NP-MRD: Showing NP-Card for morphine-3-glucuronide (NP0269398)

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Record Information

Version

2.0

Created at

2022-09-08 14:52:05 UTC

Updated at

2022-09-08 14:52:05 UTC

NP-MRD ID

NP0269398

Secondary Accession Numbers

None

Natural Product Identification

Common Name

morphine-3-glucuronide

Description

Morphine-3-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. Morphine-3-glucuronide is a very strong basic compound (based on its pKa). Morphine-3-glucuronide and uridine 5'-diphosphate can be biosynthesized from morphine and uridine diphosphate glucuronic acid; which is catalyzed by the enzymes UDP-glucuronosyltransferase 2B7 and UDP-glucuronosyltransferase 1-1. In humans, morphine-3-glucuronide is involved in morphine metabolism pathway. morphine-3-glucuronide is found in Papaver somniferum. 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.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05301311022D          

 34 39  0  0  0  0            999 V2000
    2.0483   -1.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3892    1.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8812    1.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5781    1.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7004    1.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3295    0.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1855   -0.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2648    0.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5638    0.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8520    0.9681    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4499    0.1781    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1372    2.4592    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1814    2.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0443    1.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8106    5.2832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9927    5.1761    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3122    4.6283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3341    2.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6764    4.4142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9590    2.2954    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8583    4.3072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960    3.8664    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1661    1.4555    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9088   -0.4093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8835    3.2441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1269    6.0450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4910    5.8310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1302    4.7353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5421    3.5453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3567    4.9621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4976    3.2115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6228    2.7966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1780    3.7594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7876   -0.5745    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  2  2  0  0  0  0
  7  6  1  0  0  0  0
  9  2  1  0  0  0  0
  9  8  1  0  0  0  0
 10  3  1  6  0  0  0
 11  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12  4  1  0  0  0  0
 13  5  1  0  0  0  0
 14  9  2  0  0  0  0
 16 15  1  0  0  0  0
 17 15  1  0  0  0  0
 18 13  2  0  0  0  0
 18 14  1  0  0  0  0
 19 16  1  0  0  0  0
 20 12  1  0  0  0  0
 19 21  1  6  0  0  0
 22 17  1  0  0  0  0
 23  6  1  0  0  0  0
 23 10  1  0  0  0  0
 23 14  1  1  0  0  0
 23 20  1  0  0  0  0
 24  1  1  0  0  0  0
 24  7  1  0  0  0  0
 24 11  1  0  0  0  0
 12 25  1  6  0  0  0
 15 26  1  6  0  0  0
 16 27  1  1  0  0  0
 17 28  1  1  0  0  0
 29 21  2  0  0  0  0
 30 21  1  0  0  0  0
 31 13  1  0  0  0  0
 22 31  1  6  0  0  0
 32 18  1  0  0  0  0
 20 32  1  6  0  0  0
 33 19  1  0  0  0  0
 33 22  1  0  0  0  0
 11 34  1  6  0  0  0
M  END

     RDKit          3D

 60 65  0  0  0  0  0  0  0  0999 V2000
    6.1824    1.8884    0.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7378    1.9082    0.4545 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4793    1.5083    1.7976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0770    1.0105    2.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7293   -0.0908    1.0848 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5571    0.3496    0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6401    1.1812   -0.7715 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4875    1.5216   -1.4285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7264    0.9989   -0.9807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7733    0.1440    0.1160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9352   -0.3938    0.5930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2311   -0.2072    0.1080 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0742    0.3493    1.0981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2714    0.6989    0.4865 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.0972    1.5423    1.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2152    1.9397    0.9620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6725    1.9029    2.6532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9858   -0.6008    0.1294 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2896   -0.3708   -0.2871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1536   -1.2598   -0.9633 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7817   -2.3970   -1.4184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8001   -1.5619   -0.3369 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9001   -2.0827   -1.2479 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4101   -0.1890    0.7693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7798   -0.9758    1.8546 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1777   -1.3162    1.7358 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3122   -2.5673    0.9600 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0705   -3.1918    0.8486 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8667   -2.4057   -0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5739   -1.3669   -0.8112 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8434   -0.2746    0.1260 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1108    1.0535   -0.5443 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9399    1.6915   -1.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4152    0.8308   -0.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7180    2.0105    1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4938    2.5982   -0.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2131    0.7805    2.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5997    2.4250    2.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3564    1.8552    2.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0558    0.6047    3.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4743    2.1909   -2.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6291    1.2754   -1.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3162    0.4500   -0.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0757    1.2200   -0.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9111    2.7902    3.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9657   -1.2421    1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4326   -0.6130   -1.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0550   -0.4795   -1.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1884   -3.0274   -1.8756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9825   -2.2104    0.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2955   -2.2674   -2.1399 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5877   -1.3799    2.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9475   -3.2785    1.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7263   -3.1683   -0.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6657   -3.2279   -1.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9514   -1.3141   -1.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7611   -0.5297    0.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8676    0.8364   -1.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9743    1.6432   -2.3153 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9757    2.7905   -0.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 33  1  0
 33  7  1  0
  7  6  2  0
  6 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 31  5  1  0
  5  4  1  1
  4  3  1  0
  3  2  1  0
  2  1  1  0
 24 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
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 22 23  1  0
 14 15  1  0
 15 17  1  0
 15 16  2  0
 10  9  1  0
  9  8  2  0
 31 32  1  0
 22 12  1  0
  2 32  1  0
  8  7  1  0
  5  6  1  0
  5 26  1  0
 32 58  1  6
 33 59  1  0
 33 60  1  0
 26 52  1  1
 27 53  1  1
 28 54  1  0
 29 55  1  0
 30 56  1  0
 31 57  1  1
  4 39  1  0
  4 40  1  0
  3 37  1  0
  3 38  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
 12 43  1  6
 14 44  1  6
 18 46  1  1
 19 47  1  0
 20 48  1  6
 21 49  1  0
 22 50  1  1
 23 51  1  0
 17 45  1  0
  9 42  1  0
  8 41  1  0
M  END


  Mrv0541 05301311022D          

 34 39  0  0  0  0            999 V2000
    2.0483   -1.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3892    1.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8812    1.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5781    1.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7004    1.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3295    0.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1855   -0.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2648    0.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5638    0.9416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8520    0.9681    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4499    0.1781    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1372    2.4592    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1814    2.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0443    1.5880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8106    5.2832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9927    5.1761    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3122    4.6283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3341    2.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6764    4.4142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9590    2.2954    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8583    4.3072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960    3.8664    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1661    1.4555    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9088   -0.4093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8835    3.2441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1269    6.0450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4910    5.8310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1302    4.7353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5421    3.5453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3567    4.9621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4976    3.2115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6228    2.7966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1780    3.7594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7876   -0.5745    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  2  2  0  0  0  0
  7  6  1  0  0  0  0
  9  2  1  0  0  0  0
  9  8  1  0  0  0  0
 10  3  1  6  0  0  0
 11  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12  4  1  0  0  0  0
 13  5  1  0  0  0  0
 14  9  2  0  0  0  0
 16 15  1  0  0  0  0
 17 15  1  0  0  0  0
 18 13  2  0  0  0  0
 18 14  1  0  0  0  0
 19 16  1  0  0  0  0
 20 12  1  0  0  0  0
 19 21  1  6  0  0  0
 22 17  1  0  0  0  0
 23  6  1  0  0  0  0
 23 10  1  0  0  0  0
 23 14  1  1  0  0  0
 23 20  1  0  0  0  0
 24  1  1  0  0  0  0
 24  7  1  0  0  0  0
 24 11  1  0  0  0  0
 12 25  1  6  0  0  0
 15 26  1  6  0  0  0
 16 27  1  1  0  0  0
 17 28  1  1  0  0  0
 29 21  2  0  0  0  0
 30 21  1  0  0  0  0
 31 13  1  0  0  0  0
 22 31  1  6  0  0  0
 32 18  1  0  0  0  0
 20 32  1  6  0  0  0
 33 19  1  0  0  0  0
 33 22  1  0  0  0  0
 11 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0269398

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC3=C4C(O[C@H]5[C@@H](O)C=C[C@@H]1[C@@]45CCN2C)=C(O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C23H27NO9/c1-24-7-6-23-10-3-4-12(25)20(23)32-18-13(5-2-9(14(18)23)8-11(10)24)31-22-17(28)15(26)16(27)19(33-22)21(29)30/h2-5,10-12,15-17,19-20,22,25-28H,6-8H2,1H3,(H,29,30)/t10-,11+,12-,15-,16-,17+,19-,20-,22+,23-/m0/s1

> <INCHI_KEY>
WAEXKFONHRHFBZ-ZXDZBKESSA-N

> <FORMULA>
C23H27NO9

> <MOLECULAR_WEIGHT>
461.4618

> <EXACT_MASS>
461.168581467

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
45.5118391531759

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-14-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-10-yl]oxy}oxane-2-carboxylic acid

> <ALOGPS_LOGP>
-0.63

> <JCHEM_LOGP>
-3.481938951624473

> <ALOGPS_LOGS>
-1.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.205410175123866

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.673981878897039

> <JCHEM_PKA_STRONGEST_BASIC>
9.172367845245422

> <JCHEM_POLAR_SURFACE_AREA>
149.15

> <JCHEM_REFRACTIVITY>
112.13419999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
morphine-3-glucuronide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-MAY-13         0                                  
HETATM    1  C   UNK     0       3.824  -2.282   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.193   1.920   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.645   2.086   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.079   3.468   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.774   3.348   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.482   1.608   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.213  -0.049   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.094   0.359   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.652   1.758   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.457   1.807   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.573   0.332   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.123   4.591   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.805   4.573   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.683   2.964   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.113   9.862   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.586   9.662   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.050   8.640   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.224   4.391   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.996   8.240   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.657   4.285   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.469   8.040   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.459   7.217   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.043   2.717   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       3.563  -0.764   0.000  0.00  0.00           N+0
HETATM   25  O   UNK     0       1.649   6.056   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.703  11.284   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.650  10.885   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       9.576   8.839   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.879   6.618   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.532   9.263   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       8.396   5.995   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       4.896   5.220   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       5.932   7.018   0.000  0.00  0.00           O+0
HETATM   34  H   UNK     0       5.203  -1.072   0.000  0.00  0.00           H+0
CONECT    1   24                                                            
CONECT    2    5    9                                                       
CONECT    3    4   10                                                       
CONECT    4    3   12                                                       
CONECT    5    2   13                                                       
CONECT    6    7   23                                                       
CONECT    7    6   24                                                       
CONECT    8    9   11                                                       
CONECT    9    2    8   14                                                  
CONECT   10    3   11   23                                                  
CONECT   11    8   10   24   34                                             
CONECT   12    4   20   25                                                  
CONECT   13    5   18   31                                                  
CONECT   14    9   18   23                                                  
CONECT   15   16   17   26                                                  
CONECT   16   15   19   27                                                  
CONECT   17   15   22   28                                                  
CONECT   18   13   14   32                                                  
CONECT   19   16   21   33                                                  
CONECT   20   12   23   32                                                  
CONECT   21   19   29   30                                                  
CONECT   22   17   31   33                                                  
CONECT   23    6   10   14   20                                             
CONECT   24    1    7   11                                                  
CONECT   25   12                                                            
CONECT   26   15                                                            
CONECT   27   16                                                            
CONECT   28   17                                                            
CONECT   29   21                                                            
CONECT   30   21                                                            
CONECT   31   13   22                                                       
CONECT   32   18   20                                                       
CONECT   33   19   22                                                       
CONECT   34   11                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Value	Source
Morphine 3-glucuronide(minor)	HMDB
Morphine-3beta-D-glucuronide	HMDB

Chemical Formula

C₂₃H₂₇NO₉

Average Mass

461.4618 Da

Monoisotopic Mass

461.16858 Da

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-14-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-10-yl]oxy}oxane-2-carboxylic acid

Traditional Name

morphine-3-glucuronide

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC3=C4C(O[C@H]5[C@@H](O)C=C[C@@H]1[C@@]45CCN2C)=C(O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C=C3

InChI Identifier

InChI=1S/C23H27NO9/c1-24-7-6-23-10-3-4-12(25)20(23)32-18-13(5-2-9(14(18)23)8-11(10)24)31-22-17(28)15(26)16(27)19(33-22)21(29)30/h2-5,10-12,15-17,19-20,22,25-28H,6-8H2,1H3,(H,29,30)/t10-,11+,12-,15-,16-,17+,19-,20-,22+,23-/m0/s1

InChI Key

WAEXKFONHRHFBZ-ZXDZBKESSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Papaver somniferum	LOTUS Database	35616633

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

morphinane alkaloid (CHEBI:80631 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	-0.63	ALOGPS
logP	-3.5	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	2.67	ChemAxon
pKa (Strongest Basic)	9.17	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	149.15 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	112.13 m³·mol⁻¹	ChemAxon
Polarizability	45.51 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

External Links

HMDB ID

HMDB0041936

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4588593

KEGG Compound ID

C16643

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Morphine-3-glucuronide

METLIN ID

Not Available

PubChem Compound

5484731

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for morphine-3-glucuronide (NP0269398)

MOL for NP0269398 (morphine-3-glucuronide)

3D MOL for NP0269398 (morphine-3-glucuronide)

3D SDF for NP0269398 (morphine-3-glucuronide)

3D-SDF for NP0269398 (morphine-3-glucuronide)

PDB for NP0269398 (morphine-3-glucuronide)

3D PDB for NP0269398 (morphine-3-glucuronide)

SMILES for NP0269398 (morphine-3-glucuronide)

INCHI for NP0269398 (morphine-3-glucuronide)

Structure for NP0269398 (morphine-3-glucuronide)

3D Structure for NP0269398 (morphine-3-glucuronide)