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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 02:51:49 UTC

HMDB ID

HMDB0014984

Secondary Accession Numbers

HMDB14984

Metabolite Identification

Common Name

Flurandrenolide

Description

Flurandrenolide is only found in individuals that have used or taken this drug. It is a corticosteroid used topically in the treatment of various skin disorders. It is usually employed as a cream or an ointment, and is also used as a polyethylene tape with an adhesive. (From Martindale, The Extra Pharmacopoeia, 30th ed, p733)Flurandrenolide is a topical corticosteroid. It is normally applied to a plastic tape called Cordran. Cordran is primarily effective because of its anti-inflammatory, antipruritic, and vasoconstrictive actions. Flurandrenolide, which is slowly released from the Cordran tape, binds to 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. The anti-inflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. Specifically glucocorticoids induce lipocortin-1 (annexin-1) synthesis, which then binds to cell membranes preventing the phospholipase A2 from coming into contact with its substrate arachidonic acid. This leads to diminished eicosanoid production. Cyclooxygenase (both COX-1 and COX-2) expression is also suppressed, potentiating the effect. In another words, the two main products in inflammation Prostaglandins and Leukotrienes are inhibited by the action of Glucocorticoids. Glucocorticoids also stimulate the lipocortin-1 escaping to the extracellular space, where it binds to the leukocyte membrane receptors and inhibits various inflammatory events: epithelial adhesion, emigration, chemotaxis, phagocytosis, respiratory burst and the release of various inflammatory mediators (lysosomal enzymes, cytokines, tissue plasminogen activator, chemokines etc.) from neutrophils, macrophages and mastocytes. Additionally the immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding. Like other glucocorticoid agents Fluocinolone acetonide acts as a physiological antagonist to insulin by decreasing glycogenesis (formation of glycogen). It also promotes the breakdown of lipids (lipolysis), and proteins, leading to the mobilization of extrahepatic amino acids and ketone bodies. This leads to increased circulating glucose concentrations (in the blood). There is also decreased glycogen formation in the liver.

Structure

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

846
  Mrv0541 02231215032D          

 36 40  0  0  1  0            999 V2000
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 27 31  1  0  0  0  0
M  END

HMDB0014984
     RDKit          3D
Flurandrenolide
 64 68  0  0  0  0  0  0  0  0999 V2000
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M  END

846
  Mrv0541 02231215032D          

 36 40  0  0  1  0            999 V2000
    2.4287   -0.6672    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.4742   -0.8731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 15 16  1  0  0  0  0
 17 20  1  0  0  0  0
 17 24  1  0  0  0  0
 17 25  1  1  0  0  0
 18 21  1  0  0  0  0
 20 21  1  0  0  0  0
 20 27  2  0  0  0  0
 21 36  1  1  0  0  0
 22 28  1  0  0  0  0
 23 29  1  0  0  0  0
 23 30  1  0  0  0  0
 24 26  1  0  0  0  0
 26 31  1  0  0  0  0
 27 31  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014984

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12C[C@@]3([H])[C@]4([H])C[C@]([H])(F)C5=CC(=O)CC[C@]5(C)[C@@]4([H])[C@@H](O)C[C@]3(C)[C@@]1(OC(C)(C)O2)C(=O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C24H33FO6/c1-21(2)30-19-9-14-13-8-16(25)15-7-12(27)5-6-22(15,3)20(13)17(28)10-23(14,4)24(19,31-21)18(29)11-26/h7,13-14,16-17,19-20,26,28H,5-6,8-11H2,1-4H3/t13-,14-,16-,17-,19+,20+,22-,23-,24+/m0/s1

> <INCHI_KEY>
POPFMWWJOGLOIF-XWCQMRHXSA-N

> <FORMULA>
C24H33FO6

> <MOLECULAR_WEIGHT>
436.5136

> <EXACT_MASS>
436.226116993

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
45.73639418431752

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,4R,8S,9S,11S,12S,13R,19S)-19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-17-en-16-one

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
1.5629681503333333

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.813749502050037

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.734889711078953

> <JCHEM_PKA_STRONGEST_BASIC>
-2.847062564082255

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
110.7919

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
flurandrenolide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014984
     RDKit          3D
Flurandrenolide
 64 68  0  0  0  0  0  0  0  0999 V2000
   -4.4430    1.1193   -2.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0454    0.4976   -2.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6904   -0.0870   -3.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1508    1.4706   -1.6552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998    1.5975   -0.3194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2830    1.9705    0.5567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4405    0.8334    0.2143 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8542    0.5752    0.8397 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6926    1.7898    1.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    1.2460    1.9784 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5811    2.2087    2.5611 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6159    0.3802    1.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9195    0.5580    1.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8005   -0.2153    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0078   -0.3952    0.3798 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1806   -0.7908   -1.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7164   -0.5820   -1.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9941   -0.6255    0.1781 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3300   -2.0141    0.7376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5572   -0.4207   -0.0976 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7155   -1.6564   -0.2125 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9259   -2.5819    0.8177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7442   -1.4553   -0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3349   -0.3683    0.5288 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3643   -0.7560    1.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6543    0.1258    0.0721 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7968   -0.0677    0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6488   -0.9128    0.6173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0830    0.5964    2.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3108    0.1183    2.7694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9547   -0.5179   -1.1452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1059    0.4749   -2.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8499    1.2212   -1.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4077    2.1433   -2.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5411   -0.0022   -4.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4829   -1.1895   -3.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7810    0.3618   -3.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3637    2.2028   -0.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8658    2.9415    0.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6610    2.0375    1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3253    0.8270   -0.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179    0.0352    1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0902    2.2646    0.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1127    2.4555    1.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3815    0.5739    2.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3938    1.3221    1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6745   -0.3072   -1.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4686   -1.8622   -1.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4774    0.4152   -1.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2768   -1.3339   -1.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9742   -2.1445    1.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0785   -2.8232    0.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4537   -2.1139    0.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4189    0.0846   -1.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0366   -2.1298   -1.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5810   -3.4425    0.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2624   -2.4037   -0.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0564   -1.2884   -1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2992   -1.3241    2.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1525    0.0585    2.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5721   -1.5394    2.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3802    0.4952    3.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2592    1.6954    2.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0624    0.6540    2.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  1
 24 26  1  0
 26 27  1  1
 27 28  2  0
 27 29  1  0
 29 30  1  0
 26 31  1  0
 31  2  1  0
 26  5  1  0
 24  7  1  0
 20  8  1  0
 18 12  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  5 38  1  6
  6 39  1  0
  6 40  1  0
  7 41  1  6
  8 42  1  1
  9 43  1  0
  9 44  1  0
 10 45  1  1
 13 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 19 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  6
 21 55  1  6
 22 56  1  0
 23 57  1  0
 23 58  1  0
 25 59  1  0
 25 60  1  0
 25 61  1  0
 29 62  1  0
 29 63  1  0
 30 64  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 846                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       4.534  -1.245   0.000  0.00  0.00           F+0
HETATM    2  O   UNK     0      13.952  -1.630   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.948  -3.880   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.970   3.412   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      13.526   0.970   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      16.339  -0.285   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.080   4.404   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.304  -0.438   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.970  -1.208   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.636  -0.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.439  -1.466   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.636   1.102   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.292  -2.705   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.815  -2.863   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.304   1.102   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.970   1.872   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.259   1.925   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.259  -1.262   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.638   0.332   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.864   1.134   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.864  -0.470   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.685  -0.561   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.266  -3.119   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.298   3.596   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.599   2.685   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.864   4.453   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.411   1.958   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.092  -1.189   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.034  -4.453   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.772  -2.800   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.411   3.629   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0       8.974  -1.934   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       8.646  -1.670   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       9.703   0.486   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      11.315  -3.990   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.796   0.144   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2   11   23                                                       
CONECT    3   14   23                                                       
CONECT    4   16                                                            
CONECT    5   22                                                            
CONECT    6   28                                                            
CONECT    7   31                                                            
CONECT    8    9   11   15   19                                             
CONECT    9    8   10   13   32                                             
CONECT   10    9   12   18   33                                             
CONECT   11    2    8   14   22                                             
CONECT   12   10   16   17   34                                             
CONECT   13    9   14                                                       
CONECT   14    3   11   13   35                                             
CONECT   15    8   16                                                       
CONECT   16    4   12   15                                                  
CONECT   17   12   20   24   25                                             
CONECT   18   10   21                                                       
CONECT   19    8                                                            
CONECT   20   17   21   27                                                  
CONECT   21    1   18   20   36                                             
CONECT   22    5   11   28                                                  
CONECT   23    2    3   29   30                                             
CONECT   24   17   26                                                       
CONECT   25   17                                                            
CONECT   26   24   31                                                       
CONECT   27   20   31                                                       
CONECT   28    6   22                                                       
CONECT   29   23                                                            
CONECT   30   23                                                            
CONECT   31    7   26   27                                                  
CONECT   32    9                                                            
CONECT   33   10                                                            
CONECT   34   12                                                            
CONECT   35   14                                                            
CONECT   36   21                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

COMPND    HMDB0014984
HETATM    1  C1  UNL     1      -4.443   1.119  -2.119  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.045   0.498  -2.102  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.690  -0.087  -3.432  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.151   1.471  -1.655  1.00  0.00           O  
HETATM    5  C4  UNL     1      -2.500   1.597  -0.319  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.283   1.970   0.557  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.440   0.833   0.214  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.854   0.575   0.840  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.693   1.790   1.120  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.846   1.246   1.978  1.00  0.00           C  
HETATM   11  F1  UNL     1       3.581   2.209   2.561  1.00  0.00           F  
HETATM   12  C10 UNL     1       3.616   0.380   1.039  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.920   0.558   1.005  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.801  -0.215   0.135  1.00  0.00           C  
HETATM   15  O2  UNL     1       7.008  -0.395   0.380  1.00  0.00           O  
HETATM   16  C13 UNL     1       5.181  -0.791  -1.081  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.716  -0.582  -1.176  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.994  -0.625   0.178  1.00  0.00           C  
HETATM   19  C16 UNL     1       3.330  -2.014   0.738  1.00  0.00           C  
HETATM   20  C17 UNL     1       1.557  -0.421  -0.098  1.00  0.00           C  
HETATM   21  C18 UNL     1       0.715  -1.656  -0.212  1.00  0.00           C  
HETATM   22  O3  UNL     1       0.926  -2.582   0.818  1.00  0.00           O  
HETATM   23  C19 UNL     1      -0.744  -1.455  -0.334  1.00  0.00           C  
HETATM   24  C20 UNL     1      -1.335  -0.368   0.529  1.00  0.00           C  
HETATM   25  C21 UNL     1      -1.364  -0.756   1.958  1.00  0.00           C  
HETATM   26  C22 UNL     1      -2.654   0.126   0.072  1.00  0.00           C  
HETATM   27  C23 UNL     1      -3.797  -0.068   0.979  1.00  0.00           C  
HETATM   28  O4  UNL     1      -4.649  -0.913   0.617  1.00  0.00           O  
HETATM   29  C24 UNL     1      -4.083   0.596   2.244  1.00  0.00           C  
HETATM   30  O5  UNL     1      -5.311   0.118   2.769  1.00  0.00           O  
HETATM   31  O6  UNL     1      -2.955  -0.518  -1.145  1.00  0.00           O  
HETATM   32  H1  UNL     1      -5.106   0.475  -2.755  1.00  0.00           H  
HETATM   33  H2  UNL     1      -4.850   1.221  -1.094  1.00  0.00           H  
HETATM   34  H3  UNL     1      -4.408   2.143  -2.542  1.00  0.00           H  
HETATM   35  H4  UNL     1      -3.541  -0.002  -4.149  1.00  0.00           H  
HETATM   36  H5  UNL     1      -2.483  -1.189  -3.366  1.00  0.00           H  
HETATM   37  H6  UNL     1      -1.781   0.362  -3.879  1.00  0.00           H  
HETATM   38  H7  UNL     1      -3.364   2.203  -0.107  1.00  0.00           H  
HETATM   39  H8  UNL     1      -0.866   2.941   0.214  1.00  0.00           H  
HETATM   40  H9  UNL     1      -1.661   2.037   1.575  1.00  0.00           H  
HETATM   41  H10 UNL     1      -0.325   0.827  -0.911  1.00  0.00           H  
HETATM   42  H11 UNL     1       0.718   0.035   1.800  1.00  0.00           H  
HETATM   43  H12 UNL     1       2.090   2.265   0.202  1.00  0.00           H  
HETATM   44  H13 UNL     1       1.113   2.455   1.756  1.00  0.00           H  
HETATM   45  H14 UNL     1       2.382   0.574   2.727  1.00  0.00           H  
HETATM   46  H15 UNL     1       5.394   1.322   1.656  1.00  0.00           H  
HETATM   47  H16 UNL     1       5.675  -0.307  -1.951  1.00  0.00           H  
HETATM   48  H17 UNL     1       5.469  -1.862  -1.114  1.00  0.00           H  
HETATM   49  H18 UNL     1       3.477   0.415  -1.601  1.00  0.00           H  
HETATM   50  H19 UNL     1       3.277  -1.334  -1.863  1.00  0.00           H  
HETATM   51  H20 UNL     1       2.974  -2.144   1.775  1.00  0.00           H  
HETATM   52  H21 UNL     1       3.079  -2.823   0.041  1.00  0.00           H  
HETATM   53  H22 UNL     1       4.454  -2.114   0.831  1.00  0.00           H  
HETATM   54  H23 UNL     1       1.419   0.085  -1.110  1.00  0.00           H  
HETATM   55  H24 UNL     1       1.037  -2.130  -1.195  1.00  0.00           H  
HETATM   56  H25 UNL     1       0.581  -3.443   0.522  1.00  0.00           H  
HETATM   57  H26 UNL     1      -1.262  -2.404  -0.030  1.00  0.00           H  
HETATM   58  H27 UNL     1      -1.056  -1.288  -1.382  1.00  0.00           H  
HETATM   59  H28 UNL     1      -2.299  -1.324   2.136  1.00  0.00           H  
HETATM   60  H29 UNL     1      -1.152   0.059   2.660  1.00  0.00           H  
HETATM   61  H30 UNL     1      -0.572  -1.539   2.211  1.00  0.00           H  
HETATM   62  H31 UNL     1      -3.380   0.495   3.068  1.00  0.00           H  
HETATM   63  H32 UNL     1      -4.259   1.695   2.141  1.00  0.00           H  
HETATM   64  H33 UNL     1      -6.062   0.654   2.441  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    4   31
CONECT    3   35   36   37
CONECT    4    5
CONECT    5    6   26   38
CONECT    6    7   39   40
CONECT    7    8   24   41
CONECT    8    9   20   42
CONECT    9   10   43   44
CONECT   10   11   12   45
CONECT   12   13   13   18
CONECT   13   14   46
CONECT   14   15   15   16
CONECT   16   17   47   48
CONECT   17   18   49   50
CONECT   18   19   20
CONECT   19   51   52   53
CONECT   20   21   54
CONECT   21   22   23   55
CONECT   22   56
CONECT   23   24   57   58
CONECT   24   25   26
CONECT   25   59   60   61
CONECT   26   27   31
CONECT   27   28   28   29
CONECT   29   30   62   63
CONECT   30   64
END

HMDB0014984
     RDKit          3D
Flurandrenolide
 64 68  0  0  0  0  0  0  0  0999 V2000
   -4.4430    1.1193   -2.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0454    0.4976   -2.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6904   -0.0870   -3.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1508    1.4706   -1.6552 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4998    1.5975   -0.3194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2830    1.9705    0.5567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4405    0.8334    0.2143 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8542    0.5752    0.8397 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6926    1.7898    1.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    1.2460    1.9784 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5811    2.2087    2.5611 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6159    0.3802    1.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9195    0.5580    1.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8005   -0.2153    0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0078   -0.3952    0.3798 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1806   -0.7908   -1.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7164   -0.5820   -1.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9941   -0.6255    0.1781 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3300   -2.0141    0.7376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5572   -0.4207   -0.0976 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7155   -1.6564   -0.2125 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9259   -2.5819    0.8177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7442   -1.4553   -0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3349   -0.3683    0.5288 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3643   -0.7560    1.9577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6543    0.1258    0.0721 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7968   -0.0677    0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6488   -0.9128    0.6173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0830    0.5964    2.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3108    0.1183    2.7694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9547   -0.5179   -1.1452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1059    0.4749   -2.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8499    1.2212   -1.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4077    2.1433   -2.5417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5411   -0.0022   -4.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4829   -1.1895   -3.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7810    0.3618   -3.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3637    2.2028   -0.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8658    2.9415    0.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6610    2.0375    1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3253    0.8270   -0.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7179    0.0352    1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0902    2.2646    0.2023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1127    2.4555    1.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3815    0.5739    2.7269 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3938    1.3221    1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6745   -0.3072   -1.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4686   -1.8622   -1.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4774    0.4152   -1.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2768   -1.3339   -1.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9742   -2.1445    1.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0785   -2.8232    0.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4537   -2.1139    0.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4189    0.0846   -1.1103 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0366   -2.1298   -1.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5810   -3.4425    0.5221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2624   -2.4037   -0.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0564   -1.2884   -1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2992   -1.3241    2.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1525    0.0585    2.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5721   -1.5394    2.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3802    0.4952    3.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2592    1.6954    2.1405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0624    0.6540    2.4409 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  1
 24 26  1  0
 26 27  1  1
 27 28  2  0
 27 29  1  0
 29 30  1  0
 26 31  1  0
 31  2  1  0
 26  5  1  0
 24  7  1  0
 20  8  1  0
 18 12  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  5 38  1  6
  6 39  1  0
  6 40  1  0
  7 41  1  6
  8 42  1  1
  9 43  1  0
  9 44  1  0
 10 45  1  1
 13 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 19 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  6
 21 55  1  6
 22 56  1  0
 23 57  1  0
 23 58  1  0
 25 59  1  0
 25 60  1  0
 25 61  1  0
 29 62  1  0
 29 63  1  0
 30 64  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Fludroxycortide	Kegg
Cordran	Kegg
Floudroxycortide	HMDB
Fludrossicortide	HMDB
Fludroxicortidum	HMDB
Fluorandrenolone	HMDB
Fluorandrenolone acetonide	HMDB
Flurandrenolone	HMDB
Flurandrenolone acetonide	HMDB
Haelan	HMDB
Oclassen brand OF flurandrenolone	HMDB
Typharm brand OF flurandrenolone	HMDB

Chemical Formula

C₂₄H₃₃FO₆

Average Molecular Weight

436.5136

Monoisotopic Molecular Weight

436.226116993

IUPAC Name

(1S,2S,4R,8S,9S,11S,12S,13R,19S)-19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-17-en-16-one

Traditional Name

flurandrenolide

CAS Registry Number

1524-88-5

SMILES

[H][C@@]12C[C@@]3([H])[C@]4([H])C[C@]([H])(F)C5=CC(=O)CC[C@]5(C)[C@@]4([H])[C@@H](O)C[C@]3(C)[C@@]1(OC(C)(C)O2)C(=O)CO

InChI Identifier

InChI=1S/C24H33FO6/c1-21(2)30-19-9-14-13-8-16(25)15-7-12(27)5-6-22(15,3)20(13)17(28)10-23(14,4)24(19,31-21)18(29)11-26/h7,13-14,16-17,19-20,26,28H,5-6,8-11H2,1-4H3/t13-,14-,16-,17-,19+,20+,22-,23-,24+/m0/s1

InChI Key

POPFMWWJOGLOIF-XWCQMRHXSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

21-hydroxysteroids

Alternative Parents

Substituents

Progestogin-skeleton
21-hydroxysteroid
Pregnane-skeleton
20-oxosteroid
3-oxo-delta-4-steroid
3-oxosteroid
6-halo-steroid
Halo-steroid
11-hydroxysteroid
11-beta-hydroxysteroid
Oxosteroid
Delta-4-steroid
Ketal
Cyclohexenone
Meta-dioxolane
Alpha-hydroxy ketone
Cyclic alcohol
Ketone
Secondary alcohol
Cyclic ketone
Acetal
Organoheterocyclic compound
Oxacycle
Primary alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alkyl halide
Alkyl fluoride
Alcohol
Organohalogen compound
Organofluoride
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	251 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.058 g/L	Not Available
LogP	0.6	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	201.176	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001169

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.058 g/L	ALOGPS
logP	2.02	ALOGPS
logP	1.56	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.73	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	110.79 m³·mol⁻¹	ChemAxon
Polarizability	45.74 Å³	ChemAxon
Number of Rings	5	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]-	239.584	30932474
DeepCCS	[M+Na]+	213.951	30932474
AllCCS	[M+H]+	202.8	32859911
AllCCS	[M+H-H2O]+	200.8	32859911
AllCCS	[M+NH4]+	204.6	32859911
AllCCS	[M+Na]+	205.1	32859911
AllCCS	[M-H]-	205.3	32859911
AllCCS	[M+Na-2H]-	206.2	32859911
AllCCS	[M+HCOO]-	207.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Flurandrenolide	[H][C@@]12C[C@@]3([H])[C@]4([H])C[C@]([H])(F)C5=CC(=O)CC[C@]5(C)[C@@]4([H])[C@@H](O)C[C@]3(C)[C@@]1(OC(C)(C)O2)C(=O)CO	3182.3	Standard polar	33892256
Flurandrenolide	[H][C@@]12C[C@@]3([H])[C@]4([H])C[C@]([H])(F)C5=CC(=O)CC[C@]5(C)[C@@]4([H])[C@@H](O)C[C@]3(C)[C@@]1(OC(C)(C)O2)C(=O)CO	2996.9	Standard non polar	33892256
Flurandrenolide	[H][C@@]12C[C@@]3([H])[C@]4([H])C[C@]([H])(F)C5=CC(=O)CC[C@]5(C)[C@@]4([H])[C@@H](O)C[C@]3(C)[C@@]1(OC(C)(C)O2)C(=O)CO	3680.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Flurandrenolide,1TMS,isomer #1	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=O)CO)O1	3103.1	Semi standard non polar	33892256
Flurandrenolide,1TMS,isomer #2	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)CC[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C)O1	3183.7	Semi standard non polar	33892256
Flurandrenolide,1TMS,isomer #3	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO)O1	3154.5	Semi standard non polar	33892256
Flurandrenolide,1TMS,isomer #4	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)CC[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C)O1	3202.2	Semi standard non polar	33892256
Flurandrenolide,2TMS,isomer #1	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C)O1	3076.8	Semi standard non polar	33892256
Flurandrenolide,2TMS,isomer #2	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=O)CO)O1	3052.8	Semi standard non polar	33892256
Flurandrenolide,2TMS,isomer #3	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C)O1	3107.8	Semi standard non polar	33892256
Flurandrenolide,2TMS,isomer #4	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C)O1	3136.2	Semi standard non polar	33892256
Flurandrenolide,2TMS,isomer #5	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)CC[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C)O[Si](C)(C)C)O1	3183.6	Semi standard non polar	33892256
Flurandrenolide,2TMS,isomer #6	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C)O1	3137.9	Semi standard non polar	33892256
Flurandrenolide,3TMS,isomer #1	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C)O1	3050.3	Semi standard non polar	33892256
Flurandrenolide,3TMS,isomer #1	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C)O1	3232.2	Standard non polar	33892256
Flurandrenolide,3TMS,isomer #1	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C)O1	3435.7	Standard polar	33892256
Flurandrenolide,3TMS,isomer #2	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C)O[Si](C)(C)C)O1	3085.4	Semi standard non polar	33892256
Flurandrenolide,3TMS,isomer #2	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C)O[Si](C)(C)C)O1	3232.3	Standard non polar	33892256
Flurandrenolide,3TMS,isomer #2	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C)O[Si](C)(C)C)O1	3471.9	Standard polar	33892256
Flurandrenolide,3TMS,isomer #3	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C)O1	3066.0	Semi standard non polar	33892256
Flurandrenolide,3TMS,isomer #3	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C)O1	3183.3	Standard non polar	33892256
Flurandrenolide,3TMS,isomer #3	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C)O1	3530.7	Standard polar	33892256
Flurandrenolide,3TMS,isomer #4	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C)O[Si](C)(C)C)O1	3105.1	Semi standard non polar	33892256
Flurandrenolide,3TMS,isomer #4	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C)O[Si](C)(C)C)O1	3314.9	Standard non polar	33892256
Flurandrenolide,3TMS,isomer #4	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C)O[Si](C)(C)C)O1	3555.0	Standard polar	33892256
Flurandrenolide,4TMS,isomer #1	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C)O[Si](C)(C)C)O1	3055.7	Semi standard non polar	33892256
Flurandrenolide,4TMS,isomer #1	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C)O[Si](C)(C)C)O1	3233.4	Standard non polar	33892256
Flurandrenolide,4TMS,isomer #1	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C)O[Si](C)(C)C)O1	3434.1	Standard polar	33892256
Flurandrenolide,1TBDMS,isomer #1	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=O)CO)O1	3333.7	Semi standard non polar	33892256
Flurandrenolide,1TBDMS,isomer #2	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)CC[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C(C)(C)C)O1	3448.2	Semi standard non polar	33892256
Flurandrenolide,1TBDMS,isomer #3	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO)O1	3397.8	Semi standard non polar	33892256
Flurandrenolide,1TBDMS,isomer #4	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)CC[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C(C)(C)C)O1	3426.3	Semi standard non polar	33892256
Flurandrenolide,2TBDMS,isomer #1	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C(C)(C)C)O1	3555.5	Semi standard non polar	33892256
Flurandrenolide,2TBDMS,isomer #2	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=O)CO)O1	3493.6	Semi standard non polar	33892256
Flurandrenolide,2TBDMS,isomer #3	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C(C)(C)C)O1	3548.7	Semi standard non polar	33892256
Flurandrenolide,2TBDMS,isomer #4	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C(C)(C)C)O1	3605.2	Semi standard non polar	33892256
Flurandrenolide,2TBDMS,isomer #5	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)CC[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1	3637.1	Semi standard non polar	33892256
Flurandrenolide,2TBDMS,isomer #6	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C(C)(C)C)O1	3587.1	Semi standard non polar	33892256
Flurandrenolide,3TBDMS,isomer #1	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C(C)(C)C)O1	3689.3	Semi standard non polar	33892256
Flurandrenolide,3TBDMS,isomer #1	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C(C)(C)C)O1	3847.0	Standard non polar	33892256
Flurandrenolide,3TBDMS,isomer #1	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=O)CO[Si](C)(C)C(C)(C)C)O1	3640.6	Standard polar	33892256
Flurandrenolide,3TBDMS,isomer #2	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1	3732.2	Semi standard non polar	33892256
Flurandrenolide,3TBDMS,isomer #2	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1	3853.5	Standard non polar	33892256
Flurandrenolide,3TBDMS,isomer #2	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1	3663.3	Standard polar	33892256
Flurandrenolide,3TBDMS,isomer #3	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C(C)(C)C)O1	3694.1	Semi standard non polar	33892256
Flurandrenolide,3TBDMS,isomer #3	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C(C)(C)C)O1	3761.1	Standard non polar	33892256
Flurandrenolide,3TBDMS,isomer #3	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=CO)O[Si](C)(C)C(C)(C)C)O1	3704.4	Standard polar	33892256
Flurandrenolide,3TBDMS,isomer #4	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1	3765.1	Semi standard non polar	33892256
Flurandrenolide,3TBDMS,isomer #4	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1	3877.1	Standard non polar	33892256
Flurandrenolide,3TBDMS,isomer #4	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1	3737.4	Standard polar	33892256
Flurandrenolide,4TBDMS,isomer #1	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1	3852.2	Semi standard non polar	33892256
Flurandrenolide,4TBDMS,isomer #1	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1	3948.8	Standard non polar	33892256
Flurandrenolide,4TBDMS,isomer #1	CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]5(C)[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]3(C)[C@]2(C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O1	3674.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Flurandrenolide GC-MS (2 TMS) - 70eV, Positive	splash10-014i-0242190000-938550a71054495f50e4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flurandrenolide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flurandrenolide 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 - Flurandrenolide LC-ESI-qTof , Positive-QTOF	splash10-001s-3961000000-a326b0165af296ecf245	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flurandrenolide , positive-QTOF	splash10-001s-3961000000-a326b0165af296ecf245	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flurandrenolide 45V, Positive-QTOF	splash10-0ab9-2930000000-cd90ebd8b6bcbdff0113	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flurandrenolide 30V, Positive-QTOF	splash10-0101-1892000000-4a7a3215b7b92c4b5849	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flurandrenolide 30V, Positive-QTOF	splash10-0101-1892000000-5e67e16afeb176cac16f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flurandrenolide 45V, Positive-QTOF	splash10-0ab9-2930000000-135be0b7a10b1438ca01	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flurandrenolide 75V, Positive-QTOF	splash10-054o-4900000000-698c8e0c7a2c1b17adea	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flurandrenolide 75V, Positive-QTOF	splash10-054o-4900000000-a2803e4d1a9647bfb01c	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurandrenolide 10V, Positive-QTOF	splash10-014r-0001900000-8ab0b07154fa08fbd90e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurandrenolide 20V, Positive-QTOF	splash10-0aor-2065900000-9325b21e5bdc8417f5f1	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurandrenolide 40V, Positive-QTOF	splash10-0bta-1392000000-e312185a8364edd39345	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurandrenolide 10V, Negative-QTOF	splash10-052r-1006900000-7aad85976b8cbc3f2dd7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurandrenolide 20V, Negative-QTOF	splash10-0ar9-2006900000-d7efad75f8beac5b5b6a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurandrenolide 40V, Negative-QTOF	splash10-0a4i-7119000000-7a16a8ee051b25956988	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurandrenolide 10V, Positive-QTOF	splash10-000i-0002900000-a75f37566ef563be73f5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurandrenolide 20V, Positive-QTOF	splash10-0170-0247900000-bf85161108e4ee5e5772	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurandrenolide 40V, Positive-QTOF	splash10-0ar3-2490000000-e63b46eb297d675f2717	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurandrenolide 10V, Negative-QTOF	splash10-000i-0000900000-237c434d76e103d4dd61	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurandrenolide 20V, Negative-QTOF	splash10-004r-0009500000-7662c4c1dc487a05e57a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Flurandrenolide 40V, Negative-QTOF	splash10-0bt9-9060600000-a4f103f5a13a922b4349	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 DB00846	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00846	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00846

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

14475

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Fludroxycortide

METLIN ID

Not Available

PubChem Compound

15209

PDB ID

Not Available

ChEBI ID

774963

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 Flurandrenolide (HMDB0014984)

MOL for HMDB0014984 (Flurandrenolide)

3D MOL for HMDB0014984 (Flurandrenolide)

3D SDF for HMDB0014984 (Flurandrenolide)

3D-SDF for HMDB0014984 (Flurandrenolide)

PDB for HMDB0014984 (Flurandrenolide)

3D PDB for HMDB0014984 (Flurandrenolide)

SMILES for HMDB0014984 (Flurandrenolide)

INCHI for HMDB0014984 (Flurandrenolide)

Structure for HMDB0014984 (Flurandrenolide)

3D Structure for HMDB0014984 (Flurandrenolide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra