NP-MRD: Showing NP-Card for 4E,15Z-Bilirubin IXa (NP0001295)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-08-10 02:54:44 UTC

NP-MRD ID

NP0001295

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4E,15Z-Bilirubin IXa

Description

4E,15Z-Bilirubin IXa is an isomer of bilirubin, which has antioxidative effects. When bilirubin reacts with reactive oxygen species, oxidized metabolites of bilirubin are formed, such as biliverdin and propentdyopents. A decrease in serum bilirubin concentration and an increase in serum and urinary oxidized metabolites of bilirubin may indicate the protective action of bilirubin against reactive oxygen species (PMID: 10986860 ).

Structure

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


  Mrv1652306202123373D          

 79 82  0  0  0  0            999 V2000
   -1.4935   -3.6883    5.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411   -2.7742    4.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8780   -1.4327    4.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7071   -0.4634    3.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8676   -0.5568    1.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4378    0.7423    3.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6101    1.9435    2.9224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0855    2.3284    1.6689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6810    1.8300    0.5413 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0559    2.3170   -0.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5310    1.9345   -1.9584 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6238    0.4517   -2.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4756   -0.3032   -2.2055 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7815   -1.6392   -2.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7652   -2.6350   -2.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4501   -2.5869   -1.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9794   -1.5646   -1.0263 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2881   -1.7846   -0.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0370   -1.0057   -0.1425 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6185   -3.1324   -1.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9643   -3.7133   -1.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5029   -3.6051   -1.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4599   -4.9124   -2.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5095   -5.8275   -2.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1637   -1.7368   -2.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9547   -2.9934   -2.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7009   -0.4032   -2.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1522   -0.0335   -2.4621 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7897    0.5704   -1.2221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6262   -0.2993   -0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9131   -0.0467    0.9436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3719   -1.4169   -0.0531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0179    3.1410   -0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0148    3.8378   -1.0349 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4371    3.4581   -0.7542 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6890    1.9756   -0.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0334    1.1524   -1.4602 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7981    1.6366   -0.1478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0876    3.2009    1.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2285    4.0038    2.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0236    0.4489    4.6895 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7615   -0.8326    5.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1807   -1.3506    6.1197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0563   -3.4964    5.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0452   -4.6722    4.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7573   -3.0712    3.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4961   -0.5807    0.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1687    0.2826    1.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2514   -1.4594    1.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1936    2.6995    3.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4391    1.1540    0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8611    2.3389   -2.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5056    2.4028   -2.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5425    0.0971   -2.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0330   -3.5352   -2.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5300   -0.6897   -0.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7245   -3.1109   -1.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407   -4.7364   -1.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2027   -3.7386    0.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2790   -5.1571   -3.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3131   -5.6479   -1.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5457   -6.7949   -2.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3159   -3.0888   -3.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8174   -2.9915   -1.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3608   -3.8811   -2.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7285   -0.9153   -2.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2459    0.6809   -3.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3558    1.5490   -0.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8596    0.7451   -1.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1541   -1.8781    0.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2300    3.6368   -2.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1316    4.9209   -0.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7277    3.8023    0.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932    3.9525   -1.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9154    0.6525   -0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0837    4.9398    1.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6650    3.4350    2.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7642    4.2658    3.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6102    1.0684    5.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 14  2  0  0  0  0
 22 20  2  0  0  0  0
  9 10  1  0  0  0  0
  4  3  2  0  0  0  0
  3 42  1  0  0  0  0
 42 41  1  0  0  0  0
 41  6  1  0  0  0  0
 14 13  1  0  0  0  0
 42 43  2  0  0  0  0
 10 33  2  0  0  0  0
  3  2  1  0  0  0  0
 18 19  2  0  0  0  0
 33 39  1  0  0  0  0
 20 21  1  0  0  0  0
 20 18  1  0  0  0  0
 22 23  1  0  0  0  0
 18 17  1  0  0  0  0
 23 24  2  3  0  0  0
 17 16  1  0  0  0  0
 25 26  1  0  0  0  0
 16 22  1  0  0  0  0
 33 34  1  0  0  0  0
 39  8  2  0  0  0  0
 34 35  1  0  0  0  0
 16 15  2  0  0  0  0
 35 36  1  0  0  0  0
 15 14  1  0  0  0  0
 36 37  2  0  0  0  0
  8  9  1  0  0  0  0
 36 38  1  0  0  0  0
 12 11  1  0  0  0  0
 39 40  1  0  0  0  0
 11 10  1  0  0  0  0
  2  1  2  3  0  0  0
 13 12  1  0  0  0  0
 27 28  1  0  0  0  0
  8  7  1  0  0  0  0
 28 29  1  0  0  0  0
 12 27  2  0  0  0  0
 29 30  1  0  0  0  0
  7  6  2  0  0  0  0
 30 32  1  0  0  0  0
  6  4  1  0  0  0  0
 30 31  2  0  0  0  0
 27 25  1  0  0  0  0
  4  5  1  0  0  0  0
  9 51  1  0  0  0  0
 13 54  1  0  0  0  0
 17 56  1  0  0  0  0
 15 55  1  0  0  0  0
 11 52  1  0  0  0  0
 11 53  1  0  0  0  0
  7 50  1  0  0  0  0
 41 79  1  0  0  0  0
  2 46  1  0  0  0  0
 21 57  1  0  0  0  0
 21 58  1  0  0  0  0
 21 59  1  0  0  0  0
 23 60  1  0  0  0  0
 24 61  1  0  0  0  0
 24 62  1  0  0  0  0
 26 63  1  0  0  0  0
 26 64  1  0  0  0  0
 26 65  1  0  0  0  0
 34 71  1  0  0  0  0
 34 72  1  0  0  0  0
 35 73  1  0  0  0  0
 35 74  1  0  0  0  0
 38 75  1  0  0  0  0
 40 76  1  0  0  0  0
 40 77  1  0  0  0  0
 40 78  1  0  0  0  0
  1 44  1  0  0  0  0
  1 45  1  0  0  0  0
 28 66  1  0  0  0  0
 28 67  1  0  0  0  0
 29 68  1  0  0  0  0
 29 69  1  0  0  0  0
 32 70  1  0  0  0  0
  5 47  1  0  0  0  0
  5 48  1  0  0  0  0
  5 49  1  0  0  0  0
M  END

HMDB0000488
     RDKit          3D
(4E,15Z)-Bilirubin
 79 82  0  0  0  0  0  0  0  0999 V2000
    5.3628    1.7901    4.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650    1.1392    3.5616 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0141    0.3875    2.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0347    0.1591    1.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6396    0.6591    1.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539   -0.6236    0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9754   -0.9670   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6332   -0.5946   -1.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6330   -1.4552   -1.3469 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5323   -0.8063   -1.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3158   -1.4840   -2.3299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9374   -1.3958   -1.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9173   -0.5345   -1.9897 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9737   -0.6487   -1.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1890    0.1542   -1.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6260    0.9274   -0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9910    1.0677    0.9174 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7595    1.9762    1.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5271    2.3606    2.8395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8719    2.4082    0.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9136    3.3853    1.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8024    1.7932   -0.3490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7827    2.0507   -1.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9055    1.5816   -2.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7060   -1.5937   -0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5853   -2.1052    0.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4143   -2.0647   -0.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7785   -3.0957    0.3197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6153   -4.4383   -0.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0455   -5.4379    0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0983   -5.2581    1.8239 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5516   -6.5735    0.0916 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9134    0.5360   -1.9154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0514    1.6528   -2.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4989    2.5089   -1.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1761    1.8197   -0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0837    0.6718    0.2641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1948    2.4836    0.6345 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2394    0.6694   -1.4749 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    1.9684   -1.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9372   -0.9301    0.6761 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1864   -0.2920    1.9238 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3416   -0.3701    2.4614 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2680    2.1404    4.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8555    2.1543    5.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9753    1.0666    4.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8862   -0.0030    1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3618    0.7071    2.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6282    1.7148    1.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5769   -1.6051   -1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6693   -2.4930   -1.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5916   -2.5842   -2.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1614   -1.1935   -3.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9052    0.1342   -2.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7327    0.1330   -2.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1042    0.5712    1.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0629    4.0904    0.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8114    2.7960    1.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5201    3.9569    2.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5883    2.7967   -1.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7882    1.9575   -3.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2892    0.8923   -3.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6043   -1.7266    0.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1747   -1.8529    1.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6360   -3.2280    0.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2638   -3.1576    1.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2724   -2.7356    0.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0368   -4.4258   -1.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6531   -4.7637   -0.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5112   -6.8541    0.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1518    1.2141   -2.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6097    2.2774   -3.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1643    3.3283   -0.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3484    3.0936   -1.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8628    2.8261    1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2534    2.2891   -2.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9491    1.7521   -0.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4687    2.7280   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6082   -1.4789    0.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  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  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  3
 14 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 10 33  2  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 33 39  1  0
 39 40  1  0
  6 41  1  0
 41 42  1  0
 42 43  2  0
 42  3  1  0
 39  8  2  0
 27 12  2  0
 22 16  1  0
  1 44  1  0
  1 45  1  0
  2 46  1  0
  5 47  1  0
  5 48  1  0
  5 49  1  0
  7 50  1  0
  9 51  1  0
 11 52  1  0
 11 53  1  0
 13 54  1  0
 15 55  1  0
 17 56  1  0
 21 57  1  0
 21 58  1  0
 21 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
 32 70  1  0
 34 71  1  0
 34 72  1  0
 35 73  1  0
 35 74  1  0
 38 75  1  0
 40 76  1  0
 40 77  1  0
 40 78  1  0
 41 79  1  0
M  END


  Mrv1652306202123373D          

 79 82  0  0  0  0            999 V2000
   -1.4935   -3.6883    5.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3411   -2.7742    4.0601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8780   -1.4327    4.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7071   -0.4634    3.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8676   -0.5568    1.8894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4378    0.7423    3.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6101    1.9435    2.9224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0855    2.3284    1.6689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6810    1.8300    0.5413 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0559    2.3170   -0.5836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5310    1.9345   -1.9584 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6238    0.4517   -2.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4756   -0.3032   -2.2055 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7815   -1.6392   -2.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7652   -2.6350   -2.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4501   -2.5869   -1.7499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9794   -1.5646   -1.0263 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2881   -1.7846   -0.7061 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0370   -1.0057   -0.1425 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6185   -3.1324   -1.2166 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9643   -3.7133   -1.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5029   -3.6051   -1.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4599   -4.9124   -2.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5095   -5.8275   -2.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1637   -1.7368   -2.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9547   -2.9934   -2.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7009   -0.4032   -2.3209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1522   -0.0335   -2.4621 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7897    0.5704   -1.2221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6262   -0.2993   -0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9131   -0.0467    0.9436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3719   -1.4169   -0.0531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0179    3.1410   -0.1576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0148    3.8378   -1.0349 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4371    3.4581   -0.7542 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6890    1.9756   -0.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0334    1.1524   -1.4602 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7981    1.6366   -0.1478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0876    3.2009    1.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2285    4.0038    2.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0236    0.4489    4.6895 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7615   -0.8326    5.1009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1807   -1.3506    6.1197 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0563   -3.4964    5.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0452   -4.6722    4.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7573   -3.0712    3.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4961   -0.5807    0.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1687    0.2826    1.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2514   -1.4594    1.8653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1936    2.6995    3.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4391    1.1540    0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8611    2.3389   -2.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5056    2.4028   -2.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5425    0.0971   -2.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0330   -3.5352   -2.8625 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5300   -0.6897   -0.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7245   -3.1109   -1.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407   -4.7364   -1.3806 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2027   -3.7386    0.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2790   -5.1571   -3.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3131   -5.6479   -1.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5457   -6.7949   -2.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3159   -3.0888   -3.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8174   -2.9915   -1.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3608   -3.8811   -2.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7285   -0.9153   -2.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2459    0.6809   -3.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3558    1.5490   -0.9915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8596    0.7451   -1.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1541   -1.8781    0.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2300    3.6368   -2.0898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1316    4.9209   -0.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7277    3.8023    0.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932    3.9525   -1.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9154    0.6525   -0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0837    4.9398    1.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6650    3.4350    2.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7642    4.2658    3.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6102    1.0684    5.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 14  2  0  0  0  0
 22 20  2  0  0  0  0
  9 10  1  0  0  0  0
  4  3  2  0  0  0  0
  3 42  1  0  0  0  0
 42 41  1  0  0  0  0
 41  6  1  0  0  0  0
 14 13  1  0  0  0  0
 42 43  2  0  0  0  0
 10 33  2  0  0  0  0
  3  2  1  0  0  0  0
 18 19  2  0  0  0  0
 33 39  1  0  0  0  0
 20 21  1  0  0  0  0
 20 18  1  0  0  0  0
 22 23  1  0  0  0  0
 18 17  1  0  0  0  0
 23 24  2  3  0  0  0
 17 16  1  0  0  0  0
 25 26  1  0  0  0  0
 16 22  1  0  0  0  0
 33 34  1  0  0  0  0
 39  8  2  0  0  0  0
 34 35  1  0  0  0  0
 16 15  2  0  0  0  0
 35 36  1  0  0  0  0
 15 14  1  0  0  0  0
 36 37  2  0  0  0  0
  8  9  1  0  0  0  0
 36 38  1  0  0  0  0
 12 11  1  0  0  0  0
 39 40  1  0  0  0  0
 11 10  1  0  0  0  0
  2  1  2  3  0  0  0
 13 12  1  0  0  0  0
 27 28  1  0  0  0  0
  8  7  1  0  0  0  0
 28 29  1  0  0  0  0
 12 27  2  0  0  0  0
 29 30  1  0  0  0  0
  7  6  2  0  0  0  0
 30 32  1  0  0  0  0
  6  4  1  0  0  0  0
 30 31  2  0  0  0  0
 27 25  1  0  0  0  0
  4  5  1  0  0  0  0
  9 51  1  0  0  0  0
 13 54  1  0  0  0  0
 17 56  1  0  0  0  0
 15 55  1  0  0  0  0
 11 52  1  0  0  0  0
 11 53  1  0  0  0  0
  7 50  1  0  0  0  0
 41 79  1  0  0  0  0
  2 46  1  0  0  0  0
 21 57  1  0  0  0  0
 21 58  1  0  0  0  0
 21 59  1  0  0  0  0
 23 60  1  0  0  0  0
 24 61  1  0  0  0  0
 24 62  1  0  0  0  0
 26 63  1  0  0  0  0
 26 64  1  0  0  0  0
 26 65  1  0  0  0  0
 34 71  1  0  0  0  0
 34 72  1  0  0  0  0
 35 73  1  0  0  0  0
 35 74  1  0  0  0  0
 38 75  1  0  0  0  0
 40 76  1  0  0  0  0
 40 77  1  0  0  0  0
 40 78  1  0  0  0  0
  1 44  1  0  0  0  0
  1 45  1  0  0  0  0
 28 66  1  0  0  0  0
 28 67  1  0  0  0  0
 29 68  1  0  0  0  0
 29 69  1  0  0  0  0
 32 70  1  0  0  0  0
  5 47  1  0  0  0  0
  5 48  1  0  0  0  0
  5 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001295

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])C([H])([H])C1=C(N([H])C(\C([H])=C2/N([H])C(=O)C(=C2C([H])=C([H])[H])C([H])([H])[H])=C1C([H])([H])[H])C([H])([H])C1=C(C(=C(N1[H])C(\[H])=C1\N([H])C(=O)C(C([H])=C([H])[H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])C(=O)O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C33H36N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13+,27-14-

> <INCHI_KEY>
BPYKTIZUTYGOLE-KDUUSRDASA-N

> <FORMULA>
C33H36N4O6

> <MOLECULAR_WEIGHT>
584.6621

> <EXACT_MASS>
584.263484904

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
65.37085348816532

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(2-{[3-(2-carboxyethyl)-5-{[(2E)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid

> <ALOGPS_LOGP>
3.22

> <JCHEM_LOGP>
3.119106452999999

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.630728870728111

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.027490824017337

> <JCHEM_PKA_STRONGEST_BASIC>
-2.754561928374644

> <JCHEM_POLAR_SURFACE_AREA>
164.37999999999997

> <JCHEM_REFRACTIVITY>
168.89600000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.64e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2-{[3-(2-carboxyethyl)-5-{[(2E)-4-ethenyl-3-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000488
     RDKit          3D
(4E,15Z)-Bilirubin
 79 82  0  0  0  0  0  0  0  0999 V2000
    5.3628    1.7901    4.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650    1.1392    3.5616 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0141    0.3875    2.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0347    0.1591    1.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6396    0.6591    1.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539   -0.6236    0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9754   -0.9670   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6332   -0.5946   -1.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6330   -1.4552   -1.3469 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5323   -0.8063   -1.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3158   -1.4840   -2.3299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9374   -1.3958   -1.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9173   -0.5345   -1.9897 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9737   -0.6487   -1.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1890    0.1542   -1.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6260    0.9274   -0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9910    1.0677    0.9174 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7595    1.9762    1.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5271    2.3606    2.8395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8719    2.4082    0.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9136    3.3853    1.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8024    1.7932   -0.3490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7827    2.0507   -1.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9055    1.5816   -2.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7060   -1.5937   -0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5853   -2.1052    0.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4143   -2.0647   -0.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7785   -3.0957    0.3197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6153   -4.4383   -0.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0455   -5.4379    0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0983   -5.2581    1.8239 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5516   -6.5735    0.0916 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9134    0.5360   -1.9154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0514    1.6528   -2.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4989    2.5089   -1.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1761    1.8197   -0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0837    0.6718    0.2641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1948    2.4836    0.6345 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2394    0.6694   -1.4749 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    1.9684   -1.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9372   -0.9301    0.6761 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1864   -0.2920    1.9238 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3416   -0.3701    2.4614 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2680    2.1404    4.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8555    2.1543    5.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9753    1.0666    4.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8862   -0.0030    1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3618    0.7071    2.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6282    1.7148    1.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5769   -1.6051   -1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6693   -2.4930   -1.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5916   -2.5842   -2.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1614   -1.1935   -3.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9052    0.1342   -2.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7327    0.1330   -2.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1042    0.5712    1.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0629    4.0904    0.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8114    2.7960    1.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5201    3.9569    2.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5883    2.7967   -1.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7882    1.9575   -3.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2892    0.8923   -3.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6043   -1.7266    0.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1747   -1.8529    1.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6360   -3.2280    0.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2638   -3.1576    1.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2724   -2.7356    0.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0368   -4.4258   -1.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6531   -4.7637   -0.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5112   -6.8541    0.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1518    1.2141   -2.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6097    2.2774   -3.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1643    3.3283   -0.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3484    3.0936   -1.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8628    2.8261    1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2534    2.2891   -2.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9491    1.7521   -0.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4687    2.7280   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6082   -1.4789    0.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  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  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  3
 14 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 10 33  2  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 33 39  1  0
 39 40  1  0
  6 41  1  0
 41 42  1  0
 42 43  2  0
 42  3  1  0
 39  8  2  0
 27 12  2  0
 22 16  1  0
  1 44  1  0
  1 45  1  0
  2 46  1  0
  5 47  1  0
  5 48  1  0
  5 49  1  0
  7 50  1  0
  9 51  1  0
 11 52  1  0
 11 53  1  0
 13 54  1  0
 15 55  1  0
 17 56  1  0
 21 57  1  0
 21 58  1  0
 21 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
 32 70  1  0
 34 71  1  0
 34 72  1  0
 35 73  1  0
 35 74  1  0
 38 75  1  0
 40 76  1  0
 40 77  1  0
 40 78  1  0
 41 79  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.494  -3.688   5.027  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.341  -2.774   4.060  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.878  -1.433   4.052  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.707  -0.463   3.122  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.868  -0.557   1.889  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.438   0.742   3.494  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.610   1.944   2.922  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.086   2.328   1.669  0.00  0.00           C+0
HETATM    9  N   UNK     0      -2.681   1.830   0.541  0.00  0.00           N+0
HETATM   10  C   UNK     0      -2.056   2.317  -0.584  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.531   1.935  -1.958  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.624   0.452  -2.144  0.00  0.00           C+0
HETATM   13  N   UNK     0      -1.476  -0.303  -2.205  0.00  0.00           N+0
HETATM   14  C   UNK     0      -1.782  -1.639  -2.267  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.765  -2.635  -2.314  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.450  -2.587  -1.750  0.00  0.00           C+0
HETATM   17  N   UNK     0       0.979  -1.565  -1.026  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.288  -1.785  -0.706  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.037  -1.006  -0.143  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.619  -3.132  -1.217  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.964  -3.713  -1.002  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.503  -3.605  -1.814  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.460  -4.912  -2.439  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.509  -5.827  -2.211  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.164  -1.737  -2.367  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.955  -2.993  -2.519  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.701  -0.403  -2.321  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.152  -0.034  -2.462  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.790   0.570  -1.222  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.626  -0.299  -0.015  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.913  -0.047   0.944  0.00  0.00           O+0
HETATM   32  O   UNK     0      -6.372  -1.417  -0.053  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.018   3.141  -0.158  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.015   3.838  -1.035  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.437   3.458  -0.754  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.689   1.976  -0.839  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.033   1.152  -1.460  0.00  0.00           O+0
HETATM   38  O   UNK     0       2.798   1.637  -0.148  0.00  0.00           O+0
HETATM   39  C   UNK     0      -1.088   3.201   1.278  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.229   4.004   2.193  0.00  0.00           C+0
HETATM   41  N   UNK     0      -3.024   0.449   4.689  0.00  0.00           N+0
HETATM   42  C   UNK     0      -2.761  -0.833   5.101  0.00  0.00           C+0
HETATM   43  O   UNK     0      -3.181  -1.351   6.120  0.00  0.00           O+0
HETATM   44  H   UNK     0      -2.056  -3.496   5.935  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.045  -4.672   4.930  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.757  -3.071   3.193  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.496  -0.581   0.995  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.169   0.283   1.823  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.251  -1.459   1.865  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.194   2.700   3.442  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.439   1.154   0.548  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.861   2.339  -2.725  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.506   2.403  -2.137  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.543   0.097  -2.190  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.033  -3.535  -2.862  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.530  -0.690  -0.795  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.724  -3.111  -1.509  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.041  -4.736  -1.381  0.00  0.00           H+0
HETATM   59  H   UNK     0       4.203  -3.739   0.067  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.279  -5.157  -3.113  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.313  -5.648  -1.525  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.546  -6.795  -2.702  0.00  0.00           H+0
HETATM   63  H   UNK     0      -4.316  -3.089  -3.548  0.00  0.00           H+0
HETATM   64  H   UNK     0      -4.817  -2.991  -1.846  0.00  0.00           H+0
HETATM   65  H   UNK     0      -3.361  -3.881  -2.282  0.00  0.00           H+0
HETATM   66  H   UNK     0      -5.729  -0.915  -2.767  0.00  0.00           H+0
HETATM   67  H   UNK     0      -5.246   0.681  -3.290  0.00  0.00           H+0
HETATM   68  H   UNK     0      -5.356   1.549  -0.992  0.00  0.00           H+0
HETATM   69  H   UNK     0      -6.860   0.745  -1.384  0.00  0.00           H+0
HETATM   70  H   UNK     0      -6.154  -1.878   0.785  0.00  0.00           H+0
HETATM   71  H   UNK     0      -0.230   3.637  -2.090  0.00  0.00           H+0
HETATM   72  H   UNK     0      -0.132   4.921  -0.904  0.00  0.00           H+0
HETATM   73  H   UNK     0       1.728   3.802   0.244  0.00  0.00           H+0
HETATM   74  H   UNK     0       2.093   3.953  -1.479  0.00  0.00           H+0
HETATM   75  H   UNK     0       2.915   0.653  -0.195  0.00  0.00           H+0
HETATM   76  H   UNK     0       0.084   4.940   1.720  0.00  0.00           H+0
HETATM   77  H   UNK     0       0.665   3.435   2.469  0.00  0.00           H+0
HETATM   78  H   UNK     0      -0.764   4.266   3.111  0.00  0.00           H+0
HETATM   79  H   UNK     0      -3.610   1.068   5.226  0.00  0.00           H+0
CONECT    1    2   44   45                                                  
CONECT    2    3    1   46                                                  
CONECT    3    4   42    2                                                  
CONECT    4    3    6    5                                                  
CONECT    5    4   47   48   49                                             
CONECT    6   41    7    4                                                  
CONECT    7    8    6   50                                                  
CONECT    8   39    9    7                                                  
CONECT    9   10    8   51                                                  
CONECT   10    9   33   11                                                  
CONECT   11   12   10   52   53                                             
CONECT   12   11   13   27                                                  
CONECT   13   14   12   54                                                  
CONECT   14   25   13   15                                                  
CONECT   15   16   14   55                                                  
CONECT   16   17   22   15                                                  
CONECT   17   18   16   56                                                  
CONECT   18   19   20   17                                                  
CONECT   19   18                                                            
CONECT   20   22   21   18                                                  
CONECT   21   20   57   58   59                                             
CONECT   22   20   23   16                                                  
CONECT   23   22   24   60                                                  
CONECT   24   23   61   62                                                  
CONECT   25   14   26   27                                                  
CONECT   26   25   63   64   65                                             
CONECT   27   28   12   25                                                  
CONECT   28   27   29   66   67                                             
CONECT   29   28   30   68   69                                             
CONECT   30   29   32   31                                                  
CONECT   31   30                                                            
CONECT   32   30   70                                                       
CONECT   33   10   39   34                                                  
CONECT   34   33   35   71   72                                             
CONECT   35   34   36   73   74                                             
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   75                                                       
CONECT   39   33    8   40                                                  
CONECT   40   39   76   77   78                                             
CONECT   41   42    6   79                                                  
CONECT   42    3   41   43                                                  
CONECT   43   42                                                            
CONECT   44    1                                                            
CONECT   45    1                                                            
CONECT   46    2                                                            
CONECT   47    5                                                            
CONECT   48    5                                                            
CONECT   49    5                                                            
CONECT   50    7                                                            
CONECT   51    9                                                            
CONECT   52   11                                                            
CONECT   53   11                                                            
CONECT   54   13                                                            
CONECT   55   15                                                            
CONECT   56   17                                                            
CONECT   57   21                                                            
CONECT   58   21                                                            
CONECT   59   21                                                            
CONECT   60   23                                                            
CONECT   61   24                                                            
CONECT   62   24                                                            
CONECT   63   26                                                            
CONECT   64   26                                                            
CONECT   65   26                                                            
CONECT   66   28                                                            
CONECT   67   28                                                            
CONECT   68   29                                                            
CONECT   69   29                                                            
CONECT   70   32                                                            
CONECT   71   34                                                            
CONECT   72   34                                                            
CONECT   73   35                                                            
CONECT   74   35                                                            
CONECT   75   38                                                            
CONECT   76   40                                                            
CONECT   77   40                                                            
CONECT   78   40                                                            
CONECT   79   41                                                            
MASTER        0    0    0    0    0    0    0    0   79    0  164    0
END

COMPND    HMDB0000488
HETATM    1  C1  UNL     1       5.363   1.790   4.553  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.665   1.139   3.562  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.014   0.388   2.416  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.035   0.159   1.460  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.640   0.659   1.581  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.554  -0.624   0.397  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.975  -0.967  -0.721  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.633  -0.595  -1.133  1.00  0.00           C  
HETATM    9  N1  UNL     1       2.633  -1.455  -1.347  1.00  0.00           N  
HETATM   10  C9  UNL     1       1.532  -0.806  -1.842  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.316  -1.484  -2.330  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.937  -1.396  -1.624  1.00  0.00           C  
HETATM   13  N2  UNL     1      -1.917  -0.535  -1.990  1.00  0.00           N  
HETATM   14  C12 UNL     1      -2.974  -0.649  -1.158  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.189   0.154  -1.337  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.626   0.927  -0.364  1.00  0.00           C  
HETATM   17  N3  UNL     1      -3.991   1.068   0.917  1.00  0.00           N  
HETATM   18  C15 UNL     1      -4.760   1.976   1.658  1.00  0.00           C  
HETATM   19  O1  UNL     1      -4.527   2.361   2.840  1.00  0.00           O  
HETATM   20  C16 UNL     1      -5.872   2.408   0.850  1.00  0.00           C  
HETATM   21  C17 UNL     1      -6.914   3.385   1.308  1.00  0.00           C  
HETATM   22  C18 UNL     1      -5.802   1.793  -0.349  1.00  0.00           C  
HETATM   23  C19 UNL     1      -6.783   2.051  -1.362  1.00  0.00           C  
HETATM   24  C20 UNL     1      -6.906   1.582  -2.556  1.00  0.00           C  
HETATM   25  C21 UNL     1      -2.706  -1.594  -0.232  1.00  0.00           C  
HETATM   26  C22 UNL     1      -3.585  -2.105   0.872  1.00  0.00           C  
HETATM   27  C23 UNL     1      -1.414  -2.065  -0.526  1.00  0.00           C  
HETATM   28  C24 UNL     1      -0.779  -3.096   0.320  1.00  0.00           C  
HETATM   29  C25 UNL     1      -0.615  -4.438  -0.326  1.00  0.00           C  
HETATM   30  C26 UNL     1      -0.045  -5.438   0.597  1.00  0.00           C  
HETATM   31  O2  UNL     1      -0.098  -5.258   1.824  1.00  0.00           O  
HETATM   32  O3  UNL     1       0.552  -6.573   0.092  1.00  0.00           O  
HETATM   33  C27 UNL     1       1.913   0.536  -1.915  1.00  0.00           C  
HETATM   34  C28 UNL     1       1.051   1.653  -2.270  1.00  0.00           C  
HETATM   35  C29 UNL     1       0.499   2.509  -1.211  1.00  0.00           C  
HETATM   36  C30 UNL     1      -0.176   1.820  -0.095  1.00  0.00           C  
HETATM   37  O4  UNL     1       0.084   0.672   0.264  1.00  0.00           O  
HETATM   38  O5  UNL     1      -1.195   2.484   0.635  1.00  0.00           O  
HETATM   39  C31 UNL     1       3.239   0.669  -1.475  1.00  0.00           C  
HETATM   40  C32 UNL     1       3.993   1.968  -1.470  1.00  0.00           C  
HETATM   41  N4  UNL     1       6.937  -0.930   0.676  1.00  0.00           N  
HETATM   42  C33 UNL     1       7.186  -0.292   1.924  1.00  0.00           C  
HETATM   43  O6  UNL     1       8.342  -0.370   2.461  1.00  0.00           O  
HETATM   44  H1  UNL     1       4.268   2.140   4.593  1.00  0.00           H  
HETATM   45  H2  UNL     1       5.855   2.154   5.447  1.00  0.00           H  
HETATM   46  H3  UNL     1       6.975   1.067   4.103  1.00  0.00           H  
HETATM   47  H4  UNL     1       2.886  -0.003   1.167  1.00  0.00           H  
HETATM   48  H5  UNL     1       3.362   0.707   2.694  1.00  0.00           H  
HETATM   49  H6  UNL     1       3.628   1.715   1.291  1.00  0.00           H  
HETATM   50  H7  UNL     1       5.577  -1.605  -1.412  1.00  0.00           H  
HETATM   51  H8  UNL     1       2.669  -2.493  -1.165  1.00  0.00           H  
HETATM   52  H9  UNL     1       0.592  -2.584  -2.497  1.00  0.00           H  
HETATM   53  H10 UNL     1       0.161  -1.193  -3.449  1.00  0.00           H  
HETATM   54  H11 UNL     1      -1.905   0.134  -2.794  1.00  0.00           H  
HETATM   55  H12 UNL     1      -4.733   0.133  -2.247  1.00  0.00           H  
HETATM   56  H13 UNL     1      -3.104   0.571   1.188  1.00  0.00           H  
HETATM   57  H14 UNL     1      -7.063   4.090   0.445  1.00  0.00           H  
HETATM   58  H15 UNL     1      -7.811   2.796   1.529  1.00  0.00           H  
HETATM   59  H16 UNL     1      -6.520   3.957   2.178  1.00  0.00           H  
HETATM   60  H17 UNL     1      -7.588   2.797  -1.065  1.00  0.00           H  
HETATM   61  H18 UNL     1      -7.788   1.957  -3.161  1.00  0.00           H  
HETATM   62  H19 UNL     1      -6.289   0.892  -3.046  1.00  0.00           H  
HETATM   63  H20 UNL     1      -4.604  -1.727   0.756  1.00  0.00           H  
HETATM   64  H21 UNL     1      -3.175  -1.853   1.855  1.00  0.00           H  
HETATM   65  H22 UNL     1      -3.636  -3.228   0.747  1.00  0.00           H  
HETATM   66  H23 UNL     1      -1.264  -3.158   1.310  1.00  0.00           H  
HETATM   67  H24 UNL     1       0.272  -2.736   0.550  1.00  0.00           H  
HETATM   68  H25 UNL     1       0.037  -4.426  -1.214  1.00  0.00           H  
HETATM   69  H26 UNL     1      -1.653  -4.764  -0.634  1.00  0.00           H  
HETATM   70  H27 UNL     1       1.511  -6.854   0.335  1.00  0.00           H  
HETATM   71  H28 UNL     1       0.152   1.214  -2.817  1.00  0.00           H  
HETATM   72  H29 UNL     1       1.610   2.277  -3.009  1.00  0.00           H  
HETATM   73  H30 UNL     1       1.164   3.328  -0.865  1.00  0.00           H  
HETATM   74  H31 UNL     1      -0.348   3.094  -1.713  1.00  0.00           H  
HETATM   75  H32 UNL     1      -0.863   2.826   1.528  1.00  0.00           H  
HETATM   76  H33 UNL     1       4.253   2.289  -2.497  1.00  0.00           H  
HETATM   77  H34 UNL     1       4.949   1.752  -0.955  1.00  0.00           H  
HETATM   78  H35 UNL     1       3.469   2.728  -0.864  1.00  0.00           H  
HETATM   79  H36 UNL     1       7.608  -1.479   0.118  1.00  0.00           H  
CONECT    1    2    2   44   45
CONECT    2    3   46
CONECT    3    4    4   42
CONECT    4    5    6
CONECT    5   47   48   49
CONECT    6    7    7   41
CONECT    7    8   50
CONECT    8    9   39   39
CONECT    9   10   51
CONECT   10   11   33   33
CONECT   11   12   52   53
CONECT   12   13   27   27
CONECT   13   14   54
CONECT   14   15   25   25
CONECT   15   16   16   55
CONECT   16   17   22
CONECT   17   18   56
CONECT   18   19   19   20
CONECT   20   21   22   22
CONECT   21   57   58   59
CONECT   22   23
CONECT   23   24   24   60
CONECT   24   61   62
CONECT   25   26   27
CONECT   26   63   64   65
CONECT   27   28
CONECT   28   29   66   67
CONECT   29   30   68   69
CONECT   30   31   31   32
CONECT   32   70
CONECT   33   34   39
CONECT   34   35   71   72
CONECT   35   36   73   74
CONECT   36   37   37   38
CONECT   38   75
CONECT   39   40
CONECT   40   76   77   78
CONECT   41   42   79
CONECT   42   43   43
END

HMDB0000488
     RDKit          3D
(4E,15Z)-Bilirubin
 79 82  0  0  0  0  0  0  0  0999 V2000
    5.3628    1.7901    4.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6650    1.1392    3.5616 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0141    0.3875    2.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0347    0.1591    1.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6396    0.6591    1.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5539   -0.6236    0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9754   -0.9670   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6332   -0.5946   -1.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6330   -1.4552   -1.3469 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5323   -0.8063   -1.8416 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3158   -1.4840   -2.3299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9374   -1.3958   -1.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9173   -0.5345   -1.9897 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9737   -0.6487   -1.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1890    0.1542   -1.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6260    0.9274   -0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9910    1.0677    0.9174 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7595    1.9762    1.6581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5271    2.3606    2.8395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8719    2.4082    0.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9136    3.3853    1.3084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8024    1.7932   -0.3490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7827    2.0507   -1.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9055    1.5816   -2.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7060   -1.5937   -0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5853   -2.1052    0.8717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4143   -2.0647   -0.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7785   -3.0957    0.3197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6153   -4.4383   -0.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0455   -5.4379    0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0983   -5.2581    1.8239 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5516   -6.5735    0.0916 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9134    0.5360   -1.9154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0514    1.6528   -2.2704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4989    2.5089   -1.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1761    1.8197   -0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0837    0.6718    0.2641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1948    2.4836    0.6345 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2394    0.6694   -1.4749 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    1.9684   -1.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9372   -0.9301    0.6761 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1864   -0.2920    1.9238 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3416   -0.3701    2.4614 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2680    2.1404    4.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8555    2.1543    5.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9753    1.0666    4.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8862   -0.0030    1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3618    0.7071    2.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6282    1.7148    1.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5769   -1.6051   -1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6693   -2.4930   -1.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5916   -2.5842   -2.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1614   -1.1935   -3.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9052    0.1342   -2.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7327    0.1330   -2.2473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1042    0.5712    1.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0629    4.0904    0.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8114    2.7960    1.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5201    3.9569    2.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5883    2.7967   -1.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7882    1.9575   -3.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2892    0.8923   -3.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6043   -1.7266    0.7560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1747   -1.8529    1.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6360   -3.2280    0.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2638   -3.1576    1.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2724   -2.7356    0.5498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0368   -4.4258   -1.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6531   -4.7637   -0.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5112   -6.8541    0.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1518    1.2141   -2.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6097    2.2774   -3.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1643    3.3283   -0.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3484    3.0936   -1.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8628    2.8261    1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2534    2.2891   -2.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9491    1.7521   -0.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4687    2.7280   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6082   -1.4789    0.1183 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  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  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  3
 14 25  2  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 10 33  2  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 33 39  1  0
 39 40  1  0
  6 41  1  0
 41 42  1  0
 42 43  2  0
 42  3  1  0
 39  8  2  0
 27 12  2  0
 22 16  1  0
  1 44  1  0
  1 45  1  0
  2 46  1  0
  5 47  1  0
  5 48  1  0
  5 49  1  0
  7 50  1  0
  9 51  1  0
 11 52  1  0
 11 53  1  0
 13 54  1  0
 15 55  1  0
 17 56  1  0
 21 57  1  0
 21 58  1  0
 21 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 26 63  1  0
 26 64  1  0
 26 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
 32 70  1  0
 34 71  1  0
 34 72  1  0
 35 73  1  0
 35 74  1  0
 38 75  1  0
 40 76  1  0
 40 77  1  0
 40 78  1  0
 41 79  1  0
M  END

View in JSmol

Synonyms

Value	Source
(4E)2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo--21H-biline-8,12-dipropanoic acid	ChEBI
(4E)2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo--21H-biline-8,12-dipropanoate	Generator
(4E,15Z)-Bilirubin ixa	HMDB
(4E,15Z)-Bilirubin ixalpha	HMDB
(4E,15Z)-Bilirubin ixα	HMDB
4E,15Z-Bilirubin ixa	HMDB
4E,15Z-Bilirubin ixalpha	HMDB
4E,15Z-Bilirubin ixα	HMDB
(4E,15Z)-Bilirubin	HMDB

Chemical Formula

C₃₃H₃₆N₄O₆

Average Mass

584.6621 Da

Monoisotopic Mass

584.26348 Da

IUPAC Name

3-(2-{[3-(2-carboxyethyl)-5-{[(2E)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid

Traditional Name

3-(2-{[3-(2-carboxyethyl)-5-{[(2E)-4-ethenyl-3-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid

CAS Registry Number

69853-43-6

SMILES

[H]OC(=O)C([H])([H])C([H])([H])C1=C(N([H])C(\C([H])=C2/N([H])C(=O)C(=C2C([H])=C([H])[H])C([H])([H])[H])=C1C([H])([H])[H])C([H])([H])C1=C(C(=C(N1[H])C(\[H])=C1\N([H])C(=O)C(C([H])=C([H])[H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])C(=O)O[H]

InChI Identifier

InChI=1S/C33H36N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13+,27-14-

InChI Key

BPYKTIZUTYGOLE-KDUUSRDASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Glycine max	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Solanum melongena	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Bilirubins

Direct Parent

Bilirubins

Alternative Parents

Substituents

Bilirubin skeleton
Dicarboxylic acid or derivatives
Substituted pyrrole
Pyrrole
Pyrroline
Heteroaromatic compound
Secondary carboxylic acid amide
Lactam
Carboxamide group
Azacycle
Carboxylic acid
Carboxylic acid derivative
Organopnictogen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:72719 )
biladienes (CHEBI:72719 )

Physical Properties

State

Solid

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
Water Solubility	0.0096 g/L	ALOGPS
logP	3.22	ALOGPS
logP	3.12	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	4.03	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.38 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	168.9 m³·mol⁻¹	ChemAxon
Polarizability	65.37 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0000488

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022070

KNApSAcK ID

Not Available

Chemspider ID

13628097

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bilirubin

METLIN ID

5475

PubChem Compound

21252250

PDB ID

Not Available

ChEBI ID

72719

Good Scents ID

Not Available

References

General References

Kawamoto S, Koyano K, Ozaki M, Arai T, Iwase T, Okada H, Itoh S, Murao K, Kusaka T: Effects of bilirubin configurational photoisomers on the measurement of direct bilirubin by the vanadate oxidation method. Ann Clin Biochem. 2021 Jul;58(4):311-317. doi: 10.1177/0004563221999068. Epub 2021 Mar 9. [PubMed:33588585 ]
Wang SY, Yu CP, Pan YL, Zhou XR, Xin R, Wang Y, Ma WW, Gao R, Wang C, Wu YH: Metabolomics analysis of serum from subjects after occupational exposure to acrylamide using UPLC-MS. Mol Cell Endocrinol. 2017 Mar 15;444:67-75. doi: 10.1016/j.mce.2017.02.003. Epub 2017 Feb 3. [PubMed:28163100 ]

Showing NP-Card for 4E,15Z-Bilirubin IXa (NP0001295)

MOL for NP0001295 (4E,15Z-Bilirubin IXa)

3D MOL for NP0001295 (4E,15Z-Bilirubin IXa)

3D SDF for NP0001295 (4E,15Z-Bilirubin IXa)

3D-SDF for NP0001295 (4E,15Z-Bilirubin IXa)

PDB for NP0001295 (4E,15Z-Bilirubin IXa)

3D PDB for NP0001295 (4E,15Z-Bilirubin IXa)

SMILES for NP0001295 (4E,15Z-Bilirubin IXa)

INCHI for NP0001295 (4E,15Z-Bilirubin IXa)

Structure for NP0001295 (4E,15Z-Bilirubin IXa)

3D Structure for NP0001295 (4E,15Z-Bilirubin IXa)