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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2014-04-16 20:10:16 UTC

Update Date

2021-09-14 15:42:55 UTC

HMDB ID

HMDB0061689

Secondary Accession Numbers

HMDB61689

Metabolite Identification

Common Name

4-Ketoretinoic acid glucuronide

Description

4-Ketoretinoic acid glucuronide belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. 4-Ketoretinoic acid glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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


  Mrv1652304062013172D          

 35 36  0  0  0  0            999 V2000
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1017    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5736    4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5736    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5736    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9903    6.3583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1570    6.3583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0025    4.9499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0025    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5736    2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  2 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 26 24  1  0  0  0  0
 24 27  1  0  0  0  0
 25 26  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 29 33  1  0  0  0  0
 28 34  1  0  0  0  0
 27 35  1  0  0  0  0
M  END

HMDB0061689
     RDKit          3D
4-Ketoretinoic acid glucuronide
 69 70  0  0  0  0  0  0  0  0999 V2000
   -5.6836    3.3486   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5970    2.1491   -0.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0823    0.9321   -0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6214    0.8763   -0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9829   -0.2574   -0.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5317   -0.2856   -0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6371    0.8603   -0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0351   -1.5171   -0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7073   -1.8022   -0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4697   -2.0565   -0.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8029   -1.6158   -0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0601   -0.1332   -0.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8653   -2.3923   -0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2243   -1.9601   -0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1215   -2.9024   -0.1564 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7647   -0.7108   -0.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1562   -0.4491   -0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4224    0.1328    1.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7840   -0.0759    1.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1129    0.3560    2.7943 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2341    0.8237    3.5574 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4070    0.2575    3.2791 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6720    0.5859    0.4254 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8776   -0.1530    0.4328 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1370    0.6508   -0.9632 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7443   -0.3794   -1.7085 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6329    0.5237   -1.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1127    1.8015   -0.8369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9370   -0.2631   -0.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7289   -1.1489   -1.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7261   -1.0845    1.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4111    0.0642   -0.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7977    1.3156   -0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0314    2.3989   -0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5494    3.3909    0.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2447    4.2825   -0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0398    3.2928   -1.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0692    3.3228    0.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0183    1.7704   -0.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6193   -1.1413   -0.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7854    0.7347   -0.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1483    0.9772    0.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0937    1.8453   -0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7796   -2.3633   -0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8539   -2.8991   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4647   -3.2336    0.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1248    0.3590    0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1961    0.2505   -1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8419    0.0588    0.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6613   -3.4865   -0.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7630   -1.3572   -0.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9410   -1.1897    1.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9987   -0.5244    3.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9484    1.5983    0.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3020   -0.1374   -0.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4864    1.6329   -1.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5273   -1.2498   -1.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4184    0.1758   -2.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9141    1.9225    0.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9967   -0.7361   -2.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5286   -2.2122   -1.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6770   -1.2428   -2.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8706   -0.7111    1.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6749   -1.0569    1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5188   -2.1462    0.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9859   -0.7736   -0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7716    0.1801    0.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8957    1.4475   -0.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5576    1.3294   -1.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 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  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 19 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
  3 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  2  0
 34  2  1  0
 27 17  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
  5 40  1  0
  7 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  9 45  1  0
 10 46  1  0
 12 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 17 51  1  0
 19 52  1  0
 22 53  1  0
 23 54  1  0
 24 55  1  0
 25 56  1  0
 26 57  1  0
 27 58  1  0
 28 59  1  0
 30 60  1  0
 30 61  1  0
 30 62  1  0
 31 63  1  0
 31 64  1  0
 31 65  1  0
 32 66  1  0
 32 67  1  0
 33 68  1  0
 33 69  1  0
M  END


  Mrv1652304062013172D          

 35 36  0  0  0  0            999 V2000
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1017    1.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5736    4.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5736    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5736    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9903    6.3583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1570    6.3583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0025    4.9499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0025    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5736    2.4749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  2 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 26 24  1  0  0  0  0
 24 27  1  0  0  0  0
 25 26  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 29 33  1  0  0  0  0
 28 34  1  0  0  0  0
 27 35  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061689

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C(/C)=C/C(=O)OC1OC(C(O)C(O)C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O9/c1-14(9-10-17-16(3)18(27)11-12-26(17,4)5)7-6-8-15(2)13-19(28)34-25-22(31)20(29)21(30)23(35-25)24(32)33/h6-10,13,20-23,25,29-31H,11-12H2,1-5H3,(H,32,33)/b8-6+,10-9+,14-7+,15-13+

> <INCHI_KEY>
SIKFAVWPHMSCBL-FRCNGJHJSA-N

> <FORMULA>
C26H34O9

> <MOLECULAR_WEIGHT>
490.5428

> <EXACT_MASS>
490.220282686

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
52.27475577095379

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-{[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
2.632624127666666

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.212250459730129

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3892099198186108

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6869063371000665

> <JCHEM_POLAR_SURFACE_AREA>
150.59

> <JCHEM_REFRACTIVITY>
130.78259999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-{[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061689
     RDKit          3D
4-Ketoretinoic acid glucuronide
 69 70  0  0  0  0  0  0  0  0999 V2000
   -5.6836    3.3486   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5970    2.1491   -0.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0823    0.9321   -0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6214    0.8763   -0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9829   -0.2574   -0.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5317   -0.2856   -0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6371    0.8603   -0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0351   -1.5171   -0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7073   -1.8022   -0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4697   -2.0565   -0.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8029   -1.6158   -0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0601   -0.1332   -0.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8653   -2.3923   -0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2243   -1.9601   -0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1215   -2.9024   -0.1564 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7647   -0.7108   -0.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1562   -0.4491   -0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4224    0.1328    1.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7840   -0.0759    1.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1129    0.3560    2.7943 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2341    0.8237    3.5574 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4070    0.2575    3.2791 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6720    0.5859    0.4254 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8776   -0.1530    0.4328 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1370    0.6508   -0.9632 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7443   -0.3794   -1.7085 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6329    0.5237   -1.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1127    1.8015   -0.8369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9370   -0.2631   -0.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7289   -1.1489   -1.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7261   -1.0845    1.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4111    0.0642   -0.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7977    1.3156   -0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0314    2.3989   -0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5494    3.3909    0.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2447    4.2825   -0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0398    3.2928   -1.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0692    3.3228    0.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0183    1.7704   -0.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6193   -1.1413   -0.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7854    0.7347   -0.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1483    0.9772    0.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0937    1.8453   -0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7796   -2.3633   -0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8539   -2.8991   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4647   -3.2336    0.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1248    0.3590    0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1961    0.2505   -1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8419    0.0588    0.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6613   -3.4865   -0.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7630   -1.3572   -0.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9410   -1.1897    1.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9987   -0.5244    3.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9484    1.5983    0.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3020   -0.1374   -0.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4864    1.6329   -1.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5273   -1.2498   -1.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4184    0.1758   -2.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9141    1.9225    0.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9967   -0.7361   -2.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5286   -2.2122   -1.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6770   -1.2428   -2.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8706   -0.7111    1.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6749   -1.0569    1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5188   -2.1462    0.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9859   -0.7736   -0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7716    0.1801    0.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8957    1.4475   -0.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5576    1.3294   -1.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 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  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 19 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
  3 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  2  0
 34  2  1  0
 27 17  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
  5 40  1  0
  7 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  9 45  1  0
 10 46  1  0
 12 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 17 51  1  0
 19 52  1  0
 22 53  1  0
 23 54  1  0
 24 55  1  0
 25 56  1  0
 26 57  1  0
 27 58  1  0
 28 59  1  0
 30 60  1  0
 30 61  1  0
 30 62  1  0
 31 63  1  0
 31 64  1  0
 31 65  1  0
 32 66  1  0
 32 67  1  0
 33 68  1  0
 33 69  1  0
M  END

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.611   3.670   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.057   3.670   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.337   6.160   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      14.671   3.850   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      14.671   6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.004   9.240   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      14.671   8.470   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      16.004   6.160   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.338   6.930   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.338   8.470   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.004  10.780   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      14.915  11.869   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      17.093  11.869   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      18.671   9.240   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      18.671   6.160   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      16.004   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    5   13   14                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    2   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21   24                                                       
CONECT   23   21                                                            
CONECT   24   22   26   27                                                  
CONECT   25   26   29   30                                                  
CONECT   26   24   25                                                       
CONECT   27   24   28   35                                                  
CONECT   28   27   29   34                                                  
CONECT   29   28   25   33                                                  
CONECT   30   25   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   29                                                            
CONECT   34   28                                                            
CONECT   35   27                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

COMPND    HMDB0061689
HETATM    1  C1  UNL     1      -5.684   3.349  -0.117  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.597   2.149  -0.169  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.082   0.932  -0.200  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.621   0.876  -0.182  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.983  -0.257  -0.218  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.532  -0.286  -0.196  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.637   0.860  -0.160  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.035  -1.517  -0.238  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.707  -1.802  -0.219  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.470  -2.056  -0.202  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.803  -1.616  -0.154  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.060  -0.133  -0.030  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.865  -2.392  -0.180  1.00  0.00           C  
HETATM   14  C14 UNL     1       4.224  -1.960  -0.137  1.00  0.00           C  
HETATM   15  O1  UNL     1       5.122  -2.902  -0.156  1.00  0.00           O  
HETATM   16  O2  UNL     1       4.765  -0.711  -0.079  1.00  0.00           O  
HETATM   17  C15 UNL     1       6.156  -0.449  -0.049  1.00  0.00           C  
HETATM   18  O3  UNL     1       6.422   0.133   1.211  1.00  0.00           O  
HETATM   19  C16 UNL     1       7.784  -0.076   1.431  1.00  0.00           C  
HETATM   20  C17 UNL     1       8.113   0.356   2.794  1.00  0.00           C  
HETATM   21  O4  UNL     1       7.234   0.824   3.557  1.00  0.00           O  
HETATM   22  O5  UNL     1       9.407   0.257   3.279  1.00  0.00           O  
HETATM   23  C18 UNL     1       8.672   0.586   0.425  1.00  0.00           C  
HETATM   24  O6  UNL     1       9.878  -0.153   0.433  1.00  0.00           O  
HETATM   25  C19 UNL     1       8.137   0.651  -0.963  1.00  0.00           C  
HETATM   26  O7  UNL     1       8.744  -0.379  -1.709  1.00  0.00           O  
HETATM   27  C20 UNL     1       6.633   0.524  -1.069  1.00  0.00           C  
HETATM   28  O8  UNL     1       6.113   1.801  -0.837  1.00  0.00           O  
HETATM   29  C21 UNL     1      -6.937  -0.263  -0.220  1.00  0.00           C  
HETATM   30  C22 UNL     1      -6.729  -1.149  -1.443  1.00  0.00           C  
HETATM   31  C23 UNL     1      -6.726  -1.084   1.070  1.00  0.00           C  
HETATM   32  C24 UNL     1      -8.411   0.064  -0.211  1.00  0.00           C  
HETATM   33  C25 UNL     1      -8.798   1.316  -0.914  1.00  0.00           C  
HETATM   34  C26 UNL     1      -8.031   2.399  -0.190  1.00  0.00           C  
HETATM   35  O9  UNL     1      -8.549   3.391   0.332  1.00  0.00           O  
HETATM   36  H1  UNL     1      -6.245   4.282  -0.137  1.00  0.00           H  
HETATM   37  H2  UNL     1      -5.040   3.293  -1.036  1.00  0.00           H  
HETATM   38  H3  UNL     1      -5.069   3.323   0.798  1.00  0.00           H  
HETATM   39  H4  UNL     1      -4.018   1.770  -0.135  1.00  0.00           H  
HETATM   40  H5  UNL     1      -4.619  -1.141  -0.266  1.00  0.00           H  
HETATM   41  H6  UNL     1      -0.785   0.735  -0.903  1.00  0.00           H  
HETATM   42  H7  UNL     1      -1.148   0.977   0.835  1.00  0.00           H  
HETATM   43  H8  UNL     1      -2.094   1.845  -0.396  1.00  0.00           H  
HETATM   44  H9  UNL     1      -2.780  -2.363  -0.261  1.00  0.00           H  
HETATM   45  H10 UNL     1      -0.854  -2.899  -1.131  1.00  0.00           H  
HETATM   46  H11 UNL     1       0.465  -3.234   0.140  1.00  0.00           H  
HETATM   47  H12 UNL     1       1.125   0.359   0.382  1.00  0.00           H  
HETATM   48  H13 UNL     1       2.196   0.251  -1.047  1.00  0.00           H  
HETATM   49  H14 UNL     1       2.842   0.059   0.697  1.00  0.00           H  
HETATM   50  H15 UNL     1       2.661  -3.487  -0.245  1.00  0.00           H  
HETATM   51  H16 UNL     1       6.763  -1.357  -0.086  1.00  0.00           H  
HETATM   52  H17 UNL     1       7.941  -1.190   1.331  1.00  0.00           H  
HETATM   53  H18 UNL     1       9.999  -0.524   3.029  1.00  0.00           H  
HETATM   54  H19 UNL     1       8.948   1.598   0.823  1.00  0.00           H  
HETATM   55  H20 UNL     1      10.302  -0.137  -0.469  1.00  0.00           H  
HETATM   56  H21 UNL     1       8.486   1.633  -1.394  1.00  0.00           H  
HETATM   57  H22 UNL     1       8.527  -1.250  -1.325  1.00  0.00           H  
HETATM   58  H23 UNL     1       6.418   0.176  -2.117  1.00  0.00           H  
HETATM   59  H24 UNL     1       5.914   1.922   0.134  1.00  0.00           H  
HETATM   60  H25 UNL     1      -5.997  -0.736  -2.161  1.00  0.00           H  
HETATM   61  H26 UNL     1      -6.529  -2.212  -1.153  1.00  0.00           H  
HETATM   62  H27 UNL     1      -7.677  -1.243  -2.057  1.00  0.00           H  
HETATM   63  H28 UNL     1      -5.871  -0.711   1.665  1.00  0.00           H  
HETATM   64  H29 UNL     1      -7.675  -1.057   1.628  1.00  0.00           H  
HETATM   65  H30 UNL     1      -6.519  -2.146   0.831  1.00  0.00           H  
HETATM   66  H31 UNL     1      -8.986  -0.774  -0.700  1.00  0.00           H  
HETATM   67  H32 UNL     1      -8.772   0.180   0.855  1.00  0.00           H  
HETATM   68  H33 UNL     1      -9.896   1.448  -0.733  1.00  0.00           H  
HETATM   69  H34 UNL     1      -8.558   1.329  -1.985  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3    3   34
CONECT    3    4   29
CONECT    4    5    5   39
CONECT    5    6   40
CONECT    6    7    8    8
CONECT    7   41   42   43
CONECT    8    9   44
CONECT    9   10   10   45
CONECT   10   11   46
CONECT   11   12   13   13
CONECT   12   47   48   49
CONECT   13   14   50
CONECT   14   15   15   16
CONECT   16   17
CONECT   17   18   27   51
CONECT   18   19
CONECT   19   20   23   52
CONECT   20   21   21   22
CONECT   22   53
CONECT   23   24   25   54
CONECT   24   55
CONECT   25   26   27   56
CONECT   26   57
CONECT   27   28   58
CONECT   28   59
CONECT   29   30   31   32
CONECT   30   60   61   62
CONECT   31   63   64   65
CONECT   32   33   66   67
CONECT   33   34   68   69
CONECT   34   35   35
END

HMDB0061689
     RDKit          3D
4-Ketoretinoic acid glucuronide
 69 70  0  0  0  0  0  0  0  0999 V2000
   -5.6836    3.3486   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5970    2.1491   -0.1687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0823    0.9321   -0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6214    0.8763   -0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9829   -0.2574   -0.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5317   -0.2856   -0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6371    0.8603   -0.1604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0351   -1.5171   -0.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7073   -1.8022   -0.2187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4697   -2.0565   -0.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8029   -1.6158   -0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0601   -0.1332   -0.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8653   -2.3923   -0.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2243   -1.9601   -0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1215   -2.9024   -0.1564 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7647   -0.7108   -0.0794 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1562   -0.4491   -0.0493 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4224    0.1328    1.2112 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7840   -0.0759    1.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1129    0.3560    2.7943 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2341    0.8237    3.5574 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4070    0.2575    3.2791 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6720    0.5859    0.4254 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8776   -0.1530    0.4328 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1370    0.6508   -0.9632 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7443   -0.3794   -1.7085 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6329    0.5237   -1.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1127    1.8015   -0.8369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9370   -0.2631   -0.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7289   -1.1489   -1.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7261   -1.0845    1.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4111    0.0642   -0.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7977    1.3156   -0.9142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0314    2.3989   -0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5494    3.3909    0.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2447    4.2825   -0.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0398    3.2928   -1.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0692    3.3228    0.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0183    1.7704   -0.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6193   -1.1413   -0.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7854    0.7347   -0.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1483    0.9772    0.8351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0937    1.8453   -0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7796   -2.3633   -0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8539   -2.8991   -1.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4647   -3.2336    0.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1248    0.3590    0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1961    0.2505   -1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8419    0.0588    0.6970 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6613   -3.4865   -0.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7630   -1.3572   -0.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9410   -1.1897    1.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9987   -0.5244    3.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9484    1.5983    0.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3020   -0.1374   -0.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4864    1.6329   -1.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5273   -1.2498   -1.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4184    0.1758   -2.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9141    1.9225    0.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9967   -0.7361   -2.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5286   -2.2122   -1.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6770   -1.2428   -2.0566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8706   -0.7111    1.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6749   -1.0569    1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5188   -2.1462    0.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9859   -0.7736   -0.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7716    0.1801    0.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8957    1.4475   -0.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5576    1.3294   -1.9852 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 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  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 19 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
  3 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  2  0
 34  2  1  0
 27 17  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  4 39  1  0
  5 40  1  0
  7 41  1  0
  7 42  1  0
  7 43  1  0
  8 44  1  0
  9 45  1  0
 10 46  1  0
 12 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 17 51  1  0
 19 52  1  0
 22 53  1  0
 23 54  1  0
 24 55  1  0
 25 56  1  0
 26 57  1  0
 27 58  1  0
 28 59  1  0
 30 60  1  0
 30 61  1  0
 30 62  1  0
 31 63  1  0
 31 64  1  0
 31 65  1  0
 32 66  1  0
 32 67  1  0
 33 68  1  0
 33 69  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Ketoretinoate glucuronide	Generator

Chemical Formula

C₂₆H₃₄O₉

Average Molecular Weight

490.5428

Monoisotopic Molecular Weight

490.220282686

IUPAC Name

6-{[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

6-{[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

C\C(\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C(/C)=C/C(=O)OC1OC(C(O)C(O)C1O)C(O)=O

InChI Identifier

InChI=1S/C26H34O9/c1-14(9-10-17-16(3)18(27)11-12-26(17,4)5)7-6-8-15(2)13-19(28)34-25-22(31)20(29)21(30)23(35-25)24(32)33/h6-10,13,20-23,25,29-31H,11-12H2,1-5H3,(H,32,33)/b8-6+,10-9+,14-7+,15-13+

InChI Key

SIKFAVWPHMSCBL-FRCNGJHJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Retinoid ester
Diterpenoid
Retinoid skeleton
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Beta-hydroxy acid
Fatty acid ester
Cyclohexenone
Fatty acyl
Dicarboxylic acid or derivatives
Pyran
Oxane
Hydroxy acid
Monosaccharide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic ketone
Carboxylic acid ester
Secondary alcohol
Ketone
Polyol
Carboxylic acid
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Acetal
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0061689)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.089 g/L	ALOGPS
logP	2.82	ALOGPS
logP	2.63	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	3.39	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	150.59 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	130.78 m³·mol⁻¹	ChemAxon
Polarizability	52.27 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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+H]+	219.802	30932474
DeepCCS	[M-H]-	217.407	30932474
DeepCCS	[M-2H]-	250.29	30932474
DeepCCS	[M+Na]+	225.715	30932474
AllCCS	[M+H]+	222.0	32859911
AllCCS	[M+H-H2O]+	220.0	32859911
AllCCS	[M+NH4]+	223.9	32859911
AllCCS	[M+Na]+	224.4	32859911
AllCCS	[M-H]-	216.8	32859911
AllCCS	[M+Na-2H]-	218.9	32859911
AllCCS	[M+HCOO]-	221.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.33 minutes	32390414
Predicted by Siyang on May 30, 2022	16.5858 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.21 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3304.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	233.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	166.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	177.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	124.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	637.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	628.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	83.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1337.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	619.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1609.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	446.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	484.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	216.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	197.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Ketoretinoic acid glucuronide	C\C(\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C(/C)=C/C(=O)OC1OC(C(O)C(O)C1O)C(O)=O	5650.1	Standard polar	33892256
4-Ketoretinoic acid glucuronide	C\C(\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C(/C)=C/C(=O)OC1OC(C(O)C(O)C1O)C(O)=O	3507.2	Standard non polar	33892256
4-Ketoretinoic acid glucuronide	C\C(\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C(/C)=C/C(=O)OC1OC(C(O)C(O)C1O)C(O)=O	4178.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Ketoretinoic acid glucuronide,1TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O[Si](C)(C)C)C(O)C2O)C(C)(C)CCC1=O	3919.1	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,1TMS,isomer #2	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O)C(O[Si](C)(C)C)C2O)C(C)(C)CCC1=O	3948.4	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,1TMS,isomer #3	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O)C(O)C2O[Si](C)(C)C)C(C)(C)CCC1=O	3945.0	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,1TMS,isomer #4	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C)C(O)C(O)C2O)C(C)(C)CCC1=O	3898.9	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,1TMS,isomer #5	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O)C(O)C2O)C(C)(C)CC=C1O[Si](C)(C)C	3952.6	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,2TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C2O)C(C)(C)CCC1=O	3872.8	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,2TMS,isomer #10	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C)C(O)C(O)C2O)C(C)(C)CC=C1O[Si](C)(C)C	3851.7	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,2TMS,isomer #2	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O)C(C)(C)CCC1=O	3918.5	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,2TMS,isomer #3	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O[Si](C)(C)C)C(O)C2O[Si](C)(C)C)C(C)(C)CCC1=O	3918.3	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,2TMS,isomer #4	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O[Si](C)(C)C)C(O)C2O)C(C)(C)CC=C1O[Si](C)(C)C	3895.8	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,2TMS,isomer #5	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C2O)C(C)(C)CCC1=O	3887.2	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,2TMS,isomer #6	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O)C(O[Si](C)(C)C)C2O[Si](C)(C)C)C(C)(C)CCC1=O	3933.7	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,2TMS,isomer #7	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O)C(O[Si](C)(C)C)C2O)C(C)(C)CC=C1O[Si](C)(C)C	3911.4	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,2TMS,isomer #8	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C)C(O)C(O)C2O[Si](C)(C)C)C(C)(C)CCC1=O	3887.6	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,2TMS,isomer #9	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O)C(O)C2O[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C	3923.3	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,3TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O)C(C)(C)CCC1=O	3876.0	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,3TMS,isomer #10	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C)C(O)C(O)C2O[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C	3833.7	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,3TMS,isomer #2	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C2O[Si](C)(C)C)C(C)(C)CCC1=O	3874.3	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,3TMS,isomer #3	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C2O)C(C)(C)CC=C1O[Si](C)(C)C	3815.1	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,3TMS,isomer #4	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)C(C)(C)CCC1=O	3906.8	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,3TMS,isomer #5	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O)C(C)(C)CC=C1O[Si](C)(C)C	3855.3	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,3TMS,isomer #6	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O[Si](C)(C)C)C(O)C2O[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C	3862.5	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,3TMS,isomer #7	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C2O[Si](C)(C)C)C(C)(C)CCC1=O	3879.2	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,3TMS,isomer #8	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C2O)C(C)(C)CC=C1O[Si](C)(C)C	3823.1	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,3TMS,isomer #9	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O)C(O[Si](C)(C)C)C2O[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C	3862.6	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,4TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)C(C)(C)CCC1=O	3858.7	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,4TMS,isomer #2	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O)C(C)(C)CC=C1O[Si](C)(C)C	3813.9	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,4TMS,isomer #3	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C2O[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C	3821.6	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,4TMS,isomer #4	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C	3844.0	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,4TMS,isomer #5	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C2O[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C	3812.2	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,5TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C	3796.0	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,5TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C	3635.3	Standard non polar	33892256
4-Ketoretinoic acid glucuronide,5TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C2O[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C	4096.5	Standard polar	33892256
4-Ketoretinoic acid glucuronide,1TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O[Si](C)(C)C(C)(C)C)C(O)C2O)C(C)(C)CCC1=O	4150.0	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,1TBDMS,isomer #2	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O)C(O[Si](C)(C)C(C)(C)C)C2O)C(C)(C)CCC1=O	4180.4	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,1TBDMS,isomer #3	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)C(C)(C)CCC1=O	4179.0	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,1TBDMS,isomer #4	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)C(O)C2O)C(C)(C)CCC1=O	4120.0	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,1TBDMS,isomer #5	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O)C(O)C2O)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	4173.8	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,2TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C2O)C(C)(C)CCC1=O	4323.0	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,2TBDMS,isomer #10	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)C(O)C2O)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	4290.4	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,2TBDMS,isomer #2	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O)C(C)(C)CCC1=O	4374.8	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,2TBDMS,isomer #3	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O[Si](C)(C)C(C)(C)C)C(O)C2O[Si](C)(C)C(C)(C)C)C(C)(C)CCC1=O	4369.8	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,2TBDMS,isomer #4	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O[Si](C)(C)C(C)(C)C)C(O)C2O)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	4326.0	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,2TBDMS,isomer #5	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C2O)C(C)(C)CCC1=O	4343.3	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,2TBDMS,isomer #6	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)C(C)(C)CCC1=O	4390.2	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,2TBDMS,isomer #7	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O)C(O[Si](C)(C)C(C)(C)C)C2O)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	4344.3	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,2TBDMS,isomer #8	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)C(C)(C)CCC1=O	4338.2	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,2TBDMS,isomer #9	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	4349.9	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,3TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O)C(C)(C)CCC1=O	4562.0	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,3TBDMS,isomer #10	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)C(O)C2O[Si](C)(C)C(C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	4480.8	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,3TBDMS,isomer #2	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C2O[Si](C)(C)C(C)(C)C)C(C)(C)CCC1=O	4560.3	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,3TBDMS,isomer #3	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C2O)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	4464.0	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,3TBDMS,isomer #4	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)C(C)(C)CCC1=O	4588.7	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,3TBDMS,isomer #5	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2O)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	4518.3	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,3TBDMS,isomer #6	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O[Si](C)(C)C(C)(C)C)C(O)C2O[Si](C)(C)C(C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	4519.6	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,3TBDMS,isomer #7	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)C(C)(C)CCC1=O	4565.1	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,3TBDMS,isomer #8	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C2O)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	4480.1	Semi standard non polar	33892256
4-Ketoretinoic acid glucuronide,3TBDMS,isomer #9	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)OC2OC(C(=O)O)C(O)C(O[Si](C)(C)C(C)(C)C)C2O[Si](C)(C)C(C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C	4530.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ketoretinoic acid glucuronide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0adi-9121400000-fa740a33d3378521c3aa	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ketoretinoic acid glucuronide GC-MS (2 TMS) - 70eV, Positive	splash10-01b9-6492038000-064f001b4fc21ffe7853	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ketoretinoic acid glucuronide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Ketoretinoic acid glucuronide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ketoretinoic acid glucuronide 10V, Positive-QTOF	splash10-00r2-0693500000-1c93a2e712f7e42db4e5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ketoretinoic acid glucuronide 20V, Positive-QTOF	splash10-0002-1981000000-d38a0a0c24fe50653deb	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ketoretinoic acid glucuronide 40V, Positive-QTOF	splash10-0f72-2930000000-12402f7644c1817f4597	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ketoretinoic acid glucuronide 10V, Negative-QTOF	splash10-0002-0193400000-e632d10717d4280b92e4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ketoretinoic acid glucuronide 20V, Negative-QTOF	splash10-03dj-4956200000-094ffc123fe6e74beb6e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ketoretinoic acid glucuronide 40V, Negative-QTOF	splash10-03dm-9663000000-20ba0e60cb7315df7efd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ketoretinoic acid glucuronide 10V, Negative-QTOF	splash10-000i-0001900000-a8c9368c7ac385b0a49e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ketoretinoic acid glucuronide 20V, Negative-QTOF	splash10-0170-1292200000-4b85dc33d73da2e7b002	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ketoretinoic acid glucuronide 40V, Negative-QTOF	splash10-0r00-4951100000-e95621c87c00e0b108f3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ketoretinoic acid glucuronide 10V, Positive-QTOF	splash10-0006-0452900000-e315d43e7a3da636ee90	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ketoretinoic acid glucuronide 20V, Positive-QTOF	splash10-102i-0890100000-398a7bc32d6c4cf8fd54	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Ketoretinoic acid glucuronide 40V, Positive-QTOF	splash10-014i-0921000000-9319c1f475566e5263d8	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131770407

PDB ID

Not Available

ChEBI ID

Not Available

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 4-Ketoretinoic acid glucuronide (HMDB0061689)

MOL for HMDB0061689 (4-Ketoretinoic acid glucuronide)

3D MOL for HMDB0061689 (4-Ketoretinoic acid glucuronide)

3D SDF for HMDB0061689 (4-Ketoretinoic acid glucuronide)

3D-SDF for HMDB0061689 (4-Ketoretinoic acid glucuronide)

PDB for HMDB0061689 (4-Ketoretinoic acid glucuronide)

3D PDB for HMDB0061689 (4-Ketoretinoic acid glucuronide)

SMILES for HMDB0061689 (4-Ketoretinoic acid glucuronide)

INCHI for HMDB0061689 (4-Ketoretinoic acid glucuronide)

Structure for HMDB0061689 (4-Ketoretinoic acid glucuronide)

3D Structure for HMDB0061689 (4-Ketoretinoic acid glucuronide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra