Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:00 UTC

HMDB ID

HMDB0015488

Secondary Accession Numbers

HMDB15488

Metabolite Identification

Common Name

Antrafenine

Description

Antrafenine is only found in individuals that have used or taken this drug. It is a piperazine derivative drug that acts as an analgesic and anti-inflammatory drug with similar efficacy to naproxen. It is not widely used as it has largely been replaced by newer drugs.Antrafenine is believed to be associated with the inhibition of cyclooxygenase activity. Two unique cyclooxygenases have been described in mammals. The constitutive cyclooxygenase, COX-1, synthesizes prostaglandins necessary for normal gastrointestinal and renal function. The inducible cyclooxygenase, COX-2, generates prostaglandins involved in inflammation. Inhibition of COX-1 is thought to be associated with gastrointestinal and renal toxicity while inhibition of COX-2 provides anti-inflammatory activity.

Structure

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

1419
  Mrv0541 02231215292D          

 42 46  0  0  0  0            999 V2000
    3.3000   -4.8937    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -4.8745    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.4655   -5.7090    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5636    4.2801    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.2615    5.4071    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.3886    5.7090    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.8188    0.0161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1187    1.2618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3709   -1.6173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9325   -2.4257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8475    2.4910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8570    5.0232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3614   -2.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6613   -1.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6421   -2.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9420   -1.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0901   -1.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2133   -2.8300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0997   -0.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2037   -3.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5036   -2.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4845   -4.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7844   -2.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7749   -3.6384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -4.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8284    0.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5476    1.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5571    2.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8570    3.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1195    3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2573    0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1195    4.5821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2763    2.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4050    3.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6045    3.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9765    1.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4050    4.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6905    4.5821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9860    2.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6905    3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6045    4.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9761    4.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 25  1  0  0  0  0
  2 25  1  0  0  0  0
  3 25  1  0  0  0  0
  4 42  1  0  0  0  0
  5 42  1  0  0  0  0
  6 42  1  0  0  0  0
  7 19  1  0  0  0  0
  7 26  1  0  0  0  0
  8 26  2  0  0  0  0
  9 13  1  0  0  0  0
  9 14  1  0  0  0  0
  9 17  1  0  0  0  0
 10 15  1  0  0  0  0
 10 16  1  0  0  0  0
 10 18  1  0  0  0  0
 11 28  1  0  0  0  0
 11 29  1  0  0  0  0
 12 32  2  0  0  0  0
 12 41  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 23 24  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 31  2  0  0  0  0
 28 33  2  0  0  0  0
 29 30  2  0  0  0  0
 29 35  1  0  0  0  0
 30 32  1  0  0  0  0
 30 34  1  0  0  0  0
 31 36  1  0  0  0  0
 32 37  1  0  0  0  0
 33 39  1  0  0  0  0
 34 40  2  0  0  0  0
 35 41  2  0  0  0  0
 36 39  2  0  0  0  0
 37 38  2  0  0  0  0
 38 40  1  0  0  0  0
 38 42  1  0  0  0  0
M  END

HMDB0015488
     RDKit          3D
Antrafenine
 68 72  0  0  0  0  0  0  0  0999 V2000
   -2.1274    0.5573    1.0309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3903   -0.0206    0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0008    0.0784    0.3728 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4625    0.6989    1.5474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6176    1.6330    1.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7990    1.1545    0.8998 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9407    1.9810    1.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0578    1.0808    1.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3673    0.1868    0.5223 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6234    0.1657   -0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7910    0.6624   -1.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0111    0.5876   -1.9839 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1019    0.0157   -1.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9449   -0.4870   -0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1393   -1.0929    0.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2905   -0.3664    0.3508 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.9583   -1.1129    1.9373 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.3455   -2.3729    0.1404 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.7427   -0.4049    0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2551   -0.6294    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9919   -0.2352    0.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9075   -0.7639   -0.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0715   -1.5661   -1.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5806   -2.4453   -2.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9583   -2.5399   -2.8567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7634   -1.7483   -2.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2827   -0.8650   -1.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1650    0.1225   -0.5735 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2870   -0.4480    0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9213   -1.4433    1.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9325   -1.9241    1.8546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1917   -1.3712    1.7274 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4898   -0.4221    0.8514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8000    0.0469    0.7282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1520    0.9982   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5607    1.3998   -0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3073    0.1950   -0.1570 F   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8628    2.2532    0.7341 F   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8770    1.9749   -1.5027 F   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1789    1.4875   -1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8806    1.0342   -0.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5415    0.0824   -0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679   -0.2359    2.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3813    1.0367    2.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792    2.5723    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8454    2.0106    2.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7573    2.7309    1.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3027    2.4968    0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9031    1.7462    1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6780    0.4388    2.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9758    1.1334   -1.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0946    0.9859   -3.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0513   -0.0501   -1.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6318   -0.7982    1.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4411   -1.7036    0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1040   -0.5487   -1.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1136   -0.7005    0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9989   -0.7349    1.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0174   -1.4632   -1.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105   -3.0370   -3.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3316   -3.2458   -3.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8718   -1.7676   -2.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9815    1.1220   -0.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9197   -1.8543    1.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7194   -2.6742    2.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5212   -0.3848    1.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5136    2.2083   -1.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1212    1.4050   -1.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 14 19  2  0
  9 20  1  0
 20 21  1  0
  2 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  1  0
 36 39  1  0
 35 40  2  0
 40 41  1  0
 41 42  2  0
 21  6  1  0
 27 22  1  0
 42 29  1  0
 19 10  1  0
 42 33  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  0
  5 46  1  0
  7 47  1  0
  7 48  1  0
  8 49  1  0
  8 50  1  0
 11 51  1  0
 12 52  1  0
 13 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 23 59  1  0
 24 60  1  0
 25 61  1  0
 26 62  1  0
 28 63  1  0
 30 64  1  0
 31 65  1  0
 34 66  1  0
 40 67  1  0
 41 68  1  0
M  END

1419
  Mrv0541 02231215292D          

 42 46  0  0  0  0            999 V2000
    3.3000   -4.8937    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -4.8745    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.4655   -5.7090    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.5636    4.2801    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.2615    5.4071    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.3886    5.7090    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.8188    0.0161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1187    1.2618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3709   -1.6173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9325   -2.4257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8475    2.4910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8570    5.0232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3614   -2.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6613   -1.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6421   -2.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9420   -1.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0901   -1.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2133   -2.8300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0997   -0.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2037   -3.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5036   -2.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4845   -4.0592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7844   -2.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7749   -3.6384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -4.8841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8284    0.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5476    1.2453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5571    2.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8570    3.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1195    3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2573    0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1195    4.5821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2763    2.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4050    3.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6045    3.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9765    1.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4050    4.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6905    4.5821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9860    2.0537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6905    3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6045    4.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9761    4.9946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 25  1  0  0  0  0
  2 25  1  0  0  0  0
  3 25  1  0  0  0  0
  4 42  1  0  0  0  0
  5 42  1  0  0  0  0
  6 42  1  0  0  0  0
  7 19  1  0  0  0  0
  7 26  1  0  0  0  0
  8 26  2  0  0  0  0
  9 13  1  0  0  0  0
  9 14  1  0  0  0  0
  9 17  1  0  0  0  0
 10 15  1  0  0  0  0
 10 16  1  0  0  0  0
 10 18  1  0  0  0  0
 11 28  1  0  0  0  0
 11 29  1  0  0  0  0
 12 32  2  0  0  0  0
 12 41  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 23 24  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 31  2  0  0  0  0
 28 33  2  0  0  0  0
 29 30  2  0  0  0  0
 29 35  1  0  0  0  0
 30 32  1  0  0  0  0
 30 34  1  0  0  0  0
 31 36  1  0  0  0  0
 32 37  1  0  0  0  0
 33 39  1  0  0  0  0
 34 40  2  0  0  0  0
 35 41  2  0  0  0  0
 36 39  2  0  0  0  0
 37 38  2  0  0  0  0
 38 40  1  0  0  0  0
 38 42  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015488

> <DATABASE_NAME>
hmdb

> <SMILES>
FC(F)(F)C1=CC(=CC=C1)N1CCN(CCOC(=O)C2=CC=CC=C2NC2=C3C=CC(=CC3=NC=C2)C(F)(F)F)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C30H26F6N4O2/c31-29(32,33)20-4-3-5-22(18-20)40-14-12-39(13-15-40)16-17-42-28(41)24-6-1-2-7-25(24)38-26-10-11-37-27-19-21(30(34,35)36)8-9-23(26)27/h1-11,18-19H,12-17H2,(H,37,38)

> <INCHI_KEY>
NWGGKKGAFZIVBJ-UHFFFAOYSA-N

> <FORMULA>
C30H26F6N4O2

> <MOLECULAR_WEIGHT>
588.5435

> <EXACT_MASS>
588.195995326

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
55.484876805557604

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}ethyl 2-{[7-(trifluoromethyl)quinolin-4-yl]amino}benzoate

> <ALOGPS_LOGP>
6.30

> <JCHEM_LOGP>
8.386884484333335

> <ALOGPS_LOGS>
-5.32

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.689033935415786

> <JCHEM_PKA_STRONGEST_BASIC>
7.040454055241334

> <JCHEM_POLAR_SURFACE_AREA>
57.7

> <JCHEM_REFRACTIVITY>
147.0059

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.84e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
antrafenine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015488
     RDKit          3D
Antrafenine
 68 72  0  0  0  0  0  0  0  0999 V2000
   -2.1274    0.5573    1.0309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3903   -0.0206    0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0008    0.0784    0.3728 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4625    0.6989    1.5474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6176    1.6330    1.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7990    1.1545    0.8998 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9407    1.9810    1.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0578    1.0808    1.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3673    0.1868    0.5223 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6234    0.1657   -0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7910    0.6624   -1.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0111    0.5876   -1.9839 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1019    0.0157   -1.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9449   -0.4870   -0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1393   -1.0929    0.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2905   -0.3664    0.3508 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.9583   -1.1129    1.9373 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.3455   -2.3729    0.1404 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.7427   -0.4049    0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2551   -0.6294    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9919   -0.2352    0.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9075   -0.7639   -0.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0715   -1.5661   -1.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5806   -2.4453   -2.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9583   -2.5399   -2.8567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7634   -1.7483   -2.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2827   -0.8650   -1.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1650    0.1225   -0.5735 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2870   -0.4480    0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9213   -1.4433    1.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9325   -1.9241    1.8546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1917   -1.3712    1.7274 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4898   -0.4221    0.8514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8000    0.0469    0.7282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1520    0.9982   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5607    1.3998   -0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3073    0.1950   -0.1570 F   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8628    2.2532    0.7341 F   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8770    1.9749   -1.5027 F   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1789    1.4875   -1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8806    1.0342   -0.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5415    0.0824   -0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679   -0.2359    2.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3813    1.0367    2.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792    2.5723    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8454    2.0106    2.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7573    2.7309    1.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3027    2.4968    0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9031    1.7462    1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6780    0.4388    2.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9758    1.1334   -1.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0946    0.9859   -3.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0513   -0.0501   -1.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6318   -0.7982    1.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4411   -1.7036    0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1040   -0.5487   -1.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1136   -0.7005    0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9989   -0.7349    1.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0174   -1.4632   -1.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105   -3.0370   -3.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3316   -3.2458   -3.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8718   -1.7676   -2.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9815    1.1220   -0.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9197   -1.8543    1.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7194   -2.6742    2.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5212   -0.3848    1.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5136    2.2083   -1.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1212    1.4050   -1.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 14 19  2  0
  9 20  1  0
 20 21  1  0
  2 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  1  0
 36 39  1  0
 35 40  2  0
 40 41  1  0
 41 42  2  0
 21  6  1  0
 27 22  1  0
 42 29  1  0
 19 10  1  0
 42 33  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  0
  5 46  1  0
  7 47  1  0
  7 48  1  0
  8 49  1  0
  8 50  1  0
 11 51  1  0
 12 52  1  0
 13 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 23 59  1  0
 24 60  1  0
 25 61  1  0
 26 62  1  0
 28 63  1  0
 30 64  1  0
 31 65  1  0
 34 66  1  0
 40 67  1  0
 41 68  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1419                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       6.160  -9.135   0.000  0.00  0.00           F+0
HETATM    2  F   UNK     0       3.080  -9.099   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0       4.602 -10.657   0.000  0.00  0.00           F+0
HETATM    4  F   UNK     0       6.652   7.990   0.000  0.00  0.00           F+0
HETATM    5  F   UNK     0       6.088  10.093   0.000  0.00  0.00           F+0
HETATM    6  F   UNK     0       8.192  10.657   0.000  0.00  0.00           F+0
HETATM    7  O   UNK     0      12.728   0.030   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      11.422   2.355   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      10.026  -3.019   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       7.341  -4.528   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      12.782   4.650   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      12.800   9.377   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      10.008  -4.559   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.701  -2.233   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.665  -5.313   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.358  -2.988   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.368  -2.264   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.998  -5.283   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.386  -0.724   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.980  -6.822   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.673  -4.497   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.638  -7.577   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.331  -5.252   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.313  -6.792   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.620  -9.117   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.746   1.570   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.089   2.325   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.107   3.864   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.800   6.190   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.423   7.013   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.414   1.539   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.423   8.553   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.449   4.619   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.089   6.243   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.195   6.981   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      16.756   2.294   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.089   9.323   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.756   8.553   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      16.774   3.834   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.756   7.013   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      14.195   8.585   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       7.422   9.323   0.000  0.00  0.00           C+0
CONECT    1   25                                                            
CONECT    2   25                                                            
CONECT    3   25                                                            
CONECT    4   42                                                            
CONECT    5   42                                                            
CONECT    6   42                                                            
CONECT    7   19   26                                                       
CONECT    8   26                                                            
CONECT    9   13   14   17                                                  
CONECT   10   15   16   18                                                  
CONECT   11   28   29                                                       
CONECT   12   32   41                                                       
CONECT   13    9   15                                                       
CONECT   14    9   16                                                       
CONECT   15   10   13                                                       
CONECT   16   10   14                                                       
CONECT   17    9   19                                                       
CONECT   18   10   20   21                                                  
CONECT   19    7   17                                                       
CONECT   20   18   22                                                       
CONECT   21   18   23                                                       
CONECT   22   20   24   25                                                  
CONECT   23   21   24                                                       
CONECT   24   22   23                                                       
CONECT   25    1    2    3   22                                             
CONECT   26    7    8   27                                                  
CONECT   27   26   28   31                                                  
CONECT   28   11   27   33                                                  
CONECT   29   11   30   35                                                  
CONECT   30   29   32   34                                                  
CONECT   31   27   36                                                       
CONECT   32   12   30   37                                                  
CONECT   33   28   39                                                       
CONECT   34   30   40                                                       
CONECT   35   29   41                                                       
CONECT   36   31   39                                                       
CONECT   37   32   38                                                       
CONECT   38   37   40   42                                                  
CONECT   39   33   36                                                       
CONECT   40   34   38                                                       
CONECT   41   12   35                                                       
CONECT   42    4    5    6   38                                             
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

COMPND    HMDB0015488
HETATM    1  O1  UNL     1      -2.127   0.557   1.031  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.390  -0.021   0.172  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.001   0.078   0.373  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.462   0.699   1.547  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.618   1.633   1.475  1.00  0.00           C  
HETATM    6  N1  UNL     1       2.799   1.154   0.900  1.00  0.00           N  
HETATM    7  C4  UNL     1       3.941   1.981   1.104  1.00  0.00           C  
HETATM    8  C5  UNL     1       5.058   1.081   1.649  1.00  0.00           C  
HETATM    9  N2  UNL     1       5.367   0.187   0.522  1.00  0.00           N  
HETATM   10  C6  UNL     1       6.623   0.166  -0.061  1.00  0.00           C  
HETATM   11  C7  UNL     1       6.791   0.662  -1.336  1.00  0.00           C  
HETATM   12  C8  UNL     1       8.011   0.588  -1.984  1.00  0.00           C  
HETATM   13  C9  UNL     1       9.102   0.016  -1.372  1.00  0.00           C  
HETATM   14  C10 UNL     1       8.945  -0.487  -0.079  1.00  0.00           C  
HETATM   15  C11 UNL     1      10.139  -1.093   0.580  1.00  0.00           C  
HETATM   16  F1  UNL     1      11.291  -0.366   0.351  1.00  0.00           F  
HETATM   17  F2  UNL     1       9.958  -1.113   1.937  1.00  0.00           F  
HETATM   18  F3  UNL     1      10.345  -2.373   0.140  1.00  0.00           F  
HETATM   19  C12 UNL     1       7.743  -0.405   0.539  1.00  0.00           C  
HETATM   20  C13 UNL     1       4.255  -0.629   0.091  1.00  0.00           C  
HETATM   21  C14 UNL     1       2.992  -0.235   0.838  1.00  0.00           C  
HETATM   22  C15 UNL     1      -1.907  -0.764  -0.957  1.00  0.00           C  
HETATM   23  C16 UNL     1      -1.071  -1.566  -1.729  1.00  0.00           C  
HETATM   24  C17 UNL     1      -1.581  -2.445  -2.673  1.00  0.00           C  
HETATM   25  C18 UNL     1      -2.958  -2.540  -2.857  1.00  0.00           C  
HETATM   26  C19 UNL     1      -3.763  -1.748  -2.099  1.00  0.00           C  
HETATM   27  C20 UNL     1      -3.283  -0.865  -1.160  1.00  0.00           C  
HETATM   28  N3  UNL     1      -4.165   0.123  -0.573  1.00  0.00           N  
HETATM   29  C21 UNL     1      -5.287  -0.448   0.113  1.00  0.00           C  
HETATM   30  C22 UNL     1      -4.921  -1.443   1.008  1.00  0.00           C  
HETATM   31  C23 UNL     1      -5.933  -1.924   1.855  1.00  0.00           C  
HETATM   32  N4  UNL     1      -7.192  -1.371   1.727  1.00  0.00           N  
HETATM   33  C24 UNL     1      -7.490  -0.422   0.851  1.00  0.00           C  
HETATM   34  C25 UNL     1      -8.800   0.047   0.728  1.00  0.00           C  
HETATM   35  C26 UNL     1      -9.152   0.998  -0.230  1.00  0.00           C  
HETATM   36  C27 UNL     1     -10.561   1.400  -0.283  1.00  0.00           C  
HETATM   37  F4  UNL     1     -11.307   0.195  -0.157  1.00  0.00           F  
HETATM   38  F5  UNL     1     -10.863   2.253   0.734  1.00  0.00           F  
HETATM   39  F6  UNL     1     -10.877   1.975  -1.503  1.00  0.00           F  
HETATM   40  C28 UNL     1      -8.179   1.487  -1.076  1.00  0.00           C  
HETATM   41  C29 UNL     1      -6.881   1.034  -0.961  1.00  0.00           C  
HETATM   42  C30 UNL     1      -6.542   0.082  -0.008  1.00  0.00           C  
HETATM   43  H1  UNL     1       0.868  -0.236   2.154  1.00  0.00           H  
HETATM   44  H2  UNL     1      -0.381   1.037   2.215  1.00  0.00           H  
HETATM   45  H3  UNL     1       1.279   2.572   0.916  1.00  0.00           H  
HETATM   46  H4  UNL     1       1.845   2.011   2.555  1.00  0.00           H  
HETATM   47  H5  UNL     1       3.757   2.731   1.918  1.00  0.00           H  
HETATM   48  H6  UNL     1       4.303   2.497   0.224  1.00  0.00           H  
HETATM   49  H7  UNL     1       5.903   1.746   1.909  1.00  0.00           H  
HETATM   50  H8  UNL     1       4.678   0.439   2.461  1.00  0.00           H  
HETATM   51  H9  UNL     1       5.976   1.133  -1.907  1.00  0.00           H  
HETATM   52  H10 UNL     1       8.095   0.986  -3.008  1.00  0.00           H  
HETATM   53  H11 UNL     1      10.051  -0.050  -1.866  1.00  0.00           H  
HETATM   54  H12 UNL     1       7.632  -0.798   1.544  1.00  0.00           H  
HETATM   55  H13 UNL     1       4.441  -1.704   0.272  1.00  0.00           H  
HETATM   56  H14 UNL     1       4.104  -0.549  -1.019  1.00  0.00           H  
HETATM   57  H15 UNL     1       2.114  -0.701   0.261  1.00  0.00           H  
HETATM   58  H16 UNL     1       2.999  -0.735   1.809  1.00  0.00           H  
HETATM   59  H17 UNL     1       0.017  -1.463  -1.584  1.00  0.00           H  
HETATM   60  H18 UNL     1      -0.911  -3.037  -3.248  1.00  0.00           H  
HETATM   61  H19 UNL     1      -3.332  -3.246  -3.569  1.00  0.00           H  
HETATM   62  H20 UNL     1      -4.872  -1.768  -2.208  1.00  0.00           H  
HETATM   63  H21 UNL     1      -3.981   1.122  -0.652  1.00  0.00           H  
HETATM   64  H22 UNL     1      -3.920  -1.854   1.123  1.00  0.00           H  
HETATM   65  H23 UNL     1      -5.719  -2.674   2.577  1.00  0.00           H  
HETATM   66  H24 UNL     1      -9.521  -0.385   1.392  1.00  0.00           H  
HETATM   67  H25 UNL     1      -8.514   2.208  -1.801  1.00  0.00           H  
HETATM   68  H26 UNL     1      -6.121   1.405  -1.635  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   22
CONECT    3    4
CONECT    4    5   43   44
CONECT    5    6   45   46
CONECT    6    7   21
CONECT    7    8   47   48
CONECT    8    9   49   50
CONECT    9   10   20
CONECT   10   11   11   19
CONECT   11   12   51
CONECT   12   13   13   52
CONECT   13   14   53
CONECT   14   15   19   19
CONECT   15   16   17   18
CONECT   19   54
CONECT   20   21   55   56
CONECT   21   57   58
CONECT   22   23   23   27
CONECT   23   24   59
CONECT   24   25   25   60
CONECT   25   26   61
CONECT   26   27   27   62
CONECT   27   28
CONECT   28   29   63
CONECT   29   30   30   42
CONECT   30   31   64
CONECT   31   32   32   65
CONECT   32   33
CONECT   33   34   34   42
CONECT   34   35   66
CONECT   35   36   40   40
CONECT   36   37   38   39
CONECT   40   41   67
CONECT   41   42   42   68
END

HMDB0015488
     RDKit          3D
Antrafenine
 68 72  0  0  0  0  0  0  0  0999 V2000
   -2.1274    0.5573    1.0309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3903   -0.0206    0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0008    0.0784    0.3728 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4625    0.6989    1.5474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6176    1.6330    1.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7990    1.1545    0.8998 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9407    1.9810    1.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0578    1.0808    1.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3673    0.1868    0.5223 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6234    0.1657   -0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7910    0.6624   -1.3363 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0111    0.5876   -1.9839 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1019    0.0157   -1.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9449   -0.4870   -0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1393   -1.0929    0.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2905   -0.3664    0.3508 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.9583   -1.1129    1.9373 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.3455   -2.3729    0.1404 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.7427   -0.4049    0.5387 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2551   -0.6294    0.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9919   -0.2352    0.8381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9075   -0.7639   -0.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0715   -1.5661   -1.7290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5806   -2.4453   -2.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9583   -2.5399   -2.8567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7634   -1.7483   -2.0993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2827   -0.8650   -1.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1650    0.1225   -0.5735 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2870   -0.4480    0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9213   -1.4433    1.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9325   -1.9241    1.8546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1917   -1.3712    1.7274 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4898   -0.4221    0.8514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8000    0.0469    0.7282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1520    0.9982   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5607    1.3998   -0.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3073    0.1950   -0.1570 F   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8628    2.2532    0.7341 F   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8770    1.9749   -1.5027 F   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1789    1.4875   -1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8806    1.0342   -0.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5415    0.0824   -0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8679   -0.2359    2.1539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3813    1.0367    2.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792    2.5723    0.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8454    2.0106    2.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7573    2.7309    1.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3027    2.4968    0.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9031    1.7462    1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6780    0.4388    2.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9758    1.1334   -1.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0946    0.9859   -3.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0513   -0.0501   -1.8663 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6318   -0.7982    1.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4411   -1.7036    0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1040   -0.5487   -1.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1136   -0.7005    0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9989   -0.7349    1.8091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0174   -1.4632   -1.5845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9105   -3.0370   -3.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3316   -3.2458   -3.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8718   -1.7676   -2.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9815    1.1220   -0.6518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9197   -1.8543    1.1230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7194   -2.6742    2.5770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5212   -0.3848    1.3917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5136    2.2083   -1.8006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1212    1.4050   -1.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 14 19  2  0
  9 20  1  0
 20 21  1  0
  2 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  1  0
 36 39  1  0
 35 40  2  0
 40 41  1  0
 41 42  2  0
 21  6  1  0
 27 22  1  0
 42 29  1  0
 19 10  1  0
 42 33  1  0
  4 43  1  0
  4 44  1  0
  5 45  1  0
  5 46  1  0
  7 47  1  0
  7 48  1  0
  8 49  1  0
  8 50  1  0
 11 51  1  0
 12 52  1  0
 13 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 23 59  1  0
 24 60  1  0
 25 61  1  0
 26 62  1  0
 28 63  1  0
 30 64  1  0
 31 65  1  0
 34 66  1  0
 40 67  1  0
 41 68  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Stakane	HMDB
Antrafenine dihydrochloride	HMDB
2-(4-(m-Trifluoromethyl-phenyl)-1-piperazinyl)ethyl 2-(7-trifluoromethyl-4-quinolinylamino)benzoate	HMDB

Chemical Formula

C₃₀H₂₆F₆N₄O₂

Average Molecular Weight

588.5435

Monoisotopic Molecular Weight

588.195995326

IUPAC Name

2-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}ethyl 2-{[7-(trifluoromethyl)quinolin-4-yl]amino}benzoate

Traditional Name

antrafenine

CAS Registry Number

55300-30-6

SMILES

FC(F)(F)C1=CC(=CC=C1)N1CCN(CCOC(=O)C2=CC=CC=C2NC2=C3C=CC(=CC3=NC=C2)C(F)(F)F)CC1

InChI Identifier

InChI=1S/C30H26F6N4O2/c31-29(32,33)20-4-3-5-22(18-20)40-14-12-39(13-15-40)16-17-42-28(41)24-6-1-2-7-25(24)38-26-10-11-37-27-19-21(30(34,35)36)8-9-23(26)27/h1-11,18-19H,12-17H2,(H,37,38)

InChI Key

NWGGKKGAFZIVBJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cephalosporins. Cephalosporins are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]Oct-2-ene-2-carboxylic acid moiety or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Cephalosporins

Alternative Parents

Substituents

Cephalosporin
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
2,4-disubstituted 1,3-thiazole
Meta-thiazine
1,3-thiazol-2-amine
Heteroaromatic compound
Azole
Thiazole
Tertiary carboxylic acid amide
Amino acid or derivatives
Amino acid
Azetidine
Carboxamide group
Secondary carboxylic acid amide
Thioether
Hemithioaminal
Carboxylic acid derivative
Dialkylthioether
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Azacycle
Carboxylic acid
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Primary amine
Hydrocarbon derivative
Organic oxide
Amine
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cephalosporin (CHEBI:3504 )
carboxylic acid (CHEBI:3504 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015488)
Membrane (HMDB: HMDB0015488)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Antrafenine Action Pathway (PathBank: SMP0000693)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0028 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0028 g/L	ALOGPS
logP	6.3	ALOGPS
logP	8.39	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	16.69	ChemAxon
pKa (Strongest Basic)	7.04	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.7 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	147.01 m³·mol⁻¹	ChemAxon
Polarizability	55.48 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	221.976	30932474
DeepCCS	[M-H]-	219.58	30932474
DeepCCS	[M-2H]-	252.58	30932474
DeepCCS	[M+Na]+	227.888	30932474
AllCCS	[M+H]+	232.2	32859911
AllCCS	[M+H-H2O]+	231.0	32859911
AllCCS	[M+NH4]+	233.4	32859911
AllCCS	[M+Na]+	233.7	32859911
AllCCS	[M-H]-	202.4	32859911
AllCCS	[M+Na-2H]-	202.6	32859911
AllCCS	[M+HCOO]-	203.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Antrafenine	FC(F)(F)C1=CC(=CC=C1)N1CCN(CCOC(=O)C2=CC=CC=C2NC2=C3C=CC(=CC3=NC=C2)C(F)(F)F)CC1	3930.9	Standard polar	33892256
Antrafenine	FC(F)(F)C1=CC(=CC=C1)N1CCN(CCOC(=O)C2=CC=CC=C2NC2=C3C=CC(=CC3=NC=C2)C(F)(F)F)CC1	3860.8	Standard non polar	33892256
Antrafenine	FC(F)(F)C1=CC(=CC=C1)N1CCN(CCOC(=O)C2=CC=CC=C2NC2=C3C=CC(=CC3=NC=C2)C(F)(F)F)CC1	3938.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Antrafenine,1TMS,isomer #1	C[Si](C)(C)N(C1=CC=CC=C1C(=O)OCCN1CCN(C2=CC=CC(C(F)(F)F)=C2)CC1)C1=CC=NC2=CC(C(F)(F)F)=CC=C12	3779.6	Semi standard non polar	33892256
Antrafenine,1TMS,isomer #1	C[Si](C)(C)N(C1=CC=CC=C1C(=O)OCCN1CCN(C2=CC=CC(C(F)(F)F)=C2)CC1)C1=CC=NC2=CC(C(F)(F)F)=CC=C12	3666.7	Standard non polar	33892256
Antrafenine,1TMS,isomer #1	C[Si](C)(C)N(C1=CC=CC=C1C(=O)OCCN1CCN(C2=CC=CC(C(F)(F)F)=C2)CC1)C1=CC=NC2=CC(C(F)(F)F)=CC=C12	4401.0	Standard polar	33892256
Antrafenine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)OCCN1CCN(C2=CC=CC(C(F)(F)F)=C2)CC1)C1=CC=NC2=CC(C(F)(F)F)=CC=C12	3946.8	Semi standard non polar	33892256
Antrafenine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)OCCN1CCN(C2=CC=CC(C(F)(F)F)=C2)CC1)C1=CC=NC2=CC(C(F)(F)F)=CC=C12	3806.6	Standard non polar	33892256
Antrafenine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=CC=C1C(=O)OCCN1CCN(C2=CC=CC(C(F)(F)F)=C2)CC1)C1=CC=NC2=CC(C(F)(F)F)=CC=C12	4435.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Antrafenine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ar3-2192010000-e78886973a64ef0f77a8	2017-09-01	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antrafenine 10V, Positive-QTOF	splash10-052r-0064090000-3a3f873837b9e36277d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antrafenine 20V, Positive-QTOF	splash10-0ap0-0195020000-e202288f4207ee95fde8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antrafenine 40V, Positive-QTOF	splash10-014r-2193000000-1ddcbe94c38041fd4dc2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antrafenine 10V, Negative-QTOF	splash10-000i-0064090000-8a59aea448acc191e90e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antrafenine 20V, Negative-QTOF	splash10-000i-0094040000-13fea3df8f430bfbfe67	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antrafenine 40V, Negative-QTOF	splash10-000i-1292000000-3163db928f680ec69563	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antrafenine 10V, Positive-QTOF	splash10-000i-0003090000-0643995e108396489227	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antrafenine 20V, Positive-QTOF	splash10-000i-0035090000-f556108a82ce93cbeeaf	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antrafenine 40V, Positive-QTOF	splash10-014i-0967110000-57099b829a8b1b90d12e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antrafenine 10V, Negative-QTOF	splash10-000i-0000090000-b2a5859050c4c7f5552e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antrafenine 20V, Negative-QTOF	splash10-000i-0022090000-f345c715233f7ff4d386	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Antrafenine 40V, Negative-QTOF	splash10-01p9-0193000000-c5d889108558dc0c03f4	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Antrafenine Action Pathway		Not Available

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 DB01419	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01419	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01419

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

61973

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Antrafenine

METLIN ID

Not Available

PubChem Compound

68723

PDB ID

Not Available

ChEBI ID

354983

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

Not Available

Enzymes

Enzyme Details

1. Prostaglandin G/H synthase 2

General function:: Involved in peroxidase activity
Specific function:: Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:: PTGS2
Uniprot ID:: P35354
Molecular weight:: 68995.625

References

Albertini R, Aimbire F, Villaverde AB, Silva JA Jr, Costa MS: COX-2 mRNA expression decreases in the subplantar muscle of rat paw subjected to carrageenan-induced inflammation after low level laser therapy. Inflamm Res. 2007 Jun;56(6):228-9. [PubMed:17607546 ]
Dhir A, Naidu PS, Kulkarni SK: Neuroprotective effect of nimesulide, a preferential COX-2 inhibitor, against pentylenetetrazol (PTZ)-induced chemical kindling and associated biochemical parameters in mice. Seizure. 2007 Dec;16(8):691-7. Epub 2007 Jul 2. [PubMed:17604186 ]
Kumar P, Padi SS, Naidu PS, Kumar A: Cyclooxygenase inhibition attenuates 3-nitropropionic acid-induced neurotoxicity in rats: possible antioxidant mechanisms. Fundam Clin Pharmacol. 2007 Jun;21(3):297-306. [PubMed:17521299 ]
White WB: Cardiovascular effects of the selective cyclooxygenase-2 inhibitors. Subcell Biochem. 2007;42:145-58. [PubMed:17612049 ]
Hassan-Alin M, Naesdal J, Nilsson-Pieschl C, Langstrom G, Andersson T: Lack of Pharmacokinetic Interaction between Esomeprazole and the Nonsteroidal Anti-Inflammatory Drugs Naproxen and Rofecoxib in Healthy Subjects. Clin Drug Investig. 2005;25(11):731-40. [PubMed:17532719 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Hassan SM, Olivesi A, Fish A, Turner P: A comparison of antrafenine and aspirin on platelet aggregation and frusemide-induced diuresis. Postgrad Med J. 1982 Jan;58(675):17-9. [PubMed:7088753 ]
Berry H, Coquelin JP, Gordon A, Seymour D: Antrafenine, naproxen and placebo in osteoarthritis: a comparative study. Br J Rheumatol. 1983 May;22(2):89-94. [PubMed:6342700 ]
James MJ, Cook-Johnson RJ, Cleland LG: Selective COX-2 inhibitors, eicosanoid synthesis and clinical outcomes: a case study of system failure. Lipids. 2007 Sep;42(9):779-85. Epub 2007 Jun 2. [PubMed:17541796 ]

Showing metabocard for Antrafenine (HMDB0015488)

MOL for HMDB0015488 (Antrafenine)

3D MOL for HMDB0015488 (Antrafenine)

3D SDF for HMDB0015488 (Antrafenine)

3D-SDF for HMDB0015488 (Antrafenine)

PDB for HMDB0015488 (Antrafenine)

3D PDB for HMDB0015488 (Antrafenine)

SMILES for HMDB0015488 (Antrafenine)

INCHI for HMDB0015488 (Antrafenine)

Structure for HMDB0015488 (Antrafenine)

3D Structure for HMDB0015488 (Antrafenine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References