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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (18) Show 18 proteins XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-05-17 01:22:40 UTC

Update Date

2021-09-14 15:19:06 UTC

HMDB ID

HMDB0060464

Secondary Accession Numbers

HMDB60464

Metabolite Identification

Common Name

Codeine-6-glucuronide

Description

Codeine-6-glucuronide belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic. During its metabolism, codeine is conjugated with glucuronic acid by the enzyme UDP-Glucuronosyltransferase-2B7 (UGT2B7) to form codeine-6-glucuronide. Codeine-6-glucuronide is a very strong basic compound (based on its pKa). codeine-6-glucuronide and uridine 5'-diphosphate can be biosynthesized from codeine and uridine diphosphate glucuronic acid through the action of the enzyme UDP-glucuronosyltransferase 2B7. In humans, codeine-6-glucuronide is involved in codeine metabolism pathway. C6G exhibits decreased immunosuppressive effects compared to codeine. Codeine-6-glucuronide (C6G) is a major active metabolite of codeine and may be responsible for as much as 60% of the analgesic effects of codeine.

Structure

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


  Mrv0541 06101316242D          

 35 40  0  0  1  0            999 V2000
   14.4146  -12.2277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5097  -14.3330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5167  -10.2279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9782  -14.9798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5063  -16.7337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9782  -17.6087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4662  -16.7337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7284  -15.1290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7282  -13.9799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0833  -13.1184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9644  -12.6959    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.6538  -13.1114    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.9461  -11.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2315  -13.1008    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.3684  -12.7030    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.2315  -11.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6573  -11.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6538  -12.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2278  -13.9211    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.6502  -13.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3719  -11.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2315  -10.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9355  -14.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1053  -12.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6573  -10.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9496  -10.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7443  -15.4153    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.9619  -13.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7443  -16.2902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9782  -16.7337    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2202  -15.4193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.2202  -16.2902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.8021  -10.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5589  -14.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4389  -13.6783    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 14  1  1  6  0  0  0
  1 16  1  0  0  0  0
 19  2  1  6  0  0  0
 27  2  1  1  0  0  0
  3 22  1  0  0  0  0
  3 33  1  0  0  0  0
  4 27  1  0  0  0  0
  4 31  1  0  0  0  0
 29  5  1  6  0  0  0
 30  6  1  1  0  0  0
 32  7  1  6  0  0  0
  8 34  2  0  0  0  0
  9 34  1  0  0  0  0
 15 10  1  1  0  0  0
 10 24  1  0  0  0  0
 10 28  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 11 18  1  1  0  0  0
 12 15  1  0  0  0  0
 12 20  1  0  0  0  0
 12 35  1  1  0  0  0
 13 16  2  0  0  0  0
 13 17  1  0  0  0  0
 14 19  1  0  0  0  0
 15 21  1  0  0  0  0
 16 22  1  0  0  0  0
 17 21  1  0  0  0  0
 17 25  2  0  0  0  0
 18 24  1  0  0  0  0
 19 23  1  0  0  0  0
 20 23  2  0  0  0  0
 22 26  2  0  0  0  0
 25 26  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 32  1  0  0  0  0
 31 32  1  0  0  0  0
 31 34  1  1  0  0  0
M  END

HMDB0060464
     RDKit          3D
Codeine-6-glucuronide
 63 68  0  0  0  0  0  0  0  0999 V2000
   -1.0919   -4.2133    3.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6747   -2.9854    2.7043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5981   -2.2166    2.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9355   -2.5777    1.8552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8558   -1.7913    1.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4684   -0.5942    0.6061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1621   -0.2615    0.7835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2376   -0.9973    1.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0311   -0.2832    1.3736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1711    0.7705    0.3795 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4797    0.2658   -0.8693 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5810   -0.5126   -0.4470 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7893    0.0294   -0.8330 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4493   -0.8022   -1.7014 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5334   -1.4616   -1.1775 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1636   -2.4746   -0.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1030   -3.1138    0.3767 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8519   -2.7161    0.2378 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6382   -0.5500   -0.7136 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4086   -0.1919   -1.8410 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0421    0.6767   -0.0800 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8077    1.1610    0.9744 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6212    0.4530    0.3564 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1453    1.6966    0.8279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4388   -0.5260   -1.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6935   -0.1517   -1.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1372    1.0664   -1.1704 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6282    1.2235   -1.1077 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3703    0.3071   -0.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8940    2.5972   -0.7217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0102    3.3726   -1.9620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8077    3.1849    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1431    2.2116    0.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6264    1.0006    0.2489 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6204   -4.7694    2.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764   -4.0247    4.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2676   -4.8244    3.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2296   -3.5223    2.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8774   -2.1037    1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3862    1.6319    0.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014    1.1436   -1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5661    0.9733   -1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9715   -2.0651   -2.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5914   -2.8284    1.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2922   -1.0695    0.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7705   -0.1708   -2.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0111    1.4655   -0.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0811    2.1005    0.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5316   -0.2381    1.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8758    2.2069    0.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0334   -1.4225   -2.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3424   -0.7620   -2.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7107    1.9432   -1.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0057    1.0425   -2.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9478    0.8904    0.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1318   -0.2913   -0.7310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5713    4.3895   -1.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4296    2.8979   -2.7867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0522    3.4523   -2.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0705    3.7121   -0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2563    3.9865    0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8901    1.9256    1.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3042    2.7344    1.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 11 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 34 33  1  1
  8  3  1  0
 34 10  1  0
 29  6  1  0
 34  7  1  0
 23 13  1  0
 34 27  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  5 39  1  0
 10 40  1  1
 11 41  1  6
 13 42  1  6
 15 43  1  6
 18 44  1  0
 19 45  1  1
 20 46  1  0
 21 47  1  6
 22 48  1  0
 23 49  1  1
 24 50  1  0
 25 51  1  0
 26 52  1  0
 27 53  1  6
 28 54  1  6
 29 55  1  0
 29 56  1  0
 31 57  1  0
 31 58  1  0
 31 59  1  0
 32 60  1  0
 32 61  1  0
 33 62  1  0
 33 63  1  0
M  END


  Mrv0541 06101316242D          

 35 40  0  0  1  0            999 V2000
   14.4146  -12.2277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5097  -14.3330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5167  -10.2279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9782  -14.9798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5063  -16.7337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9782  -17.6087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4662  -16.7337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7284  -15.1290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7282  -13.9799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0833  -13.1184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9644  -12.6959    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.6538  -13.1114    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.9461  -11.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2315  -13.1008    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.3684  -12.7030    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.2315  -11.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6573  -11.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6538  -12.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2278  -13.9211    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.6502  -13.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3719  -11.8791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2315  -10.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9355  -14.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1053  -12.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6573  -10.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9496  -10.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7443  -15.4153    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.9619  -13.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7443  -16.2902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.9782  -16.7337    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2202  -15.4193    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.2202  -16.2902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.8021  -10.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5589  -14.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4389  -13.6783    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 14  1  1  6  0  0  0
  1 16  1  0  0  0  0
 19  2  1  6  0  0  0
 27  2  1  1  0  0  0
  3 22  1  0  0  0  0
  3 33  1  0  0  0  0
  4 27  1  0  0  0  0
  4 31  1  0  0  0  0
 29  5  1  6  0  0  0
 30  6  1  1  0  0  0
 32  7  1  6  0  0  0
  8 34  2  0  0  0  0
  9 34  1  0  0  0  0
 15 10  1  1  0  0  0
 10 24  1  0  0  0  0
 10 28  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 11 18  1  1  0  0  0
 12 15  1  0  0  0  0
 12 20  1  0  0  0  0
 12 35  1  1  0  0  0
 13 16  2  0  0  0  0
 13 17  1  0  0  0  0
 14 19  1  0  0  0  0
 15 21  1  0  0  0  0
 16 22  1  0  0  0  0
 17 21  1  0  0  0  0
 17 25  2  0  0  0  0
 18 24  1  0  0  0  0
 19 23  1  0  0  0  0
 20 23  2  0  0  0  0
 22 26  2  0  0  0  0
 25 26  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 32  1  0  0  0  0
 31 32  1  0  0  0  0
 31 34  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0060464

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12C=C[C@H](O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@H]3OC4=C5C(C[C@H]1N(C)CC[C@@]235)=CC=C4OC

> <INCHI_IDENTIFIER>
InChI=1S/C24H29NO9/c1-25-8-7-24-11-4-6-14(32-23-18(28)16(26)17(27)20(34-23)22(29)30)21(24)33-19-13(31-2)5-3-10(15(19)24)9-12(11)25/h3-6,11-12,14,16-18,20-21,23,26-28H,7-9H2,1-2H3,(H,29,30)/t11-,12+,14-,16-,17-,18+,20-,21-,23+,24-/m0/s1

> <INCHI_KEY>
CRWVOYRJXPDBPM-HSCJLHHPSA-N

> <FORMULA>
C24H29NO9

> <MOLECULAR_WEIGHT>
475.4884

> <EXACT_MASS>
475.184231531

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
47.274081047802625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7,9,11(18),15-tetraen-14-yl]oxy}oxane-2-carboxylic acid

> <ALOGPS_LOGP>
-0.23

> <JCHEM_LOGP>
-2.8388618238247267

> <ALOGPS_LOGS>
-2.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.22736554053497

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.871113725857091

> <JCHEM_PKA_STRONGEST_BASIC>
9.192381718880771

> <JCHEM_POLAR_SURFACE_AREA>
138.15

> <JCHEM_REFRACTIVITY>
116.88539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.31e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
codeine-6-glucuronide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060464
     RDKit          3D
Codeine-6-glucuronide
 63 68  0  0  0  0  0  0  0  0999 V2000
   -1.0919   -4.2133    3.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6747   -2.9854    2.7043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5981   -2.2166    2.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9355   -2.5777    1.8552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8558   -1.7913    1.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4684   -0.5942    0.6061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1621   -0.2615    0.7835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2376   -0.9973    1.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0311   -0.2832    1.3736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1711    0.7705    0.3795 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4797    0.2658   -0.8693 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5810   -0.5126   -0.4470 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7893    0.0294   -0.8330 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4493   -0.8022   -1.7014 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5334   -1.4616   -1.1775 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1636   -2.4746   -0.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1030   -3.1138    0.3767 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8519   -2.7161    0.2378 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6382   -0.5500   -0.7136 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4086   -0.1919   -1.8410 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0421    0.6767   -0.0800 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8077    1.1610    0.9744 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6212    0.4530    0.3564 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1453    1.6966    0.8279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4388   -0.5260   -1.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6935   -0.1517   -1.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1372    1.0664   -1.1704 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6282    1.2235   -1.1077 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3703    0.3071   -0.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8940    2.5972   -0.7217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0102    3.3726   -1.9620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8077    3.1849    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1431    2.2116    0.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6264    1.0006    0.2489 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6204   -4.7694    2.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764   -4.0247    4.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2676   -4.8244    3.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2296   -3.5223    2.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8774   -2.1037    1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3862    1.6319    0.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014    1.1436   -1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5661    0.9733   -1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9715   -2.0651   -2.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5914   -2.8284    1.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2922   -1.0695    0.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7705   -0.1708   -2.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0111    1.4655   -0.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0811    2.1005    0.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5316   -0.2381    1.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8758    2.2069    0.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0334   -1.4225   -2.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3424   -0.7620   -2.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7107    1.9432   -1.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0057    1.0425   -2.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9478    0.8904    0.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1318   -0.2913   -0.7310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5713    4.3895   -1.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4296    2.8979   -2.7867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0522    3.4523   -2.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0705    3.7121   -0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2563    3.9865    0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8901    1.9256    1.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3042    2.7344    1.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 11 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 34 33  1  1
  8  3  1  0
 34 10  1  0
 29  6  1  0
 34  7  1  0
 23 13  1  0
 34 27  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  5 39  1  0
 10 40  1  1
 11 41  1  6
 13 42  1  6
 15 43  1  6
 18 44  1  0
 19 45  1  1
 20 46  1  0
 21 47  1  6
 22 48  1  0
 23 49  1  1
 24 50  1  0
 25 51  1  0
 26 52  1  0
 27 53  1  6
 28 54  1  6
 29 55  1  0
 29 56  1  0
 31 57  1  0
 31 58  1  0
 31 59  1  0
 32 60  1  0
 32 61  1  0
 33 62  1  0
 33 63  1  0
M  END

HEADER    PROTEIN                                 10-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-JUN-13         0                                  
HETATM    1  O   UNK     0      26.907 -22.825   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      27.085 -26.755   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      27.098 -19.092   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      24.226 -27.962   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      27.078 -31.236   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      24.226 -32.870   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      21.404 -31.236   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      20.026 -28.241   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      21.893 -26.096   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      33.755 -24.488   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      29.800 -23.699   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.087 -24.475   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      29.766 -22.168   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.432 -24.455   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.421 -23.712   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.432 -21.405   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      31.094 -21.405   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      31.087 -22.917   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.425 -25.986   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      31.080 -26.006   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      32.428 -22.174   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      28.432 -19.861   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      29.746 -26.762   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      33.797 -22.971   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      31.094 -19.861   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      29.773 -19.092   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      25.656 -28.775   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      35.396 -24.488   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      25.656 -30.408   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      24.226 -31.236   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      22.811 -28.783   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      22.811 -30.408   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      25.764 -19.861   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      21.577 -27.707   0.000  0.00  0.00           C+0
HETATM   35  H   UNK     0      32.553 -25.533   0.000  0.00  0.00           H+0
CONECT    1   14   16                                                       
CONECT    2   19   27                                                       
CONECT    3   22   33                                                       
CONECT    4   27   31                                                       
CONECT    5   29                                                            
CONECT    6   30                                                            
CONECT    7   32                                                            
CONECT    8   34                                                            
CONECT    9   34                                                            
CONECT   10   15   24   28                                                  
CONECT   11   12   13   14   18                                             
CONECT   12   11   15   20   35                                             
CONECT   13   11   16   17                                                  
CONECT   14    1   11   19                                                  
CONECT   15   10   12   21                                                  
CONECT   16    1   13   22                                                  
CONECT   17   13   21   25                                                  
CONECT   18   11   24                                                       
CONECT   19    2   14   23                                                  
CONECT   20   12   23                                                       
CONECT   21   15   17                                                       
CONECT   22    3   16   26                                                  
CONECT   23   19   20                                                       
CONECT   24   10   18                                                       
CONECT   25   17   26                                                       
CONECT   26   22   25                                                       
CONECT   27    2    4   29                                                  
CONECT   28   10                                                            
CONECT   29    5   27   30                                                  
CONECT   30    6   29   32                                                  
CONECT   31    4   32   34                                                  
CONECT   32    7   30   31                                                  
CONECT   33    3                                                            
CONECT   34    8    9   31                                                  
CONECT   35   12                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

COMPND    HMDB0060464
HETATM    1  C1  UNL     1      -1.092  -4.213   3.271  1.00  0.00           C  
HETATM    2  O1  UNL     1      -0.675  -2.985   2.704  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.598  -2.217   2.023  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.936  -2.578   1.855  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.856  -1.791   1.164  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.468  -0.594   0.606  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.162  -0.261   0.783  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.238  -0.997   1.445  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.031  -0.283   1.374  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.171   0.771   0.379  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.480   0.266  -0.869  1.00  0.00           C  
HETATM   12  O3  UNL     1       1.581  -0.513  -0.447  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.789   0.029  -0.833  1.00  0.00           C  
HETATM   14  O4  UNL     1       3.449  -0.802  -1.701  1.00  0.00           O  
HETATM   15  C11 UNL     1       4.533  -1.462  -1.178  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.164  -2.475  -0.145  1.00  0.00           C  
HETATM   17  O5  UNL     1       5.103  -3.114   0.377  1.00  0.00           O  
HETATM   18  O6  UNL     1       2.852  -2.716   0.238  1.00  0.00           O  
HETATM   19  C13 UNL     1       5.638  -0.550  -0.714  1.00  0.00           C  
HETATM   20  O7  UNL     1       6.409  -0.192  -1.841  1.00  0.00           O  
HETATM   21  C14 UNL     1       5.042   0.677  -0.080  1.00  0.00           C  
HETATM   22  O8  UNL     1       5.808   1.161   0.974  1.00  0.00           O  
HETATM   23  C15 UNL     1       3.621   0.453   0.356  1.00  0.00           C  
HETATM   24  O9  UNL     1       3.145   1.697   0.828  1.00  0.00           O  
HETATM   25  C16 UNL     1      -0.439  -0.526  -1.709  1.00  0.00           C  
HETATM   26  C17 UNL     1      -1.693  -0.152  -1.861  1.00  0.00           C  
HETATM   27  C18 UNL     1      -2.137   1.066  -1.170  1.00  0.00           C  
HETATM   28  C19 UNL     1      -3.628   1.223  -1.108  1.00  0.00           C  
HETATM   29  C20 UNL     1      -4.370   0.307  -0.189  1.00  0.00           C  
HETATM   30  N1  UNL     1      -3.894   2.597  -0.722  1.00  0.00           N  
HETATM   31  C21 UNL     1      -4.010   3.373  -1.962  1.00  0.00           C  
HETATM   32  C22 UNL     1      -2.808   3.185   0.026  1.00  0.00           C  
HETATM   33  C23 UNL     1      -2.143   2.212   0.963  1.00  0.00           C  
HETATM   34  C24 UNL     1      -1.626   1.001   0.249  1.00  0.00           C  
HETATM   35  H1  UNL     1      -1.620  -4.769   2.457  1.00  0.00           H  
HETATM   36  H2  UNL     1      -1.876  -4.025   4.052  1.00  0.00           H  
HETATM   37  H3  UNL     1      -0.268  -4.824   3.642  1.00  0.00           H  
HETATM   38  H4  UNL     1      -3.230  -3.522   2.299  1.00  0.00           H  
HETATM   39  H5  UNL     1      -4.877  -2.104   1.056  1.00  0.00           H  
HETATM   40  H6  UNL     1       0.386   1.632   0.811  1.00  0.00           H  
HETATM   41  H7  UNL     1       0.901   1.144  -1.423  1.00  0.00           H  
HETATM   42  H8  UNL     1       2.566   0.973  -1.397  1.00  0.00           H  
HETATM   43  H9  UNL     1       4.971  -2.065  -2.026  1.00  0.00           H  
HETATM   44  H10 UNL     1       2.591  -2.828   1.228  1.00  0.00           H  
HETATM   45  H11 UNL     1       6.292  -1.069   0.007  1.00  0.00           H  
HETATM   46  H12 UNL     1       5.770  -0.171  -2.602  1.00  0.00           H  
HETATM   47  H13 UNL     1       5.011   1.465  -0.874  1.00  0.00           H  
HETATM   48  H14 UNL     1       6.081   2.100   0.816  1.00  0.00           H  
HETATM   49  H15 UNL     1       3.532  -0.238   1.217  1.00  0.00           H  
HETATM   50  H16 UNL     1       2.876   2.207   0.013  1.00  0.00           H  
HETATM   51  H17 UNL     1      -0.033  -1.422  -2.190  1.00  0.00           H  
HETATM   52  H18 UNL     1      -2.342  -0.762  -2.490  1.00  0.00           H  
HETATM   53  H19 UNL     1      -1.711   1.943  -1.671  1.00  0.00           H  
HETATM   54  H20 UNL     1      -4.006   1.043  -2.158  1.00  0.00           H  
HETATM   55  H21 UNL     1      -4.948   0.890   0.582  1.00  0.00           H  
HETATM   56  H22 UNL     1      -5.132  -0.291  -0.731  1.00  0.00           H  
HETATM   57  H23 UNL     1      -3.571   4.389  -1.827  1.00  0.00           H  
HETATM   58  H24 UNL     1      -3.430   2.898  -2.787  1.00  0.00           H  
HETATM   59  H25 UNL     1      -5.052   3.452  -2.305  1.00  0.00           H  
HETATM   60  H26 UNL     1      -2.071   3.712  -0.629  1.00  0.00           H  
HETATM   61  H27 UNL     1      -3.256   3.987   0.660  1.00  0.00           H  
HETATM   62  H28 UNL     1      -2.890   1.926   1.731  1.00  0.00           H  
HETATM   63  H29 UNL     1      -1.304   2.734   1.448  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   38
CONECT    5    6    6   39
CONECT    6    7   29
CONECT    7    8    8   34
CONECT    8    9
CONECT    9   10
CONECT   10   11   34   40
CONECT   11   12   25   41
CONECT   12   13
CONECT   13   14   23   42
CONECT   14   15
CONECT   15   16   19   43
CONECT   16   17   17   18
CONECT   18   44
CONECT   19   20   21   45
CONECT   20   46
CONECT   21   22   23   47
CONECT   22   48
CONECT   23   24   49
CONECT   24   50
CONECT   25   26   26   51
CONECT   26   27   52
CONECT   27   28   34   53
CONECT   28   29   30   54
CONECT   29   55   56
CONECT   30   31   32
CONECT   31   57   58   59
CONECT   32   33   60   61
CONECT   33   34   62   63
END

HMDB0060464
     RDKit          3D
Codeine-6-glucuronide
 63 68  0  0  0  0  0  0  0  0999 V2000
   -1.0919   -4.2133    3.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6747   -2.9854    2.7043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5981   -2.2166    2.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9355   -2.5777    1.8552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8558   -1.7913    1.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4684   -0.5942    0.6061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1621   -0.2615    0.7835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2376   -0.9973    1.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0311   -0.2832    1.3736 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1711    0.7705    0.3795 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4797    0.2658   -0.8693 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5810   -0.5126   -0.4470 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7893    0.0294   -0.8330 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4493   -0.8022   -1.7014 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5334   -1.4616   -1.1775 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1636   -2.4746   -0.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1030   -3.1138    0.3767 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8519   -2.7161    0.2378 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6382   -0.5500   -0.7136 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4086   -0.1919   -1.8410 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0421    0.6767   -0.0800 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8077    1.1610    0.9744 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6212    0.4530    0.3564 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1453    1.6966    0.8279 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4388   -0.5260   -1.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6935   -0.1517   -1.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1372    1.0664   -1.1704 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6282    1.2235   -1.1077 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3703    0.3071   -0.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8940    2.5972   -0.7217 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0102    3.3726   -1.9620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8077    3.1849    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1431    2.2116    0.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6264    1.0006    0.2489 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6204   -4.7694    2.4573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8764   -4.0247    4.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2676   -4.8244    3.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2296   -3.5223    2.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8774   -2.1037    1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3862    1.6319    0.8110 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014    1.1436   -1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5661    0.9733   -1.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9715   -2.0651   -2.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5914   -2.8284    1.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2922   -1.0695    0.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7705   -0.1708   -2.6019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0111    1.4655   -0.8741 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0811    2.1005    0.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5316   -0.2381    1.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8758    2.2069    0.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0334   -1.4225   -2.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3424   -0.7620   -2.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7107    1.9432   -1.6715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0057    1.0425   -2.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9478    0.8904    0.5824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1318   -0.2913   -0.7310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5713    4.3895   -1.8267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4296    2.8979   -2.7867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0522    3.4523   -2.3046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0705    3.7121   -0.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2563    3.9865    0.6603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8901    1.9256    1.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3042    2.7344    1.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 11 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 34 33  1  1
  8  3  1  0
 34 10  1  0
 29  6  1  0
 34  7  1  0
 23 13  1  0
 34 27  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  4 38  1  0
  5 39  1  0
 10 40  1  1
 11 41  1  6
 13 42  1  6
 15 43  1  6
 18 44  1  0
 19 45  1  1
 20 46  1  0
 21 47  1  6
 22 48  1  0
 23 49  1  1
 24 50  1  0
 25 51  1  0
 26 52  1  0
 27 53  1  6
 28 54  1  6
 29 55  1  0
 29 56  1  0
 31 57  1  0
 31 58  1  0
 31 59  1  0
 32 60  1  0
 32 61  1  0
 33 62  1  0
 33 63  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₄H₂₉NO₉

Average Molecular Weight

475.4884

Monoisotopic Molecular Weight

475.184231531

IUPAC Name

(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7,9,11(18),15-tetraen-14-yl]oxy}oxane-2-carboxylic acid

Traditional Name

codeine-6-glucuronide

CAS Registry Number

20736-11-2

SMILES

[H][C@]12C=C[C@H](O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@H]3OC4=C5C(C[C@H]1N(C)CC[C@@]235)=CC=C4OC

InChI Identifier

InChI=1S/C24H29NO9/c1-25-8-7-24-11-4-6-14(32-23-18(28)16(26)17(27)20(34-23)22(29)30)21(24)33-19-13(31-2)5-3-10(15(19)24)9-12(11)25/h3-6,11-12,14,16-18,20-21,23,26-28H,7-9H2,1-2H3,(H,29,30)/t11-,12+,14-,16-,17-,18+,20-,21-,23+,24-/m0/s1

InChI Key

CRWVOYRJXPDBPM-HSCJLHHPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Morphinans

Sub Class

Not Available

Direct Parent

Morphinans

Alternative Parents

Substituents

Morphinan
O-glucuronide
1-o-glucuronide
Phenanthrene
Glucuronic acid or derivatives
O-glycosyl compound
Glycosyl compound
Tetralin
Coumaran
Anisole
Alkyl aryl ether
Beta-hydroxy acid
Aralkylamine
Hydroxy acid
Oxane
Monosaccharide
Piperidine
Benzenoid
Pyran
Amino acid or derivatives
Amino acid
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Acetal
Carboxylic acid derivative
Carboxylic acid
Ether
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Polyol
Organic nitrogen compound
Alcohol
Amine
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Organic oxide
Carbonyl group
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

morphinane alkaloid (CHEBI:80580 )

Ontology

Not Available

Liver (HMDB: HMDB0060464)
Kidney (HMDB: HMDB0060464)

Excreta

Biofluid or Excreta

Urine (PMID: 16258895)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 9448068)

Cellular substructure

Microsomes (HMDB: HMDB0060464)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Codeine Action Pathway (PathBank: SMP0000405)

Metabolic pathway

Codeine Metabolism Pathway (PathBank: SMP0000621)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	248-250°C	http://www.buyersguidechem.com/cas_supplier/20736-11-2.html
Boiling Point	Not Available	Not Available
Water Solubility	0	Toronto Research Chemicals, 2013
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.31 g/L	ALOGPS
logP	-0.23	ALOGPS
logP	-2.8	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	2.87	ChemAxon
pKa (Strongest Basic)	9.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	138.15 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	116.89 m³·mol⁻¹	ChemAxon
Polarizability	47.27 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	245.264	30932474
DeepCCS	[M+Na]+	219.037	30932474
AllCCS	[M+H]+	211.3	32859911
AllCCS	[M+H-H2O]+	209.4	32859911
AllCCS	[M+NH4]+	213.0	32859911
AllCCS	[M+Na]+	213.5	32859911
AllCCS	[M-H]-	204.6	32859911
AllCCS	[M+Na-2H]-	205.2	32859911
AllCCS	[M+HCOO]-	206.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Codeine-6-glucuronide	[H][C@]12C=C[C@H](O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@H]3OC4=C5C(C[C@H]1N(C)CC[C@@]235)=CC=C4OC	4738.4	Standard polar	33892256
Codeine-6-glucuronide	[H][C@]12C=C[C@H](O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@H]3OC4=C5C(C[C@H]1N(C)CC[C@@]235)=CC=C4OC	3622.6	Standard non polar	33892256
Codeine-6-glucuronide	[H][C@]12C=C[C@H](O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@H]3OC4=C5C(C[C@H]1N(C)CC[C@@]235)=CC=C4OC	3871.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Codeine-6-glucuronide,1TMS,isomer #1	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C	3693.3	Semi standard non polar	33892256
Codeine-6-glucuronide,1TMS,isomer #2	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C	3705.3	Semi standard non polar	33892256
Codeine-6-glucuronide,1TMS,isomer #3	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]5O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C	3692.9	Semi standard non polar	33892256
Codeine-6-glucuronide,1TMS,isomer #4	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C	3644.5	Semi standard non polar	33892256
Codeine-6-glucuronide,2TMS,isomer #1	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C	3635.5	Semi standard non polar	33892256
Codeine-6-glucuronide,2TMS,isomer #2	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C	3674.2	Semi standard non polar	33892256
Codeine-6-glucuronide,2TMS,isomer #3	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C	3664.3	Semi standard non polar	33892256
Codeine-6-glucuronide,2TMS,isomer #4	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C	3632.6	Semi standard non polar	33892256
Codeine-6-glucuronide,2TMS,isomer #5	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C	3664.4	Semi standard non polar	33892256
Codeine-6-glucuronide,2TMS,isomer #6	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]5O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C	3622.0	Semi standard non polar	33892256
Codeine-6-glucuronide,3TMS,isomer #1	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[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]5O)[C@@H]5OC1=C2[C@@]54CCN3C	3637.7	Semi standard non polar	33892256
Codeine-6-glucuronide,3TMS,isomer #2	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]5O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C	3633.5	Semi standard non polar	33892256
Codeine-6-glucuronide,3TMS,isomer #3	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C	3658.9	Semi standard non polar	33892256
Codeine-6-glucuronide,3TMS,isomer #4	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]5O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C	3623.9	Semi standard non polar	33892256
Codeine-6-glucuronide,4TMS,isomer #1	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[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]5O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C	3644.2	Semi standard non polar	33892256
Codeine-6-glucuronide,1TBDMS,isomer #1	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C	3919.5	Semi standard non polar	33892256
Codeine-6-glucuronide,1TBDMS,isomer #2	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C	3937.7	Semi standard non polar	33892256
Codeine-6-glucuronide,1TBDMS,isomer #3	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]5O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C	3923.0	Semi standard non polar	33892256
Codeine-6-glucuronide,1TBDMS,isomer #4	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]5O)[C@@H]5OC1=C2[C@@]54CCN3C	3887.5	Semi standard non polar	33892256
Codeine-6-glucuronide,2TBDMS,isomer #1	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[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]5O)[C@@H]5OC1=C2[C@@]54CCN3C	4091.6	Semi standard non polar	33892256
Codeine-6-glucuronide,2TBDMS,isomer #2	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[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]5O)[C@@H]5OC1=C2[C@@]54CCN3C	4111.8	Semi standard non polar	33892256
Codeine-6-glucuronide,2TBDMS,isomer #3	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]5O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C	4111.9	Semi standard non polar	33892256
Codeine-6-glucuronide,2TBDMS,isomer #4	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[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]5O)[C@@H]5OC1=C2[C@@]54CCN3C	4096.4	Semi standard non polar	33892256
Codeine-6-glucuronide,2TBDMS,isomer #5	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]5O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C	4107.1	Semi standard non polar	33892256
Codeine-6-glucuronide,2TBDMS,isomer #6	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]5O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C	4089.6	Semi standard non polar	33892256
Codeine-6-glucuronide,3TBDMS,isomer #1	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[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]5O)[C@@H]5OC1=C2[C@@]54CCN3C	4256.5	Semi standard non polar	33892256
Codeine-6-glucuronide,3TBDMS,isomer #2	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[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]5O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C	4268.9	Semi standard non polar	33892256
Codeine-6-glucuronide,3TBDMS,isomer #3	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[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]5O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C	4279.6	Semi standard non polar	33892256
Codeine-6-glucuronide,3TBDMS,isomer #4	COC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[C@@H]5O[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]5O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3C	4260.1	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 - Codeine-6-glucuronide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9202300000-c0e5abf76f3d3777bf71	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Codeine-6-glucuronide GC-MS (3 TMS) - 70eV, Positive	splash10-004i-5251029000-7a0f671ad644403d7704	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Codeine-6-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 - Codeine-6-glucuronide 10V, Positive-QTOF	splash10-0zi0-0156900000-94e266093e29f563d412	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine-6-glucuronide 20V, Positive-QTOF	splash10-0ue9-0189100000-506af8b6b31a10be8b3e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine-6-glucuronide 40V, Positive-QTOF	splash10-001l-1191000000-97b95309ab6cb729c927	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine-6-glucuronide 10V, Negative-QTOF	splash10-00dj-2240900000-97f310bd2d4e910d5386	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine-6-glucuronide 20V, Negative-QTOF	splash10-000t-1290300000-addb13b052bca1e8d8cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine-6-glucuronide 40V, Negative-QTOF	splash10-001m-3190000000-1a066b69fdc8045d7592	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine-6-glucuronide 10V, Positive-QTOF	splash10-001i-0091800000-f683f5fbf7057a476377	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine-6-glucuronide 20V, Positive-QTOF	splash10-001i-0256900000-c792ae5e958b1756378f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine-6-glucuronide 40V, Positive-QTOF	splash10-01q9-6498500000-ff04bfeeb8802cc45c22	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine-6-glucuronide 10V, Negative-QTOF	splash10-00di-0010900000-f61069a4327f438acbc5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine-6-glucuronide 20V, Negative-QTOF	splash10-0002-5984700000-0a2873e05408ba63e5be	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Codeine-6-glucuronide 40V, Negative-QTOF	splash10-059t-9373200000-b8019fef538f241a652d	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Microsomes

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Codeine Action Pathway		Not Available
Codeine Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Available	Not Available	collected 0–6 h after oral intake of 60 mg of codeine	9448068	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Arrested for driving under the influence of drugs.	9448068	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	femoral vein blood in a typical case of fatal heroin overdose.	9448068	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Female	Heroine addict	16258895	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C16577

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Codeine-6-glucuronide

METLIN ID

Not Available

PubChem Compound

5489029

PDB ID

Not Available

ChEBI ID

80580

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Srinivasan, Vinayak; Wielbo, Donna; Simpkins, James; Karlix, Janet; Sloan, Kenneth; Tebbett, Ian, 1996: Analgesic and immunomodulatory effects of codeine and codeine 6-glucuronide. Pharmaceutical Research (new York). 13(2): 296-300

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Murphy CM, Huestis MA: LC-ESI-MS/MS analysis for the quantification of morphine, codeine, morphine-3-beta-D-glucuronide, morphine-6-beta-D-glucuronide, and codeine-6-beta-D-glucuronide in human urine. J Mass Spectrom. 2005 Nov;40(11):1412-6. [PubMed:16258895 ]
Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
Srinivasan V, Wielbo D, Tebbett IR: Analgesic effects of codeine-6-glucuronide after intravenous administration. Eur J Pain. 1997;1(3):185-90. [PubMed:15102399 ]
Vree TB, van Dongen RT, Koopman-Kimenai PM: Codeine analgesia is due to codeine-6-glucuronide, not morphine. Int J Clin Pract. 2000 Jul-Aug;54(6):395-8. [PubMed:11092114 ]
Raungrut P, Uchaipichat V, Elliot DJ, Janchawee B, Somogyi AA, Miners JO: In vitro-in vivo extrapolation predicts drug-drug interactions arising from inhibition of codeine glucuronidation by dextropropoxyphene, fluconazole, ketoconazole, and methadone in humans. J Pharmacol Exp Ther. 2010 Aug;334(2):609-18. doi: 10.1124/jpet.110.167916. Epub 2010 May 18. [PubMed:20484152 ]
Bogusz MJ, Maier RD, Erkens M, Driessen S: Determination of morphine and its 3- and 6-glucuronides, codeine, codeine-glucuronide and 6-monoacetylmorphine in body fluids by liquid chromatography atmospheric pressure chemical ionization mass spectrometry. J Chromatogr B Biomed Sci Appl. 1997 Dec 5;703(1-2):115-27. [PubMed:9448068 ]

Only showing the first 10 proteins. There are 18 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

Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronide	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

Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronide	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

Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronide	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

Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronide	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

Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronide	details

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

Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronide	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

Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronide	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

Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronide	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

Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronide	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

Uridine diphosphate glucuronic acid + Codeine → Uridine 5'-diphosphate + Codeine-6-glucuronide	details

Only showing the first 10 proteins. There are 18 proteins in total.

Show all enzymes and transporters

Showing metabocard for Codeine-6-glucuronide (HMDB0060464)

MOL for HMDB0060464 (Codeine-6-glucuronide)

3D MOL for HMDB0060464 (Codeine-6-glucuronide)

3D SDF for HMDB0060464 (Codeine-6-glucuronide)

3D-SDF for HMDB0060464 (Codeine-6-glucuronide)

PDB for HMDB0060464 (Codeine-6-glucuronide)

3D PDB for HMDB0060464 (Codeine-6-glucuronide)

SMILES for HMDB0060464 (Codeine-6-glucuronide)

INCHI for HMDB0060464 (Codeine-6-glucuronide)

Structure for HMDB0060464 (Codeine-6-glucuronide)

3D Structure for HMDB0060464 (Codeine-6-glucuronide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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