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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:38 UTC

HMDB ID

HMDB0014469

Secondary Accession Numbers

HMDB14469

Metabolite Identification

Common Name

Fluorometholone

Description

Fluorometholone is only found in individuals that have used or taken this drug. It is a glucocorticoid employed, usually as eye drops, in the treatment of allergic and inflammatory conditions of the eye. It has also been used topically in the treatment of various skin disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p732)There is no generally accepted explanation for the mechanism of action of ocular corticosteroids. 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. Their primary target is the cytosolic glucocorticoid receptor. After binding the receptor the newly formed receptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing the increase in expression of specific target genes.

Structure

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

324
  Mrv0541 02231214362D          

 29 32  0  0  1  0            999 V2000
    4.1400    0.7077    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.6263    1.9371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9559    1.3132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4634    2.4564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0993    0.9007    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0993    0.0757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3849   -0.3368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6703    0.0757    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8799    1.1521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3849    1.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6703    0.9007    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8799   -0.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9196   -0.3425    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3614    0.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3981   -1.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6572   -1.6314    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0993    1.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9130   -1.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5482    1.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6434    0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1550    0.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6603   -2.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1413   -1.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729   -0.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3660   -1.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1691   -0.5806    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9589   -0.6624    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  6  0  0  0
 10  2  1  6  0  0  0
 12  3  1  1  0  0  0
  4 20  2  0  0  0  0
  5 27  2  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 18  1  1  0  0  0
  7  8  1  0  0  0  0
  7 13  1  0  0  0  0
  7 28  1  6  0  0  0
  8  9  1  0  0  0  0
  8 16  1  0  0  0  0
  8 29  1  1  0  0  0
  9 12  1  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  0  0  0  0
 10 20  1  0  0  0  0
 11 12  1  0  0  0  0
 13 15  1  0  0  0  0
 14 19  1  0  0  0  0
 14 21  1  1  0  0  0
 14 22  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
 17 23  1  6  0  0  0
 19 24  2  0  0  0  0
 20 26  1  0  0  0  0
 22 25  2  0  0  0  0
 24 27  1  0  0  0  0
 25 27  1  0  0  0  0
M  END

HMDB0014469
     RDKit          3D
Fluorometholone
 56 59  0  0  0  0  0  0  0  0999 V2000
    5.4232   -0.4594   -1.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2225    0.2935   -0.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0794    1.4186   -1.0677 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2376   -0.2894    0.3375 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5965   -1.5445    0.7610 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1627    0.7341    1.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8765    1.5135    1.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0343    0.3811    0.7382 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2791    0.6457    0.0755 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0883    1.7013    0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3867    1.8246   -0.0689 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2464    2.9502    0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0578    0.4961    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1429    0.4716    0.8629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8030   -0.8123    1.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8582   -0.8685    1.7765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1586   -1.9809    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0537   -1.9418   -0.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3636   -0.6638   -0.4670 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3108   -0.3955   -1.9669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9788   -0.6927    0.1519 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2212   -0.8845    1.5262 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1590   -1.8442   -0.3218 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6448   -2.2000   -1.5972 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2980   -1.7221   -0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8669   -0.3382   -0.2932 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8651    0.2885   -1.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2892   -0.3039   -0.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1110   -1.5149   -1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7121   -0.1134   -2.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5520   -1.7012    0.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9397    0.1741    2.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0331    1.3814    1.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1062    2.2514    0.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5573    2.0512    2.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9183   -0.3063    1.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1674    0.9315   -0.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5636    2.6688    0.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3512    1.3422    1.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0900    1.9627   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3638    3.0387    1.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2258    2.8528   -0.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7971    3.8954   -0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5645    1.4028    1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6151   -2.9753    0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6618   -2.8964   -0.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5805   -1.3050   -2.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3433    0.0023   -2.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0854    0.3552   -2.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4085   -2.7412    0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4326   -3.1484   -1.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062   -2.1658   -1.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8056   -2.3256    0.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8286    1.3726   -1.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166   -0.1760   -2.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7649   -0.0912   -2.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  6
 26  4  1  0
 26  8  1  0
 21  9  1  0
 19 13  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  1
  9 37  1  6
 10 38  1  0
 10 39  1  0
 11 40  1  6
 12 41  1  0
 12 42  1  0
 12 43  1  0
 14 44  1  0
 17 45  1  0
 18 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 23 50  1  1
 24 51  1  0
 25 52  1  0
 25 53  1  0
 27 54  1  0
 27 55  1  0
 27 56  1  0
M  END

324
  Mrv0541 02231214362D          

 29 32  0  0  1  0            999 V2000
    4.1400    0.7077    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.6263    1.9371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9559    1.3132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4634    2.4564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0993    0.9007    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0993    0.0757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3849   -0.3368    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6703    0.0757    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8799    1.1521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3849    1.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6703    0.9007    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8799   -0.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9196   -0.3425    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3614    0.4882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3981   -1.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6572   -1.6314    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0993    1.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9130   -1.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5482    1.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6434    0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1550    0.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6603   -2.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1413   -1.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729   -0.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3660   -1.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1691   -0.5806    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9589   -0.6624    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  6  0  0  0
 10  2  1  6  0  0  0
 12  3  1  1  0  0  0
  4 20  2  0  0  0  0
  5 27  2  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  0  0  0  0
  6 11  1  0  0  0  0
  6 18  1  1  0  0  0
  7  8  1  0  0  0  0
  7 13  1  0  0  0  0
  7 28  1  6  0  0  0
  8  9  1  0  0  0  0
  8 16  1  0  0  0  0
  8 29  1  1  0  0  0
  9 12  1  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  0  0  0  0
 10 20  1  0  0  0  0
 11 12  1  0  0  0  0
 13 15  1  0  0  0  0
 14 19  1  0  0  0  0
 14 21  1  1  0  0  0
 14 22  1  0  0  0  0
 16 17  1  0  0  0  0
 17 19  1  0  0  0  0
 17 23  1  6  0  0  0
 19 24  2  0  0  0  0
 20 26  1  0  0  0  0
 22 25  2  0  0  0  0
 24 27  1  0  0  0  0
 25 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014469

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H29FO4/c1-12-9-17-15-6-8-21(27,13(2)24)20(15,4)11-18(26)22(17,23)19(3)7-5-14(25)10-16(12)19/h5,7,10,12,15,17-18,26-27H,6,8-9,11H2,1-4H3/t12-,15-,17-,18-,19-,20-,21-,22-/m0/s1

> <INCHI_KEY>
FAOZLTXFLGPHNG-KNAQIMQKSA-N

> <FORMULA>
C22H29FO4

> <MOLECULAR_WEIGHT>
376.4617

> <EXACT_MASS>
376.204987621

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
40.05095368504851

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
2.4208639956666667

> <ALOGPS_LOGS>
-4.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.6935060053532

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.648286467835149

> <JCHEM_PKA_STRONGEST_BASIC>
-3.393381973387413

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
100.86769999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fluorometholone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014469
     RDKit          3D
Fluorometholone
 56 59  0  0  0  0  0  0  0  0999 V2000
    5.4232   -0.4594   -1.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2225    0.2935   -0.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0794    1.4186   -1.0677 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2376   -0.2894    0.3375 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5965   -1.5445    0.7610 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1627    0.7341    1.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8765    1.5135    1.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0343    0.3811    0.7382 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2791    0.6457    0.0755 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0883    1.7013    0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3867    1.8246   -0.0689 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2464    2.9502    0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0578    0.4961    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1429    0.4716    0.8629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8030   -0.8123    1.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8582   -0.8685    1.7765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1586   -1.9809    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0537   -1.9418   -0.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3636   -0.6638   -0.4670 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3108   -0.3955   -1.9669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9788   -0.6927    0.1519 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2212   -0.8845    1.5262 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1590   -1.8442   -0.3218 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6448   -2.2000   -1.5972 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2980   -1.7221   -0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8669   -0.3382   -0.2932 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8651    0.2885   -1.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2892   -0.3039   -0.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1110   -1.5149   -1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7121   -0.1134   -2.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5520   -1.7012    0.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9397    0.1741    2.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0331    1.3814    1.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1062    2.2514    0.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5573    2.0512    2.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9183   -0.3063    1.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1674    0.9315   -0.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5636    2.6688    0.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3512    1.3422    1.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0900    1.9627   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3638    3.0387    1.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2258    2.8528   -0.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7971    3.8954   -0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5645    1.4028    1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6151   -2.9753    0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6618   -2.8964   -0.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5805   -1.3050   -2.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3433    0.0023   -2.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0854    0.3552   -2.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4085   -2.7412    0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4326   -3.1484   -1.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062   -2.1658   -1.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8056   -2.3256    0.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8286    1.3726   -1.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166   -0.1760   -2.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7649   -0.0912   -2.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  6
 26  4  1  0
 26  8  1  0
 21  9  1  0
 19 13  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  1
  9 37  1  6
 10 38  1  0
 10 39  1  0
 11 40  1  6
 12 41  1  0
 12 42  1  0
 12 43  1  0
 14 44  1  0
 17 45  1  0
 18 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 23 50  1  1
 24 51  1  0
 25 52  1  0
 25 53  1  0
 27 54  1  0
 27 55  1  0
 27 56  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 324                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       7.728   1.321   0.000  0.00  0.00           F+0
HETATM    2  O   UNK     0      12.369   3.616   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.384   2.451   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      13.932   4.585   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.080  -3.019   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      11.385   1.681   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.385   0.141   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.052  -0.629   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.718   0.141   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.842   2.151   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.052   2.451   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.718   1.681   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.842  -0.328   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.317  -0.639   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.741   0.911   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.076  -2.233   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.693  -3.045   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.385   3.221   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.304  -2.243   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.090   3.053   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.801   0.812   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.889   0.229   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.699  -4.585   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.864  -3.090   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.429  -0.584   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.496   2.425   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.417  -2.255   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0      11.516  -1.084   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      11.123  -1.236   0.000  0.00  0.00           H+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   12                                                            
CONECT    4   20                                                            
CONECT    5   27                                                            
CONECT    6    7   10   11   18                                             
CONECT    7    6    8   13   28                                             
CONECT    8    7    9   16   29                                             
CONECT    9    1    8   12   14                                             
CONECT   10    2    6   15   20                                             
CONECT   11    6   12                                                       
CONECT   12    3    9   11                                                  
CONECT   13    7   15                                                       
CONECT   14    9   19   21   22                                             
CONECT   15   10   13                                                       
CONECT   16    8   17                                                       
CONECT   17   16   19   23                                                  
CONECT   18    6                                                            
CONECT   19   14   17   24                                                  
CONECT   20    4   10   26                                                  
CONECT   21   14                                                            
CONECT   22   14   25                                                       
CONECT   23   17                                                            
CONECT   24   19   27                                                       
CONECT   25   22   27                                                       
CONECT   26   20                                                            
CONECT   27    5   24   25                                                  
CONECT   28    7                                                            
CONECT   29    8                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

COMPND    HMDB0014469
HETATM    1  C1  UNL     1       5.423  -0.459  -1.085  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.222   0.293  -0.622  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.079   1.419  -1.068  1.00  0.00           O  
HETATM    4  C3  UNL     1       3.238  -0.289   0.338  1.00  0.00           C  
HETATM    5  O2  UNL     1       3.596  -1.544   0.761  1.00  0.00           O  
HETATM    6  C4  UNL     1       3.163   0.734   1.476  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.876   1.514   1.131  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.034   0.381   0.738  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.279   0.646   0.076  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.088   1.701   0.742  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.387   1.825  -0.069  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.246   2.950   0.367  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.058   0.496   0.164  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.143   0.472   0.863  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.803  -0.812   1.103  1.00  0.00           C  
HETATM   16  O3  UNL     1      -5.858  -0.868   1.777  1.00  0.00           O  
HETATM   17  C14 UNL     1      -4.159  -1.981   0.517  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.054  -1.942  -0.195  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.364  -0.664  -0.467  1.00  0.00           C  
HETATM   20  C17 UNL     1      -2.311  -0.396  -1.967  1.00  0.00           C  
HETATM   21  C18 UNL     1      -0.979  -0.693   0.152  1.00  0.00           C  
HETATM   22  F1  UNL     1      -1.221  -0.885   1.526  1.00  0.00           F  
HETATM   23  C19 UNL     1      -0.159  -1.844  -0.322  1.00  0.00           C  
HETATM   24  O4  UNL     1      -0.645  -2.200  -1.597  1.00  0.00           O  
HETATM   25  C20 UNL     1       1.298  -1.722  -0.398  1.00  0.00           C  
HETATM   26  C21 UNL     1       1.867  -0.338  -0.293  1.00  0.00           C  
HETATM   27  C22 UNL     1       1.865   0.288  -1.649  1.00  0.00           C  
HETATM   28  H1  UNL     1       6.289  -0.304  -0.443  1.00  0.00           H  
HETATM   29  H2  UNL     1       5.111  -1.515  -1.199  1.00  0.00           H  
HETATM   30  H3  UNL     1       5.712  -0.113  -2.109  1.00  0.00           H  
HETATM   31  H4  UNL     1       4.552  -1.701   0.845  1.00  0.00           H  
HETATM   32  H5  UNL     1       2.940   0.174   2.396  1.00  0.00           H  
HETATM   33  H6  UNL     1       4.033   1.381   1.518  1.00  0.00           H  
HETATM   34  H7  UNL     1       2.106   2.251   0.368  1.00  0.00           H  
HETATM   35  H8  UNL     1       1.557   2.051   2.046  1.00  0.00           H  
HETATM   36  H9  UNL     1       0.918  -0.306   1.598  1.00  0.00           H  
HETATM   37  H10 UNL     1      -0.167   0.932  -0.980  1.00  0.00           H  
HETATM   38  H11 UNL     1      -0.564   2.669   0.745  1.00  0.00           H  
HETATM   39  H12 UNL     1      -1.351   1.342   1.767  1.00  0.00           H  
HETATM   40  H13 UNL     1      -2.090   1.963  -1.119  1.00  0.00           H  
HETATM   41  H14 UNL     1      -3.364   3.039   1.465  1.00  0.00           H  
HETATM   42  H15 UNL     1      -4.226   2.853  -0.118  1.00  0.00           H  
HETATM   43  H16 UNL     1      -2.797   3.895  -0.058  1.00  0.00           H  
HETATM   44  H17 UNL     1      -4.564   1.403   1.272  1.00  0.00           H  
HETATM   45  H18 UNL     1      -4.615  -2.975   0.672  1.00  0.00           H  
HETATM   46  H19 UNL     1      -2.662  -2.896  -0.582  1.00  0.00           H  
HETATM   47  H20 UNL     1      -2.581  -1.305  -2.545  1.00  0.00           H  
HETATM   48  H21 UNL     1      -1.343   0.002  -2.307  1.00  0.00           H  
HETATM   49  H22 UNL     1      -3.085   0.355  -2.220  1.00  0.00           H  
HETATM   50  H23 UNL     1      -0.408  -2.741   0.321  1.00  0.00           H  
HETATM   51  H24 UNL     1      -0.433  -3.148  -1.791  1.00  0.00           H  
HETATM   52  H25 UNL     1       1.706  -2.166  -1.346  1.00  0.00           H  
HETATM   53  H26 UNL     1       1.806  -2.326   0.414  1.00  0.00           H  
HETATM   54  H27 UNL     1       1.829   1.373  -1.679  1.00  0.00           H  
HETATM   55  H28 UNL     1       1.017  -0.176  -2.234  1.00  0.00           H  
HETATM   56  H29 UNL     1       2.765  -0.091  -2.219  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3    3    4
CONECT    4    5    6   26
CONECT    5   31
CONECT    6    7   32   33
CONECT    7    8   34   35
CONECT    8    9   26   36
CONECT    9   10   21   37
CONECT   10   11   38   39
CONECT   11   12   13   40
CONECT   12   41   42   43
CONECT   13   14   14   19
CONECT   14   15   44
CONECT   15   16   16   17
CONECT   17   18   18   45
CONECT   18   19   46
CONECT   19   20   21
CONECT   20   47   48   49
CONECT   21   22   23
CONECT   23   24   25   50
CONECT   24   51
CONECT   25   26   52   53
CONECT   26   27
CONECT   27   54   55   56
END

HMDB0014469
     RDKit          3D
Fluorometholone
 56 59  0  0  0  0  0  0  0  0999 V2000
    5.4232   -0.4594   -1.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2225    0.2935   -0.6224 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0794    1.4186   -1.0677 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2376   -0.2894    0.3375 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5965   -1.5445    0.7610 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1627    0.7341    1.4757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8765    1.5135    1.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0343    0.3811    0.7382 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2791    0.6457    0.0755 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0883    1.7013    0.7425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3867    1.8246   -0.0689 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2464    2.9502    0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0578    0.4961    0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1429    0.4716    0.8629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8030   -0.8123    1.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8582   -0.8685    1.7765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1586   -1.9809    0.5172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0537   -1.9418   -0.1954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3636   -0.6638   -0.4670 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3108   -0.3955   -1.9669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9788   -0.6927    0.1519 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2212   -0.8845    1.5262 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1590   -1.8442   -0.3218 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6448   -2.2000   -1.5972 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2980   -1.7221   -0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8669   -0.3382   -0.2932 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8651    0.2885   -1.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2892   -0.3039   -0.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1110   -1.5149   -1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7121   -0.1134   -2.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5520   -1.7012    0.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9397    0.1741    2.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0331    1.3814    1.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1062    2.2514    0.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5573    2.0512    2.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9183   -0.3063    1.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1674    0.9315   -0.9800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5636    2.6688    0.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3512    1.3422    1.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0900    1.9627   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3638    3.0387    1.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2258    2.8528   -0.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7971    3.8954   -0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5645    1.4028    1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6151   -2.9753    0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6618   -2.8964   -0.5823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5805   -1.3050   -2.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3433    0.0023   -2.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0854    0.3552   -2.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4085   -2.7412    0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4326   -3.1484   -1.7906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062   -2.1658   -1.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8056   -2.3256    0.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8286    1.3726   -1.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166   -0.1760   -2.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7649   -0.0912   -2.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  6
 26  4  1  0
 26  8  1  0
 21  9  1  0
 19 13  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  1
  9 37  1  6
 10 38  1  0
 10 39  1  0
 11 40  1  6
 12 41  1  0
 12 42  1  0
 12 43  1  0
 14 44  1  0
 17 45  1  0
 18 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 23 50  1  1
 24 51  1  0
 25 52  1  0
 25 53  1  0
 27 54  1  0
 27 55  1  0
 27 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9-Fluoro-11beta,17-dihydroxy-6alpha-methylpregna-1,4-diene-3,20-dione	ChEBI
Fluor-OP	ChEBI
Fluorometholon	ChEBI
Fluorometholonum	ChEBI
Fluorometolona	ChEBI
NSC 33001	ChEBI
Oxylone	ChEBI
Fml	Kegg
9-Fluoro-11b,17-dihydroxy-6a-methylpregna-1,4-diene-3,20-dione	Generator
9-Fluoro-11β,17-dihydroxy-6α-methylpregna-1,4-diene-3,20-dione	Generator
Fluormetholon	HMDB
Fluormetholone	HMDB
Fluoromethalone	HMDB
Fluor OP	HMDB
Fluoro ophtal	HMDB
Pharm-allergan brand OF fluorometholone	HMDB
Pharmascience brand OF fluorometholone	HMDB
Ursapharm brand OF fluorometholone	HMDB
Cortisdin	HMDB
Efflumidex	HMDB
FML Forte	HMDB
Fluoro-ophtal	HMDB
Isopto flucon	HMDB
PMS Fluorometholone	HMDB
PMS-Fluorometholone	HMDB
Pharm allergan brand OF fluorometholone	HMDB
Allergan brand 1 OF fluorometholone	HMDB
Allergan brand 2 OF fluorometholone	HMDB
FML Liquifilm	HMDB
Flucon, isopto	HMDB
Fluoropos	HMDB
Winzer brand OF fluorometholone	HMDB
Alcon brand OF fluorometholone	HMDB
Allergan brand 3 OF fluorometholone	HMDB
Flucon	HMDB
Isdin brand OF fluorometholone	HMDB
Novartis brand OF fluorometholone	HMDB

Chemical Formula

C₂₂H₂₉FO₄

Average Molecular Weight

376.4617

Monoisotopic Molecular Weight

376.204987621

IUPAC Name

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

Traditional Name

fluorometholone

CAS Registry Number

426-13-1

SMILES

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

InChI Identifier

InChI=1S/C22H29FO4/c1-12-9-17-15-6-8-21(27,13(2)24)20(15,4)11-18(26)22(17,23)19(3)7-5-14(25)10-16(12)19/h5,7,10,12,15,17-18,26-27H,6,8-9,11H2,1-4H3/t12-,15-,17-,18-,19-,20-,21-,22-/m0/s1

InChI Key

FAOZLTXFLGPHNG-KNAQIMQKSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

11beta-hydroxy steroid (CHEBI:31625 )
17alpha-hydroxy steroid (CHEBI:31625 )
glucocorticoid (CHEBI:31625 )
20-oxo steroid (CHEBI:31625 )
fluorinated steroid (CHEBI:31625 )
3-oxo-Delta(1),Delta(4)-steroid (CHEBI:31625 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	297 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.017 g/L	Not Available
LogP	2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.017 g/L	ALOGPS
logP	2.34	ALOGPS
logP	2.42	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	12.65	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	1	ChemAxon
Refractivity	100.87 m³·mol⁻¹	ChemAxon
Polarizability	40.05 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]-	223.497	30932474
DeepCCS	[M+Na]+	197.581	30932474
AllCCS	[M+H]+	190.0	32859911
AllCCS	[M+H-H2O]+	187.4	32859911
AllCCS	[M+NH4]+	192.4	32859911
AllCCS	[M+Na]+	193.1	32859911
AllCCS	[M-H]-	195.6	32859911
AllCCS	[M+Na-2H]-	196.1	32859911
AllCCS	[M+HCOO]-	196.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Fluorometholone	[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](C)C2=CC(=O)C=C[C@]12C	4017.4	Standard polar	33892256
Fluorometholone	[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](C)C2=CC(=O)C=C[C@]12C	2730.6	Standard non polar	33892256
Fluorometholone	[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](C)C2=CC(=O)C=C[C@]12C	2929.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Fluorometholone,1TMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C	3116.8	Semi standard non polar	33892256
Fluorometholone,1TMS,isomer #2	CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C	3048.0	Semi standard non polar	33892256
Fluorometholone,1TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C	3026.0	Semi standard non polar	33892256
Fluorometholone,2TMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C	3034.4	Semi standard non polar	33892256
Fluorometholone,2TMS,isomer #2	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C	3017.0	Semi standard non polar	33892256
Fluorometholone,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C	2931.5	Semi standard non polar	33892256
Fluorometholone,3TMS,isomer #1	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C	2964.4	Semi standard non polar	33892256
Fluorometholone,3TMS,isomer #1	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C	3055.7	Standard non polar	33892256
Fluorometholone,3TMS,isomer #1	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@@]21C	3254.3	Standard polar	33892256
Fluorometholone,1TBDMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C	3347.6	Semi standard non polar	33892256
Fluorometholone,1TBDMS,isomer #2	CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3288.8	Semi standard non polar	33892256
Fluorometholone,1TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C	3259.0	Semi standard non polar	33892256
Fluorometholone,2TBDMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3495.7	Semi standard non polar	33892256
Fluorometholone,2TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C	3476.3	Semi standard non polar	33892256
Fluorometholone,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3397.0	Semi standard non polar	33892256
Fluorometholone,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3634.4	Semi standard non polar	33892256
Fluorometholone,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3703.8	Standard non polar	33892256
Fluorometholone,3TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3C[C@H](C)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3482.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Fluorometholone GC-MS (Non-derivatized) - 70eV, Positive	splash10-01qd-2923000000-d51e17b0fa8439e2bc18	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fluorometholone GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-4646090000-fd4d299c79b87e200eea	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Fluorometholone 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 - Fluorometholone LC-ESI-qTof , Positive-QTOF	splash10-0079-2960000000-57c1831d283834b32701	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluorometholone , positive-QTOF	splash10-0079-2960000000-57c1831d283834b32701	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluorometholone 60V, Positive-QTOF	splash10-059i-2930000000-4f8bf4616616ac38dbe2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluorometholone 50V, Positive-QTOF	splash10-0079-0950000000-553575697067e4b2ea74	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluorometholone 30V, Positive-QTOF	splash10-002r-0691000000-e9d333f14892b5c60042	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluorometholone 20V, Positive-QTOF	splash10-004r-0394000000-2093403203c2b0fc9c10	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluorometholone 75V, Positive-QTOF	splash10-0avu-2920000000-7eaf4c211285e06ae8cc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluorometholone 60V, Positive-QTOF	splash10-059i-2930000000-c99fa5c5e166ee859f74	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluorometholone 90V, Positive-QTOF	splash10-00kf-3910000000-b4846c764fd5be25b954	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluorometholone 40V, Positive-QTOF	splash10-01p9-0980000000-b0a88a5603fd3efe6849	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluorometholone 30V, Positive-QTOF	splash10-002r-0791000000-77abf92c461f1ad29d3b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluorometholone 45V, Positive-QTOF	splash10-000i-1960000000-4594ec630c6854d76672	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluorometholone 15V, Positive-QTOF	splash10-009i-0389000000-cf127fcfcee4a744f76a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluorometholone 50V, Positive-QTOF	splash10-0079-0950000000-362de078c079eaec2b48	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluorometholone 10V, Positive-QTOF	splash10-004i-0019000000-186c4dfe4b7e61670d08	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluorometholone 20V, Positive-QTOF	splash10-004r-0394000000-07ae4bf52b68e15af517	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluorometholone 40V, Positive-QTOF	splash10-01p9-0980000000-c3c01780614bd50c5d7c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Fluorometholone 30V, Positive-QTOF	splash10-002r-0691000000-55e76cdcb25ab8d35c0c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluorometholone 10V, Positive-QTOF	splash10-056r-0009000000-531774f624efd22f7096	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluorometholone 20V, Positive-QTOF	splash10-0a6u-0129000000-87f7ef0f82ebc7d60851	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluorometholone 40V, Positive-QTOF	splash10-008i-0392000000-d6c8be250e0763166290	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluorometholone 10V, Negative-QTOF	splash10-004i-0009000000-e9871ab3d4408fc89668	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluorometholone 20V, Negative-QTOF	splash10-05rr-0009000000-edd2f8db34c792d235cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluorometholone 40V, Negative-QTOF	splash10-0ldr-0129000000-09e9dc7990d339033e84	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Fluorometholone 10V, Positive-QTOF	splash10-056r-0009000000-44db180c7fb54e31ed64	2021-09-23	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 DB00324	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00324	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00324

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9494

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fluorometholone

METLIN ID

Not Available

PubChem Compound

9878

PDB ID

Not Available

ChEBI ID

31625

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)

Download (PDF)

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 3A4

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

References

El-Sankary W, Bombail V, Gibson GG, Plant N: Glucocorticoid-mediated induction of CYP3A4 is decreased by disruption of a protein: DNA interaction distinct from the pregnane X receptor response element. Drug Metab Dispos. 2002 Sep;30(9):1029-34. [PubMed:12167569 ]

Showing metabocard for Fluorometholone (HMDB0014469)

MOL for HMDB0014469 (Fluorometholone)

3D MOL for HMDB0014469 (Fluorometholone)

3D SDF for HMDB0014469 (Fluorometholone)

3D-SDF for HMDB0014469 (Fluorometholone)

PDB for HMDB0014469 (Fluorometholone)

3D PDB for HMDB0014469 (Fluorometholone)

SMILES for HMDB0014469 (Fluorometholone)

INCHI for HMDB0014469 (Fluorometholone)

Structure for HMDB0014469 (Fluorometholone)

3D Structure for HMDB0014469 (Fluorometholone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References