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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:53 UTC

HMDB ID

HMDB0015148

Secondary Accession Numbers

HMDB15148

Metabolite Identification

Common Name

Clobetasol

Description

Clobetasol is only found in individuals that have used or taken this drug. It is a derivative of prednisolone with high glucocorticoid activity and low mineralocorticoid activity. Absorbed through the skin faster than fluocinonide, it is used topically in treatment of psoriasis but may cause marked adrenocortical suppression. [PubChem]The precise mechanism of the antiinflammatory activity of topical steroids in the treatment of steroid-responsive dermatoses, in general, is uncertain. However, corticosteroids are thought to act by the induction of phospholipase A₂ inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A₂. Initially, however, clobetasol, like other corticosteroids, bind to the glucocorticoid receptor, which complexes, enteres the cell nucleus and modifies genetic transcription (transrepression/transactivation).

Structure

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

  Mrv0541 09041214292D          

 30 33  0  0  1  0            999 V2000
    8.3346   -4.3826    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3346   -5.2076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6399   -3.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3346   -3.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6399   -5.6418    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9017   -4.3826    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9017   -5.2076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6399   -6.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1636   -3.9484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1636   -5.6418    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9017   -6.0760    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.9017   -6.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1636   -6.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4254   -5.2076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1636   -4.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4254   -6.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7307   -5.6418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7307   -6.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9925   -6.9010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3346   -6.0760    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5965   -4.7734    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1192   -5.4626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6041   -4.7951    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1193   -4.1277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.1148   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8269   -2.8836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3980   -2.8914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5437   -3.2921    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.9179   -3.9374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4291   -4.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  1  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  1  0  0  0
  7 10  1  0  0  0  0
  7 11  1  6  0  0  0
  8 12  1  0  0  0  0
 10 13  1  0  0  0  0
 10 14  1  0  0  0  0
 10 15  1  1  0  0  0
 13 16  2  0  0  0  0
 14 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
  6  7  1  0  0  0  0
 12 13  1  0  0  0  0
 17 18  1  0  0  0  0
  2 20  1  6  0  0  0
  5 21  1  1  0  0  0
 22  2  1  0  0  0  0
  1  2  1  0  0  0  0
 23 22  1  0  0  0  0
 24  1  1  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 26 28  1  0  0  0  0
 24 29  1  6  0  0  0
 23 30  1  1  0  0  0
M  END

HMDB0015148
     RDKit          3D
Clobetasol
 56 59  0  0  0  0  0  0  0  0999 V2000
    3.8733   -2.1138   -0.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7329   -1.2263   -1.0867 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3812   -1.8580   -0.7407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5967   -0.6463   -0.4793 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7673   -0.7994    0.0896 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5521   -1.8843   -0.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9370   -1.9359    0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5105   -0.5839   -0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5849   -0.5232   -0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2180    0.7247   -1.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2444    0.7012   -2.1025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5757    1.9508   -0.9551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4946    1.8366   -0.2173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8326    0.6197    0.2290 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0769    0.6014    1.7615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3680    0.6052   -0.0666 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1726    0.9577   -1.3851 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5814    1.5476    0.7797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7542    1.3695    2.1502 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933    1.5399    0.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875    0.1671    0.4098 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7616   -0.4356    1.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7590    0.1287   -0.4358 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5625    1.1073   -1.4269 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9599    0.4299    0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3760   -0.2490    1.2438 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7757    1.6327   -0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1876    1.8208    1.0251 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7500   -2.6742    0.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9686   -2.8778   -1.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8067   -1.5154   -0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292   -1.1177   -2.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9494   -2.3837   -1.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591   -2.5755    0.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5038   -0.0706   -1.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7739   -0.9856    1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0124   -2.8237   -0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7357   -1.6654   -1.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5542   -2.7399   -0.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7967   -1.9452    1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0585   -1.4441   -1.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9919    2.9003   -1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0539    2.8210    0.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4989   -0.1681    2.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0550    1.6092    2.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1597    0.2856    1.8512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9423    2.5751    0.5560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0483    1.5917    2.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3944    2.0707    1.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1554    2.0929   -0.4335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3581   -1.3544    1.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8796   -0.6656    2.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3718    0.2851    2.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3111    1.1253   -2.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1294    2.5582    0.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1412    1.6066   -1.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 23  2  1  0
 21  4  1  0
 16  5  1  0
 14  8  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  6
  3 33  1  0
  3 34  1  0
  4 35  1  6
  5 36  1  1
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  9 41  1  0
 12 42  1  0
 13 43  1  0
 15 44  1  0
 15 45  1  0
 15 46  1  0
 18 47  1  6
 19 48  1  0
 20 49  1  0
 20 50  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 24 54  1  0
 27 55  1  0
 27 56  1  0
M  END

  Mrv0541 09041214292D          

 30 33  0  0  1  0            999 V2000
    8.3346   -4.3826    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3346   -5.2076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6399   -3.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3346   -3.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6399   -5.6418    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9017   -4.3826    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9017   -5.2076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6399   -6.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1636   -3.9484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1636   -5.6418    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9017   -6.0760    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.9017   -6.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1636   -6.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4254   -5.2076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1636   -4.8168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4254   -6.9010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7307   -5.6418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7307   -6.4668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9925   -6.9010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3346   -6.0760    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5965   -4.7734    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1192   -5.4626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6041   -4.7951    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1193   -4.1277    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.1148   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8269   -2.8836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3980   -2.8914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5437   -3.2921    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.9179   -3.9374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4291   -4.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  1  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  1  0  0  0
  7 10  1  0  0  0  0
  7 11  1  6  0  0  0
  8 12  1  0  0  0  0
 10 13  1  0  0  0  0
 10 14  1  0  0  0  0
 10 15  1  1  0  0  0
 13 16  2  0  0  0  0
 14 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
  6  7  1  0  0  0  0
 12 13  1  0  0  0  0
 17 18  1  0  0  0  0
  2 20  1  6  0  0  0
  5 21  1  1  0  0  0
 22  2  1  0  0  0  0
  1  2  1  0  0  0  0
 23 22  1  0  0  0  0
 24  1  1  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 26 28  1  0  0  0  0
 24 29  1  6  0  0  0
 23 30  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0015148

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H28ClFO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,24)17(26)10-20(16,3)22(12,28)18(27)11-23/h6-7,9,12,15-17,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1

> <INCHI_KEY>
FCSHDIVRCWTZOX-DVTGEIKXSA-N

> <FORMULA>
C22H28ClFO4

> <MOLECULAR_WEIGHT>
410.907

> <EXACT_MASS>
410.166015296

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
41.97303287213109

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
3.0361615356666674

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.654881865556526

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.468411647136076

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3933767917789623

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
105.54389999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
clobetasol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015148
     RDKit          3D
Clobetasol
 56 59  0  0  0  0  0  0  0  0999 V2000
    3.8733   -2.1138   -0.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7329   -1.2263   -1.0867 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3812   -1.8580   -0.7407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5967   -0.6463   -0.4793 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7673   -0.7994    0.0896 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5521   -1.8843   -0.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9370   -1.9359    0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5105   -0.5839   -0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5849   -0.5232   -0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2180    0.7247   -1.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2444    0.7012   -2.1025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5757    1.9508   -0.9551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4946    1.8366   -0.2173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8326    0.6197    0.2290 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0769    0.6014    1.7615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3680    0.6052   -0.0666 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1726    0.9577   -1.3851 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5814    1.5476    0.7797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7542    1.3695    2.1502 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933    1.5399    0.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875    0.1671    0.4098 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7616   -0.4356    1.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7590    0.1287   -0.4358 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5625    1.1073   -1.4269 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9599    0.4299    0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3760   -0.2490    1.2438 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7757    1.6327   -0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1876    1.8208    1.0251 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7500   -2.6742    0.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9686   -2.8778   -1.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8067   -1.5154   -0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292   -1.1177   -2.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9494   -2.3837   -1.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591   -2.5755    0.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5038   -0.0706   -1.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7739   -0.9856    1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0124   -2.8237   -0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7357   -1.6654   -1.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5542   -2.7399   -0.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7967   -1.9452    1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0585   -1.4441   -1.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9919    2.9003   -1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0539    2.8210    0.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4989   -0.1681    2.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0550    1.6092    2.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1597    0.2856    1.8512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9423    2.5751    0.5560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0483    1.5917    2.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3944    2.0707    1.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1554    2.0929   -0.4335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3581   -1.3544    1.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8796   -0.6656    2.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3718    0.2851    2.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3111    1.1253   -2.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1294    2.5582    0.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1412    1.6066   -1.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 23  2  1  0
 21  4  1  0
 16  5  1  0
 14  8  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  6
  3 33  1  0
  3 34  1  0
  4 35  1  6
  5 36  1  1
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  9 41  1  0
 12 42  1  0
 13 43  1  0
 15 44  1  0
 15 45  1  0
 15 46  1  0
 18 47  1  6
 19 48  1  0
 20 49  1  0
 20 50  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 24 54  1  0
 27 55  1  0
 27 56  1  0
M  END

HEADER    PROTEIN                                 04-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-12         0                                  
HETATM    1  C   UNK     0      15.558  -8.181   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.558  -9.721   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.261  -7.370   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.558  -6.641   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.261 -10.531   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.883  -8.181   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.883  -9.721   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.261 -12.071   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.505  -7.370   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      11.505 -10.531   0.000  0.00  0.00           C+0
HETATM   11  F   UNK     0      12.883 -11.342   0.000  0.00  0.00           F+0
HETATM   12  C   UNK     0      12.883 -12.882   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.505 -12.071   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.127  -9.721   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.505  -8.991   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.127 -12.882   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.831 -10.531   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.831 -12.071   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.453 -12.882   0.000  0.00  0.00           O+0
HETATM   20  H   UNK     0      15.558 -11.342   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0      14.180  -8.910   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      17.023 -10.197   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.928  -8.951   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.023  -7.705   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.014  -6.160   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.344  -5.383   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      15.676  -5.397   0.000  0.00  0.00           O+0
HETATM   28 Cl   UNK     0      19.682  -6.145   0.000  0.00  0.00          Cl+0
HETATM   29  O   UNK     0      18.513  -7.350   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      19.468  -8.951   0.000  0.00  0.00           C+0
CONECT    1    3    4    2   24                                             
CONECT    2    5   20   22    1                                             
CONECT    3    1    6                                                       
CONECT    4    1                                                            
CONECT    5    2    7    8   21                                             
CONECT    6    3    9    7                                                  
CONECT    7    5   10   11    6                                             
CONECT    8    5   12                                                       
CONECT    9    6                                                            
CONECT   10    7   13   14   15                                             
CONECT   11    7                                                            
CONECT   12    8   13                                                       
CONECT   13   10   16   12                                                  
CONECT   14   10   17                                                       
CONECT   15   10                                                            
CONECT   16   13   18                                                       
CONECT   17   14   18                                                       
CONECT   18   16   19   17                                                  
CONECT   19   18                                                            
CONECT   20    2                                                            
CONECT   21    5                                                            
CONECT   22    2   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24    1   23   25   29                                             
CONECT   25   24   26   27                                                  
CONECT   26   25   28                                                       
CONECT   27   25                                                            
CONECT   28   26                                                            
CONECT   29   24                                                            
CONECT   30   23                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0015148
HETATM    1  C1  UNL     1       3.873  -2.114  -0.729  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.733  -1.226  -1.087  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.381  -1.858  -0.741  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.597  -0.646  -0.479  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.767  -0.799   0.090  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.552  -1.884  -0.554  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.937  -1.936   0.107  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.510  -0.584  -0.259  1.00  0.00           C  
HETATM    9  C9  UNL     1      -4.585  -0.523  -0.989  1.00  0.00           C  
HETATM   10  C10 UNL     1      -5.218   0.725  -1.405  1.00  0.00           C  
HETATM   11  O1  UNL     1      -6.244   0.701  -2.103  1.00  0.00           O  
HETATM   12  C11 UNL     1      -4.576   1.951  -0.955  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.495   1.837  -0.217  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.833   0.620   0.229  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.077   0.601   1.762  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.368   0.605  -0.067  1.00  0.00           C  
HETATM   17  F1  UNL     1      -1.173   0.958  -1.385  1.00  0.00           F  
HETATM   18  C16 UNL     1      -0.581   1.548   0.780  1.00  0.00           C  
HETATM   19  O2  UNL     1      -0.754   1.369   2.150  1.00  0.00           O  
HETATM   20  C17 UNL     1       0.893   1.540   0.492  1.00  0.00           C  
HETATM   21  C18 UNL     1       1.487   0.167   0.410  1.00  0.00           C  
HETATM   22  C19 UNL     1       1.762  -0.436   1.740  1.00  0.00           C  
HETATM   23  C20 UNL     1       2.759   0.129  -0.436  1.00  0.00           C  
HETATM   24  O3  UNL     1       2.562   1.107  -1.427  1.00  0.00           O  
HETATM   25  C21 UNL     1       3.960   0.430   0.321  1.00  0.00           C  
HETATM   26  O4  UNL     1       4.376  -0.249   1.244  1.00  0.00           O  
HETATM   27  C22 UNL     1       4.776   1.633  -0.005  1.00  0.00           C  
HETATM   28 CL1  UNL     1       6.188   1.821   1.025  1.00  0.00          CL  
HETATM   29  H1  UNL     1       3.750  -2.674   0.214  1.00  0.00           H  
HETATM   30  H2  UNL     1       3.969  -2.878  -1.531  1.00  0.00           H  
HETATM   31  H3  UNL     1       4.807  -1.515  -0.754  1.00  0.00           H  
HETATM   32  H4  UNL     1       2.729  -1.118  -2.192  1.00  0.00           H  
HETATM   33  H5  UNL     1       0.949  -2.384  -1.637  1.00  0.00           H  
HETATM   34  H6  UNL     1       1.459  -2.576   0.070  1.00  0.00           H  
HETATM   35  H7  UNL     1       0.504  -0.071  -1.444  1.00  0.00           H  
HETATM   36  H8  UNL     1      -0.774  -0.986   1.193  1.00  0.00           H  
HETATM   37  H9  UNL     1      -1.012  -2.824  -0.405  1.00  0.00           H  
HETATM   38  H10 UNL     1      -1.736  -1.665  -1.627  1.00  0.00           H  
HETATM   39  H11 UNL     1      -3.554  -2.740  -0.273  1.00  0.00           H  
HETATM   40  H12 UNL     1      -2.797  -1.945   1.199  1.00  0.00           H  
HETATM   41  H13 UNL     1      -5.058  -1.444  -1.323  1.00  0.00           H  
HETATM   42  H14 UNL     1      -4.992   2.900  -1.231  1.00  0.00           H  
HETATM   43  H15 UNL     1      -3.054   2.821   0.088  1.00  0.00           H  
HETATM   44  H16 UNL     1      -2.499  -0.168   2.263  1.00  0.00           H  
HETATM   45  H17 UNL     1      -3.055   1.609   2.184  1.00  0.00           H  
HETATM   46  H18 UNL     1      -4.160   0.286   1.851  1.00  0.00           H  
HETATM   47  H19 UNL     1      -0.942   2.575   0.556  1.00  0.00           H  
HETATM   48  H20 UNL     1       0.048   1.592   2.674  1.00  0.00           H  
HETATM   49  H21 UNL     1       1.394   2.071   1.329  1.00  0.00           H  
HETATM   50  H22 UNL     1       1.155   2.093  -0.433  1.00  0.00           H  
HETATM   51  H23 UNL     1       2.358  -1.354   1.654  1.00  0.00           H  
HETATM   52  H24 UNL     1       0.880  -0.666   2.340  1.00  0.00           H  
HETATM   53  H25 UNL     1       2.372   0.285   2.321  1.00  0.00           H  
HETATM   54  H26 UNL     1       3.311   1.125  -2.072  1.00  0.00           H  
HETATM   55  H27 UNL     1       4.129   2.558   0.029  1.00  0.00           H  
HETATM   56  H28 UNL     1       5.141   1.607  -1.072  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3   23   32
CONECT    3    4   33   34
CONECT    4    5   21   35
CONECT    5    6   16   36
CONECT    6    7   37   38
CONECT    7    8   39   40
CONECT    8    9    9   14
CONECT    9   10   41
CONECT   10   11   11   12
CONECT   12   13   13   42
CONECT   13   14   43
CONECT   14   15   16
CONECT   15   44   45   46
CONECT   16   17   18
CONECT   18   19   20   47
CONECT   19   48
CONECT   20   21   49   50
CONECT   21   22   23
CONECT   22   51   52   53
CONECT   23   24   25
CONECT   24   54
CONECT   25   26   26   27
CONECT   27   28   55   56
END

HMDB0015148
     RDKit          3D
Clobetasol
 56 59  0  0  0  0  0  0  0  0999 V2000
    3.8733   -2.1138   -0.7292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7329   -1.2263   -1.0867 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3812   -1.8580   -0.7407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5967   -0.6463   -0.4793 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7673   -0.7994    0.0896 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5521   -1.8843   -0.5544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9370   -1.9359    0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5105   -0.5839   -0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5849   -0.5232   -0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2180    0.7247   -1.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2444    0.7012   -2.1025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5757    1.9508   -0.9551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4946    1.8366   -0.2173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8326    0.6197    0.2290 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0769    0.6014    1.7615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3680    0.6052   -0.0666 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1726    0.9577   -1.3851 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5814    1.5476    0.7797 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7542    1.3695    2.1502 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933    1.5399    0.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875    0.1671    0.4098 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7616   -0.4356    1.7404 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7590    0.1287   -0.4358 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5625    1.1073   -1.4269 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9599    0.4299    0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3760   -0.2490    1.2438 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7757    1.6327   -0.0052 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1876    1.8208    1.0251 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.7500   -2.6742    0.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9686   -2.8778   -1.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8067   -1.5154   -0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292   -1.1177   -2.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9494   -2.3837   -1.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591   -2.5755    0.0696 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5038   -0.0706   -1.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7739   -0.9856    1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0124   -2.8237   -0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7357   -1.6654   -1.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5542   -2.7399   -0.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7967   -1.9452    1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0585   -1.4441   -1.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9919    2.9003   -1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0539    2.8210    0.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4989   -0.1681    2.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0550    1.6092    2.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1597    0.2856    1.8512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9423    2.5751    0.5560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0483    1.5917    2.6739 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3944    2.0707    1.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1554    2.0929   -0.4335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3581   -1.3544    1.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8796   -0.6656    2.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3718    0.2851    2.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3111    1.1253   -2.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1294    2.5582    0.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1412    1.6066   -1.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  1
 14 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  6
 23 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 23  2  1  0
 21  4  1  0
 16  5  1  0
 14  8  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  6
  3 33  1  0
  3 34  1  0
  4 35  1  6
  5 36  1  1
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
  9 41  1  0
 12 42  1  0
 13 43  1  0
 15 44  1  0
 15 45  1  0
 15 46  1  0
 18 47  1  6
 19 48  1  0
 20 49  1  0
 20 50  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
 24 54  1  0
 27 55  1  0
 27 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(11beta,16beta)-21-Chloro-9-fluoro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dione	ChEBI
Clobetasolum	ChEBI
Clobecort amex	Kegg
(11b,16b)-21-Chloro-9-fluoro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dione	Generator
(11Β,16β)-21-chloro-9-fluoro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dione	Generator
Clobetasol 17 propionate	HMDB
Clobetasol 17-propionate	HMDB
Clobetasol propionate	HMDB
Clobex	HMDB
Clofenazon	HMDB
Cormax	HMDB
Dermovate	HMDB
Embeline	HMDB
Embeline e	HMDB
OLUX	HMDB
Temovate	HMDB

Chemical Formula

C₂₂H₂₈ClFO₄

Average Molecular Weight

410.907

Monoisotopic Molecular Weight

410.166015296

IUPAC Name

(1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one

Traditional Name

clobetasol

CAS Registry Number

25122-46-7

SMILES

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

InChI Identifier

InChI=1S/C22H28ClFO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,24)17(26)10-20(16,3)22(12,28)18(27)11-23/h6-7,9,12,15-17,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1

InChI Key

FCSHDIVRCWTZOX-DVTGEIKXSA-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
Hydroxysteroid
Halo-steroid
9-halo-steroid
Oxosteroid
11-beta-hydroxysteroid
11-hydroxysteroid
3-oxo-delta-1,4-steroid
3-oxosteroid
17-hydroxysteroid
Delta-1,4-steroid
Alpha-haloketone
Cyclic alcohol
Alpha-hydroxy ketone
Tertiary alcohol
Alpha-chloroketone
Cyclic ketone
Secondary alcohol
Fluorohydrin
Halohydrin
Ketone
Organooxygen compound
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alkyl halide
Alkyl fluoride
Organofluoride
Organochloride
Organohalogen compound
Alkyl chloride
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

11beta-hydroxy steroid (CHEBI:205919 )
17alpha-hydroxy steroid (CHEBI:205919 )
glucocorticoid (CHEBI:205919 )
20-oxo steroid (CHEBI:205919 )
fluorinated steroid (CHEBI:205919 )
3-oxo-Delta(1),Delta(4)-steroid (CHEBI:205919 )
chlorinated steroid (CHEBI:205919 )

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: HMDB0015148)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	195.5 - 197 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.014 g/L	Not Available
LogP	3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	2.72	ALOGPS
logP	3.04	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	12.47	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	105.54 m³·mol⁻¹	ChemAxon
Polarizability	41.97 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 Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	228.981	30932474
DeepCCS	[M+Na]+	203.926	30932474
AllCCS	[M+H]+	194.9	32859911
AllCCS	[M+H-H2O]+	192.5	32859911
AllCCS	[M+NH4]+	197.1	32859911
AllCCS	[M+Na]+	197.7	32859911
AllCCS	[M-H]-	199.0	32859911
AllCCS	[M+Na-2H]-	199.8	32859911
AllCCS	[M+HCOO]-	200.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Clobetasol	[H][C@@]12C[C@H](C)[C@](O)(C(=O)CCl)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C	4146.8	Standard polar	33892256
Clobetasol	[H][C@@]12C[C@H](C)[C@](O)(C(=O)CCl)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C	2910.8	Standard non polar	33892256
Clobetasol	[H][C@@]12C[C@H](C)[C@](O)(C(=O)CCl)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C	3096.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Clobetasol,1TMS,isomer #1	C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O[Si](C)(C)C)C(=O)CCl	3365.2	Semi standard non polar	33892256
Clobetasol,1TMS,isomer #2	C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@@]1(O)C(=O)CCl	3291.1	Semi standard non polar	33892256
Clobetasol,1TMS,isomer #3	C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=CCl)O[Si](C)(C)C	3272.8	Semi standard non polar	33892256
Clobetasol,2TMS,isomer #1	C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@@]1(O[Si](C)(C)C)C(=O)CCl	3291.7	Semi standard non polar	33892256
Clobetasol,2TMS,isomer #2	C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O[Si](C)(C)C)C(=CCl)O[Si](C)(C)C	3282.3	Semi standard non polar	33892256
Clobetasol,2TMS,isomer #3	C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@@]1(O)C(=CCl)O[Si](C)(C)C	3193.4	Semi standard non polar	33892256
Clobetasol,3TMS,isomer #1	C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@@]1(O[Si](C)(C)C)C(=CCl)O[Si](C)(C)C	3194.5	Semi standard non polar	33892256
Clobetasol,3TMS,isomer #1	C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@@]1(O[Si](C)(C)C)C(=CCl)O[Si](C)(C)C	3203.2	Standard non polar	33892256
Clobetasol,3TMS,isomer #1	C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@@]1(O[Si](C)(C)C)C(=CCl)O[Si](C)(C)C	3346.8	Standard polar	33892256
Clobetasol,1TBDMS,isomer #1	C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O[Si](C)(C)C(C)(C)C)C(=O)CCl	3586.0	Semi standard non polar	33892256
Clobetasol,1TBDMS,isomer #2	C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@@]1(O)C(=O)CCl	3520.3	Semi standard non polar	33892256
Clobetasol,1TBDMS,isomer #3	C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=CCl)O[Si](C)(C)C(C)(C)C	3508.0	Semi standard non polar	33892256
Clobetasol,2TBDMS,isomer #1	C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@@]1(O[Si](C)(C)C(C)(C)C)C(=O)CCl	3749.5	Semi standard non polar	33892256
Clobetasol,2TBDMS,isomer #2	C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O[Si](C)(C)C(C)(C)C)C(=CCl)O[Si](C)(C)C(C)(C)C	3737.0	Semi standard non polar	33892256
Clobetasol,2TBDMS,isomer #3	C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@@]1(O)C(=CCl)O[Si](C)(C)C(C)(C)C	3649.3	Semi standard non polar	33892256
Clobetasol,3TBDMS,isomer #1	C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@@]1(O[Si](C)(C)C(C)(C)C)C(=CCl)O[Si](C)(C)C(C)(C)C	3860.3	Semi standard non polar	33892256
Clobetasol,3TBDMS,isomer #1	C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@@]1(O[Si](C)(C)C(C)(C)C)C(=CCl)O[Si](C)(C)C(C)(C)C	3844.0	Standard non polar	33892256
Clobetasol,3TBDMS,isomer #1	C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@@]1(O[Si](C)(C)C(C)(C)C)C(=CCl)O[Si](C)(C)C(C)(C)C	3554.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Clobetasol GC-MS (Non-derivatized) - 70eV, Positive	splash10-05ur-1922000000-1a2dff27fd4359dcf1ff	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clobetasol GC-MS (2 TMS) - 70eV, Positive	splash10-000l-3545390000-45a386f33671c09db1ef	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clobetasol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobetasol 50V, Positive-QTOF	splash10-00dj-0960000000-a22cd2cf411698d4cb20	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobetasol 10V, Positive-QTOF	splash10-01ox-0009400000-e9436fb9bac8eda3bf10	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobetasol 50V, Positive-QTOF	splash10-00dj-0960000000-6443ffdb9b79ef387dc3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobetasol 30V, Positive-QTOF	splash10-01w1-0692000000-4a54671d4895c5118cc1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobetasol 30V, Positive-QTOF	splash10-01w1-0692000000-ee83dc8cb91bcf54300f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobetasol 40V, Positive-QTOF	splash10-022a-0890000000-38b8d519ad2a9ba13b3d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobetasol 20V, Positive-QTOF	splash10-00di-0469000000-31fce0ad107cfd522ffc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Clobetasol 10V, Positive-QTOF	splash10-01ox-0009400000-8d3f1a9dbe178961f1a3	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobetasol 10V, Positive-QTOF	splash10-03ec-0009300000-eabf4bbbde18aa470559	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobetasol 20V, Positive-QTOF	splash10-06vl-0139100000-5851c4786f4f11dac8a4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobetasol 40V, Positive-QTOF	splash10-0i6r-0396000000-ce80f2ae92c03b288ae7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobetasol 10V, Negative-QTOF	splash10-0a4i-0005900000-08f019701c8687b3adfa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobetasol 20V, Negative-QTOF	splash10-05fr-1009200000-83699a43939ad9dd09a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobetasol 40V, Negative-QTOF	splash10-0gc0-1029000000-d3f4258d8f19313ca5a9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobetasol 10V, Positive-QTOF	splash10-03dl-0009700000-1851cdf5907155e33c20	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobetasol 20V, Positive-QTOF	splash10-03dl-0869400000-ff98ebd4c04b608835cd	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobetasol 40V, Positive-QTOF	splash10-0a4u-2891000000-106ece766a3163e1226b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobetasol 10V, Negative-QTOF	splash10-0ab9-0009800000-d247e43fa37d759961e6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobetasol 20V, Negative-QTOF	splash10-001i-1009000000-d289c7e30bdafdb38a90	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clobetasol 40V, Negative-QTOF	splash10-001i-1019000000-0e4b816a146275aa7238	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 DB01013	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01013	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB11750

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4470588

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Clobetasol propionate

METLIN ID

Not Available

PubChem Compound

5311051

PDB ID

Not Available

ChEBI ID

205919

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

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. Cytochrome P450 1A1

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

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

2. Cytochrome P450 1A2

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

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 ]

Showing metabocard for Clobetasol (HMDB0015148)

MOL for HMDB0015148 (Clobetasol)

3D MOL for HMDB0015148 (Clobetasol)

3D SDF for HMDB0015148 (Clobetasol)

3D-SDF for HMDB0015148 (Clobetasol)

PDB for HMDB0015148 (Clobetasol)

3D PDB for HMDB0015148 (Clobetasol)

SMILES for HMDB0015148 (Clobetasol)

INCHI for HMDB0015148 (Clobetasol)

Structure for HMDB0015148 (Clobetasol)

3D Structure for HMDB0015148 (Clobetasol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References