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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (22) Show 22 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:36 UTC

Update Date

2021-09-14 15:39:02 UTC

HMDB ID

HMDB0003141

Secondary Accession Numbers

HMDB03141

Metabolite Identification

Common Name

Retinoyl b-glucuronide

Description

Retinoyl beta-glucuronide is a naturally occurring, biologically active metabolite of vitamin A. Although retinoyl beta-glucuronide is regarded as a detoxification product of retinoic acid, it plays several roles in the functions of vitamin A. It can serve as a source of retinoic acid, and it may be a vehicle for transport of retinoic acid to target tissues. Topically applied retinoyl beta-glucuronide is comparable in efficacy to retinoic acid in the treatment of acne in humans, without the same side effects. Retinoyl beta-glucuronide may or may not be teratogenic, depending on the mode of administration and the species in which it is used. It may be a valuable therapeutic compound for the treatment of skin disorders and certain types of cancers.

Structure

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


  Mrv0541 02231219392D          

 34 35  0  0  1  0            999 V2000
   22.6791  -17.1507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6791  -18.8007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1080  -19.6257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5370  -18.8007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5370  -16.3256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1080  -17.1507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2515  -17.5632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3935  -15.9131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5192   -9.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9317  -10.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6791  -14.6756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2500  -12.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3921  -12.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1067  -10.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3935  -17.5632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.3935  -18.3882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.1080  -18.8007    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.8225  -18.3882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.8225  -17.5632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.3921   -9.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6776  -10.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6776  -10.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5370  -17.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6791  -16.3256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9646  -15.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5356  -12.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9646  -15.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5356  -13.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2500  -14.6756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2500  -13.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8211  -12.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8211  -11.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3921  -11.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1067  -10.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15  1  1  6  0  0  0
  1 24  1  0  0  0  0
 16  2  1  1  0  0  0
 17  3  1  6  0  0  0
 18  4  1  1  0  0  0
  5 23  1  0  0  0  0
  6 15  1  0  0  0  0
  6 19  1  0  0  0  0
  7 23  2  0  0  0  0
  8 24  2  0  0  0  0
  9 14  1  0  0  0  0
 10 14  1  0  0  0  0
 11 25  1  0  0  0  0
 12 26  1  0  0  0  0
 13 33  1  0  0  0  0
 14 20  1  0  0  0  0
 14 34  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 23  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 33  1  0  0  0  0
 24 27  1  0  0  0  0
 25 27  2  0  0  0  0
 25 29  1  0  0  0  0
 26 28  2  0  0  0  0
 26 31  1  0  0  0  0
 28 30  1  0  0  0  0
 29 30  2  0  0  0  0
 31 32  2  0  0  0  0
 32 34  1  0  0  0  0
 33 34  2  0  0  0  0
M  END

HMDB0003141
     RDKit          3D
Retinoyl b-glucuronide
 70 71  0  0  0  0  0  0  0  0999 V2000
   -6.3613    0.5733   -3.7421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7628    1.8664   -4.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5725    2.1984   -3.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0690    1.2215   -2.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9655    1.1854   -1.8901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6724    0.0156   -0.9885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6725   -1.0098   -0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4622   -0.0136   -0.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085   -1.0847    0.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2135   -1.0116    0.9597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8731   -1.9250    1.8579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1166   -3.0673    2.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1244   -1.7380    2.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8813   -2.6278    3.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4346   -3.6325    3.6434 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2194   -2.3207    3.3591 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0854   -3.0971    4.1541 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5413   -2.3620    5.1832 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5268   -1.4571    5.0890 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8998   -0.1141    5.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7149    0.0987    5.5886 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7185    0.9940    5.0307 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1768   -1.4730    3.7281 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.4612   -0.9046    3.9253 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4459   -2.9240    3.4089 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2590   -3.1304    2.3250 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1726   -3.7216    3.2713 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4510   -5.0178    3.7139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0488    3.4721   -3.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7408    4.0003   -3.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0876    4.5326   -3.3829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0675    3.5241   -5.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4721    3.5327   -5.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4163    2.6739   -5.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3209    0.4436   -4.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6230    0.4663   -2.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6649   -0.2511   -4.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6776    0.2968   -2.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2928    1.9967   -1.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9831   -1.3982   -1.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3561   -1.8708   -0.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6008   -0.6091   -0.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7374    0.6148   -0.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5841   -1.9812    0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.1047    0.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9833   -2.9623    2.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4234   -3.9902    1.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2560   -3.1515    3.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6044   -0.8624    1.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5294   -3.9873    4.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3129   -1.6109    5.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4875    1.8416    5.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5756   -0.9358    3.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5582   -0.5034    4.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0082   -3.3132    4.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1511   -3.5489    2.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8360   -3.6504    2.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8411   -5.3023    4.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7294    4.3748   -2.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5522    4.9808   -4.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8306    3.4410   -3.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2326    5.2914   -4.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6995    5.0004   -2.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0350    4.0530   -3.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4448    2.6827   -5.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5697    4.4658   -5.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4136    3.1607   -6.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8333    4.5518   -5.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3156    3.2232   -4.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8245    1.8917   -5.8897 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  2  1  0
 27 17  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  5 39  1  0
  7 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 12 46  1  0
 12 47  1  0
 12 48  1  0
 13 49  1  0
 17 50  1  1
 19 51  1  1
 22 52  1  0
 23 53  1  6
 24 54  1  0
 25 55  1  1
 26 56  1  0
 27 57  1  6
 28 58  1  0
 30 59  1  0
 30 60  1  0
 30 61  1  0
 31 62  1  0
 31 63  1  0
 31 64  1  0
 32 65  1  0
 32 66  1  0
 33 67  1  0
 33 68  1  0
 34 69  1  0
 34 70  1  0
M  END


  Mrv0541 02231219392D          

 34 35  0  0  1  0            999 V2000
   22.6791  -17.1507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6791  -18.8007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1080  -19.6257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5370  -18.8007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5370  -16.3256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1080  -17.1507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2515  -17.5632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3935  -15.9131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5192   -9.4235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9317  -10.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6791  -14.6756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2500  -12.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3921  -12.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1067  -10.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3935  -17.5632    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.3935  -18.3882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.1080  -18.8007    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.8225  -18.3882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.8225  -17.5632    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.3921   -9.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6776  -10.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6776  -10.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5370  -17.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6791  -16.3256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9646  -15.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5356  -12.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9646  -15.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5356  -13.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2500  -14.6756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2500  -13.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8211  -12.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8211  -11.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3921  -11.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1067  -10.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15  1  1  6  0  0  0
  1 24  1  0  0  0  0
 16  2  1  1  0  0  0
 17  3  1  6  0  0  0
 18  4  1  1  0  0  0
  5 23  1  0  0  0  0
  6 15  1  0  0  0  0
  6 19  1  0  0  0  0
  7 23  2  0  0  0  0
  8 24  2  0  0  0  0
  9 14  1  0  0  0  0
 10 14  1  0  0  0  0
 11 25  1  0  0  0  0
 12 26  1  0  0  0  0
 13 33  1  0  0  0  0
 14 20  1  0  0  0  0
 14 34  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 23  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 33  1  0  0  0  0
 24 27  1  0  0  0  0
 25 27  2  0  0  0  0
 25 29  1  0  0  0  0
 26 28  2  0  0  0  0
 26 31  1  0  0  0  0
 28 30  1  0  0  0  0
 29 30  2  0  0  0  0
 31 32  2  0  0  0  0
 32 34  1  0  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003141

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@@H]1[C@@H](O)[C@@H](O[C@H](C(O)=O)[C@H]1O)OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C26H36O8/c1-15(11-12-18-17(3)10-7-13-26(18,4)5)8-6-9-16(2)14-19(27)33-25-22(30)20(28)21(29)23(34-25)24(31)32/h6,8-9,11-12,14,20-23,25,28-30H,7,10,13H2,1-5H3,(H,31,32)/b9-6+,12-11+,15-8+,16-14+/t20-,21-,22+,23-,25+/m0/s1

> <INCHI_KEY>
MTGFYEHKPMOVNE-NEFMKCFNSA-N

> <FORMULA>
C26H36O8

> <MOLECULAR_WEIGHT>
476.5592

> <EXACT_MASS>
476.241018128

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
51.85115996977926

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.57

> <JCHEM_LOGP>
3.2999074889999997

> <ALOGPS_LOGS>
-4.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.212250468844253

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.389209916695899

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6869063371000665

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
130.0894

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glucuronide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0003141
     RDKit          3D
Retinoyl b-glucuronide
 70 71  0  0  0  0  0  0  0  0999 V2000
   -6.3613    0.5733   -3.7421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7628    1.8664   -4.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5725    2.1984   -3.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0690    1.2215   -2.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9655    1.1854   -1.8901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6724    0.0156   -0.9885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6725   -1.0098   -0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4622   -0.0136   -0.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085   -1.0847    0.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2135   -1.0116    0.9597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8731   -1.9250    1.8579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1166   -3.0673    2.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1244   -1.7380    2.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8813   -2.6278    3.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4346   -3.6325    3.6434 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2194   -2.3207    3.3591 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0854   -3.0971    4.1541 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5413   -2.3620    5.1832 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5268   -1.4571    5.0890 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8998   -0.1141    5.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7149    0.0987    5.5886 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7185    0.9940    5.0307 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1768   -1.4730    3.7281 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.4612   -0.9046    3.9253 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4459   -2.9240    3.4089 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2590   -3.1304    2.3250 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1726   -3.7216    3.2713 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4510   -5.0178    3.7139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0488    3.4721   -3.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7408    4.0003   -3.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0876    4.5326   -3.3829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0675    3.5241   -5.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4721    3.5327   -5.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4163    2.6739   -5.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3209    0.4436   -4.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6230    0.4663   -2.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6649   -0.2511   -4.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6776    0.2968   -2.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2928    1.9967   -1.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9831   -1.3982   -1.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3561   -1.8708   -0.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6008   -0.6091   -0.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7374    0.6148   -0.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5841   -1.9812    0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.1047    0.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9833   -2.9623    2.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4234   -3.9902    1.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2560   -3.1515    3.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6044   -0.8624    1.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5294   -3.9873    4.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3129   -1.6109    5.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4875    1.8416    5.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5756   -0.9358    3.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5582   -0.5034    4.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0082   -3.3132    4.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1511   -3.5489    2.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8360   -3.6504    2.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8411   -5.3023    4.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7294    4.3748   -2.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5522    4.9808   -4.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8306    3.4410   -3.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2326    5.2914   -4.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6995    5.0004   -2.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0350    4.0530   -3.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4448    2.6827   -5.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5697    4.4658   -5.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4136    3.1607   -6.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8333    4.5518   -5.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3156    3.2232   -4.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8245    1.8917   -5.8897 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  2  1  0
 27 17  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  5 39  1  0
  7 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 12 46  1  0
 12 47  1  0
 12 48  1  0
 13 49  1  0
 17 50  1  1
 19 51  1  1
 22 52  1  0
 23 53  1  6
 24 54  1  0
 25 55  1  1
 26 56  1  0
 27 57  1  6
 28 58  1  0
 30 59  1  0
 30 60  1  0
 30 61  1  0
 31 62  1  0
 31 63  1  0
 31 64  1  0
 32 65  1  0
 32 66  1  0
 33 67  1  0
 33 68  1  0
 34 69  1  0
 34 70  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      42.334 -32.015   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      42.334 -35.095   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      45.002 -36.635   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      47.669 -35.095   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      47.669 -30.474   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      45.002 -32.015   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      49.003 -32.785   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      43.668 -29.704   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      36.436 -17.591   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      37.206 -18.924   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      42.334 -27.394   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      39.667 -22.774   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      34.332 -22.774   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.666 -18.924   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      43.668 -32.785   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      43.668 -34.325   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      45.002 -35.095   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      46.335 -34.325   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      46.335 -32.785   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      34.332 -18.154   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      32.998 -18.924   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      32.998 -20.464   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      47.669 -32.015   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      42.334 -30.474   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      41.001 -28.164   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      38.333 -23.544   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      41.001 -29.704   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      38.333 -25.084   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      39.667 -27.394   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      39.667 -25.854   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      36.999 -22.774   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      36.999 -21.234   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      34.332 -21.234   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      35.666 -20.464   0.000  0.00  0.00           C+0
CONECT    1   15   24                                                       
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4   18                                                            
CONECT    5   23                                                            
CONECT    6   15   19                                                       
CONECT    7   23                                                            
CONECT    8   24                                                            
CONECT    9   14                                                            
CONECT   10   14                                                            
CONECT   11   25                                                            
CONECT   12   26                                                            
CONECT   13   33                                                            
CONECT   14    9   10   20   34                                             
CONECT   15    1    6   16                                                  
CONECT   16    2   15   17                                                  
CONECT   17    3   16   18                                                  
CONECT   18    4   17   19                                                  
CONECT   19    6   18   23                                                  
CONECT   20   14   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   33                                                       
CONECT   23    5    7   19                                                  
CONECT   24    1    8   27                                                  
CONECT   25   11   27   29                                                  
CONECT   26   12   28   31                                                  
CONECT   27   24   25                                                       
CONECT   28   26   30                                                       
CONECT   29   25   30                                                       
CONECT   30   28   29                                                       
CONECT   31   26   32                                                       
CONECT   32   31   34                                                       
CONECT   33   13   22   34                                                  
CONECT   34   14   32   33                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

COMPND    HMDB0003141
HETATM    1  C1  UNL     1      -6.361   0.573  -3.742  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.763   1.866  -4.103  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.572   2.198  -3.501  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.069   1.221  -2.594  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.966   1.185  -1.890  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.672   0.016  -0.989  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.673  -1.010  -0.740  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.462  -0.014  -0.440  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.008  -1.085   0.475  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.214  -1.012   0.960  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.873  -1.925   1.858  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.117  -3.067   2.433  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.124  -1.738   2.200  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.881  -2.628   3.103  1.00  0.00           C  
HETATM   15  O1  UNL     1       2.435  -3.633   3.643  1.00  0.00           O  
HETATM   16  O2  UNL     1       4.219  -2.321   3.359  1.00  0.00           O  
HETATM   17  C15 UNL     1       5.085  -3.097   4.154  1.00  0.00           C  
HETATM   18  O3  UNL     1       5.541  -2.362   5.183  1.00  0.00           O  
HETATM   19  C16 UNL     1       6.527  -1.457   5.089  1.00  0.00           C  
HETATM   20  C17 UNL     1       5.900  -0.114   5.260  1.00  0.00           C  
HETATM   21  O4  UNL     1       4.715   0.099   5.589  1.00  0.00           O  
HETATM   22  O5  UNL     1       6.719   0.994   5.031  1.00  0.00           O  
HETATM   23  C18 UNL     1       7.177  -1.473   3.728  1.00  0.00           C  
HETATM   24  O6  UNL     1       8.461  -0.905   3.925  1.00  0.00           O  
HETATM   25  C19 UNL     1       7.446  -2.924   3.409  1.00  0.00           C  
HETATM   26  O7  UNL     1       8.259  -3.130   2.325  1.00  0.00           O  
HETATM   27  C20 UNL     1       6.173  -3.722   3.271  1.00  0.00           C  
HETATM   28  O8  UNL     1       6.451  -5.018   3.714  1.00  0.00           O  
HETATM   29  C21 UNL     1      -4.049   3.472  -3.862  1.00  0.00           C  
HETATM   30  C22 UNL     1      -2.741   4.000  -3.457  1.00  0.00           C  
HETATM   31  C23 UNL     1      -5.088   4.533  -3.383  1.00  0.00           C  
HETATM   32  C24 UNL     1      -4.067   3.524  -5.414  1.00  0.00           C  
HETATM   33  C25 UNL     1      -5.472   3.533  -5.917  1.00  0.00           C  
HETATM   34  C26 UNL     1      -6.416   2.674  -5.131  1.00  0.00           C  
HETATM   35  H1  UNL     1      -7.321   0.444  -4.299  1.00  0.00           H  
HETATM   36  H2  UNL     1      -6.623   0.466  -2.666  1.00  0.00           H  
HETATM   37  H3  UNL     1      -5.665  -0.251  -4.004  1.00  0.00           H  
HETATM   38  H4  UNL     1      -4.678   0.297  -2.395  1.00  0.00           H  
HETATM   39  H5  UNL     1      -2.293   1.997  -1.959  1.00  0.00           H  
HETATM   40  H6  UNL     1      -3.983  -1.398  -1.751  1.00  0.00           H  
HETATM   41  H7  UNL     1      -3.356  -1.871  -0.175  1.00  0.00           H  
HETATM   42  H8  UNL     1      -4.601  -0.609  -0.237  1.00  0.00           H  
HETATM   43  H9  UNL     1      -0.737   0.615  -0.896  1.00  0.00           H  
HETATM   44  H10 UNL     1      -1.584  -1.981   0.629  1.00  0.00           H  
HETATM   45  H11 UNL     1       0.785  -0.105   0.587  1.00  0.00           H  
HETATM   46  H12 UNL     1      -0.983  -2.962   2.238  1.00  0.00           H  
HETATM   47  H13 UNL     1       0.423  -3.990   1.908  1.00  0.00           H  
HETATM   48  H14 UNL     1       0.256  -3.151   3.535  1.00  0.00           H  
HETATM   49  H15 UNL     1       2.604  -0.862   1.760  1.00  0.00           H  
HETATM   50  H16 UNL     1       4.529  -3.987   4.590  1.00  0.00           H  
HETATM   51  H17 UNL     1       7.313  -1.611   5.888  1.00  0.00           H  
HETATM   52  H18 UNL     1       6.487   1.842   5.555  1.00  0.00           H  
HETATM   53  H19 UNL     1       6.576  -0.936   3.008  1.00  0.00           H  
HETATM   54  H20 UNL     1       8.558  -0.503   4.830  1.00  0.00           H  
HETATM   55  H21 UNL     1       8.008  -3.313   4.318  1.00  0.00           H  
HETATM   56  H22 UNL     1       9.151  -3.549   2.536  1.00  0.00           H  
HETATM   57  H23 UNL     1       5.836  -3.650   2.229  1.00  0.00           H  
HETATM   58  H24 UNL     1       5.841  -5.302   4.458  1.00  0.00           H  
HETATM   59  H25 UNL     1      -2.729   4.375  -2.399  1.00  0.00           H  
HETATM   60  H26 UNL     1      -2.552   4.981  -4.047  1.00  0.00           H  
HETATM   61  H27 UNL     1      -1.831   3.441  -3.594  1.00  0.00           H  
HETATM   62  H28 UNL     1      -5.233   5.291  -4.163  1.00  0.00           H  
HETATM   63  H29 UNL     1      -4.700   5.000  -2.467  1.00  0.00           H  
HETATM   64  H30 UNL     1      -6.035   4.053  -3.126  1.00  0.00           H  
HETATM   65  H31 UNL     1      -3.445   2.683  -5.737  1.00  0.00           H  
HETATM   66  H32 UNL     1      -3.570   4.466  -5.683  1.00  0.00           H  
HETATM   67  H33 UNL     1      -5.414   3.161  -6.991  1.00  0.00           H  
HETATM   68  H34 UNL     1      -5.833   4.552  -5.973  1.00  0.00           H  
HETATM   69  H35 UNL     1      -7.316   3.223  -4.848  1.00  0.00           H  
HETATM   70  H36 UNL     1      -6.824   1.892  -5.890  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3    3   34
CONECT    3    4   29
CONECT    4    5    5   38
CONECT    5    6   39
CONECT    6    7    8    8
CONECT    7   40   41   42
CONECT    8    9   43
CONECT    9   10   10   44
CONECT   10   11   45
CONECT   11   12   13   13
CONECT   12   46   47   48
CONECT   13   14   49
CONECT   14   15   15   16
CONECT   16   17
CONECT   17   18   27   50
CONECT   18   19
CONECT   19   20   23   51
CONECT   20   21   21   22
CONECT   22   52
CONECT   23   24   25   53
CONECT   24   54
CONECT   25   26   27   55
CONECT   26   56
CONECT   27   28   57
CONECT   28   58
CONECT   29   30   31   32
CONECT   30   59   60   61
CONECT   31   62   63   64
CONECT   32   33   65   66
CONECT   33   34   67   68
CONECT   34   69   70
END

HMDB0003141
     RDKit          3D
Retinoyl b-glucuronide
 70 71  0  0  0  0  0  0  0  0999 V2000
   -6.3613    0.5733   -3.7421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7628    1.8664   -4.1030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5725    2.1984   -3.5012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0690    1.2215   -2.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9655    1.1854   -1.8901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6724    0.0156   -0.9885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6725   -1.0098   -0.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4622   -0.0136   -0.4403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085   -1.0847    0.4750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2135   -1.0116    0.9597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8731   -1.9250    1.8579 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1166   -3.0673    2.4334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1244   -1.7380    2.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8813   -2.6278    3.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4346   -3.6325    3.6434 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2194   -2.3207    3.3591 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0854   -3.0971    4.1541 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5413   -2.3620    5.1832 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5268   -1.4571    5.0890 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8998   -0.1141    5.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7149    0.0987    5.5886 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7185    0.9940    5.0307 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1768   -1.4730    3.7281 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.4612   -0.9046    3.9253 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4459   -2.9240    3.4089 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2590   -3.1304    2.3250 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1726   -3.7216    3.2713 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4510   -5.0178    3.7139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0488    3.4721   -3.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7408    4.0003   -3.4575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0876    4.5326   -3.3829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0675    3.5241   -5.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4721    3.5327   -5.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4163    2.6739   -5.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3209    0.4436   -4.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6230    0.4663   -2.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6649   -0.2511   -4.0038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6776    0.2968   -2.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2928    1.9967   -1.9593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9831   -1.3982   -1.7509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3561   -1.8708   -0.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6008   -0.6091   -0.2374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7374    0.6148   -0.8963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5841   -1.9812    0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.1047    0.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9833   -2.9623    2.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4234   -3.9902    1.9084 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2560   -3.1515    3.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6044   -0.8624    1.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5294   -3.9873    4.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3129   -1.6109    5.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4875    1.8416    5.5549 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5756   -0.9358    3.0078 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5582   -0.5034    4.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0082   -3.3132    4.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1511   -3.5489    2.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8360   -3.6504    2.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8411   -5.3023    4.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7294    4.3748   -2.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5522    4.9808   -4.0472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8306    3.4410   -3.5938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2326    5.2914   -4.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6995    5.0004   -2.4670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0350    4.0530   -3.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4448    2.6827   -5.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5697    4.4658   -5.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4136    3.1607   -6.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8333    4.5518   -5.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3156    3.2232   -4.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8245    1.8917   -5.8897 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  2  1  0
 27 17  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  5 39  1  0
  7 40  1  0
  7 41  1  0
  7 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 12 46  1  0
 12 47  1  0
 12 48  1  0
 13 49  1  0
 17 50  1  1
 19 51  1  1
 22 52  1  0
 23 53  1  6
 24 54  1  0
 25 55  1  1
 26 56  1  0
 27 57  1  6
 28 58  1  0
 30 59  1  0
 30 60  1  0
 30 61  1  0
 31 62  1  0
 31 63  1  0
 31 64  1  0
 32 65  1  0
 32 66  1  0
 33 67  1  0
 33 68  1  0
 34 69  1  0
 34 70  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
all-trans-Retinoyl-beta-glucuronide	ChEBI
Retinoyl glucuronide	ChEBI
all-trans-Retinoyl-b-glucuronide	Generator
all-trans-Retinoyl-β-glucuronide	Generator
13-cis-Retinoate	HMDB
13-cis-Retinoic acid	HMDB
13-cis-Retinoic acid acyl beta-D-glucuronide	HMDB
13-cis-Retinoic acid acyl beta-delta-glucuronide	HMDB
13-cis-Retinoyl glucuronide	HMDB
13-cis-Retinoyl-beta-D-glucuronide	HMDB
13-cis-Retinoyl-beta-delta-glucuronide	HMDB
13-cis-Retinoyl-beta-glucuronide	HMDB
9-cis-Retinoyl-beta-D-glucuronide	HMDB
9-cis-Retinoyl-beta-delta-glucuronide	HMDB
all-trans-Retinoyl-beta-D-glucuronide	HMDB
all-trans-Retinoyl-beta-delta-glucuronide	HMDB
Glucuronide	HMDB
Retinoate	HMDB
Retinoic acid	HMDB
Retinoic acid beta-D-glucuronide	HMDB
Retinoic acid beta-delta-glucuronide	HMDB
Retinoyl beta-glucuronide	HMDB
Retinoyl-beta-glucuronide	HMDB
trans-Retinoyl glucuronide	MeSH, HMDB

Chemical Formula

C₂₆H₃₆O₈

Average Molecular Weight

476.5592

Monoisotopic Molecular Weight

476.241018128

IUPAC Name

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

Traditional Name

glucuronide

CAS Registry Number

401-10-5

SMILES

O[C@@H]1[C@@H](O)[C@@H](O[C@H](C(O)=O)[C@H]1O)OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

InChI Identifier

InChI=1S/C26H36O8/c1-15(11-12-18-17(3)10-7-13-26(18,4)5)8-6-9-16(2)14-19(27)33-25-22(30)20(28)21(29)23(34-25)24(31)32/h6,8-9,11-12,14,20-23,25,28-30H,7,10,13H2,1-5H3,(H,31,32)/b9-6+,12-11+,15-8+,16-14+/t20-,21-,22+,23-,25+/m0/s1

InChI Key

MTGFYEHKPMOVNE-NEFMKCFNSA-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
Dicarboxylic acid or derivatives
Fatty acyl
Hydroxy acid
Monosaccharide
Oxane
Pyran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organoheterocyclic compound
Polyol
Oxacycle
Acetal
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

glucuronic acids (CHEBI:28870 )

Ontology

Not Available

Adipose Tissue (HMDB: HMDB0003141)

Epithelium

Epidermis (HMDB: HMDB0003141)

Cell

Fibroblasts (HMDB: HMDB0003141)

Fibroblast

Fibroblast (HMDB: HMDB0003141)

Organ

Biofluid or Excreta

Non-excretory biofluid

Blood (PMID: 2756924)

Excreta

Urine (HMDB: HMDB0003141)

Blood (HMDB: HMDB0003141)
Urine (HMDB: HMDB0003141)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0003141)

Cytoplasm (HMDB: HMDB0003141)
Extracellular (HMDB: HMDB0003141)
Membrane (HMDB: HMDB0003141)
Endoplasmic reticulum (HMDB: HMDB0003141)
Kidney (HMDB: HMDB0003141)
Liver (HMDB: HMDB0003141)
Intestine (HMDB: HMDB0003141)
Pancreas (HMDB: HMDB0003141)
Skin (HMDB: HMDB0003141)
Cell membrane (HMDB: HMDB0003141)

Tissue substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0003141)

Source

Endogenous

Endogenous (HMDB: HMDB0003141)

Animal

Animal (HMDB: HMDB0003141)

Exogenous

Food

Food (HMDB: HMDB0003141)

Animal origin

Poultry

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

Role

Biological role

Membrane stabilizer (HMDB: HMDB0003141)

Nutrient

Nutrient (HMDB: HMDB0003141)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0003141)

Emulsifier (HMDB: HMDB0003141)

Physical Properties

State

Solid

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	0.046 g/L	ALOGPS
logP	3.57	ALOGPS
logP	3.3	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	3.39	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	130.09 m³·mol⁻¹	ChemAxon
Polarizability	51.85 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
DarkChem	[M+H]+	217.695	31661259
DarkChem	[M-H]-	209.286	31661259
DeepCCS	[M+H]+	218.507	30932474
DeepCCS	[M-H]-	216.612	30932474
DeepCCS	[M-2H]-	249.852	30932474
DeepCCS	[M+Na]+	224.136	30932474
AllCCS	[M+H]+	220.7	32859911
AllCCS	[M+H-H2O]+	218.6	32859911
AllCCS	[M+NH4]+	222.6	32859911
AllCCS	[M+Na]+	223.2	32859911
AllCCS	[M-H]-	214.5	32859911
AllCCS	[M+Na-2H]-	216.6	32859911
AllCCS	[M+HCOO]-	219.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Retinoyl b-glucuronide	O[C@@H]1[C@@H](O)[C@@H](O[C@H](C(O)=O)[C@H]1O)OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C	5236.0	Standard polar	33892256
Retinoyl b-glucuronide	O[C@@H]1[C@@H](O)[C@@H](O[C@H](C(O)=O)[C@H]1O)OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C	3534.3	Standard non polar	33892256
Retinoyl b-glucuronide	O[C@@H]1[C@@H](O)[C@@H](O[C@H](C(O)=O)[C@H]1O)OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C	3846.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Retinoyl b-glucuronide,1TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)C(C)(C)CCC1	3755.3	Semi standard non polar	33892256
Retinoyl b-glucuronide,1TMS,isomer #2	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)C(C)(C)CCC1	3766.5	Semi standard non polar	33892256
Retinoyl b-glucuronide,1TMS,isomer #3	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)C(C)(C)CCC1	3728.3	Semi standard non polar	33892256
Retinoyl b-glucuronide,1TMS,isomer #4	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)C(C)(C)CCC1	3753.6	Semi standard non polar	33892256
Retinoyl b-glucuronide,2TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O)C(C)(C)CCC1	3701.5	Semi standard non polar	33892256
Retinoyl b-glucuronide,2TMS,isomer #2	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O)C(C)(C)CCC1	3700.9	Semi standard non polar	33892256
Retinoyl b-glucuronide,2TMS,isomer #3	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C(C)(C)CCC1	3704.8	Semi standard non polar	33892256
Retinoyl b-glucuronide,2TMS,isomer #4	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C)C(C)(C)CCC1	3702.8	Semi standard non polar	33892256
Retinoyl b-glucuronide,2TMS,isomer #5	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)C(C)(C)CCC1	3711.0	Semi standard non polar	33892256
Retinoyl b-glucuronide,2TMS,isomer #6	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O)C(C)(C)CCC1	3701.0	Semi standard non polar	33892256
Retinoyl b-glucuronide,3TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O)C(C)(C)CCC1	3666.9	Semi standard non polar	33892256
Retinoyl b-glucuronide,3TMS,isomer #2	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C(C)(C)CCC1	3675.2	Semi standard non polar	33892256
Retinoyl b-glucuronide,3TMS,isomer #3	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C(C)(C)CCC1	3691.6	Semi standard non polar	33892256
Retinoyl b-glucuronide,3TMS,isomer #4	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C)C(C)(C)CCC1	3683.0	Semi standard non polar	33892256
Retinoyl b-glucuronide,4TMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]2O[Si](C)(C)C)C(C)(C)CCC1	3660.4	Semi standard non polar	33892256
Retinoyl b-glucuronide,1TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C(C)(C)CCC1	3972.8	Semi standard non polar	33892256
Retinoyl b-glucuronide,1TBDMS,isomer #2	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C(C)(C)CCC1	3985.2	Semi standard non polar	33892256
Retinoyl b-glucuronide,1TBDMS,isomer #3	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O)C(C)(C)CCC1	3963.1	Semi standard non polar	33892256
Retinoyl b-glucuronide,1TBDMS,isomer #4	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O)C(C)(C)CCC1	3971.5	Semi standard non polar	33892256
Retinoyl b-glucuronide,2TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C(C)(C)CCC1	4136.6	Semi standard non polar	33892256
Retinoyl b-glucuronide,2TBDMS,isomer #2	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C(C)(C)CCC1	4131.9	Semi standard non polar	33892256
Retinoyl b-glucuronide,2TBDMS,isomer #3	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C(C)(C)CCC1	4137.1	Semi standard non polar	33892256
Retinoyl b-glucuronide,2TBDMS,isomer #4	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C(C)(C)CCC1	4139.7	Semi standard non polar	33892256
Retinoyl b-glucuronide,2TBDMS,isomer #5	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C(C)(C)CCC1	4140.2	Semi standard non polar	33892256
Retinoyl b-glucuronide,2TBDMS,isomer #6	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O)C(C)(C)CCC1	4139.5	Semi standard non polar	33892256
Retinoyl b-glucuronide,3TBDMS,isomer #1	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C(C)(C)CCC1	4278.8	Semi standard non polar	33892256
Retinoyl b-glucuronide,3TBDMS,isomer #2	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C(C)(C)CCC1	4291.5	Semi standard non polar	33892256
Retinoyl b-glucuronide,3TBDMS,isomer #3	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C(C)(C)CCC1	4290.9	Semi standard non polar	33892256
Retinoyl b-glucuronide,3TBDMS,isomer #4	CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[C@@H]2O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C(C)(C)CCC1	4313.7	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 - Retinoyl b-glucuronide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9432400000-25dd7257fa97ce57c686	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Retinoyl b-glucuronide GC-MS (3 TMS) - 70eV, Positive	splash10-004i-3051009000-fd7898490f7303f898cc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Retinoyl b-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 - Retinoyl b-glucuronide 10V, Positive-QTOF	splash10-0ke9-0693400000-31eed182f08fe6786169	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 20V, Positive-QTOF	splash10-052u-0891000000-ca789901418c22bb0493	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 40V, Positive-QTOF	splash10-000i-1920000000-e38e08d95bad4a423551	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 10V, Negative-QTOF	splash10-001i-1190200000-9141a0351cb4c8689ff4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 20V, Negative-QTOF	splash10-000t-3690100000-f02b84b6d3b8cceeb6cf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 40V, Negative-QTOF	splash10-0535-8590000000-12eae5811075d2fce9f9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 10V, Positive-QTOF	splash10-057r-0565900000-0aac4f4c541ab0976b56	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 20V, Positive-QTOF	splash10-009f-0923100000-bb8c1ba6dc7f05b15be7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 40V, Positive-QTOF	splash10-0ac0-2900000000-b37fb8c36dde85ab4488	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 10V, Negative-QTOF	splash10-0059-0390700000-eddabec40f40511d435f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 20V, Negative-QTOF	splash10-0a6s-2391400000-4b33ff2150a642a78136	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinoyl b-glucuronide 40V, Negative-QTOF	splash10-0r01-3390000000-158c7d14c4f6713d87da	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)
Endoplasmic reticulum

Biospecimen Locations

Blood
Urine

Tissue Locations

Adipose Tissue
Epidermis
Fibroblasts
Intestine
Kidney
Liver
Pancreas
Placenta

Pathways

Name	SMPDB/PathBank	KEGG
Retinol Metabolism
Vitamin A Deficiency		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0066 +/- 0.0025 uM	Adult (>18 years old)	Both	Normal	2756924	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

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

FDB023112

KNApSAcK ID

Not Available

Chemspider ID

4445170

KEGG Compound ID

C11061

BioCyc ID

Not Available

BiGG ID

2304843

Wikipedia Link

Not Available

METLIN ID

2280

PubChem Compound

5281877

PDB ID

Not Available

ChEBI ID

28870

Food Biomarker Ontology

Not Available

VMH ID

RETNGLC

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Yamanaka H, Nakajima M, Katoh M, Kanoh A, Tamura O, Ishibashi H, Yokoi T: Trans-3'-hydroxycotinine O- and N-glucuronidations in human liver microsomes. Drug Metab Dispos. 2005 Jan;33(1):23-30. Epub 2004 Oct 6. [PubMed:15470160 ]
Matsushima S, Maeda K, Kondo C, Hirano M, Sasaki M, Suzuki H, Sugiyama Y: Identification of the hepatic efflux transporters of organic anions using double-transfected Madin-Darby canine kidney II cells expressing human organic anion-transporting polypeptide 1B1 (OATP1B1)/multidrug resistance-associated protein 2, OATP1B1/multidrug resistance 1, and OATP1B1/breast cancer resistance protein. J Pharmacol Exp Ther. 2005 Sep;314(3):1059-67. Epub 2005 May 18. [PubMed:15901800 ]
Kosoglou T, Statkevich P, Johnson-Levonas AO, Paolini JF, Bergman AJ, Alton KB: Ezetimibe: a review of its metabolism, pharmacokinetics and drug interactions. Clin Pharmacokinet. 2005;44(5):467-94. [PubMed:15871634 ]
Kochansky CJ, Xia YQ, Wang S, Cato B, Creighton M, Vincent SH, Franklin RB, Reed JR: Species differences in the elimination of a peroxisome proliferator-activated receptor agonist highlighted by oxidative metabolism of its acyl glucuronide. Drug Metab Dispos. 2005 Dec;33(12):1894-904. Epub 2005 Sep 23. [PubMed:16183782 ]
Ghosal A, Yuan Y, Hapangama N, Su AD, Alvarez N, Chowdhury SK, Alton KB, Patrick JE, Zbaida S: Identification of human UDP-glucuronosyltransferase enzyme(s) responsible for the glucuronidation of 3-hydroxydesloratadine. Biopharm Drug Dispos. 2004 Sep;25(6):243-52. [PubMed:15334623 ]
Brunelle FM, Verbeeck RK: Glucuronidation of diflunisal in liver and kidney microsomes of rat and man. Xenobiotica. 1996 Feb;26(2):123-31. [PubMed:8867997 ]
Niles RM, Cook CP, Meadows GG, Fu YM, McLaughlin JL, Rankin GO: Resveratrol is rapidly metabolized in athymic (nu/nu) mice and does not inhibit human melanoma xenograft tumor growth. J Nutr. 2006 Oct;136(10):2542-6. [PubMed:16988123 ]
Sass JO, Masgrau E, Saurat JH, Nau H: Metabolism of oral 9-cis-retinoic acid in the human. Identification of 9-cis-retinoyl-beta-glucuronide and 9-cis-4-oxo-retinoyl-beta-glucuronide as urinary metabolites. Drug Metab Dispos. 1995 Sep;23(9):887-91. [PubMed:8565776 ]
Calabrese CR, Loadman PM, Lim LS, Bibby MC, Double JA, Brown JE, Lamb JH: In vivo metabolism of the antitumor imidazoacridinone C1311 in the mouse and in vitro comparison with humans. Drug Metab Dispos. 1999 Feb;27(2):240-5. [PubMed:9929509 ]
Sperker B, Murdter TE, Schick M, Eckhardt K, Bosslet K, Kroemer HK: Interindividual variability in expression and activity of human beta-glucuronidase in liver and kidney: consequences for drug metabolism. J Pharmacol Exp Ther. 1997 May;281(2):914-20. [PubMed:9152401 ]
Moss T, Howes D, Williams FM: Percutaneous penetration and dermal metabolism of triclosan (2,4, 4'-trichloro-2'-hydroxydiphenyl ether). Food Chem Toxicol. 2000 Apr;38(4):361-70. [PubMed:10722890 ]
Cunha PD, Lord RS, Johnson ST, Wilker PR, Aster RH, Bougie DW: Immune hemolytic anemia caused by sensitivity to a metabolite of etodolac, a nonsteroidal anti-inflammatory drug. Transfusion. 2000 Jun;40(6):663-8. [PubMed:10864985 ]
Nordin C, Bertilsson L: Active hydroxymetabolites of antidepressants. Emphasis on E-10-hydroxy-nortriptyline. Clin Pharmacokinet. 1995 Jan;28(1):26-40. [PubMed:7712660 ]
Johnson AG, Rigby RJ, Taylor PJ, Jones CE, Allen J, Franzen K, Falk MC, Nicol D: The kinetics of mycophenolic acid and its glucuronide metabolite in adult kidney transplant recipients. Clin Pharmacol Ther. 1999 Nov;66(5):492-500. [PubMed:10579476 ]
Oswald S, Haenisch S, Fricke C, Sudhop T, Remmler C, Giessmann T, Jedlitschky G, Adam U, Dazert E, Warzok R, Wacke W, Cascorbi I, Kroemer HK, Weitschies W, von Bergmann K, Siegmund W: Intestinal expression of P-glycoprotein (ABCB1), multidrug resistance associated protein 2 (ABCC2), and uridine diphosphate-glucuronosyltransferase 1A1 predicts the disposition and modulates the effects of the cholesterol absorption inhibitor ezetimibe in humans. Clin Pharmacol Ther. 2006 Mar;79(3):206-17. Epub 2006 Feb 7. [PubMed:16513445 ]
Kenny JR, Maggs JL, Tettey JN, Harrell AW, Parker SG, Clarke SE, Park BK: Formation and protein binding of the acyl glucuronide of a leukotriene B4 antagonist (SB-209247): relation to species differences in hepatotoxicity. Drug Metab Dispos. 2005 Feb;33(2):271-81. Epub 2004 Nov 2. [PubMed:15523047 ]
Qiao GL, Williams PL, Riviere JE: Percutaneous absorption, biotransformation, and systemic disposition of parathion in vivo in swine. I. Comprehensive pharmacokinetic model. Drug Metab Dispos. 1994 May-Jun;22(3):459-71. [PubMed:8070325 ]
Ethell BT, Riedel J, Englert H, Jantz H, Oekonomopulos R, Burchell B: Glucuronidation of HMR1098 in human microsomes: evidence for the involvement of UGT1A1 in the formation of S-glucuronides. Drug Metab Dispos. 2003 Aug;31(8):1027-34. [PubMed:12867491 ]
Andersen A: Final report on the safety assessment of sodium p-chloro-m-cresol, p-chloro-m-cresol, chlorothymol, mixed cresols, m-cresol, o-cresol, p-cresol, isopropyl cresols, thymol, o-cymen-5-ol, and carvacrol. Int J Toxicol. 2006;25 Suppl 1:29-127. [PubMed:16835130 ]
Sallustio BC, Sabordo L, Evans AM, Nation RL: Hepatic disposition of electrophilic acyl glucuronide conjugates. Curr Drug Metab. 2000 Sep;1(2):163-80. [PubMed:11465081 ]

Only showing the first 10 proteins. There are 22 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 2B28

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:: UGT2B28
Uniprot ID:: Q9BY64
Molecular weight:: 38742.9

Reactions

all-trans-Retinoic acid + Uridine diphosphate glucuronic acid → Retinoyl b-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

2. UDP-glucuronosyltransferase 2B4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:: UGT2B4
Uniprot ID:: P06133
Molecular weight:: 60512.035

Reactions

all-trans-Retinoic acid + Uridine diphosphate glucuronic acid → Retinoyl b-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

3. UDP-glucuronosyltransferase 1-4

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:: UGT1A4
Uniprot ID:: P22310
Molecular weight:: 60024.535

Reactions

all-trans-Retinoic acid + Uridine diphosphate glucuronic acid → Retinoyl b-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

4. UDP-glucuronosyltransferase 2B10

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:: UGT2B10
Uniprot ID:: P36537
Molecular weight:: 60773.485

Reactions

all-trans-Retinoic acid + Uridine diphosphate glucuronic acid → Retinoyl b-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

5. UDP-glucuronosyltransferase 2B7

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:: UGT2B7
Uniprot ID:: P16662
Molecular weight:: 60720.15

Reactions

all-trans-Retinoic acid + Uridine diphosphate glucuronic acid → Retinoyl b-glucuronide + Uridine 5'-diphosphate	details

References

Gestl SA, Green MD, Shearer DA, Frauenhoffer E, Tephly TR, Weisz J: Expression of UGT2B7, a UDP-glucuronosyltransferase implicated in the metabolism of 4-hydroxyestrone and all-trans retinoic acid, in normal human breast parenchyma and in invasive and in situ breast cancers. Am J Pathol. 2002 Apr;160(4):1467-79. [PubMed:11943730 ]

Enzyme Details

6. UDP-glucuronosyltransferase 2B15

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:: UGT2B15
Uniprot ID:: P54855
Molecular weight:: 61035.815

Reactions

all-trans-Retinoic acid + Uridine diphosphate glucuronic acid → Retinoyl b-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

7. UDP-glucuronosyltransferase 2A1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:: UGT2A1
Uniprot ID:: Q9Y4X1
Molecular weight:: 60771.605

Reactions

all-trans-Retinoic acid + Uridine diphosphate glucuronic acid → Retinoyl b-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

8. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

all-trans-Retinoic acid + Uridine diphosphate glucuronic acid → Retinoyl b-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

9. UDP-glucuronosyltransferase 1-9

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:: UGT1A9
Uniprot ID:: O60656
Molecular weight:: 59940.495

Reactions

all-trans-Retinoic acid + Uridine diphosphate glucuronic acid → Retinoyl b-glucuronide + Uridine 5'-diphosphate	details

Enzyme Details

10. UDP-glucuronosyltransferase 1-8

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:: UGT1A8
Uniprot ID:: Q9HAW9
Molecular weight:: 59741.035

Reactions

all-trans-Retinoic acid + Uridine diphosphate glucuronic acid → Retinoyl b-glucuronide + Uridine 5'-diphosphate	details

Only showing the first 10 proteins. There are 22 proteins in total.

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Showing metabocard for Retinoyl b-glucuronide (HMDB0003141)

MOL for HMDB0003141 (Retinoyl b-glucuronide)

3D MOL for HMDB0003141 (Retinoyl b-glucuronide)

3D SDF for HMDB0003141 (Retinoyl b-glucuronide)

3D-SDF for HMDB0003141 (Retinoyl b-glucuronide)

PDB for HMDB0003141 (Retinoyl b-glucuronide)

3D PDB for HMDB0003141 (Retinoyl b-glucuronide)

SMILES for HMDB0003141 (Retinoyl b-glucuronide)

INCHI for HMDB0003141 (Retinoyl b-glucuronide)

Structure for HMDB0003141 (Retinoyl b-glucuronide)

3D Structure for HMDB0003141 (Retinoyl b-glucuronide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

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GC-MS Spectra

MS/MS Spectra

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