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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

2008-09-15 17:30:22 UTC

Update Date

2021-09-14 15:39:02 UTC

HMDB ID

HMDB0010340

Secondary Accession Numbers

HMDB10340

Metabolite Identification

Common Name

Retinyl beta-glucuronide

Description

Retinyl beta-glucuronide is a natural human metabolite of retinoic acid generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.

Structure

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


  Mrv0541 02241200512D          

 33 34  0  0  1  0            999 V2000
   18.4775  -10.8034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0485  -10.8034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4775  -13.2785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9064  -12.4535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0485  -12.4535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9064   -9.9784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6209  -11.2159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6195   -5.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9050   -4.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9050   -3.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3341   -4.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6195   -3.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3341   -3.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2070   -5.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0320   -5.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4775  -12.4535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.1920  -12.0410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7630  -12.0410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.0485   -5.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1920  -11.2159    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0485   -3.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7630  -11.2159    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0485   -5.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9064  -10.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7630   -6.2658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0485   -9.9784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3341   -9.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4775   -5.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7630   -7.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3341   -8.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0485   -7.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0485   -8.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6195   -8.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  1 22  1  0  0  0  0
 22  2  1  6  0  0  0
  2 26  1  0  0  0  0
 16  3  1  6  0  0  0
 17  4  1  1  0  0  0
 18  5  1  1  0  0  0
  6 24  1  0  0  0  0
  7 24  2  0  0  0  0
  8  9  1  0  0  0  0
  8 11  1  0  0  0  0
  8 14  1  0  0  0  0
  8 15  1  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  2  0  0  0  0
 11 19  1  0  0  0  0
 12 13  1  0  0  0  0
 13 21  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 20 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 28  1  0  0  0  0
 25 29  2  0  0  0  0
 26 27  1  0  0  0  0
 27 30  2  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 31 32  2  0  0  0  0
M  END

HMDB0010340
     RDKit          3D
Retinyl beta-glucuronide
 71 72  0  0  0  0  0  0  0  0999 V2000
   -6.4817    0.5588    2.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2035    0.8524    1.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9461    0.6358    0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9719    0.1396    1.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1627   -0.2571    2.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2112   -0.7338    3.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6367   -1.4948    4.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9274   -0.6965    2.9976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4082   -0.1564    1.7713 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9306   -0.1295    1.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5353    0.3853    0.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7514    0.8786   -0.7395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8442    0.4414    0.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7885   -0.0378    1.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5178   -1.0658    0.6467 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3483   -0.5334   -0.3619 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9036   -0.7713   -1.6220 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7738   -0.2751   -2.5918 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1958   -0.5057   -3.9529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9301   -0.5684   -4.0539 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9532   -0.6603   -5.0926 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1230   -0.8272   -2.5044 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0838    0.1916   -2.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4876   -1.4919   -1.2106 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2406   -2.8812   -1.3242 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7494   -0.9094   -0.0324 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4725    0.1040    0.5858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6798    0.7821   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5413   -0.1409   -1.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4080    2.1905   -1.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8988    0.2587   -1.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0910    1.1051   -1.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2662    1.3597    0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8658    1.2118    3.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5781    0.7855    2.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3642   -0.5210    2.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9899    0.1870    0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1400   -0.2588    3.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5000   -2.1200    4.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0279   -0.8100    5.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8265   -2.1113    4.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2366   -1.1218    3.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9565    0.2284    0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5174   -0.5526    2.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2786    0.5111   -1.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2332    0.3753   -0.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851    1.9623   -0.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3099    0.8224   -0.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3090   -0.4454    2.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4895    0.7915    1.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2284    0.5938   -0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7793    0.8438   -2.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0153   -1.6714   -5.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2866   -1.5625   -3.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9055    1.0095   -2.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5619   -1.4083   -1.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2126   -3.2651   -0.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7232   -1.7478    0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9015    0.5271    1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7781   -0.3427   -2.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5570    0.3389   -1.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6242   -1.0543   -0.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6360    2.6556   -0.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2906    2.8366   -1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9035    2.1653   -2.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6771    0.1652   -2.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1071   -0.7841   -1.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0267    0.6101   -1.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0132    2.0465   -1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2423    0.8919    0.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4240    2.4704    0.2643 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  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
  3 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
 31 32  1  0
 32 33  1  0
 33  2  1  0
 26 16  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  5 38  1  0
  7 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 12 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 16 51  1  1
 18 52  1  1
 21 53  1  0
 22 54  1  6
 23 55  1  0
 24 56  1  1
 25 57  1  0
 26 58  1  1
 27 59  1  0
 29 60  1  0
 29 61  1  0
 29 62  1  0
 30 63  1  0
 30 64  1  0
 30 65  1  0
 31 66  1  0
 31 67  1  0
 32 68  1  0
 32 69  1  0
 33 70  1  0
 33 71  1  0
M  END


  Mrv0541 02241200512D          

 33 34  0  0  1  0            999 V2000
   18.4775  -10.8034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0485  -10.8034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4775  -13.2785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9064  -12.4535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0485  -12.4535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9064   -9.9784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6209  -11.2159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6195   -5.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9050   -4.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9050   -3.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3341   -4.6158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6195   -3.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3341   -3.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2070   -5.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0320   -5.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4775  -12.4535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.1920  -12.0410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.7630  -12.0410    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.0485   -5.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1920  -11.2159    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0485   -3.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7630  -11.2159    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.0485   -5.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9064  -10.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7630   -6.2658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0485   -9.9784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3341   -9.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4775   -5.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7630   -7.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3341   -8.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0485   -7.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0485   -8.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6195   -8.3283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 20  1  0  0  0  0
  1 22  1  0  0  0  0
 22  2  1  6  0  0  0
  2 26  1  0  0  0  0
 16  3  1  6  0  0  0
 17  4  1  1  0  0  0
 18  5  1  1  0  0  0
  6 24  1  0  0  0  0
  7 24  2  0  0  0  0
  8  9  1  0  0  0  0
  8 11  1  0  0  0  0
  8 14  1  0  0  0  0
  8 15  1  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  2  0  0  0  0
 11 19  1  0  0  0  0
 12 13  1  0  0  0  0
 13 21  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 17 20  1  0  0  0  0
 18 22  1  0  0  0  0
 19 23  2  0  0  0  0
 20 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 28  1  0  0  0  0
 25 29  2  0  0  0  0
 26 27  1  0  0  0  0
 27 30  2  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 31 32  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0010340

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@@H]1[C@@H](O)[C@H](OC\C=C(\C)/C=C/C=C(/C)\C=C\C2=C(C)CCCC2(C)C)O[C@H](C(O)=O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H38O7/c1-16(11-12-19-18(3)10-7-14-26(19,4)5)8-6-9-17(2)13-15-32-25-22(29)20(27)21(28)23(33-25)24(30)31/h6,8-9,11-13,20-23,25,27-29H,7,10,14-15H2,1-5H3,(H,30,31)/b9-6+,12-11+,16-8-,17-13-/t20-,21-,22+,23-,25+/m0/s1

> <INCHI_KEY>
IYHVRAMISWFIRU-GMBUFXMQSA-N

> <FORMULA>
C26H38O7

> <MOLECULAR_WEIGHT>
462.5757

> <EXACT_MASS>
462.26175357

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
51.80278027974174

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.93

> <JCHEM_LOGP>
3.2435320653333344

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.227564433624972

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5842401096475314

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686499907687752

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
130.20409999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.94e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
retinyl β-glucuronide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0010340
     RDKit          3D
Retinyl beta-glucuronide
 71 72  0  0  0  0  0  0  0  0999 V2000
   -6.4817    0.5588    2.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2035    0.8524    1.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9461    0.6358    0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9719    0.1396    1.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1627   -0.2571    2.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2112   -0.7338    3.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6367   -1.4948    4.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9274   -0.6965    2.9976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4082   -0.1564    1.7713 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9306   -0.1295    1.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5353    0.3853    0.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7514    0.8786   -0.7395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8442    0.4414    0.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7885   -0.0378    1.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5178   -1.0658    0.6467 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3483   -0.5334   -0.3619 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9036   -0.7713   -1.6220 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7738   -0.2751   -2.5918 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1958   -0.5057   -3.9529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9301   -0.5684   -4.0539 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9532   -0.6603   -5.0926 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1230   -0.8272   -2.5044 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0838    0.1916   -2.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4876   -1.4919   -1.2106 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2406   -2.8812   -1.3242 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7494   -0.9094   -0.0324 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4725    0.1040    0.5858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6798    0.7821   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5413   -0.1409   -1.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4080    2.1905   -1.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8988    0.2587   -1.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0910    1.1051   -1.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2662    1.3597    0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8658    1.2118    3.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5781    0.7855    2.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3642   -0.5210    2.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9899    0.1870    0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1400   -0.2588    3.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5000   -2.1200    4.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0279   -0.8100    5.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8265   -2.1113    4.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2366   -1.1218    3.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9565    0.2284    0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5174   -0.5526    2.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2786    0.5111   -1.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2332    0.3753   -0.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851    1.9623   -0.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3099    0.8224   -0.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3090   -0.4454    2.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4895    0.7915    1.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2284    0.5938   -0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7793    0.8438   -2.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0153   -1.6714   -5.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2866   -1.5625   -3.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9055    1.0095   -2.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5619   -1.4083   -1.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2126   -3.2651   -0.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7232   -1.7478    0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9015    0.5271    1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7781   -0.3427   -2.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5570    0.3389   -1.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6242   -1.0543   -0.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6360    2.6556   -0.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2906    2.8366   -1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9035    2.1653   -2.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6771    0.1652   -2.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1071   -0.7841   -1.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0267    0.6101   -1.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0132    2.0465   -1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2423    0.8919    0.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4240    2.4704    0.2643 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  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
  3 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
 31 32  1  0
 32 33  1  0
 33  2  1  0
 26 16  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  5 38  1  0
  7 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 12 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 16 51  1  1
 18 52  1  1
 21 53  1  0
 22 54  1  6
 23 55  1  0
 24 56  1  1
 25 57  1  0
 26 58  1  1
 27 59  1  0
 29 60  1  0
 29 61  1  0
 29 62  1  0
 30 63  1  0
 30 64  1  0
 30 65  1  0
 31 66  1  0
 31 67  1  0
 32 68  1  0
 32 69  1  0
 33 70  1  0
 33 71  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      34.491 -20.166   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      31.824 -20.166   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      34.491 -24.787   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      37.159 -23.247   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      31.824 -23.247   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      37.159 -18.626   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      38.492 -20.936   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      29.156  -9.386   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.823  -8.616   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.823  -7.076   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.490  -8.616   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      29.156  -6.306   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      30.490  -7.076   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.386 -10.720   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      29.926 -10.720   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      34.491 -23.247   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      35.825 -22.477   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      33.158 -22.477   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      31.824  -9.386   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      35.825 -20.936   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      31.824  -6.306   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      33.158 -20.936   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      31.824 -10.926   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      37.159 -20.166   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      33.158 -11.696   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      31.824 -18.626   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      30.490 -17.856   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      34.491 -10.926   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      33.158 -13.236   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      30.490 -16.316   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      31.824 -14.006   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      31.824 -15.546   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      29.156 -15.546   0.000  0.00  0.00           C+0
CONECT    1   20   22                                                       
CONECT    2   22   26                                                       
CONECT    3   16                                                            
CONECT    4   17                                                            
CONECT    5   18                                                            
CONECT    6   24                                                            
CONECT    7   24                                                            
CONECT    8    9   11   14   15                                             
CONECT    9    8   10                                                       
CONECT   10    9   12                                                       
CONECT   11    8   13   19                                                  
CONECT   12   10   13                                                       
CONECT   13   11   12   21                                                  
CONECT   14    8                                                            
CONECT   15    8                                                            
CONECT   16    3   17   18                                                  
CONECT   17    4   16   20                                                  
CONECT   18    5   16   22                                                  
CONECT   19   11   23                                                       
CONECT   20    1   17   24                                                  
CONECT   21   13                                                            
CONECT   22    1    2   18                                                  
CONECT   23   19   25                                                       
CONECT   24    6    7   20                                                  
CONECT   25   23   28   29                                                  
CONECT   26    2   27                                                       
CONECT   27   26   30                                                       
CONECT   28   25                                                            
CONECT   29   25   31                                                       
CONECT   30   27   32   33                                                  
CONECT   31   29   32                                                       
CONECT   32   30   31                                                       
CONECT   33   30                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

COMPND    HMDB0010340
HETATM    1  C1  UNL     1      -6.482   0.559   2.467  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.203   0.852   1.020  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.946   0.636   0.608  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.972   0.140   1.576  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.163  -0.257   2.329  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.211  -0.734   3.244  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.637  -1.495   4.523  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.927  -0.696   2.998  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.408  -0.156   1.771  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.931  -0.129   1.592  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.535   0.385   0.422  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.751   0.879  -0.739  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.844   0.441   0.253  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.788  -0.038   1.293  1.00  0.00           C  
HETATM   15  O1  UNL     1       4.518  -1.066   0.647  1.00  0.00           O  
HETATM   16  C15 UNL     1       5.348  -0.533  -0.362  1.00  0.00           C  
HETATM   17  O2  UNL     1       4.904  -0.771  -1.622  1.00  0.00           O  
HETATM   18  C16 UNL     1       5.774  -0.275  -2.592  1.00  0.00           C  
HETATM   19  C17 UNL     1       5.196  -0.506  -3.953  1.00  0.00           C  
HETATM   20  O3  UNL     1       3.930  -0.568  -4.054  1.00  0.00           O  
HETATM   21  O4  UNL     1       5.953  -0.660  -5.093  1.00  0.00           O  
HETATM   22  C18 UNL     1       7.123  -0.827  -2.504  1.00  0.00           C  
HETATM   23  O5  UNL     1       8.084   0.192  -2.808  1.00  0.00           O  
HETATM   24  C19 UNL     1       7.488  -1.492  -1.211  1.00  0.00           C  
HETATM   25  O6  UNL     1       7.241  -2.881  -1.324  1.00  0.00           O  
HETATM   26  C20 UNL     1       6.749  -0.909  -0.032  1.00  0.00           C  
HETATM   27  O7  UNL     1       7.473   0.104   0.586  1.00  0.00           O  
HETATM   28  C21 UNL     1      -4.680   0.782  -0.825  1.00  0.00           C  
HETATM   29  C22 UNL     1      -3.541  -0.141  -1.314  1.00  0.00           C  
HETATM   30  C23 UNL     1      -4.408   2.190  -1.190  1.00  0.00           C  
HETATM   31  C24 UNL     1      -5.899   0.259  -1.584  1.00  0.00           C  
HETATM   32  C25 UNL     1      -7.091   1.105  -1.319  1.00  0.00           C  
HETATM   33  C26 UNL     1      -7.266   1.360   0.163  1.00  0.00           C  
HETATM   34  H1  UNL     1      -5.866   1.212   3.130  1.00  0.00           H  
HETATM   35  H2  UNL     1      -7.578   0.785   2.632  1.00  0.00           H  
HETATM   36  H3  UNL     1      -6.364  -0.521   2.656  1.00  0.00           H  
HETATM   37  H4  UNL     1      -2.990   0.187   0.605  1.00  0.00           H  
HETATM   38  H5  UNL     1      -4.140  -0.259   3.307  1.00  0.00           H  
HETATM   39  H6  UNL     1      -3.500  -2.120   4.084  1.00  0.00           H  
HETATM   40  H7  UNL     1      -3.028  -0.810   5.249  1.00  0.00           H  
HETATM   41  H8  UNL     1      -1.827  -2.111   4.853  1.00  0.00           H  
HETATM   42  H9  UNL     1      -0.237  -1.122   3.771  1.00  0.00           H  
HETATM   43  H10 UNL     1      -0.957   0.228   0.974  1.00  0.00           H  
HETATM   44  H11 UNL     1       1.517  -0.553   2.410  1.00  0.00           H  
HETATM   45  H12 UNL     1       1.279   0.511  -1.689  1.00  0.00           H  
HETATM   46  H13 UNL     1      -0.233   0.375  -0.805  1.00  0.00           H  
HETATM   47  H14 UNL     1       0.685   1.962  -0.712  1.00  0.00           H  
HETATM   48  H15 UNL     1       3.310   0.822  -0.650  1.00  0.00           H  
HETATM   49  H16 UNL     1       3.309  -0.445   2.135  1.00  0.00           H  
HETATM   50  H17 UNL     1       4.490   0.791   1.538  1.00  0.00           H  
HETATM   51  H18 UNL     1       5.228   0.594  -0.216  1.00  0.00           H  
HETATM   52  H19 UNL     1       5.779   0.844  -2.428  1.00  0.00           H  
HETATM   53  H20 UNL     1       6.015  -1.671  -5.476  1.00  0.00           H  
HETATM   54  H21 UNL     1       7.287  -1.562  -3.341  1.00  0.00           H  
HETATM   55  H22 UNL     1       7.905   1.010  -2.315  1.00  0.00           H  
HETATM   56  H23 UNL     1       8.562  -1.408  -1.040  1.00  0.00           H  
HETATM   57  H24 UNL     1       7.213  -3.265  -0.414  1.00  0.00           H  
HETATM   58  H25 UNL     1       6.723  -1.748   0.740  1.00  0.00           H  
HETATM   59  H26 UNL     1       6.902   0.527   1.289  1.00  0.00           H  
HETATM   60  H27 UNL     1      -3.778  -0.343  -2.405  1.00  0.00           H  
HETATM   61  H28 UNL     1      -2.557   0.339  -1.264  1.00  0.00           H  
HETATM   62  H29 UNL     1      -3.624  -1.054  -0.699  1.00  0.00           H  
HETATM   63  H30 UNL     1      -3.636   2.656  -0.507  1.00  0.00           H  
HETATM   64  H31 UNL     1      -5.291   2.837  -1.303  1.00  0.00           H  
HETATM   65  H32 UNL     1      -3.903   2.165  -2.200  1.00  0.00           H  
HETATM   66  H33 UNL     1      -5.677   0.165  -2.644  1.00  0.00           H  
HETATM   67  H34 UNL     1      -6.107  -0.784  -1.176  1.00  0.00           H  
HETATM   68  H35 UNL     1      -8.027   0.610  -1.748  1.00  0.00           H  
HETATM   69  H36 UNL     1      -7.013   2.046  -1.922  1.00  0.00           H  
HETATM   70  H37 UNL     1      -8.242   0.892   0.430  1.00  0.00           H  
HETATM   71  H38 UNL     1      -7.424   2.470   0.264  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3    3   33
CONECT    3    4   28
CONECT    4    5    5   37
CONECT    5    6   38
CONECT    6    7    8    8
CONECT    7   39   40   41
CONECT    8    9   42
CONECT    9   10   10   43
CONECT   10   11   44
CONECT   11   12   13   13
CONECT   12   45   46   47
CONECT   13   14   48
CONECT   14   15   49   50
CONECT   15   16
CONECT   16   17   26   51
CONECT   17   18
CONECT   18   19   22   52
CONECT   19   20   20   21
CONECT   21   53
CONECT   22   23   24   54
CONECT   23   55
CONECT   24   25   26   56
CONECT   25   57
CONECT   26   27   58
CONECT   27   59
CONECT   28   29   30   31
CONECT   29   60   61   62
CONECT   30   63   64   65
CONECT   31   32   66   67
CONECT   32   33   68   69
CONECT   33   70   71
END

HMDB0010340
     RDKit          3D
Retinyl beta-glucuronide
 71 72  0  0  0  0  0  0  0  0999 V2000
   -6.4817    0.5588    2.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2035    0.8524    1.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9461    0.6358    0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9719    0.1396    1.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1627   -0.2571    2.3286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2112   -0.7338    3.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6367   -1.4948    4.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9274   -0.6965    2.9976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4082   -0.1564    1.7713 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9306   -0.1295    1.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5353    0.3853    0.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7514    0.8786   -0.7395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8442    0.4414    0.2531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7885   -0.0378    1.2928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5178   -1.0658    0.6467 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3483   -0.5334   -0.3619 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9036   -0.7713   -1.6220 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7738   -0.2751   -2.5918 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1958   -0.5057   -3.9529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9301   -0.5684   -4.0539 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9532   -0.6603   -5.0926 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1230   -0.8272   -2.5044 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0838    0.1916   -2.8076 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4876   -1.4919   -1.2106 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2406   -2.8812   -1.3242 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7494   -0.9094   -0.0324 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4725    0.1040    0.5858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6798    0.7821   -0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5413   -0.1409   -1.3142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4080    2.1905   -1.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8988    0.2587   -1.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0910    1.1051   -1.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2662    1.3597    0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8658    1.2118    3.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5781    0.7855    2.6320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3642   -0.5210    2.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9899    0.1870    0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1400   -0.2588    3.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5000   -2.1200    4.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0279   -0.8100    5.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8265   -2.1113    4.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2366   -1.1218    3.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9565    0.2284    0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5174   -0.5526    2.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2786    0.5111   -1.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2332    0.3753   -0.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6851    1.9623   -0.7123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3099    0.8224   -0.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3090   -0.4454    2.1348 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4895    0.7915    1.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2284    0.5938   -0.2160 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7793    0.8438   -2.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0153   -1.6714   -5.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2866   -1.5625   -3.3405 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9055    1.0095   -2.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5619   -1.4083   -1.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2126   -3.2651   -0.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7232   -1.7478    0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9015    0.5271    1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7781   -0.3427   -2.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5570    0.3389   -1.2644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6242   -1.0543   -0.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6360    2.6556   -0.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2906    2.8366   -1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9035    2.1653   -2.2004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6771    0.1652   -2.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1071   -0.7841   -1.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0267    0.6101   -1.7484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0132    2.0465   -1.9216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2423    0.8919    0.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4240    2.4704    0.2643 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  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 18 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
  3 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
 31 32  1  0
 32 33  1  0
 33  2  1  0
 26 16  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  5 38  1  0
  7 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  9 43  1  0
 10 44  1  0
 12 45  1  0
 12 46  1  0
 12 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 16 51  1  1
 18 52  1  1
 21 53  1  0
 22 54  1  6
 23 55  1  0
 24 56  1  1
 25 57  1  0
 26 58  1  1
 27 59  1  0
 29 60  1  0
 29 61  1  0
 29 62  1  0
 30 63  1  0
 30 64  1  0
 30 65  1  0
 31 66  1  0
 31 67  1  0
 32 68  1  0
 32 69  1  0
 33 70  1  0
 33 71  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Retinyl b-glucuronide	Generator
Retinyl β-glucuronide	Generator
Retinylglucuronide	HMDB
(2S,3S,4S,5R,6R)-6-{[(2Z,4E,6Z)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate	HMDB
Retinyl beta-glucuronide	MeSH

Chemical Formula

C₂₆H₃₈O₇

Average Molecular Weight

462.5757

Monoisotopic Molecular Weight

462.26175357

IUPAC Name

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

Traditional Name

retinyl β-glucuronide

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](O)[C@H](OC\C=C(\C)/C=C/C=C(/C)\C=C\C2=C(C)CCCC2(C)C)O[C@H](C(O)=O)[C@H]1O

InChI Identifier

InChI=1S/C26H38O7/c1-16(11-12-19-18(3)10-7-14-26(19,4)5)8-6-9-17(2)13-15-32-25-22(29)20(27)21(28)23(33-25)24(30)31/h6,8-9,11-13,20-23,25,27-29H,7,10,14-15H2,1-5H3,(H,30,31)/b9-6+,12-11+,16-8-,17-13-/t20-,21-,22+,23-,25+/m0/s1

InChI Key

IYHVRAMISWFIRU-GMBUFXMQSA-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
Diterpenoid
Retinoid skeleton
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Beta-hydroxy acid
Fatty acyl
Pyran
Hydroxy acid
Monosaccharide
Oxane
Secondary alcohol
Polyol
Organoheterocyclic compound
Acetal
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 2756924)

Organ

Liver (HMDB: HMDB0010340)
Kidney (HMDB: HMDB0010340)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0010340)
Feces (PMID: 26848182)

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0010340)

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

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	0.039 g/L	ALOGPS
logP	3.93	ALOGPS
logP	3.24	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	3.58	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	130.2 m³·mol⁻¹	ChemAxon
Polarizability	51.8 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]+	212.351	31661259
DarkChem	[M-H]-	205.454	31661259
DeepCCS	[M+H]+	209.594	30932474
DeepCCS	[M-H]-	207.199	30932474
DeepCCS	[M-2H]-	240.082	30932474
DeepCCS	[M+Na]+	215.507	30932474
AllCCS	[M+H]+	218.5	32859911
AllCCS	[M+H-H2O]+	216.3	32859911
AllCCS	[M+NH4]+	220.5	32859911
AllCCS	[M+Na]+	221.0	32859911
AllCCS	[M-H]-	212.3	32859911
AllCCS	[M+Na-2H]-	214.4	32859911
AllCCS	[M+HCOO]-	216.9	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.	6.4 minutes	32390414
Predicted by Siyang on May 30, 2022	19.3957 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.01 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3630.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	317.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	190.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	186.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	161.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	755.5 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	733.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	90.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1607.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	688.0 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	1673.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	596.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	520.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	214.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	306.1 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	9.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Retinyl beta-glucuronide	O[C@@H]1[C@@H](O)[C@H](OC\C=C(\C)/C=C/C=C(/C)\C=C\C2=C(C)CCCC2(C)C)O[C@H](C(O)=O)[C@H]1O	5051.4	Standard polar	33892256
Retinyl beta-glucuronide	O[C@@H]1[C@@H](O)[C@H](OC\C=C(\C)/C=C/C=C(/C)\C=C\C2=C(C)CCCC2(C)C)O[C@H](C(O)=O)[C@H]1O	3564.5	Standard non polar	33892256
Retinyl beta-glucuronide	O[C@@H]1[C@@H](O)[C@H](OC\C=C(\C)/C=C/C=C(/C)\C=C\C2=C(C)CCCC2(C)C)O[C@H](C(O)=O)[C@H]1O	3782.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Retinyl beta-glucuronide,1TMS,isomer #1	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	3719.6	Semi standard non polar	33892256
Retinyl beta-glucuronide,1TMS,isomer #2	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	3730.3	Semi standard non polar	33892256
Retinyl beta-glucuronide,1TMS,isomer #3	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	3694.4	Semi standard non polar	33892256
Retinyl beta-glucuronide,1TMS,isomer #4	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	3715.3	Semi standard non polar	33892256
Retinyl beta-glucuronide,2TMS,isomer #1	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	3668.6	Semi standard non polar	33892256
Retinyl beta-glucuronide,2TMS,isomer #2	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	3664.7	Semi standard non polar	33892256
Retinyl beta-glucuronide,2TMS,isomer #3	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	3667.4	Semi standard non polar	33892256
Retinyl beta-glucuronide,2TMS,isomer #4	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	3670.6	Semi standard non polar	33892256
Retinyl beta-glucuronide,2TMS,isomer #5	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	3681.8	Semi standard non polar	33892256
Retinyl beta-glucuronide,2TMS,isomer #6	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	3666.4	Semi standard non polar	33892256
Retinyl beta-glucuronide,3TMS,isomer #1	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	3617.4	Semi standard non polar	33892256
Retinyl beta-glucuronide,3TMS,isomer #2	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	3625.4	Semi standard non polar	33892256
Retinyl beta-glucuronide,3TMS,isomer #3	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	3638.6	Semi standard non polar	33892256
Retinyl beta-glucuronide,3TMS,isomer #4	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	3645.8	Semi standard non polar	33892256
Retinyl beta-glucuronide,4TMS,isomer #1	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	3602.0	Semi standard non polar	33892256
Retinyl beta-glucuronide,1TBDMS,isomer #1	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	3931.7	Semi standard non polar	33892256
Retinyl beta-glucuronide,1TBDMS,isomer #2	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	3952.3	Semi standard non polar	33892256
Retinyl beta-glucuronide,1TBDMS,isomer #3	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	3931.6	Semi standard non polar	33892256
Retinyl beta-glucuronide,1TBDMS,isomer #4	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	3933.9	Semi standard non polar	33892256
Retinyl beta-glucuronide,2TBDMS,isomer #1	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	4099.2	Semi standard non polar	33892256
Retinyl beta-glucuronide,2TBDMS,isomer #2	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	4086.9	Semi standard non polar	33892256
Retinyl beta-glucuronide,2TBDMS,isomer #3	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	4088.3	Semi standard non polar	33892256
Retinyl beta-glucuronide,2TBDMS,isomer #4	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	4106.9	Semi standard non polar	33892256
Retinyl beta-glucuronide,2TBDMS,isomer #5	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	4101.5	Semi standard non polar	33892256
Retinyl beta-glucuronide,2TBDMS,isomer #6	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	4097.9	Semi standard non polar	33892256
Retinyl beta-glucuronide,3TBDMS,isomer #1	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	4223.3	Semi standard non polar	33892256
Retinyl beta-glucuronide,3TBDMS,isomer #2	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	4235.2	Semi standard non polar	33892256
Retinyl beta-glucuronide,3TBDMS,isomer #3	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	4233.2	Semi standard non polar	33892256
Retinyl beta-glucuronide,3TBDMS,isomer #4	CC1=C(/C=C/C(C)=C\C=C\C(C)=C/CO[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	4264.8	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 - Retinyl beta-glucuronide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9417500000-fb337d0040baffcd1d91	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Retinyl beta-glucuronide GC-MS (3 TMS) - 70eV, Positive	splash10-03di-5162039000-e99f016f764d9c5bd86e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Retinyl beta-glucuronide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Retinyl beta-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 - Retinyl beta-glucuronide 10V, Positive-QTOF	splash10-01p2-0361900000-9580eec2fb7747637d3b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl beta-glucuronide 20V, Positive-QTOF	splash10-00kr-1971200000-6c240334f3dd3bdd4286	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl beta-glucuronide 40V, Positive-QTOF	splash10-002r-4920100000-cc19503557a0b71cd9fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl beta-glucuronide 10V, Negative-QTOF	splash10-03xr-2331900000-f032e18ef6357a405038	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl beta-glucuronide 20V, Negative-QTOF	splash10-004v-4931300000-975bb93eab639e62fb7e	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl beta-glucuronide 40V, Negative-QTOF	splash10-0a4m-9430000000-c64c697b73c4d7f182fa	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl beta-glucuronide 10V, Negative-QTOF	splash10-03dl-0100900000-99edc85ce251eb4e8660	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl beta-glucuronide 20V, Negative-QTOF	splash10-06vr-9652300000-2e1a8e4b74afa81bac68	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl beta-glucuronide 40V, Negative-QTOF	splash10-0a4r-5390000000-4e0597f224f6fb6d1fa2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl beta-glucuronide 10V, Positive-QTOF	splash10-03fr-0942600000-9d9399245f1cc0c0a078	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl beta-glucuronide 20V, Positive-QTOF	splash10-00rb-1921100000-4b9eeada09794cc68398	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retinyl beta-glucuronide 40V, Positive-QTOF	splash10-0101-2910000000-636d65a3f001924dcb1d	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0068 +/- 0.004 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

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohns disease	26848182	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Iron deficiency	26848182	details

Associated Disorders and Diseases

Disease References

Crohn's disease
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Iron deficiency
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]

Associated OMIM IDs

266600 (Crohn's disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027492

KNApSAcK ID

Not Available

Chemspider ID

4945190

KEGG Compound ID

Not Available

BioCyc ID

Beta-D-Glucuronides

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6440956

PDB ID

Not Available

ChEBI ID

88739

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

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

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

References

Genchi G, Wang W, Barua A, Bidlack WR, Olson JA: Formation of beta-glucuronides and of beta-galacturonides of various retinoids catalyzed by induced and noninduced microsomal UDP-glucuronosyltransferases of rat liver. Biochim Biophys Acta. 1996 Mar 15;1289(2):284-90. [PubMed:8600986 ]

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

References

Genchi G, Wang W, Barua A, Bidlack WR, Olson JA: Formation of beta-glucuronides and of beta-galacturonides of various retinoids catalyzed by induced and noninduced microsomal UDP-glucuronosyltransferases of rat liver. Biochim Biophys Acta. 1996 Mar 15;1289(2):284-90. [PubMed:8600986 ]

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

References

Genchi G, Wang W, Barua A, Bidlack WR, Olson JA: Formation of beta-glucuronides and of beta-galacturonides of various retinoids catalyzed by induced and noninduced microsomal UDP-glucuronosyltransferases of rat liver. Biochim Biophys Acta. 1996 Mar 15;1289(2):284-90. [PubMed:8600986 ]

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

References

Genchi G, Wang W, Barua A, Bidlack WR, Olson JA: Formation of beta-glucuronides and of beta-galacturonides of various retinoids catalyzed by induced and noninduced microsomal UDP-glucuronosyltransferases of rat liver. Biochim Biophys Acta. 1996 Mar 15;1289(2):284-90. [PubMed:8600986 ]

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

References

Genchi G, Wang W, Barua A, Bidlack WR, Olson JA: Formation of beta-glucuronides and of beta-galacturonides of various retinoids catalyzed by induced and noninduced microsomal UDP-glucuronosyltransferases of rat liver. Biochim Biophys Acta. 1996 Mar 15;1289(2):284-90. [PubMed:8600986 ]

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

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

References

Genchi G, Wang W, Barua A, Bidlack WR, Olson JA: Formation of beta-glucuronides and of beta-galacturonides of various retinoids catalyzed by induced and noninduced microsomal UDP-glucuronosyltransferases of rat liver. Biochim Biophys Acta. 1996 Mar 15;1289(2):284-90. [PubMed:8600986 ]

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

References

Genchi G, Wang W, Barua A, Bidlack WR, Olson JA: Formation of beta-glucuronides and of beta-galacturonides of various retinoids catalyzed by induced and noninduced microsomal UDP-glucuronosyltransferases of rat liver. Biochim Biophys Acta. 1996 Mar 15;1289(2):284-90. [PubMed:8600986 ]

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

References

Genchi G, Wang W, Barua A, Bidlack WR, Olson JA: Formation of beta-glucuronides and of beta-galacturonides of various retinoids catalyzed by induced and noninduced microsomal UDP-glucuronosyltransferases of rat liver. Biochim Biophys Acta. 1996 Mar 15;1289(2):284-90. [PubMed:8600986 ]

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

Show all enzymes and transporters

Showing metabocard for Retinyl beta-glucuronide (HMDB0010340)

MOL for HMDB0010340 (Retinyl beta-glucuronide)

3D MOL for HMDB0010340 (Retinyl beta-glucuronide)

3D SDF for HMDB0010340 (Retinyl beta-glucuronide)

3D-SDF for HMDB0010340 (Retinyl beta-glucuronide)

PDB for HMDB0010340 (Retinyl beta-glucuronide)

3D PDB for HMDB0010340 (Retinyl beta-glucuronide)

SMILES for HMDB0010340 (Retinyl beta-glucuronide)

INCHI for HMDB0010340 (Retinyl beta-glucuronide)

Structure for HMDB0010340 (Retinyl beta-glucuronide)

3D Structure for HMDB0010340 (Retinyl beta-glucuronide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References