MiMeDB: Showing metabocard for Biliverdin (MMDBc0000382)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:33 UTC

Update Date

2024-10-13 06:59:05 UTC

Metabolite ID

MMDBc0000382

Metabolite Identification

Common Name

Biliverdin

Description

Biliverdin is a green pigment formed as a byproduct of hemoglobin breakdown. It consists of four linearly connected pyrrole rings (a tetrapyrrole). Biliverdin is formed when the heme group in hemoglobin is cleaved at its alpha-methene bridge. The resulting biliverdin is then reduced to bilirubin, a yellow pigment, by the enzyme biliverdin reductase. The changing color of a bruise from deep purple to yellow over time is a graphical indicator of this reaction. Biliverdin occurs in the bile of amphibia and of birds, but not in normal human bile or serum.

Structure

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


  Mrv1652309042000172D          

 43 46  0  0  0  0            999 V2000
    1.8296   -1.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7497   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0046   -1.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0846   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8692   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4171   -2.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0858    1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9790    0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1720    0.2597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8395    1.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0110    2.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3914    0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2120    0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5475    1.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3713    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8196   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8995   -1.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0745   -1.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1544   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9391   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4870   -2.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4870   -3.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2014   -3.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4870   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2014   -4.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9159   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0349   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0489    0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4613    0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2818    0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9093    1.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0809    2.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8655    2.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2419    0.2597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1556    1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4412    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3146   -0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3844   -0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4171   -3.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1316   -3.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8460   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1316   -4.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4171   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 37  1  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  6  2  2  0  0  0  0
  3  2  1  0  0  0  0
  2 27  1  0  0  0  0
  4  6  1  0  0  0  0
  4  5  1  0  0  0  0
  6 39  1  0  0  0  0
 15  7  2  0  0  0  0
  7  9  1  0  0  0  0
 10  7  1  0  0  0  0
  8 37  2  0  0  0  0
  9  8  1  0  0  0  0
 12  8  1  0  0  0  0
 10 12  2  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 16 27  2  0  0  0  0
 18 16  1  0  0  0  0
 21 16  1  0  0  0  0
 38 17  1  0  0  0  0
 18 17  2  0  0  0  0
 19 17  1  0  0  0  0
 19 21  2  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 25  1  0  0  0  0
 25 24  1  0  0  0  0
 25 26  2  0  0  0  0
 28 34  1  0  0  0  0
 29 28  1  0  0  0  0
 38 28  2  0  0  0  0
 31 29  2  0  0  0  0
 29 30  1  0  0  0  0
 31 35  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 39 40  1  0  0  0  0
 40 42  1  0  0  0  0
 42 41  1  0  0  0  0
 42 43  2  0  0  0  0
M  END

HMDB0001008
     RDKit          3D
Biliverdin
 77 80  0  0  0  0  0  0  0  0999 V2000
    6.8895    5.7479    0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8941    5.2566   -0.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939    3.9620    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2878    3.3809   -0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5894    3.9652   -1.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9446    2.0975    0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9300    1.3295   -0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5373    0.0648    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2928   -0.3555    0.1510 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0380   -1.5939    0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1195   -2.2440    0.5866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1804   -1.6049   -0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6126   -0.3396   -0.0815 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5565   -0.0768   -0.9589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3664    1.1171   -1.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9791    1.7860   -0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8749    1.3646    1.0969 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6280    2.2970    1.8473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7704    2.2509    3.1090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1690    3.2594    0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0192    4.3981    1.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8013    2.9830   -0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1839    3.7476   -1.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9538    3.6592   -2.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7907   -1.2251   -1.7109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7319   -1.4060   -2.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9216   -2.1836   -1.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7745   -3.5463   -1.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2802   -4.6589   -0.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7028   -4.6532   -0.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5520   -3.8033   -0.8763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1456   -5.7503    0.2455 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2393   -1.9994    1.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405   -3.2534    2.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4745   -4.4177    1.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6798   -5.6846    1.9427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8101   -5.6475    3.1763 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7212   -6.8696    1.2583 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1226   -0.9876    1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5319   -1.2137    1.6474 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8480    1.9449    1.1891 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7056    3.1106    1.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6168    3.2432    2.0608 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3080    5.2370    1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2831    6.6979    0.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4744    5.8068   -1.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5174    3.6379   -1.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0676    3.5276   -2.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6452    5.0631   -1.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2454    1.7749   -0.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2589   -3.1998    1.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2174    0.3611    0.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4818    1.4823   -2.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3523    0.5263    1.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3400    5.2743    1.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5946    4.2067    2.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7655    4.6772    0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8422    4.6358   -1.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3899    2.9605   -3.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4319    4.4611   -3.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7366   -1.7226   -2.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8082   -0.4354   -3.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3152   -2.1190   -3.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3095   -3.6423   -2.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7109   -3.7833   -1.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0912   -5.6238   -1.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6558   -4.7805    0.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2993   -6.6038   -0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5925   -3.3628    2.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3907   -3.2064    2.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3291   -4.2171    0.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5562   -4.5402    0.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9731   -7.7745    1.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7428   -2.3353    1.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1924   -0.7493    0.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6544   -0.8830    2.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8558    1.1976    1.8593 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  2  0
  9 10  1  0
 10 11  2  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  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 33 39  2  0
 39 40  1  0
  6 41  1  0
 41 42  1  0
 42 43  2  0
 42  3  1  0
 39  8  1  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
 11 51  1  0
 13 52  1  0
 15 53  1  0
 17 54  1  0
 21 55  1  0
 21 56  1  0
 21 57  1  0
 23 58  1  0
 24 59  1  0
 24 60  1  0
 26 61  1  0
 26 62  1  0
 26 63  1  0
 28 64  1  0
 28 65  1  0
 29 66  1  0
 29 67  1  0
 32 68  1  0
 34 69  1  0
 34 70  1  0
 35 71  1  0
 35 72  1  0
 38 73  1  0
 40 74  1  0
 40 75  1  0
 40 76  1  0
 41 77  1  0
M  END


  Mrv1652309042000172D          

 43 46  0  0  0  0            999 V2000
    1.8296   -1.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7497   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0046   -1.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0846   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8692   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4171   -2.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0858    1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9790    0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1720    0.2597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8395    1.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0110    2.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3914    0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2120    0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5475    1.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3713    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8196   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8995   -1.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0745   -1.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1544   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9391   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4870   -2.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4870   -3.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2014   -3.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4870   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2014   -4.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9159   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0349   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0489    0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4613    0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2818    0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9093    1.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0809    2.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8655    2.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2419    0.2597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1556    1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4412    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3146   -0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3844   -0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4171   -3.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1316   -3.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8460   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1316   -4.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4171   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 37  1  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  6  2  2  0  0  0  0
  3  2  1  0  0  0  0
  2 27  1  0  0  0  0
  4  6  1  0  0  0  0
  4  5  1  0  0  0  0
  6 39  1  0  0  0  0
 15  7  2  0  0  0  0
  7  9  1  0  0  0  0
 10  7  1  0  0  0  0
  8 37  2  0  0  0  0
  9  8  1  0  0  0  0
 12  8  1  0  0  0  0
 10 12  2  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 16 27  2  0  0  0  0
 18 16  1  0  0  0  0
 21 16  1  0  0  0  0
 38 17  1  0  0  0  0
 18 17  2  0  0  0  0
 19 17  1  0  0  0  0
 19 21  2  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 25  1  0  0  0  0
 25 24  1  0  0  0  0
 25 26  2  0  0  0  0
 28 34  1  0  0  0  0
 29 28  1  0  0  0  0
 38 28  2  0  0  0  0
 31 29  2  0  0  0  0
 29 30  1  0  0  0  0
 31 35  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 39 40  1  0  0  0  0
 40 42  1  0  0  0  0
 42 41  1  0  0  0  0
 42 43  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000382

> <DATABASE_NAME>
MIME

> <SMILES>
CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(N1)\C=C1/N=C(/C=C2\NC(=O)C(C=C)=C2C)C(C)=C1CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C33H34N4O6/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/h7-8,13-15,35H,1-2,9-12H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14-,28-15-

> <INCHI_KEY>
QBUVFDKTZJNUPP-BBROENKCSA-N

> <FORMULA>
C33H34N4O6

> <MOLECULAR_WEIGHT>
582.657

> <EXACT_MASS>
582.247834831

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
64.76179351109342

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(2-{[(2Z)-3-(2-carboxyethyl)-5-{[(2Z)-4-ethenyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene]methyl}-4-methyl-2H-pyrrol-2-ylidene]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>
3.44

> <JCHEM_LOGP>
0.5727987549162802

> <ALOGPS_LOGS>
-4.65

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.462128056457106

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.868581374117636

> <JCHEM_PKA_STRONGEST_BASIC>
5.8592066222604196

> <JCHEM_POLAR_SURFACE_AREA>
160.95

> <JCHEM_REFRACTIVITY>
169.35510000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
biliverdine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001008
     RDKit          3D
Biliverdin
 77 80  0  0  0  0  0  0  0  0999 V2000
    6.8895    5.7479    0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8941    5.2566   -0.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939    3.9620    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2878    3.3809   -0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5894    3.9652   -1.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9446    2.0975    0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9300    1.3295   -0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5373    0.0648    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2928   -0.3555    0.1510 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0380   -1.5939    0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1195   -2.2440    0.5866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1804   -1.6049   -0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6126   -0.3396   -0.0815 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5565   -0.0768   -0.9589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3664    1.1171   -1.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9791    1.7860   -0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8749    1.3646    1.0969 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6280    2.2970    1.8473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7704    2.2509    3.1090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1690    3.2594    0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0192    4.3981    1.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8013    2.9830   -0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1839    3.7476   -1.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9538    3.6592   -2.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7907   -1.2251   -1.7109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7319   -1.4060   -2.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9216   -2.1836   -1.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7745   -3.5463   -1.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2802   -4.6589   -0.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7028   -4.6532   -0.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5520   -3.8033   -0.8763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1456   -5.7503    0.2455 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2393   -1.9994    1.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405   -3.2534    2.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4745   -4.4177    1.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6798   -5.6846    1.9427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8101   -5.6475    3.1763 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7212   -6.8696    1.2583 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1226   -0.9876    1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5319   -1.2137    1.6474 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8480    1.9449    1.1891 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7056    3.1106    1.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6168    3.2432    2.0608 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3080    5.2370    1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2831    6.6979    0.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4744    5.8068   -1.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5174    3.6379   -1.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0676    3.5276   -2.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6452    5.0631   -1.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2454    1.7749   -0.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2589   -3.1998    1.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2174    0.3611    0.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4818    1.4823   -2.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3523    0.5263    1.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3400    5.2743    1.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5946    4.2067    2.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7655    4.6772    0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8422    4.6358   -1.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3899    2.9605   -3.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4319    4.4611   -3.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7366   -1.7226   -2.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8082   -0.4354   -3.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3152   -2.1190   -3.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3095   -3.6423   -2.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7109   -3.7833   -1.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0912   -5.6238   -1.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6558   -4.7805    0.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2993   -6.6038   -0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5925   -3.3628    2.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3907   -3.2064    2.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3291   -4.2171    0.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5562   -4.5402    0.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9731   -7.7745    1.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7428   -2.3353    1.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1924   -0.7493    0.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6544   -0.8830    2.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8558    1.1976    1.8593 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  2  0
  9 10  1  0
 10 11  2  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  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 33 39  2  0
 39 40  1  0
  6 41  1  0
 41 42  1  0
 42 43  2  0
 42  3  1  0
 39  8  1  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
 11 51  1  0
 13 52  1  0
 15 53  1  0
 17 54  1  0
 21 55  1  0
 21 56  1  0
 21 57  1  0
 23 58  1  0
 24 59  1  0
 24 60  1  0
 26 61  1  0
 26 62  1  0
 26 63  1  0
 28 64  1  0
 28 65  1  0
 29 66  1  0
 29 67  1  0
 32 68  1  0
 34 69  1  0
 34 70  1  0
 35 71  1  0
 35 72  1  0
 38 73  1  0
 40 74  1  0
 40 75  1  0
 40 76  1  0
 41 77  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0       3.415  -2.488   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.399  -3.953   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.875  -2.488   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       3.891  -3.953   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.356  -4.429   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.645  -4.858   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.027   2.016   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.694   0.165   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.188   0.485   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.434   2.642   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.754   4.149   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.464   1.498   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.996   1.659   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.622   3.066   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.693   2.786   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.530  -3.953   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.546  -2.488   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -2.006  -2.488   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -4.022  -3.953   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.486  -4.429   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.776  -4.858   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.776  -6.398   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.109  -7.168   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.776  -9.478   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.109  -8.708   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.443  -9.478   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.065  -4.429   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.825   0.165   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.594   1.498   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.126   1.659   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.564   2.642   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.884   4.149   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.349   4.625   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      -2.318   0.485   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0      -2.157   2.016   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -0.824   2.786   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.321  -1.242   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -4.451  -1.242   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.645  -6.398   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.979  -7.168   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       5.313  -9.478   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       3.979  -8.708   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       2.645  -9.478   0.000  0.00  0.00           O+0
CONECT    1   37    3    4                                                  
CONECT    2    6    3   27                                                  
CONECT    3    1    2                                                       
CONECT    4    1    6    5                                                  
CONECT    5    4                                                            
CONECT    6    2    4   39                                                  
CONECT    7   15    9   10                                                  
CONECT    8   37    9   12                                                  
CONECT    9    7    8                                                       
CONECT   10    7   12   11                                                  
CONECT   11   10                                                            
CONECT   12    8   10   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15    7                                                            
CONECT   16   27   18   21                                                  
CONECT   17   38   18   19                                                  
CONECT   18   16   17                                                       
CONECT   19   17   21   20                                                  
CONECT   20   19                                                            
CONECT   21   16   19   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   25                                                       
CONECT   24   25                                                            
CONECT   25   23   24   26                                                  
CONECT   26   25                                                            
CONECT   27    2   16                                                       
CONECT   28   34   29   38                                                  
CONECT   29   28   31   30                                                  
CONECT   30   29                                                            
CONECT   31   29   35   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   28   35                                                       
CONECT   35   31   34   36                                                  
CONECT   36   35                                                            
CONECT   37    1    8                                                       
CONECT   38   17   28                                                       
CONECT   39    6   40                                                       
CONECT   40   39   42                                                       
CONECT   41   42                                                            
CONECT   42   40   41   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   92    0
END

COMPND    HMDB0001008
HETATM    1  C1  UNL     1       6.890   5.748   0.441  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.894   5.257  -0.236  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.294   3.962   0.117  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.288   3.381  -0.501  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.589   3.965  -1.681  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.945   2.097   0.115  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.930   1.330  -0.110  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.537   0.065   0.422  1.00  0.00           C  
HETATM    9  N1  UNL     1       1.293  -0.355   0.151  1.00  0.00           N  
HETATM   10  C9  UNL     1       1.038  -1.594   0.705  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.119  -2.244   0.587  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.180  -1.605  -0.180  1.00  0.00           C  
HETATM   13  N2  UNL     1      -1.613  -0.340  -0.081  1.00  0.00           N  
HETATM   14  C12 UNL     1      -2.556  -0.077  -0.959  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.366   1.117  -1.233  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.979   1.786  -0.260  1.00  0.00           C  
HETATM   17  N3  UNL     1      -3.875   1.365   1.097  1.00  0.00           N  
HETATM   18  C15 UNL     1      -4.628   2.297   1.847  1.00  0.00           C  
HETATM   19  O1  UNL     1      -4.770   2.251   3.109  1.00  0.00           O  
HETATM   20  C16 UNL     1      -5.169   3.259   0.917  1.00  0.00           C  
HETATM   21  C17 UNL     1      -6.019   4.398   1.313  1.00  0.00           C  
HETATM   22  C18 UNL     1      -4.801   2.983  -0.349  1.00  0.00           C  
HETATM   23  C19 UNL     1      -5.184   3.748  -1.499  1.00  0.00           C  
HETATM   24  C20 UNL     1      -4.954   3.659  -2.746  1.00  0.00           C  
HETATM   25  C21 UNL     1      -2.791  -1.225  -1.711  1.00  0.00           C  
HETATM   26  C22 UNL     1      -3.732  -1.406  -2.842  1.00  0.00           C  
HETATM   27  C23 UNL     1      -1.922  -2.184  -1.214  1.00  0.00           C  
HETATM   28  C24 UNL     1      -1.775  -3.546  -1.718  1.00  0.00           C  
HETATM   29  C25 UNL     1      -2.280  -4.659  -0.869  1.00  0.00           C  
HETATM   30  C26 UNL     1      -3.703  -4.653  -0.543  1.00  0.00           C  
HETATM   31  O2  UNL     1      -4.552  -3.803  -0.876  1.00  0.00           O  
HETATM   32  O3  UNL     1      -4.146  -5.750   0.246  1.00  0.00           O  
HETATM   33  C27 UNL     1       2.239  -1.999   1.377  1.00  0.00           C  
HETATM   34  C28 UNL     1       2.440  -3.253   2.150  1.00  0.00           C  
HETATM   35  C29 UNL     1       2.474  -4.418   1.197  1.00  0.00           C  
HETATM   36  C30 UNL     1       2.680  -5.685   1.943  1.00  0.00           C  
HETATM   37  O4  UNL     1       2.810  -5.648   3.176  1.00  0.00           O  
HETATM   38  O5  UNL     1       2.721  -6.870   1.258  1.00  0.00           O  
HETATM   39  C31 UNL     1       3.123  -0.988   1.183  1.00  0.00           C  
HETATM   40  C32 UNL     1       4.532  -1.214   1.647  1.00  0.00           C  
HETATM   41  N4  UNL     1       4.848   1.945   1.189  1.00  0.00           N  
HETATM   42  C33 UNL     1       5.706   3.111   1.202  1.00  0.00           C  
HETATM   43  O6  UNL     1       6.617   3.243   2.061  1.00  0.00           O  
HETATM   44  H1  UNL     1       7.308   5.237   1.271  1.00  0.00           H  
HETATM   45  H2  UNL     1       7.283   6.698   0.136  1.00  0.00           H  
HETATM   46  H3  UNL     1       5.474   5.807  -1.101  1.00  0.00           H  
HETATM   47  H4  UNL     1       2.517   3.638  -1.635  1.00  0.00           H  
HETATM   48  H5  UNL     1       4.068   3.528  -2.589  1.00  0.00           H  
HETATM   49  H6  UNL     1       3.645   5.063  -1.671  1.00  0.00           H  
HETATM   50  H7  UNL     1       2.245   1.775  -0.899  1.00  0.00           H  
HETATM   51  H8  UNL     1      -0.259  -3.200   1.062  1.00  0.00           H  
HETATM   52  H9  UNL     1      -1.217   0.361   0.616  1.00  0.00           H  
HETATM   53  H10 UNL     1      -3.482   1.482  -2.231  1.00  0.00           H  
HETATM   54  H11 UNL     1      -3.352   0.526   1.449  1.00  0.00           H  
HETATM   55  H12 UNL     1      -5.340   5.274   1.509  1.00  0.00           H  
HETATM   56  H13 UNL     1      -6.595   4.207   2.247  1.00  0.00           H  
HETATM   57  H14 UNL     1      -6.766   4.677   0.551  1.00  0.00           H  
HETATM   58  H15 UNL     1      -5.842   4.636  -1.244  1.00  0.00           H  
HETATM   59  H16 UNL     1      -4.390   2.960  -3.286  1.00  0.00           H  
HETATM   60  H17 UNL     1      -5.432   4.461  -3.388  1.00  0.00           H  
HETATM   61  H18 UNL     1      -4.737  -1.723  -2.577  1.00  0.00           H  
HETATM   62  H19 UNL     1      -3.808  -0.435  -3.426  1.00  0.00           H  
HETATM   63  H20 UNL     1      -3.315  -2.119  -3.617  1.00  0.00           H  
HETATM   64  H21 UNL     1      -2.310  -3.642  -2.707  1.00  0.00           H  
HETATM   65  H22 UNL     1      -0.711  -3.783  -1.989  1.00  0.00           H  
HETATM   66  H23 UNL     1      -2.091  -5.624  -1.434  1.00  0.00           H  
HETATM   67  H24 UNL     1      -1.656  -4.781   0.046  1.00  0.00           H  
HETATM   68  H25 UNL     1      -4.299  -6.604  -0.296  1.00  0.00           H  
HETATM   69  H26 UNL     1       1.592  -3.363   2.887  1.00  0.00           H  
HETATM   70  H27 UNL     1       3.391  -3.206   2.712  1.00  0.00           H  
HETATM   71  H28 UNL     1       3.329  -4.217   0.502  1.00  0.00           H  
HETATM   72  H29 UNL     1       1.556  -4.540   0.616  1.00  0.00           H  
HETATM   73  H30 UNL     1       2.973  -7.774   1.646  1.00  0.00           H  
HETATM   74  H31 UNL     1       4.743  -2.335   1.583  1.00  0.00           H  
HETATM   75  H32 UNL     1       5.192  -0.749   0.881  1.00  0.00           H  
HETATM   76  H33 UNL     1       4.654  -0.883   2.676  1.00  0.00           H  
HETATM   77  H34 UNL     1       4.856   1.198   1.859  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    9   39
CONECT    9   10
CONECT   10   11   11   33
CONECT   11   12   51
CONECT   12   13   27   27
CONECT   13   14   52
CONECT   14   15   25   25
CONECT   15   16   16   53
CONECT   16   17   22
CONECT   17   18   54
CONECT   18   19   19   20
CONECT   20   21   22   22
CONECT   21   55   56   57
CONECT   22   23
CONECT   23   24   24   58
CONECT   24   59   60
CONECT   25   26   27
CONECT   26   61   62   63
CONECT   27   28
CONECT   28   29   64   65
CONECT   29   30   66   67
CONECT   30   31   31   32
CONECT   32   68
CONECT   33   34   39   39
CONECT   34   35   69   70
CONECT   35   36   71   72
CONECT   36   37   37   38
CONECT   38   73
CONECT   39   40
CONECT   40   74   75   76
CONECT   41   42   77
CONECT   42   43   43
END

HMDB0001008
     RDKit          3D
Biliverdin
 77 80  0  0  0  0  0  0  0  0999 V2000
    6.8895    5.7479    0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8941    5.2566   -0.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939    3.9620    0.1166 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2878    3.3809   -0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5894    3.9652   -1.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9446    2.0975    0.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9300    1.3295   -0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5373    0.0648    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2928   -0.3555    0.1510 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0380   -1.5939    0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1195   -2.2440    0.5866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1804   -1.6049   -0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6126   -0.3396   -0.0815 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5565   -0.0768   -0.9589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3664    1.1171   -1.2328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9791    1.7860   -0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8749    1.3646    1.0969 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6280    2.2970    1.8473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7704    2.2509    3.1090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1690    3.2594    0.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0192    4.3981    1.3127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8013    2.9830   -0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1839    3.7476   -1.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9538    3.6592   -2.7459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7907   -1.2251   -1.7109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7319   -1.4060   -2.8421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9216   -2.1836   -1.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7745   -3.5463   -1.7177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2802   -4.6589   -0.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7028   -4.6532   -0.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5520   -3.8033   -0.8763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1456   -5.7503    0.2455 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2393   -1.9994    1.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405   -3.2534    2.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4745   -4.4177    1.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6798   -5.6846    1.9427 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8101   -5.6475    3.1763 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7212   -6.8696    1.2583 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1226   -0.9876    1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5319   -1.2137    1.6474 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8480    1.9449    1.1891 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7056    3.1106    1.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6168    3.2432    2.0608 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3080    5.2370    1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2831    6.6979    0.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4744    5.8068   -1.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5174    3.6379   -1.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0676    3.5276   -2.5892 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6452    5.0631   -1.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2454    1.7749   -0.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2589   -3.1998    1.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2174    0.3611    0.6157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4818    1.4823   -2.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3523    0.5263    1.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3400    5.2743    1.5093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5946    4.2067    2.2470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7655    4.6772    0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8422    4.6358   -1.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3899    2.9605   -3.2862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4319    4.4611   -3.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7366   -1.7226   -2.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8082   -0.4354   -3.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3152   -2.1190   -3.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3095   -3.6423   -2.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7109   -3.7833   -1.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0912   -5.6238   -1.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6558   -4.7805    0.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2993   -6.6038   -0.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5925   -3.3628    2.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3907   -3.2064    2.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3291   -4.2171    0.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5562   -4.5402    0.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9731   -7.7745    1.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7428   -2.3353    1.5830 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1924   -0.7493    0.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6544   -0.8830    2.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8558    1.1976    1.8593 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  2  0
  9 10  1  0
 10 11  2  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  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  2  0
 36 38  1  0
 33 39  2  0
 39 40  1  0
  6 41  1  0
 41 42  1  0
 42 43  2  0
 42  3  1  0
 39  8  1  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
 11 51  1  0
 13 52  1  0
 15 53  1  0
 17 54  1  0
 21 55  1  0
 21 56  1  0
 21 57  1  0
 23 58  1  0
 24 59  1  0
 24 60  1  0
 26 61  1  0
 26 62  1  0
 26 63  1  0
 28 64  1  0
 28 65  1  0
 29 66  1  0
 29 67  1  0
 32 68  1  0
 34 69  1  0
 34 70  1  0
 35 71  1  0
 35 72  1  0
 38 73  1  0
 40 74  1  0
 40 75  1  0
 40 76  1  0
 41 77  1  0
M  END

Synonyms

Value	Source
8,12-Bis(2-carboxyethyl)-2,7,13,17-tetramethyl-3,18-divinylbilin-1(19)(21H,24H)-dione	ChEBI
Biliverdin IX alpha	ChEBI
Biliverdin ixalpha	ChEBI
Biliverdine	ChEBI
BILIVERDINE IX ALPHA	ChEBI
Biliverdin IX a	Generator
Biliverdin IX α	Generator
BILIVERDINE IX a	Generator
BILIVERDINE IX α	Generator
Biliverdin IX	HMDB
1,3,6,7-Tetramethyl-4,5-dicarboxyethyl-2,8-divinylbilenone	HMDB
Dehydrobilirubin	HMDB
Protobiliverdin IX	HMDB
Uteroverdine	HMDB

Molecular Formula

C₃₃H₃₄N₄O₆

Average Mass

582.657

Monoisotopic Mass

582.247834831

IUPAC Name

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

biliverdine

CAS Registry Number

Not Available

SMILES

CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(N1)\C=C1/N=C(/C=C2\NC(=O)C(C=C)=C2C)C(C)=C1CCC(O)=O

InChI Identifier

InChI=1S/C33H34N4O6/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/h7-8,13-15,35H,1-2,9-12H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14-,28-15-

InChI Key

QBUVFDKTZJNUPP-BBROENKCSA-N

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
Dipyrrin
Dicarboxylic acid or derivatives
Substituted pyrrole
Pyrrole
Pyrroline
Heteroaromatic compound
Carboxamide group
Ketimine
Lactam
Secondary carboxylic acid amide
Azacycle
Organic 1,3-dipolar compound
Carboxylic acid derivative
Carboxylic acid
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Imine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

bilins (CHEBI:17033 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	3.44	ALOGPS
logP	0.57	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	5.86	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	160.95 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	169.36 m³·mol⁻¹	ChemAxon
Polarizability	64.76 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

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Membrane
Nucleus

Biospecimen Locations

Feces
Neuron
Placenta
Prostate

Tissue Locations

Neuron
Placenta
Prostate

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191822	Heme oxygenase 2	Unknown	P30519	Homo sapiens
MMDBp0191869	Heme oxygenase 1	Unknown	P09601	Homo sapiens
MMDBp0192339	Biliverdin reductase A	Unknown	P53004	Homo sapiens
MMDBp0192340	Flavin reductase (NADPH)	Unknown	P30043	Homo sapiens
MMDBp0193303	Aryl hydrocarbon receptor	Unknown	P35869	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0019750	Heme	Carbon monoxide	Unknown Protein		PathBank	31602464
MMDBr0019751	Biliverdin	Bilirubin	Unknown Protein		PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Firmicutes	2	Human feces; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Neuron	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified	Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0001008

DrugBank ID

DB02073

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022366

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17033

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Beruter J, Colombo JP, Schlunegger UP: Isolation and identification of the urinary pigment uroerythrin. Eur J Biochem. 1975 Aug 1;56(1):239-44. doi: 10.1111/j.1432-1033.1975.tb02226.x. [PubMed:1175621 ]
Trull FR, Ibars O, Lightner DA: Conformation inversion of bilirubin formed by reduction of the biliverdin-human serum albumin complex: evidence from circular dichroism. Arch Biochem Biophys. 1992 Nov 1;298(2):710-4. doi: 10.1016/0003-9861(92)90470-h. [PubMed:1416999 ]
Chrastil J: Spectrophotometric determination of cysteine and cystine in urine. Analyst. 1990 Oct;115(10):1383-4. doi: 10.1039/an9901501383. [PubMed:2270876 ]
Odrcich MJ, Graham CH, Kimura KA, McLaughlin BE, Marks GS, Nakatsu K, Brien JF: Heme oxygenase and nitric oxide synthase in the placenta of the guinea-pig during gestation. Placenta. 1998 Sep;19(7):509-16. doi: 10.1016/s0143-4004(98)91044-x. [PubMed:9778124 ]
Kunikata T, Itoh S, Ozaki T, Kondo M, Isobe K, Onishi S: Formation of propentdyopents and biliverdin, oxidized metabolites of bilirubin, in infants receiving oxygen therapy. Pediatr Int. 2000 Aug;42(4):331-6. doi: 10.1046/j.1442-200x.2000.01246.x. [PubMed:10986860 ]
Briz O, Macias RI, Serrano MA, Gonzalez-Gallego J, Bayon JE, Marin JJ: Excretion of foetal bilirubin by the rat placenta-maternal liver tandem. Placenta. 2003 May;24(5):462-72. doi: 10.1053/plac.2002.0959. [PubMed:12744922 ]
Poon HF, Calabrese V, Scapagnini G, Butterfield DA: Free radicals: key to brain aging and heme oxygenase as a cellular response to oxidative stress. J Gerontol A Biol Sci Med Sci. 2004 May;59(5):478-93. doi: 10.1093/gerona/59.5.m478. [PubMed:15123759 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Biliverdin (MMDBc0000382)

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Structure for #<Metabolite:0x00007f9205d6c3f8>

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