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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:48 UTC

HMDB ID

HMDB0014976

Secondary Accession Numbers

HMDB14976

Metabolite Identification

Common Name

Clocortolone

Description

Clocortolone is only found in individuals that have used or taken this drug. It is a medium potency corticosteroid that is often used as a topical cream for the relief of inflammatory oand pruritic (itching) arising from steroid-responsive dermatoses of the scalp.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. These enzyme transcriptional changes are mediated by the drug binding first to the glucocorticoid receptor. This complex can migrate to the cell nucleus which then binds to DNA initiating genetic activation and repression of various genes.

Structure

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


  Mrv0541 04191212152D          

 30 33  0  0  1  0            999 V2000
    5.7755   -5.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7755   -6.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4868   -6.9891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1981   -6.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1981   -5.7759    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4868   -5.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9092   -6.9891    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5786   -6.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5786   -5.7759    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9092   -5.3575    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2898   -5.3575    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2898   -4.5626    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5786   -4.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9092   -4.5626    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9092   -7.8258    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.9092   -6.1942    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.2898   -6.1942    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2480   -3.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1981   -4.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0644   -6.9891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1981   -4.1443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5786   -4.9810    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0458   -4.3170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.5129   -4.9601    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0459   -5.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3008   -3.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1079   -3.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7486   -2.9191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6598   -3.9739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3381   -4.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
  7 15  1  6  0  0  0
 10 16  1  6  0  0  0
 11 17  1  6  0  0  0
 12 18  1  1  0  0  0
  5 19  1  1  0  0  0
  2 20  2  0  0  0  0
 14 21  1  1  0  0  0
  9 22  1  1  0  0  0
 23 12  1  0  0  0  0
 11 12  1  0  0  0  0
 24 23  1  0  0  0  0
 25 11  1  0  0  0  0
 25 24  1  0  0  0  0
 23 26  1  1  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 27 29  1  0  0  0  0
 24 30  1  6  0  0  0
M  END

HMDB0014976
     RDKit          3D
Clocortolone
 56 59  0  0  0  0  0  0  0  0999 V2000
   -2.9852    0.3032   -2.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7810    0.7534   -1.1617 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4401    1.4887   -1.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5569    0.4400   -0.5871 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7663    0.8411   -0.0160 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5168    1.7671   -0.8873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8951    1.9941   -0.3115 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6430    2.8909   -0.9875 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5022    0.5988   -0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4930    0.3728   -1.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1389   -0.9508   -1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1074   -1.1720   -2.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5642   -1.9831   -0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5475   -1.7078    0.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8996   -0.4176    0.5166 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1765   -0.0280    1.9946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4207   -0.4720    0.3482 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1035   -1.6936   -0.9438 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6859   -1.0097    1.5539 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7760   -0.2398    2.6846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7767   -1.2892    1.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4145   -0.1084    0.5298 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9542    0.9346    1.4530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5937   -0.5332   -0.3551 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7707   -0.9196    0.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7355   -1.0246    1.6094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0385   -1.1904   -0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0352   -1.5407    0.5709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3786    0.9464   -3.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6278   -0.7325   -2.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0380    0.3411   -2.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6075    1.3632   -0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566    1.8176   -2.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5037    2.3984   -0.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4798   -0.3773   -1.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5513    1.3953    0.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6034    1.3809   -1.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0023    2.7512   -0.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8179    2.2403    0.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9014    1.1878   -1.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9537   -3.0177   -0.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1580   -2.5817    0.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2808    0.1273    2.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7091    0.8980    2.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9543   -0.9324    2.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0849   -2.0310    1.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2127    0.5398    2.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8311   -2.2017    0.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2984   -1.4600    2.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1512    0.4691    2.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3474    1.8606    1.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9742    1.3159    1.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2271   -1.3573   -0.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8976   -1.9334   -1.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3951   -0.2572   -0.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4700   -0.7261    0.9063 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 24  2  1  0
 22  4  1  0
 17  5  1  0
 15  9  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  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  1
 10 40  1  0
 13 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 19 46  1  1
 20 47  1  0
 21 48  1  0
 21 49  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  6
 27 54  1  0
 27 55  1  0
 28 56  1  0
M  END


  Mrv0541 04191212152D          

 30 33  0  0  1  0            999 V2000
    5.7755   -5.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7755   -6.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4868   -6.9891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1981   -6.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1981   -5.7759    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4868   -5.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9092   -6.9891    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5786   -6.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5786   -5.7759    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9092   -5.3575    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2898   -5.3575    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2898   -4.5626    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.5786   -4.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9092   -4.5626    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9092   -7.8258    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.9092   -6.1942    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.2898   -6.1942    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2480   -3.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1981   -4.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0644   -6.9891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1981   -4.1443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5786   -4.9810    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0458   -4.3170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.5129   -4.9601    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0459   -5.6032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3008   -3.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1079   -3.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7486   -2.9191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6598   -3.9739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3381   -4.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
  7 15  1  6  0  0  0
 10 16  1  6  0  0  0
 11 17  1  6  0  0  0
 12 18  1  1  0  0  0
  5 19  1  1  0  0  0
  2 20  2  0  0  0  0
 14 21  1  1  0  0  0
  9 22  1  1  0  0  0
 23 12  1  0  0  0  0
 11 12  1  0  0  0  0
 24 23  1  0  0  0  0
 25 11  1  0  0  0  0
 25 24  1  0  0  0  0
 23 26  1  1  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 27 29  1  0  0  0  0
 24 30  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0014976

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(Cl)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C22H28ClFO4/c1-11-6-13-14-8-16(24)15-7-12(26)4-5-21(15,3)22(14,23)18(28)9-20(13,2)19(11)17(27)10-25/h4-5,7,11,13-14,16,18-19,25,28H,6,8-10H2,1-3H3/t11-,13+,14+,16+,18+,19-,20+,21+,22+/m1/s1

> <INCHI_KEY>
YMTMADLUXIRMGX-RFPWEZLHSA-N

> <FORMULA>
C22H28ClFO4

> <MOLECULAR_WEIGHT>
410.907

> <EXACT_MASS>
410.166015296

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
41.79875113918743

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,8S,10S,11S,13R,14S,15S,17S)-1-chloro-8-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
2.474821861666665

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.09578395865979

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.533640659774612

> <JCHEM_PKA_STRONGEST_BASIC>
-3.295502639455157

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
105.73639999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
clocortolona

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014976
     RDKit          3D
Clocortolone
 56 59  0  0  0  0  0  0  0  0999 V2000
   -2.9852    0.3032   -2.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7810    0.7534   -1.1617 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4401    1.4887   -1.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5569    0.4400   -0.5871 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7663    0.8411   -0.0160 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5168    1.7671   -0.8873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8951    1.9941   -0.3115 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6430    2.8909   -0.9875 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5022    0.5988   -0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4930    0.3728   -1.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1389   -0.9508   -1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1074   -1.1720   -2.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5642   -1.9831   -0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5475   -1.7078    0.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8996   -0.4176    0.5166 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1765   -0.0280    1.9946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4207   -0.4720    0.3482 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1035   -1.6936   -0.9438 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6859   -1.0097    1.5539 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7760   -0.2398    2.6846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7767   -1.2892    1.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4145   -0.1084    0.5298 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9542    0.9346    1.4530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5937   -0.5332   -0.3551 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7707   -0.9196    0.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7355   -1.0246    1.6094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0385   -1.1904   -0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0352   -1.5407    0.5709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3786    0.9464   -3.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6278   -0.7325   -2.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0380    0.3411   -2.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6075    1.3632   -0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566    1.8176   -2.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5037    2.3984   -0.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4798   -0.3773   -1.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5513    1.3953    0.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6034    1.3809   -1.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0023    2.7512   -0.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8179    2.2403    0.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9014    1.1878   -1.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9537   -3.0177   -0.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1580   -2.5817    0.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2808    0.1273    2.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7091    0.8980    2.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9543   -0.9324    2.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0849   -2.0310    1.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2127    0.5398    2.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8311   -2.2017    0.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2984   -1.4600    2.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1512    0.4691    2.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3474    1.8606    1.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9742    1.3159    1.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2271   -1.3573   -0.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8976   -1.9334   -1.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3951   -0.2572   -0.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4700   -0.7261    0.9063 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 24  2  1  0
 22  4  1  0
 17  5  1  0
 15  9  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  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  1
 10 40  1  0
 13 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 19 46  1  1
 20 47  1  0
 21 48  1  0
 21 49  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  6
 27 54  1  0
 27 55  1  0
 28 56  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      10.781 -10.782   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.781 -12.265   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.109 -13.046   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.436 -12.265   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.436 -10.782   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.109 -10.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.764 -13.046   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.013 -12.265   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.013 -10.782   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.764 -10.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.341 -10.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.341  -8.517   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.013  -7.736   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.764  -8.517   0.000  0.00  0.00           C+0
HETATM   15  F   UNK     0      14.764 -14.608   0.000  0.00  0.00           F+0
HETATM   16 Cl   UNK     0      14.764 -11.563   0.000  0.00  0.00          Cl+0
HETATM   17  H   UNK     0      17.341 -11.563   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0      17.263  -6.955   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.436  -9.298   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.454 -13.046   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      13.436  -7.736   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0      16.013  -9.298   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0      18.752  -8.058   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.624  -9.259   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      18.752 -10.459   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      19.228  -6.594   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.735  -6.273   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      18.197  -5.449   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      21.765  -7.418   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      21.164  -9.259   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   19                                             
CONECT    6    5    1                                                       
CONECT    7    4    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11   22                                             
CONECT   10    9    5   14   16                                             
CONECT   11    9   17   12   25                                             
CONECT   12   13   18   23   11                                             
CONECT   13   12   14                                                       
CONECT   14   13   10   21                                                  
CONECT   15    7                                                            
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19    5                                                            
CONECT   20    2                                                            
CONECT   21   14                                                            
CONECT   22    9                                                            
CONECT   23   12   24   26                                                  
CONECT   24   23   25   30                                                  
CONECT   25   11   24                                                       
CONECT   26   23   27   28                                                  
CONECT   27   26   29                                                       
CONECT   28   26                                                            
CONECT   29   27                                                            
CONECT   30   24                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0014976
HETATM    1  C1  UNL     1      -2.985   0.303  -2.605  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.781   0.753  -1.162  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.440   1.489  -1.119  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.557   0.440  -0.587  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.766   0.841  -0.016  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.517   1.767  -0.887  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.895   1.994  -0.311  1.00  0.00           C  
HETATM    8  F1  UNL     1       3.643   2.891  -0.988  1.00  0.00           F  
HETATM    9  C8  UNL     1       3.502   0.599  -0.361  1.00  0.00           C  
HETATM   10  C9  UNL     1       4.493   0.373  -1.142  1.00  0.00           C  
HETATM   11  C10 UNL     1       5.139  -0.951  -1.265  1.00  0.00           C  
HETATM   12  O1  UNL     1       6.107  -1.172  -2.025  1.00  0.00           O  
HETATM   13  C11 UNL     1       4.564  -1.983  -0.433  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.548  -1.708   0.360  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.900  -0.418   0.517  1.00  0.00           C  
HETATM   16  C14 UNL     1       3.177  -0.028   1.995  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.421  -0.472   0.348  1.00  0.00           C  
HETATM   18 CL1  UNL     1       1.104  -1.694  -0.944  1.00  0.00          CL  
HETATM   19  C16 UNL     1       0.686  -1.010   1.554  1.00  0.00           C  
HETATM   20  O2  UNL     1       0.776  -0.240   2.685  1.00  0.00           O  
HETATM   21  C17 UNL     1      -0.777  -1.289   1.200  1.00  0.00           C  
HETATM   22  C18 UNL     1      -1.414  -0.108   0.530  1.00  0.00           C  
HETATM   23  C19 UNL     1      -1.954   0.935   1.453  1.00  0.00           C  
HETATM   24  C20 UNL     1      -2.594  -0.533  -0.355  1.00  0.00           C  
HETATM   25  C21 UNL     1      -3.771  -0.920   0.405  1.00  0.00           C  
HETATM   26  O3  UNL     1      -3.735  -1.025   1.609  1.00  0.00           O  
HETATM   27  C22 UNL     1      -5.038  -1.190  -0.311  1.00  0.00           C  
HETATM   28  O4  UNL     1      -6.035  -1.541   0.571  1.00  0.00           O  
HETATM   29  H1  UNL     1      -2.379   0.946  -3.305  1.00  0.00           H  
HETATM   30  H2  UNL     1      -2.628  -0.733  -2.769  1.00  0.00           H  
HETATM   31  H3  UNL     1      -4.038   0.341  -2.910  1.00  0.00           H  
HETATM   32  H4  UNL     1      -3.608   1.363  -0.798  1.00  0.00           H  
HETATM   33  H5  UNL     1      -1.157   1.818  -2.139  1.00  0.00           H  
HETATM   34  H6  UNL     1      -1.504   2.398  -0.501  1.00  0.00           H  
HETATM   35  H7  UNL     1      -0.480  -0.377  -1.348  1.00  0.00           H  
HETATM   36  H8  UNL     1       0.551   1.395   0.939  1.00  0.00           H  
HETATM   37  H9  UNL     1       1.603   1.381  -1.929  1.00  0.00           H  
HETATM   38  H10 UNL     1       1.002   2.751  -0.856  1.00  0.00           H  
HETATM   39  H11 UNL     1       2.818   2.240   0.765  1.00  0.00           H  
HETATM   40  H12 UNL     1       4.901   1.188  -1.763  1.00  0.00           H  
HETATM   41  H13 UNL     1       4.954  -3.018  -0.438  1.00  0.00           H  
HETATM   42  H14 UNL     1       3.158  -2.582   0.971  1.00  0.00           H  
HETATM   43  H15 UNL     1       4.281   0.127   2.120  1.00  0.00           H  
HETATM   44  H16 UNL     1       2.709   0.898   2.284  1.00  0.00           H  
HETATM   45  H17 UNL     1       2.954  -0.932   2.579  1.00  0.00           H  
HETATM   46  H18 UNL     1       1.085  -2.031   1.839  1.00  0.00           H  
HETATM   47  H19 UNL     1       0.213   0.540   2.745  1.00  0.00           H  
HETATM   48  H20 UNL     1      -0.831  -2.202   0.587  1.00  0.00           H  
HETATM   49  H21 UNL     1      -1.298  -1.460   2.163  1.00  0.00           H  
HETATM   50  H22 UNL     1      -2.151   0.469   2.444  1.00  0.00           H  
HETATM   51  H23 UNL     1      -1.347   1.861   1.509  1.00  0.00           H  
HETATM   52  H24 UNL     1      -2.974   1.316   1.140  1.00  0.00           H  
HETATM   53  H25 UNL     1      -2.227  -1.357  -0.988  1.00  0.00           H  
HETATM   54  H26 UNL     1      -4.898  -1.933  -1.124  1.00  0.00           H  
HETATM   55  H27 UNL     1      -5.395  -0.257  -0.838  1.00  0.00           H  
HETATM   56  H28 UNL     1      -6.470  -0.726   0.906  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3   24   32
CONECT    3    4   33   34
CONECT    4    5   22   35
CONECT    5    6   17   36
CONECT    6    7   37   38
CONECT    7    8    9   39
CONECT    9   10   10   15
CONECT   10   11   40
CONECT   11   12   12   13
CONECT   13   14   14   41
CONECT   14   15   42
CONECT   15   16   17
CONECT   16   43   44   45
CONECT   17   18   19
CONECT   19   20   21   46
CONECT   20   47
CONECT   21   22   48   49
CONECT   22   23   24
CONECT   23   50   51   52
CONECT   24   25   53
CONECT   25   26   26   27
CONECT   27   28   54   55
CONECT   28   56
END

HMDB0014976
     RDKit          3D
Clocortolone
 56 59  0  0  0  0  0  0  0  0999 V2000
   -2.9852    0.3032   -2.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7810    0.7534   -1.1617 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4401    1.4887   -1.1195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5569    0.4400   -0.5871 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7663    0.8411   -0.0160 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5168    1.7671   -0.8873 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8951    1.9941   -0.3115 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6430    2.8909   -0.9875 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5022    0.5988   -0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4930    0.3728   -1.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1389   -0.9508   -1.2650 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1074   -1.1720   -2.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5642   -1.9831   -0.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5475   -1.7078    0.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8996   -0.4176    0.5166 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1765   -0.0280    1.9946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4207   -0.4720    0.3482 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1035   -1.6936   -0.9438 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6859   -1.0097    1.5539 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7760   -0.2398    2.6846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7767   -1.2892    1.1997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4145   -0.1084    0.5298 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9542    0.9346    1.4530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5937   -0.5332   -0.3551 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7707   -0.9196    0.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7355   -1.0246    1.6094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0385   -1.1904   -0.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0352   -1.5407    0.5709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3786    0.9464   -3.3052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6278   -0.7325   -2.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0380    0.3411   -2.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6075    1.3632   -0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566    1.8176   -2.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5037    2.3984   -0.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4798   -0.3773   -1.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5513    1.3953    0.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6034    1.3809   -1.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0023    2.7512   -0.8561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8179    2.2403    0.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9014    1.1878   -1.7627 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9537   -3.0177   -0.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1580   -2.5817    0.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2808    0.1273    2.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7091    0.8980    2.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9543   -0.9324    2.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0849   -2.0310    1.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2127    0.5398    2.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8311   -2.2017    0.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2984   -1.4600    2.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1512    0.4691    2.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3474    1.8606    1.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9742    1.3159    1.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2271   -1.3573   -0.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8976   -1.9334   -1.1243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3951   -0.2572   -0.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4700   -0.7261    0.9063 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 24  2  1  0
 22  4  1  0
 17  5  1  0
 15  9  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  1
  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  1
 10 40  1  0
 13 41  1  0
 14 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 19 46  1  1
 20 47  1  0
 21 48  1  0
 21 49  1  0
 23 50  1  0
 23 51  1  0
 23 52  1  0
 24 53  1  6
 27 54  1  0
 27 55  1  0
 28 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9-Chloro-6alpha-fluoro-11beta,21-dihydroxy-16alpha-methyl-1,4-pregnadien-3,20-dione	ChEBI
9-Chloro-6alpha-fluoro-16alpha-methyl-1,4-pregnadiene-11beta,21-diol-3,20-dione	ChEBI
Clocortolona	ChEBI
Clocortolonum	ChEBI
9-Chloro-6a-fluoro-11b,21-dihydroxy-16a-methyl-1,4-pregnadien-3,20-dione	Generator
9-Chloro-6α-fluoro-11β,21-dihydroxy-16α-methyl-1,4-pregnadien-3,20-dione	Generator
9-Chloro-6a-fluoro-16a-methyl-1,4-pregnadiene-11b,21-diol-3,20-dione	Generator
9-Chloro-6α-fluoro-16α-methyl-1,4-pregnadiene-11β,21-diol-3,20-dione	Generator
Clocortolone pivalate	HMDB
Clocortolone acetate	HMDB

Chemical Formula

C₂₂H₂₈ClFO₄

Average Molecular Weight

410.907

Monoisotopic Molecular Weight

410.166015296

IUPAC Name

(1R,2S,8S,10S,11S,13R,14S,15S,17S)-1-chloro-8-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one

Traditional Name

clocortolona

CAS Registry Number

34097-16-0

SMILES

[H][C@@]12C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(Cl)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C

InChI Identifier

InChI=1S/C22H28ClFO4/c1-11-6-13-14-8-16(24)15-7-12(26)4-5-21(15,3)22(14,23)18(28)9-20(13,2)19(11)17(27)10-25/h4-5,7,11,13-14,16,18-19,25,28H,6,8-10H2,1-3H3/t11-,13+,14+,16+,18+,19-,20+,21+,22+/m1/s1

InChI Key

YMTMADLUXIRMGX-RFPWEZLHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

21-hydroxysteroids

Alternative Parents

Substituents

21-hydroxysteroid
Progestogin-skeleton
20-oxosteroid
Pregnane-skeleton
6-halo-steroid
Halo-steroid
3-oxo-delta-1,4-steroid
9-halo-steroid
3-oxosteroid
Oxosteroid
11-beta-hydroxysteroid
11-hydroxysteroid
Delta-1,4-steroid
Cyclic alcohol
Alpha-hydroxy ketone
Halohydrin
Chlorohydrin
Secondary alcohol
Ketone
Cyclic ketone
Organic oxygen compound
Organohalogen compound
Organochloride
Organofluoride
Organooxygen compound
Primary alcohol
Carbonyl group
Hydrocarbon derivative
Alkyl halide
Alkyl fluoride
Alkyl chloride
Alcohol
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

11beta-hydroxy steroid (CHEBI:59582 )
glucocorticoid (CHEBI:59582 )
20-oxo steroid (CHEBI:59582 )
fluorinated steroid (CHEBI:59582 )
3-oxo-Delta(1),Delta(4)-steroid (CHEBI:59582 )
chlorinated steroid (CHEBI:59582 )
21-hydroxy steroid (CHEBI:59582 )

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: HMDB0014976)

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	0.015 g/L	Not Available
LogP	3.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.015 g/L	ALOGPS
logP	2.73	ALOGPS
logP	2.47	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	13.53	ChemAxon
pKa (Strongest Basic)	-3.3	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	105.74 m³·mol⁻¹	ChemAxon
Polarizability	41.8 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]-	225.739	30932474
DeepCCS	[M+Na]+	200.028	30932474
AllCCS	[M+H]+	194.7	32859911
AllCCS	[M+H-H2O]+	192.4	32859911
AllCCS	[M+NH4]+	196.9	32859911
AllCCS	[M+Na]+	197.5	32859911
AllCCS	[M-H]-	199.0	32859911
AllCCS	[M+Na-2H]-	199.8	32859911
AllCCS	[M+HCOO]-	200.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.64 minutes	32390414
Predicted by Siyang on May 30, 2022	14.2558 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.15 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2700.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	256.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	193.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	183.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	155.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	601.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	540.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	93.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1150.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	500.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1583.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	371.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	438.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	265.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	356.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	16.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Clocortolone	[H][C@@]12C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(Cl)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C	3811.4	Standard polar	33892256
Clocortolone	[H][C@@]12C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(Cl)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C	2871.4	Standard non polar	33892256
Clocortolone	[H][C@@]12C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(Cl)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C	3323.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Clocortolone,1TMS,isomer #1	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)[C@H]1C(=O)CO[Si](C)(C)C	3283.1	Semi standard non polar	33892256
Clocortolone,1TMS,isomer #2	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@H]1C(=O)CO	3247.1	Semi standard non polar	33892256
Clocortolone,1TMS,isomer #3	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)C1=C(CO)O[Si](C)(C)C	3209.5	Semi standard non polar	33892256
Clocortolone,1TMS,isomer #4	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)[C@H]1C(=CO)O[Si](C)(C)C	3225.7	Semi standard non polar	33892256
Clocortolone,2TMS,isomer #1	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@H]1C(=O)CO[Si](C)(C)C	3222.7	Semi standard non polar	33892256
Clocortolone,2TMS,isomer #2	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)C1=C(CO[Si](C)(C)C)O[Si](C)(C)C	3163.6	Semi standard non polar	33892256
Clocortolone,2TMS,isomer #3	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C)O[Si](C)(C)C	3214.2	Semi standard non polar	33892256
Clocortolone,2TMS,isomer #4	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C)C[C@]2(C)C1=C(CO)O[Si](C)(C)C	3138.0	Semi standard non polar	33892256
Clocortolone,2TMS,isomer #5	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@H]1C(=CO)O[Si](C)(C)C	3155.5	Semi standard non polar	33892256
Clocortolone,3TMS,isomer #1	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C)C[C@]2(C)C1=C(CO[Si](C)(C)C)O[Si](C)(C)C	3137.0	Semi standard non polar	33892256
Clocortolone,3TMS,isomer #1	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C)C[C@]2(C)C1=C(CO[Si](C)(C)C)O[Si](C)(C)C	3216.0	Standard non polar	33892256
Clocortolone,3TMS,isomer #1	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C)C[C@]2(C)C1=C(CO[Si](C)(C)C)O[Si](C)(C)C	3464.8	Standard polar	33892256
Clocortolone,3TMS,isomer #2	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C)O[Si](C)(C)C	3183.5	Semi standard non polar	33892256
Clocortolone,3TMS,isomer #2	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C)O[Si](C)(C)C	3175.2	Standard non polar	33892256
Clocortolone,3TMS,isomer #2	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C)O[Si](C)(C)C	3505.8	Standard polar	33892256
Clocortolone,1TBDMS,isomer #1	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)[C@H]1C(=O)CO[Si](C)(C)C(C)(C)C	3510.2	Semi standard non polar	33892256
Clocortolone,1TBDMS,isomer #2	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@H]1C(=O)CO	3445.1	Semi standard non polar	33892256
Clocortolone,1TBDMS,isomer #3	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)C1=C(CO)O[Si](C)(C)C(C)(C)C	3443.3	Semi standard non polar	33892256
Clocortolone,1TBDMS,isomer #4	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)[C@H]1C(=CO)O[Si](C)(C)C(C)(C)C	3441.2	Semi standard non polar	33892256
Clocortolone,2TBDMS,isomer #1	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@H]1C(=O)CO[Si](C)(C)C(C)(C)C	3681.3	Semi standard non polar	33892256
Clocortolone,2TBDMS,isomer #2	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)C1=C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3609.9	Semi standard non polar	33892256
Clocortolone,2TBDMS,isomer #3	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3620.3	Semi standard non polar	33892256
Clocortolone,2TBDMS,isomer #4	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)C1=C(CO)O[Si](C)(C)C(C)(C)C	3587.2	Semi standard non polar	33892256
Clocortolone,2TBDMS,isomer #5	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@H]1C(=CO)O[Si](C)(C)C(C)(C)C	3588.1	Semi standard non polar	33892256
Clocortolone,3TBDMS,isomer #1	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)C1=C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3773.5	Semi standard non polar	33892256
Clocortolone,3TBDMS,isomer #1	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)C1=C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3828.8	Standard non polar	33892256
Clocortolone,3TBDMS,isomer #1	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)C1=C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3678.8	Standard polar	33892256
Clocortolone,3TBDMS,isomer #2	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3813.4	Semi standard non polar	33892256
Clocortolone,3TBDMS,isomer #2	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3788.8	Standard non polar	33892256
Clocortolone,3TBDMS,isomer #2	C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3709.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Clocortolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fts-0902000000-db049b3ec73de5a11c55	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clocortolone GC-MS (2 TMS) - 70eV, Positive	splash10-000l-2422090000-e26ab64c097ac3a8a28e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Clocortolone 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clocortolone 10V, Positive-QTOF	splash10-03dl-0009300000-10e0e49fc29a66a2e173	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clocortolone 20V, Positive-QTOF	splash10-06tf-0109100000-752aaf06820544efd7db	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clocortolone 40V, Positive-QTOF	splash10-001j-3119000000-2d31623d437f3f01cadb	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clocortolone 10V, Negative-QTOF	splash10-0a4i-0004900000-88750b9c66302d7f4b0f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clocortolone 20V, Negative-QTOF	splash10-0a4l-1009200000-dd9fd4ec78332b3082e7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clocortolone 40V, Negative-QTOF	splash10-0a4i-4509000000-3061fb46de1c491f79dc	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clocortolone 10V, Positive-QTOF	splash10-03di-0007900000-097eefd9651f8cee538b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clocortolone 20V, Positive-QTOF	splash10-0ik9-0009100000-9e7fed184555a49f52dc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clocortolone 40V, Positive-QTOF	splash10-0zmi-2986000000-95acec09a45b047de6e3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clocortolone 10V, Negative-QTOF	splash10-0a4i-0007900000-9048ab14b535e5d00a42	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clocortolone 20V, Negative-QTOF	splash10-005a-0009000000-767fa69916370947b930	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Clocortolone 40V, Negative-QTOF	splash10-0f6w-0009000000-63e23b0c3d6fdff57bb7	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 DB00838	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00838	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00838

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4470589

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Clocortolone

METLIN ID

Not Available

PubChem Compound

5311052

PDB ID

Not Available

ChEBI ID

59582

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.

Showing metabocard for Clocortolone (HMDB0014976)

MOL for HMDB0014976 (Clocortolone)

3D MOL for HMDB0014976 (Clocortolone)

3D SDF for HMDB0014976 (Clocortolone)

3D-SDF for HMDB0014976 (Clocortolone)

PDB for HMDB0014976 (Clocortolone)

3D PDB for HMDB0014976 (Clocortolone)

SMILES for HMDB0014976 (Clocortolone)

INCHI for HMDB0014976 (Clocortolone)

Structure for HMDB0014976 (Clocortolone)

3D Structure for HMDB0014976 (Clocortolone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra