5820    2.3267   -0.9307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7354    1.4989   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8020    0.7132   -0.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8841    0.8395   -2.1429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7886   -0.1992   -0.3003 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0842   -0.3002    1.0622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0926   -1.6076    1.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4228    1.7305    0.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7274    2.4790   -0.8121 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1756    1.1533    0.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2773   -1.5095    0.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
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  8  9  2  0
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 37 80  1  0
 39 81  1  0
 39 82  1  0
 39 83  1  0
M  END

1410
  Mrv0541 02231215282D          

 43 48  0  0  1  0            999 V2000
    7.4742   -0.4840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9363   -1.6895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3411    2.2169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2956    1.0199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6383   -0.4039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0556    0.1544    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.6266    0.1544    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6637   -0.3960    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6266    0.9794    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3294   -1.1450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    5.3411    1.3919    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8891    1.4204    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    6.5859    0.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0617   -1.7483    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  1 20  1  0  0  0  0
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  2 20  1  0  0  0  0
 16  3  1  1  0  0  0
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 34 35  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015480

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12C[C@@]3([H])[C@]4([H])CCC5=CC(=O)C=C[C@]5(C)[C@@]4([H])[C@@H](O)C[C@]3(C)[C@@]1(OC(O2)C1CCCCC1)C(=O)COC(=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C32H44O7/c1-18(2)28(36)37-17-25(35)32-26(38-29(39-32)19-8-6-5-7-9-19)15-23-22-11-10-20-14-21(33)12-13-30(20,3)27(22)24(34)16-31(23,32)4/h12-14,18-19,22-24,26-27,29,34H,5-11,15-17H2,1-4H3/t22-,23-,24-,26+,27+,29?,30-,31-,32+/m0/s1

> <INCHI_KEY>
LUKZNWIVRBCLON-FOMURGDPSA-N

> <FORMULA>
C32H44O7

> <MOLECULAR_WEIGHT>
540.6876

> <EXACT_MASS>
540.308703762

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
60.20727833660553

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1S,2S,4R,8S,9S,11S,12S,13R)-6-cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-14,17-dien-8-yl]-2-oxoethyl 2-methylpropanoate

> <ALOGPS_LOGP>
4.08

> <JCHEM_LOGP>
5.323272522666668

> <ALOGPS_LOGS>
-5.54

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.562094998808288

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.778522590506018

> <JCHEM_PKA_STRONGEST_BASIC>
-2.851415363085546

> <JCHEM_POLAR_SURFACE_AREA>
99.13

> <JCHEM_REFRACTIVITY>
146.27890000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.57e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ciclesonide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015480
     RDKit          3D
Ciclesonide
 83 88  0  0  0  0  0  0  0  0999 V2000
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 39 83  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1410                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      13.952  -0.903   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      12.948  -3.154   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.970   4.138   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      13.618   1.904   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      16.074   1.101   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.080   5.131   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      17.991  -0.754   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.304   0.288   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.970  -0.482   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.636   0.288   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.439  -0.739   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.636   1.828   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.815  -2.137   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.292  -1.979   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.304   1.828   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.970   2.598   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.260   2.651   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.260  -0.535   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.294   1.468   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.266  -2.393   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.509   0.368   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.864   0.256   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.864   1.860   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.599   3.411   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.672  -3.020   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.298   4.322   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.004  -0.006   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.411   2.684   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.832  -4.552   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.919  -2.116   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.864   5.180   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.411   4.355   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      17.238  -5.180   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      18.325  -2.744   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      18.484  -4.276   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      17.568   0.727   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      18.639   1.834   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      20.133   1.460   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      18.216   3.314   0.000  0.00  0.00           C+0
HETATM   40  H   UNK     0       8.974  -1.207   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0       8.646  -0.944   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0       9.703   1.212   0.000  0.00  0.00           H+0
HETATM   43  H   UNK     0      11.315  -3.263   0.000  0.00  0.00           H+0
CONECT    1   11   20                                                       
CONECT    2   13   20                                                       
CONECT    3   16                                                            
CONECT    4   21                                                            
CONECT    5   27   36                                                       
CONECT    6   32                                                            
CONECT    7   36                                                            
CONECT    8    9   11   15   19                                             
CONECT    9    8   10   14   40                                             
CONECT   10    9   12   18   41                                             
CONECT   11    1    8   13   21                                             
CONECT   12   10   16   17   42                                             
CONECT   13    2   11   14   43                                             
CONECT   14    9   13                                                       
CONECT   15    8   16                                                       
CONECT   16    3   12   15                                                  
CONECT   17   12   23   24   26                                             
CONECT   18   10   22                                                       
CONECT   19    8                                                            
CONECT   20    1    2   25                                                  
CONECT   21    4   11   27                                                  
CONECT   22   18   23                                                       
CONECT   23   17   22   28                                                  
CONECT   24   17                                                            
CONECT   25   20   29   30                                                  
CONECT   26   17   31                                                       
CONECT   27    5   21                                                       
CONECT   28   23   32                                                       
CONECT   29   25   33                                                       
CONECT   30   25   34                                                       
CONECT   31   26   32                                                       
CONECT   32    6   28   31                                                  
CONECT   33   29   35                                                       
CONECT   34   30   35                                                       
CONECT   35   33   34                                                       
CONECT   36    5    7   37                                                  
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40    9                                                            
CONECT   41   10                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

COMPND    HMDB0015480
HETATM    1  C1  UNL     1      -6.344   4.725   0.067  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.449   4.015  -0.925  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.688   5.061  -1.696  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.498   3.100  -0.225  1.00  0.00           C  
HETATM    5  O1  UNL     1      -4.563   3.061   1.030  1.00  0.00           O  
HETATM    6  O2  UNL     1      -3.582   2.327  -0.931  1.00  0.00           O  
HETATM    7  C5  UNL     1      -2.735   1.499  -0.117  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.802   0.713  -0.927  1.00  0.00           C  
HETATM    9  O3  UNL     1      -1.884   0.839  -2.143  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.789  -0.199  -0.300  1.00  0.00           C  
HETATM   11  O4  UNL     1      -1.084  -0.300   1.062  1.00  0.00           O  
HETATM   12  C8  UNL     1      -1.093  -1.608   1.414  1.00  0.00           C  
HETATM   13  C9  UNL     1      -2.338  -2.074   2.188  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.058  -3.511   2.521  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.251  -4.387   2.653  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.961  -4.323   1.291  1.00  0.00           C  
HETATM   17  C13 UNL     1      -4.528  -2.923   1.225  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.523  -1.841   1.345  1.00  0.00           C  
HETATM   19  O5  UNL     1      -0.996  -2.393   0.293  1.00  0.00           O  
HETATM   20  C15 UNL     1      -0.839  -1.582  -0.828  1.00  0.00           C  
HETATM   21  C16 UNL     1       0.580  -1.925  -1.336  1.00  0.00           C  
HETATM   22  C17 UNL     1       1.398  -1.018  -0.508  1.00  0.00           C  
HETATM   23  C18 UNL     1       2.829  -0.803  -0.963  1.00  0.00           C  
HETATM   24  C19 UNL     1       3.580  -2.085  -0.721  1.00  0.00           C  
HETATM   25  C20 UNL     1       5.064  -1.979  -0.709  1.00  0.00           C  
HETATM   26  C21 UNL     1       5.591  -0.683  -0.196  1.00  0.00           C  
HETATM   27  C22 UNL     1       6.689  -0.740   0.528  1.00  0.00           C  
HETATM   28  C23 UNL     1       7.216   0.508   1.040  1.00  0.00           C  
HETATM   29  O6  UNL     1       8.263   0.522   1.738  1.00  0.00           O  
HETATM   30  C24 UNL     1       6.511   1.736   0.730  1.00  0.00           C  
HETATM   31  C25 UNL     1       5.423   1.730   0.003  1.00  0.00           C  
HETATM   32  C26 UNL     1       4.830   0.523  -0.555  1.00  0.00           C  
HETATM   33  C27 UNL     1       4.880   0.573  -2.100  1.00  0.00           C  
HETATM   34  C28 UNL     1       3.427   0.268  -0.083  1.00  0.00           C  
HETATM   35  C29 UNL     1       2.606   1.471   0.139  1.00  0.00           C  
HETATM   36  O7  UNL     1       2.727   2.479  -0.812  1.00  0.00           O  
HETATM   37  C30 UNL     1       1.176   1.153   0.500  1.00  0.00           C  
HETATM   38  C31 UNL     1       0.606   0.265  -0.570  1.00  0.00           C  
HETATM   39  C32 UNL     1       0.675   0.905  -1.930  1.00  0.00           C  
HETATM   40  H1  UNL     1      -6.734   5.679  -0.332  1.00  0.00           H  
HETATM   41  H2  UNL     1      -7.190   4.113   0.409  1.00  0.00           H  
HETATM   42  H3  UNL     1      -5.772   4.997   0.999  1.00  0.00           H  
HETATM   43  H4  UNL     1      -6.117   3.426  -1.594  1.00  0.00           H  
HETATM   44  H5  UNL     1      -3.594   4.920  -1.507  1.00  0.00           H  
HETATM   45  H6  UNL     1      -4.952   6.068  -1.375  1.00  0.00           H  
HETATM   46  H7  UNL     1      -4.858   4.874  -2.775  1.00  0.00           H  
HETATM   47  H8  UNL     1      -3.404   0.861   0.440  1.00  0.00           H  
HETATM   48  H9  UNL     1      -2.154   2.213   0.505  1.00  0.00           H  
HETATM   49  H10 UNL     1      -0.189  -1.818   2.059  1.00  0.00           H  
HETATM   50  H11 UNL     1      -2.335  -1.493   3.131  1.00  0.00           H  
HETATM   51  H12 UNL     1      -1.397  -3.966   1.752  1.00  0.00           H  
HETATM   52  H13 UNL     1      -1.482  -3.554   3.482  1.00  0.00           H  
HETATM   53  H14 UNL     1      -2.894  -5.434   2.738  1.00  0.00           H  
HETATM   54  H15 UNL     1      -3.957  -4.096   3.443  1.00  0.00           H  
HETATM   55  H16 UNL     1      -4.765  -5.050   1.210  1.00  0.00           H  
HETATM   56  H17 UNL     1      -3.147  -4.469   0.540  1.00  0.00           H  
HETATM   57  H18 UNL     1      -5.282  -2.850   2.039  1.00  0.00           H  
HETATM   58  H19 UNL     1      -5.069  -2.865   0.238  1.00  0.00           H  
HETATM   59  H20 UNL     1      -3.277  -1.510   0.300  1.00  0.00           H  
HETATM   60  H21 UNL     1      -4.073  -0.957   1.794  1.00  0.00           H  
HETATM   61  H22 UNL     1      -1.593  -1.737  -1.599  1.00  0.00           H  
HETATM   62  H23 UNL     1       0.684  -1.673  -2.403  1.00  0.00           H  
HETATM   63  H24 UNL     1       0.780  -3.005  -1.178  1.00  0.00           H  
HETATM   64  H25 UNL     1       1.484  -1.319   0.557  1.00  0.00           H  
HETATM   65  H26 UNL     1       2.895  -0.586  -2.040  1.00  0.00           H  
HETATM   66  H27 UNL     1       3.251  -2.886  -1.451  1.00  0.00           H  
HETATM   67  H28 UNL     1       3.288  -2.533   0.276  1.00  0.00           H  
HETATM   68  H29 UNL     1       5.459  -2.122  -1.728  1.00  0.00           H  
HETATM   69  H30 UNL     1       5.532  -2.833  -0.122  1.00  0.00           H  
HETATM   70  H31 UNL     1       7.191  -1.702   0.737  1.00  0.00           H  
HETATM   71  H32 UNL     1       6.907   2.707   1.122  1.00  0.00           H  
HETATM   72  H33 UNL     1       4.963   2.732  -0.169  1.00  0.00           H  
HETATM   73  H34 UNL     1       4.102   1.195  -2.528  1.00  0.00           H  
HETATM   74  H35 UNL     1       4.825  -0.432  -2.540  1.00  0.00           H  
HETATM   75  H36 UNL     1       5.885   1.028  -2.357  1.00  0.00           H  
HETATM   76  H37 UNL     1       3.538  -0.232   0.931  1.00  0.00           H  
HETATM   77  H38 UNL     1       3.010   1.956   1.092  1.00  0.00           H  
HETATM   78  H39 UNL     1       2.451   3.344  -0.416  1.00  0.00           H  
HETATM   79  H40 UNL     1       0.646   2.143   0.561  1.00  0.00           H  
HETATM   80  H41 UNL     1       1.162   0.615   1.455  1.00  0.00           H  
HETATM   81  H42 UNL     1       1.742   1.029  -2.284  1.00  0.00           H  
HETATM   82  H43 UNL     1       0.154   1.870  -1.915  1.00  0.00           H  
HETATM   83  H44 UNL     1       0.220   0.250  -2.687  1.00  0.00           H  
CONECT    1    2   40   41   42
CONECT    2    3    4   43
CONECT    3   44   45   46
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8   47   48
CONECT    8    9    9   10
CONECT   10   11   20   38
CONECT   11   12
CONECT   12   13   19   49
CONECT   13   14   18   50
CONECT   14   15   51   52
CONECT   15   16   53   54
CONECT   16   17   55   56
CONECT   17   18   57   58
CONECT   18   59   60
CONECT   19   20
CONECT   20   21   61
CONECT   21   22   62   63
CONECT   22   23   38   64
CONECT   23   24   34   65
CONECT   24   25   66   67
CONECT   25   26   68   69
CONECT   26   27   27   32
CONECT   27   28   70
CONECT   28   29   29   30
CONECT   30   31   31   71
CONECT   31   32   72
CONECT   32   33   34
CONECT   33   73   74   75
CONECT   34   35   76
CONECT   35   36   37   77
CONECT   36   78
CONECT   37   38   79   80
CONECT   38   39
CONECT   39   81   82   83
END

HMDB0015480
     RDKit          3D
Ciclesonide
 83 88  0  0  0  0  0  0  0  0999 V2000
   -6.3438    4.7249    0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4491    4.0151   -0.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6875    5.0611   -1.6962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4981    3.1000   -0.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5632    3.0609    1.0301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5820    2.3267   -0.9307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7354    1.4989   -0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8020    0.7132   -0.9269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8841    0.8395   -2.1429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7886   -0.1992   -0.3003 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0842   -0.3002    1.0622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0926   -1.6076    1.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3380   -2.0743    2.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0585   -3.5112    2.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2515   -4.3867    2.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9613   -4.3228    1.2910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5281   -2.9231    1.2248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5231   -1.8409    1.3449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9956   -2.3934    0.2931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8389   -1.5819   -0.8277 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5795   -1.9251   -1.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3983   -1.0185   -0.5079 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8293   -0.8028   -0.9628 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5804   -2.0851   -0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0642   -1.9788   -0.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5912   -0.6831   -0.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6892   -0.7405    0.5277 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2157    0.5077    1.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2629    0.5215    1.7376 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5110    1.7365    0.7302 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4228    1.7305    0.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8301    0.5232   -0.5554 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8801    0.5734   -2.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4272    0.2681   -0.0829 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6062    1.4714    0.1389 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7274    2.4790   -0.8121 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1756    1.1533    0.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6063    0.2653   -0.5699 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6753    0.9052   -1.9297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7342    5.6792   -0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1905    4.1135    0.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7720    4.9971    0.9990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1165    3.4256   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5936    4.9200   -1.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9524    6.0684   -1.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8580    4.8744   -2.7749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4040    0.8610    0.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1543    2.2128    0.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1891   -1.8176    2.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3351   -1.4932    3.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3966   -3.9659    1.7518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4820   -3.5535    3.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8942   -5.4341    2.7380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9567   -4.0961    3.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7650   -5.0498    1.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1474   -4.4694    0.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2817   -2.8499    2.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0694   -2.8649    0.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2773   -1.5095    0.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0730   -0.9575    1.7943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5930   -1.7369   -1.5987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6840   -1.6735   -2.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7799   -3.0054   -1.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4837   -1.3192    0.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8953   -0.5862   -2.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2508   -2.8857   -1.4507 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2879   -2.5327    0.2760 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4592   -2.1221   -1.7284 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5319   -2.8330   -0.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1905   -1.7019    0.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9071    2.7069    1.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9632    2.7323   -0.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1023    1.1954   -2.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8247   -0.4321   -2.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8846    1.0277   -2.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5378   -0.2320    0.9314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0103    1.9562    1.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4509    3.3444   -0.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6460    2.1433    0.5606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1622    0.6150    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7422    1.0292   -2.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1540    1.8695   -1.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2205    0.2498   -2.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
 10  8  1  6
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 12 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  6
 32 34  1  0
 34 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 38 39  1  6
 20 10  1  0
 38 22  1  0
 38 10  1  0
 18 13  1  0
 34 23  1  0
 32 26  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  2 43  1  0
  3 44  1  0
  3 45  1  0
  3 46  1  0
  7 47  1  0
  7 48  1  0
 12 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  0
 16 56  1  0
 17 57  1  0
 17 58  1  0
 18 59  1  0
 18 60  1  0
 20 61  1  6
 21 62  1  0
 21 63  1  0
 22 64  1  1
 23 65  1  6
 24 66  1  0
 24 67  1  0
 25 68  1  0
 25 69  1  0
 27 70  1  0
 30 71  1  0
 31 72  1  0
 33 73  1  0
 33 74  1  0
 33 75  1  0
 34 76  1  1
 35 77  1  1
 36 78  1  0
 37 79  1  0
 37 80  1  0
 39 81  1  0
 39 82  1  0
 39 83  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(R)-11beta,16alpha,17,21-Tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with cyclohexanecarboxaldehyde, 21-isobutyrate	HMDB
Alvesco	HMDB
Omnaris	HMDB
2-[(1S,2S,4R,8S,9S,11S,12S,13R)-6-Cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-14,17-dien-8-yl]-2-oxoethyl 2-methylpropanoic acid	HMDB
2-[(1S,2S,4R,8S,9S,11S,12S,13R)-6-Cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0,.0,.0,]icosa-14,17-dien-8-yl]-2-oxoethyl 2-methylpropanoic acid	HMDB

Chemical Formula

C₃₂H₄₄O₇

Average Molecular Weight

540.6876

Monoisotopic Molecular Weight

540.308703762

IUPAC Name

2-[(1S,2S,4R,8S,9S,11S,12S,13R)-6-cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-14,17-dien-8-yl]-2-oxoethyl 2-methylpropanoate

Traditional Name

ciclesonide

CAS Registry Number

141845-82-1

SMILES

[H][C@@]12C[C@@]3([H])[C@]4([H])CCC5=CC(=O)C=C[C@]5(C)[C@@]4([H])[C@@H](O)C[C@]3(C)[C@@]1(OC(O2)C1CCCCC1)C(=O)COC(=O)C(C)C

InChI Identifier

InChI=1S/C32H44O7/c1-18(2)28(36)37-17-25(35)32-26(38-29(39-32)19-8-6-5-7-9-19)15-23-22-11-10-20-14-21(33)12-13-30(20,3)27(22)24(34)16-31(23,32)4/h12-14,18-19,22-24,26-27,29,34H,5-11,15-17H2,1-4H3/t22-,23-,24-,26+,27+,29?,30-,31-,32+/m0/s1

InChI Key

LUKZNWIVRBCLON-FOMURGDPSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
3-oxo-delta-1,4-steroid
3-oxosteroid
11-hydroxysteroid
11-beta-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-1,4-steroid
Alpha-acyloxy ketone
Meta-dioxolane
Cyclic alcohol
Carboxylic acid ester
Cyclic ketone
Secondary alcohol
Ketone
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015480)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0016 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0016 g/L	ALOGPS
logP	4.08	ALOGPS
logP	5.32	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	14.78	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	146.28 m³·mol⁻¹	ChemAxon
Polarizability	60.21 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	259.858	30932474
DeepCCS	[M+Na]+	234.006	30932474
AllCCS	[M+H]+	225.5	32859911
AllCCS	[M+H-H2O]+	224.3	32859911
AllCCS	[M+NH4]+	226.6	32859911
AllCCS	[M+Na]+	226.9	32859911
AllCCS	[M-H]-	213.9	32859911
AllCCS	[M+Na-2H]-	216.2	32859911
AllCCS	[M+HCOO]-	218.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ciclesonide	[H][C@@]12C[C@@]3([H])[C@]4([H])CCC5=CC(=O)C=C[C@]5(C)[C@@]4([H])[C@@H](O)C[C@]3(C)[C@@]1(OC(O2)C1CCCCC1)C(=O)COC(=O)C(C)C	4794.8	Standard polar	33892256
Ciclesonide	[H][C@@]12C[C@@]3([H])[C@]4([H])CCC5=CC(=O)C=C[C@]5(C)[C@@]4([H])[C@@H](O)C[C@]3(C)[C@@]1(OC(O2)C1CCCCC1)C(=O)COC(=O)C(C)C	3796.5	Standard non polar	33892256
Ciclesonide	[H][C@@]12C[C@@]3([H])[C@]4([H])CCC5=CC(=O)C=C[C@]5(C)[C@@]4([H])[C@@H](O)C[C@]3(C)[C@@]1(OC(O2)C1CCCCC1)C(=O)COC(=O)C(C)C	4404.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ciclesonide,1TMS,isomer #1	CC(C)C(=O)OCC(=O)[C@@]12OC(C3CCCCC3)O[C@@H]1C[C@H]1[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@@]12C	4075.6	Semi standard non polar	33892256
Ciclesonide,1TMS,isomer #2	CC(C)C(=O)OC=C(O[Si](C)(C)C)[C@@]12OC(C3CCCCC3)O[C@@H]1C[C@H]1[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O)C[C@@]12C	4096.8	Semi standard non polar	33892256
Ciclesonide,2TMS,isomer #1	CC(C)C(=O)OC=C(O[Si](C)(C)C)[C@@]12OC(C3CCCCC3)O[C@@H]1C[C@H]1[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@@]12C	3958.4	Semi standard non polar	33892256
Ciclesonide,2TMS,isomer #1	CC(C)C(=O)OC=C(O[Si](C)(C)C)[C@@]12OC(C3CCCCC3)O[C@@H]1C[C@H]1[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@@]12C	3933.7	Standard non polar	33892256
Ciclesonide,2TMS,isomer #1	CC(C)C(=O)OC=C(O[Si](C)(C)C)[C@@]12OC(C3CCCCC3)O[C@@H]1C[C@H]1[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@@]12C	4762.0	Standard polar	33892256
Ciclesonide,1TBDMS,isomer #1	CC(C)C(=O)OCC(=O)[C@@]12OC(C3CCCCC3)O[C@@H]1C[C@H]1[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]12C	4317.3	Semi standard non polar	33892256
Ciclesonide,1TBDMS,isomer #2	CC(C)C(=O)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]12OC(C3CCCCC3)O[C@@H]1C[C@H]1[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O)C[C@@]12C	4325.1	Semi standard non polar	33892256
Ciclesonide,2TBDMS,isomer #1	CC(C)C(=O)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]12OC(C3CCCCC3)O[C@@H]1C[C@H]1[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]12C	4402.9	Semi standard non polar	33892256
Ciclesonide,2TBDMS,isomer #1	CC(C)C(=O)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]12OC(C3CCCCC3)O[C@@H]1C[C@H]1[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]12C	4322.2	Standard non polar	33892256
Ciclesonide,2TBDMS,isomer #1	CC(C)C(=O)OC=C(O[Si](C)(C)C(C)(C)C)[C@@]12OC(C3CCCCC3)O[C@@H]1C[C@H]1[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]12C	4893.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ciclesonide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0016-9861410000-a67890c0fa5cdc01cbb9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ciclesonide GC-MS (1 TMS) - 70eV, Positive	splash10-00gm-9306150000-a60ff93ad43f322301b6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ciclesonide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ciclesonide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ciclesonide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ciclesonide GC-MS ("Ciclesonide,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclesonide 10V, Positive-QTOF	splash10-00dl-5100690000-558aa84dc4e52e89f5be	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclesonide 20V, Positive-QTOF	splash10-00du-9231530000-40ea30ede80e6943ebad	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclesonide 40V, Positive-QTOF	splash10-0006-9200000000-3f46dd50bf208489a9a1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclesonide 10V, Negative-QTOF	splash10-000i-9101470000-588b08c76a85183d97f6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclesonide 20V, Negative-QTOF	splash10-000i-9000200000-0b002a191145f0fcb1d8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclesonide 40V, Negative-QTOF	splash10-000i-9003200000-106aed5a2431a2a36272	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclesonide 10V, Positive-QTOF	splash10-01p6-0001950000-159b4f38473b16b13bbd	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclesonide 20V, Positive-QTOF	splash10-03dl-4203930000-bc04875f57aaba9e2269	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclesonide 40V, Positive-QTOF	splash10-03el-9840500000-b59a6775b4435bfdcbe5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclesonide 10V, Negative-QTOF	splash10-000i-9000010000-e5544ec5e9a99db8375d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclesonide 20V, Negative-QTOF	splash10-000i-9000000000-6e075c0ec9445ad48a7d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ciclesonide 40V, Negative-QTOF	splash10-000f-9000100000-9d8d178fd958fb7859ab	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01410	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01410	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

392056

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ciclesonide

METLIN ID

Not Available

PubChem Compound

444033

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Mutch E, Nave R, McCracken N, Zech K, Williams FM: The role of esterases in the metabolism of ciclesonide to desisobutyryl-ciclesonide in human tissue. Biochem Pharmacol. 2007 May 15;73(10):1657-64. Epub 2007 Jan 28. [PubMed:17331475 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

Enzyme Details

1. Liver carboxylesterase 1

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:: CES1
Uniprot ID:: P23141
Molecular weight:: 62520.62

References

Mutch E, Nave R, McCracken N, Zech K, Williams FM: The role of esterases in the metabolism of ciclesonide to desisobutyryl-ciclesonide in human tissue. Biochem Pharmacol. 2007 May 15;73(10):1657-64. Epub 2007 Jan 28. [PubMed:17331475 ]

Enzyme Details

2. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Peet CF, Enos T, Nave R, Zech K, Hall M: Identification of enzymes involved in phase I metabolism of ciclesonide by human liver microsomes. Eur J Drug Metab Pharmacokinet. 2005 Oct-Dec;30(4):275-86. [PubMed:16435573 ]

Showing metabocard for Ciclesonide (HMDB0015480)

MOL for HMDB0015480 (Ciclesonide)

3D MOL for HMDB0015480 (Ciclesonide)

3D SDF for HMDB0015480 (Ciclesonide)

3D-SDF for HMDB0015480 (Ciclesonide)

PDB for HMDB0015480 (Ciclesonide)

3D PDB for HMDB0015480 (Ciclesonide)

SMILES for HMDB0015480 (Ciclesonide)

INCHI for HMDB0015480 (Ciclesonide)

Structure for HMDB0015480 (Ciclesonide)

3D Structure for HMDB0015480 (Ciclesonide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References