NP-MRD: Showing NP-Card for Bilirubin (NP0000301)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-07-01 14:26:57 UTC

NP-MRD ID

NP0000301

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bilirubin

Description

Bilirubin is a yellow bile pigment that is a degradation product of heme. It occurs in the normal catabolic pathway that breaks down heme in vertebrates. This catabolism is a necessary process in the body's clearance of waste products that arise from the destruction of aged or abnormal red blood cells. Bilirubin has been found in all vertebrates and in certain plants including Strelitzia nicolai (PMID: 28573242 ). Bilirubin levels in humans are elevated in certain diseases such as jaundice and liver disease and it is responsible for the yellow color of bruises and the yellow discoloration in jaundice. Bilirubin breakdown products, such as stercobilin, cause the brown color of feces. A different breakdown product, urobilin, is the main component of the straw-yellow color in urine. Bilirubin consists of an open chain of four pyrroles (tetrapyrrole). It is formed by oxidative cleavage of a porphyrin in heme, which leads to biliverdin, a green tetrapyrrolic bile pigment that is also a product of heme catabolism. Biliverdin is then reduced to bilirubin via biliverdin reductase. After conjugation with glucuronic acid, bilirubin can be excreted in the urine. Bilirubin is structurally similar to the pigment phycobilin used by certain algae to capture light energy, and to the pigment phytochrome used by plants to sense light. Elevated bilirubin levels in humans are associated with Crigler-Najjar syndrome type I, which is an inborn error of metabolism. Crigler-Najjar syndrome is a rare genetic disorder characterized by an inability to properly convert and clear bilirubin from the body. Affected individuals cannot convert unconjugated bilirubin to the conjugated form because they lack a specific liver enzyme required to break down (metabolize) bilirubin. Since they cannot convert bilirubin, they develop abnormally high levels of unconjugated bilirubin in the blood (hyperbilirubinemia). Crigler-Najjar syndrome is caused by mutations in the UGT1A1 gene. The hallmark finding of Crigler-Najjar syndrome is a persistent yellowing of the skin, mucous membranes and whites of the eyes (jaundice). Elevation of both alanine aminotransferase and bilirubin levels in serum or plasma can be indicative of serious liver injury. High levels of bilirubin are indicative of jaundice, which is easily recognizable due to a yellowing of the skin and eyes. Bilirubin is also an antioxidant. Bilirubin's antioxidant activity may be particularly important in the brain, where it prevents excitotoxicity and neuronal death by scavenging superoxide during N-methyl-D-aspartic acid neurotransmission (PMID: 31353321 ).

Structure

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

  Mrv1652303182019232D          

 43 46  0  0  0  0            999 V2000
   -1.8645   -1.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395   -1.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9041   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -2.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1207    1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0139    0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8744    1.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4264    0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2469    0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5824    1.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4062    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1195   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4520   -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
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 12 13  1  0  0  0  0
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 16 27  1  0  0  0  0
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 21 16  2  0  0  0  0
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 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  2  0  0  0  0
 42 43  1  0  0  0  0
M  END

HMDB0000054
     RDKit          3D
Bilirubin
 79 82  0  0  0  0  0  0  0  0999 V2000
   -9.3811    3.3987   -0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3929    2.7185    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2364    1.9224    0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3549    1.8953   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5131    2.6246   -2.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2223    1.0212   -0.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2542    0.7063   -1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1414   -0.1633   -1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8594    0.1075   -1.3868 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0346   -0.9606   -1.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3193    0.2944   -0.9184 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5081    0.1525   -0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6648    1.0322   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7496    2.2742    0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6024    3.0600    0.3953 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0297    4.3927    0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3325    5.3928    0.9803 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4513    4.4268    0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3119    5.6543    0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5564   -1.1255    0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3716   -1.8146   -0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2324   -3.2660    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5760   -6.0990   -1.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8538   -1.8698   -0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4827   -3.1529    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9678   -2.9509    1.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9866    1.1764   -1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6234    0.5512   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6390    2.6994    0.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9713    5.7768   -0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9185    5.5520    1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6961    6.5552    0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9528    3.8260   -0.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5386    0.8984   -0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9774    1.9581   -0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4339   -0.9406    1.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3785   -2.1856    1.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2606   -2.5002    0.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8904   -3.8731   -1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6610   -5.7236   -0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3866   -3.8229    0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0854   -2.2523    1.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6842   -3.9369    1.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0204   -0.3022    2.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2066   -3.3006   -0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5004   -2.3223    1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8154   -0.0528    1.3511 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
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 18 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 23 24  2  3
 14 25  2  0
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 25 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
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 10 33  2  0
 33 34  1  0
 34 35  1  0
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 36 38  1  0
 33 39  1  0
 39 40  1  0
  6 41  1  0
 41 42  1  0
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 42  3  1  0
 39  8  2  0
 27 12  2  0
 22 16  1  0
  1 44  1  0
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  5 47  1  0
  5 48  1  0
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  7 50  1  0
  9 51  1  0
 11 52  1  0
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 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

  Mrv1652303182019232D          

 43 46  0  0  0  0            999 V2000
   -1.8645   -1.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0395   -1.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9041   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -2.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1207    1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0139    0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2069    0.2597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8744    1.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0459    2.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4264    0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2469    0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5824    1.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4062    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8646   -1.3329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0396   -1.3329    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1195   -2.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -2.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -3.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1666   -3.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1666   -4.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8809   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0139    0.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4265    0.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2469    0.8889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8744    1.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0460    2.2227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8306    2.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2070    0.2597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1207    1.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4063    1.4927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3495   -0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3495   -0.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -3.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1665   -3.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809   -5.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1665   -4.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4520   -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  1  0  0  0  0
 18 16  1  0  0  0  0
 21 16  2  0  0  0  0
 38 17  1  0  0  0  0
 18 17  1  0  0  0  0
 19 17  2  0  0  0  0
 19 21  1  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  2  0  0  0  0
 25 26  1  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  2  0  0  0  0
 42 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000301

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(N2)\C=C2/NC(=O)C(C=C)=C2C)N1

> <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-IFADSCNNSA-N

> <FORMULA>
C33H36N4O6

> <MOLECULAR_WEIGHT>
584.6621

> <EXACT_MASS>
584.263484904

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
66.1582703894841

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-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>
bilirubin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000054
     RDKit          3D
Bilirubin
 79 82  0  0  0  0  0  0  0  0999 V2000
   -9.3811    3.3987   -0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3929    2.7185    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2364    1.9224    0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3549    1.8953   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5131    2.6246   -2.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2223    1.0212   -0.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2542    0.7063   -1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1414   -0.1633   -1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8594    0.1075   -1.3868 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0346   -0.9606   -1.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3297   -0.9988   -1.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5856   -0.8971   -0.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193    0.2944   -0.9184 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5081    0.1525   -0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6648    1.0322   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7496    2.2742    0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6024    3.0600    0.3953 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0297    4.3927    0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3325    5.3928    0.9803 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4513    4.4268    0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3119    5.6543    0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8817    3.1801    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2503    2.9293   -0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8749    1.8697   -0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5564   -1.1255    0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7080   -1.7266    0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3716   -1.8146   -0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2324   -3.2660    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7795   -4.0694   -1.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336   -5.5123   -0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5760   -6.0990   -1.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7672   -6.2305   -0.4374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8538   -1.8698   -0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4827   -3.1529    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9678   -2.9509    1.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0083   -2.4041    2.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8307   -3.1799    3.0521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1378   -1.0539    2.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1749   -1.3932   -0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3245   -2.2311    0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4373    0.5387    0.7706 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6784    1.0880    1.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1755    0.8429    2.3559 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2168    3.9181   -0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0050    3.9725   -1.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9904    2.2043    1.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7853    3.6976   -1.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5081    2.7100   -2.6901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1889    2.1286   -2.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2984    1.1357   -2.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5803    0.9918   -1.8409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4130   -2.0492   -2.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3749   -0.3520   -2.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9866    1.1764   -1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6234    0.5512   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6390    2.6994    0.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9713    5.7768   -0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9185    5.5520    1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6961    6.5552    0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9528    3.8260   -0.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5386    0.8984   -0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9774    1.9581   -0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4339   -0.9406    1.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3785   -2.1856    1.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2606   -2.5002    0.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9445   -3.5187    0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2904   -3.6440    0.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2769   -3.7796   -2.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904   -3.8731   -1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6610   -5.7236   -0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3866   -3.8229    0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897   -3.7388   -0.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0854   -2.2523    1.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6842   -3.9369    1.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0204   -0.3022    2.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2066   -3.3006   -0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5004   -2.3223    1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2203   -1.8801   -0.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8154   -0.0528    1.3511 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                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  C   UNK     0      -3.480  -2.488   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.465  -3.953   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -1.940  -2.488   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -3.956  -3.953   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.421  -4.429   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.710  -4.858   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.092   2.016   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.759   0.165   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -2.253   0.485   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -3.499   2.642   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.819   4.149   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.529   1.498   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.061   1.659   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.687   3.066   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.758   2.786   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.465  -3.953   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.481  -2.488   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       1.941  -2.488   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       3.956  -3.953   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.421  -4.429   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.711  -4.858   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.711  -6.398   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.044  -7.168   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.711  -9.478   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.044  -8.708   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.378  -9.478   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.000  -4.429   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.759   0.165   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.529   1.498   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.061   1.659   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.499   2.642   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.819   4.149   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.284   4.625   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0       2.253   0.485   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       2.092   2.016   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       0.758   2.786   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -4.386  -1.242   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.386  -1.242   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.710  -6.398   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -4.044  -7.168   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -5.378  -9.478   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -4.044  -8.708   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -2.710  -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    HMDB0000054
HETATM    1  C1  UNL     1      -9.381   3.399  -0.124  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.393   2.718   0.011  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.236   1.922   0.168  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.355   1.895  -0.888  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.513   2.625  -2.170  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.222   1.021  -0.534  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.254   0.706  -1.350  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.141  -0.163  -1.018  1.00  0.00           C  
HETATM    9  N1  UNL     1      -1.859   0.108  -1.387  1.00  0.00           N  
HETATM   10  C9  UNL     1      -1.035  -0.961  -1.050  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.330  -0.999  -1.512  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.586  -0.897  -0.843  1.00  0.00           C  
HETATM   13  N2  UNL     1       2.319   0.294  -0.918  1.00  0.00           N  
HETATM   14  C12 UNL     1       3.508   0.153  -0.342  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.665   1.032  -0.299  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.750   2.274   0.005  1.00  0.00           C  
HETATM   17  N3  UNL     1       3.602   3.060   0.395  1.00  0.00           N  
HETATM   18  C15 UNL     1       4.030   4.393   0.625  1.00  0.00           C  
HETATM   19  O1  UNL     1       3.333   5.393   0.980  1.00  0.00           O  
HETATM   20  C16 UNL     1       5.451   4.427   0.377  1.00  0.00           C  
HETATM   21  C17 UNL     1       6.312   5.654   0.511  1.00  0.00           C  
HETATM   22  C18 UNL     1       5.882   3.180   0.011  1.00  0.00           C  
HETATM   23  C19 UNL     1       7.250   2.929  -0.321  1.00  0.00           C  
HETATM   24  C20 UNL     1       7.875   1.870  -0.668  1.00  0.00           C  
HETATM   25  C21 UNL     1       3.556  -1.126   0.124  1.00  0.00           C  
HETATM   26  C22 UNL     1       4.708  -1.727   0.862  1.00  0.00           C  
HETATM   27  C23 UNL     1       2.372  -1.815  -0.175  1.00  0.00           C  
HETATM   28  C24 UNL     1       2.232  -3.266   0.084  1.00  0.00           C  
HETATM   29  C25 UNL     1       2.780  -4.069  -1.095  1.00  0.00           C  
HETATM   30  C26 UNL     1       2.634  -5.512  -0.862  1.00  0.00           C  
HETATM   31  O2  UNL     1       1.576  -6.099  -1.025  1.00  0.00           O  
HETATM   32  O3  UNL     1       3.767  -6.230  -0.437  1.00  0.00           O  
HETATM   33  C27 UNL     1      -1.854  -1.870  -0.455  1.00  0.00           C  
HETATM   34  C28 UNL     1      -1.483  -3.153   0.153  1.00  0.00           C  
HETATM   35  C29 UNL     1      -0.968  -2.951   1.554  1.00  0.00           C  
HETATM   36  C30 UNL     1      -2.008  -2.404   2.452  1.00  0.00           C  
HETATM   37  O4  UNL     1      -2.831  -3.180   3.052  1.00  0.00           O  
HETATM   38  O5  UNL     1      -2.138  -1.054   2.673  1.00  0.00           O  
HETATM   39  C31 UNL     1      -3.175  -1.393  -0.433  1.00  0.00           C  
HETATM   40  C32 UNL     1      -4.325  -2.231   0.002  1.00  0.00           C  
HETATM   41  N4  UNL     1      -5.437   0.539   0.771  1.00  0.00           N  
HETATM   42  C33 UNL     1      -6.678   1.088   1.202  1.00  0.00           C  
HETATM   43  O6  UNL     1      -7.175   0.843   2.356  1.00  0.00           O  
HETATM   44  H1  UNL     1     -10.217   3.918  -0.149  1.00  0.00           H  
HETATM   45  H2  UNL     1      -9.005   3.972  -1.301  1.00  0.00           H  
HETATM   46  H3  UNL     1      -8.990   2.204   1.175  1.00  0.00           H  
HETATM   47  H4  UNL     1      -6.785   3.698  -1.968  1.00  0.00           H  
HETATM   48  H5  UNL     1      -5.508   2.710  -2.690  1.00  0.00           H  
HETATM   49  H6  UNL     1      -7.189   2.129  -2.887  1.00  0.00           H  
HETATM   50  H7  UNL     1      -4.298   1.136  -2.383  1.00  0.00           H  
HETATM   51  H8  UNL     1      -1.580   0.992  -1.841  1.00  0.00           H  
HETATM   52  H9  UNL     1       0.413  -2.049  -2.135  1.00  0.00           H  
HETATM   53  H10 UNL     1       0.375  -0.352  -2.510  1.00  0.00           H  
HETATM   54  H11 UNL     1       1.987   1.176  -1.350  1.00  0.00           H  
HETATM   55  H12 UNL     1       5.623   0.551  -0.586  1.00  0.00           H  
HETATM   56  H13 UNL     1       2.639   2.699   0.495  1.00  0.00           H  
HETATM   57  H14 UNL     1       6.971   5.777  -0.364  1.00  0.00           H  
HETATM   58  H15 UNL     1       6.918   5.552   1.445  1.00  0.00           H  
HETATM   59  H16 UNL     1       5.696   6.555   0.631  1.00  0.00           H  
HETATM   60  H17 UNL     1       7.953   3.826  -0.283  1.00  0.00           H  
HETATM   61  H18 UNL     1       7.539   0.898  -0.801  1.00  0.00           H  
HETATM   62  H19 UNL     1       8.977   1.958  -0.888  1.00  0.00           H  
HETATM   63  H20 UNL     1       5.434  -0.941   1.116  1.00  0.00           H  
HETATM   64  H21 UNL     1       4.378  -2.186   1.847  1.00  0.00           H  
HETATM   65  H22 UNL     1       5.261  -2.500   0.276  1.00  0.00           H  
HETATM   66  H23 UNL     1       2.944  -3.519   0.943  1.00  0.00           H  
HETATM   67  H24 UNL     1       1.290  -3.644   0.386  1.00  0.00           H  
HETATM   68  H25 UNL     1       2.277  -3.780  -2.008  1.00  0.00           H  
HETATM   69  H26 UNL     1       3.890  -3.873  -1.152  1.00  0.00           H  
HETATM   70  H27 UNL     1       4.661  -5.724  -0.302  1.00  0.00           H  
HETATM   71  H28 UNL     1      -2.387  -3.823   0.279  1.00  0.00           H  
HETATM   72  H29 UNL     1      -0.790  -3.739  -0.468  1.00  0.00           H  
HETATM   73  H30 UNL     1      -0.085  -2.252   1.604  1.00  0.00           H  
HETATM   74  H31 UNL     1      -0.684  -3.937   1.968  1.00  0.00           H  
HETATM   75  H32 UNL     1      -2.020  -0.302   2.034  1.00  0.00           H  
HETATM   76  H33 UNL     1      -4.207  -3.301  -0.396  1.00  0.00           H  
HETATM   77  H34 UNL     1      -4.500  -2.322   1.060  1.00  0.00           H  
HETATM   78  H35 UNL     1      -5.220  -1.880  -0.589  1.00  0.00           H  
HETATM   79  H36 UNL     1      -4.815  -0.053   1.351  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

HMDB0000054
     RDKit          3D
Bilirubin
 79 82  0  0  0  0  0  0  0  0999 V2000
   -9.3811    3.3987   -0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3929    2.7185    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2364    1.9224    0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3549    1.8953   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5131    2.6246   -2.1704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2223    1.0212   -0.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2542    0.7063   -1.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1414   -0.1633   -1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8594    0.1075   -1.3868 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0346   -0.9606   -1.0501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3297   -0.9988   -1.5120 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5856   -0.8971   -0.8432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193    0.2944   -0.9184 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5081    0.1525   -0.3420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6648    1.0322   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7496    2.2742    0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6024    3.0600    0.3953 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0297    4.3927    0.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3325    5.3928    0.9803 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4513    4.4268    0.3765 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3119    5.6543    0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8817    3.1801    0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2503    2.9293   -0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8749    1.8697   -0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5564   -1.1255    0.1243 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7080   -1.7266    0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3716   -1.8146   -0.1750 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2324   -3.2660    0.0844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7795   -4.0694   -1.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6336   -5.5123   -0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5760   -6.0990   -1.0253 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7672   -6.2305   -0.4374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8538   -1.8698   -0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4827   -3.1529    0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9678   -2.9509    1.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0083   -2.4041    2.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8307   -3.1799    3.0521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1378   -1.0539    2.6731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1749   -1.3932   -0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3245   -2.2311    0.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4373    0.5387    0.7706 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6784    1.0880    1.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1755    0.8429    2.3559 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2168    3.9181   -0.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0050    3.9725   -1.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9904    2.2043    1.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7853    3.6976   -1.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5081    2.7100   -2.6901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1889    2.1286   -2.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2984    1.1357   -2.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5803    0.9918   -1.8409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4130   -2.0492   -2.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3749   -0.3520   -2.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9866    1.1764   -1.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6234    0.5512   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6390    2.6994    0.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9713    5.7768   -0.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9185    5.5520    1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6961    6.5552    0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9528    3.8260   -0.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5386    0.8984   -0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9774    1.9581   -0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4339   -0.9406    1.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3785   -2.1856    1.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2606   -2.5002    0.2756 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9445   -3.5187    0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2904   -3.6440    0.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2769   -3.7796   -2.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904   -3.8731   -1.1520 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6610   -5.7236   -0.3017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3866   -3.8229    0.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897   -3.7388   -0.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0854   -2.2523    1.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6842   -3.9369    1.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0204   -0.3022    2.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2066   -3.3006   -0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5004   -2.3223    1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2203   -1.8801   -0.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8154   -0.0528    1.3511 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
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 20 21  1  0
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 14 25  2  0
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 27 28  1  0
 28 29  1  0
 29 30  1  0
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 30 32  1  0
 10 33  2  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
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 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
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 13 54  1  0
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 21 57  1  0
 21 58  1  0
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 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
1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionic acid	ChEBI
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
2,7,13,17-Tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoic acid	ChEBI
8,12-Bis(2-carboxyethyl)-2,7,13,17-tetramethyl-3,18-divinylbiladiene-ac-1,19(21H,24H)-dione	ChEBI
Bilirubin(Z,Z)	ChEBI
Bilirubin-ixalpha	ChEBI
1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionate	Generator
2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoate	Generator
2,7,13,17-Tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoate	Generator
Bilirubin ixalpha	HMDB
(4Z,15Z)-Bilirubin ixa	HMDB
(Z,Z)-Bilirubin ixa	HMDB
1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-biline-8,12-dipropionate	HMDB
1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-biline-8,12-dipropionic acid	HMDB
3-(2-((3-(2-Carboxyethyl)-4-methyl-5-((3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-2-yl)methyl)-4-methyl-5-((4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-3-yl)propanoate	HMDB
3-(2-((3-(2-Carboxyethyl)-4-methyl-5-((3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-2-yl)methyl)-4-methyl-5-((4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl)-1H-pyrrol-3-yl)propanoic acid	HMDB
3-(2-((3-(2-Carboxyethyl)-4-methyl-5-[(Z)-(3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl]-1H-pyrrol-2-yl)methyl)-4-methyl-5-[(Z)-(4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene	HMDB
3-[2-[[3-(2-Carboxyethyl)-5-[(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoate	HMDB
3-[2-[[3-(2-Carboxyethyl)-5-[(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid	HMDB
3-[2-[[3-(2-Carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoate	HMDB
3-[2-[[3-(2-Carboxyethyl)-5-[(Z)-(3-ethenyl-4-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methyl]-5-[(Z)-(4-ethenyl-3-methyl-5-oxo-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-3-yl]propanoic acid	HMDB
Bilirubin IX-alpha	HMDB
Cholerythrin	HMDB
Hematoidin	HMDB
Bilirubin IX alpha	HMDB

Chemical Formula

C₃₃H₃₆N₄O₆

Average Mass

584.6621 Da

Monoisotopic Mass

584.26348 Da

IUPAC Name

3-(2-{[3-(2-carboxyethyl)-5-{[(2Z)-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

bilirubin

CAS Registry Number

635-65-4

SMILES

CC1=C(C=C)\C(NC1=O)=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(N2)\C=C2/NC(=O)C(C=C)=C2C)N1

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-IFADSCNNSA-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
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
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Species Where Detected

Species Name	Source	Reference
Bos taurus domesticus GMELIN	KNApSAcK Database	22123792

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:16990 )
biladienes (CHEBI:16990 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.009 mg/mL at 25 °C	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	66.16 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

HMDB0000054

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

5280352

PDB ID

Not Available

ChEBI ID

16990

Good Scents ID

rw1223461

References

General References

Randeberg LL, Roll EB, Nilsen LT, Christensen T, Svaasand LO: In vivo spectroscopy of jaundiced newborn skin reveals more than a bilirubin index. Acta Paediatr. 2005 Jan;94(1):65-71. [PubMed:15858963 ]
Bayes Garcia R, Maldonado Lozano J, Molina Font JA: [Interrelation of bilirubin and free fatty acids in newborn infants with pathologic conditions]. An Esp Pediatr. 1989 Jan;30(1):27-31. [PubMed:2648917 ]
Yamamoto S, Kubo S, Hai S, Uenishi T, Yamamoto T, Shuto T, Takemura S, Tanaka H, Yamazaki O, Hirohashi K, Tanaka T: Hepatitis C virus infection as a likely etiology of intrahepatic cholangiocarcinoma. Cancer Sci. 2004 Jul;95(7):592-5. [PubMed:15245596 ]
Kabicek P: Importance of serum bile acids determination in adolescents with juvenile hyperbilirubinaemia. Cent Eur J Public Health. 2004 Jun;12(2):102-9. [PubMed:15242029 ]
Tiribelli C, Ostrow JD: New concepts in bilirubin and jaundice: report of the Third International Bilirubin Workshop, April 6-8, 1995, Trieste, Italy. Hepatology. 1996 Nov;24(5):1296-311. [PubMed:8903413 ]
Zhan X, Wang SY, Wang L, Qu P: [Decreased peripheral nerve conduction velocity may be associated with lower-serum level of vitamin E in patients with infantile hepatitis syndrome]. Zhonghua Er Ke Za Zhi. 2004 May;42(5):362-6. [PubMed:15189696 ]
Deja M, Hildebrandt B, Ahlers O, Riess H, Wust P, Gerlach H, Kerner T: Goal-directed therapy of cardiac preload in induced whole-body hyperthermia. Chest. 2005 Aug;128(2):580-6. [PubMed:16100141 ]
Kikuchi S, Hata M, Fukumoto K, Yamane Y, Matsui T, Tamura A, Yonemura S, Yamagishi H, Keppler D, Tsukita S, Tsukita S: Radixin deficiency causes conjugated hyperbilirubinemia with loss of Mrp2 from bile canalicular membranes. Nat Genet. 2002 Jul;31(3):320-5. Epub 2002 Jun 17. [PubMed:12068294 ]
Lin JM, Jiang CQ: [Clinical manifestation and ultrasonic characteristics of five patients with acute arsenic poisoning]. Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2003 Dec;21(6):420-2. [PubMed:14761351 ]
Azer SA: A multimedia CD-ROM tool to improve student understanding of bile salts and bilirubin metabolism: evaluation of its use in a medical hybrid PBL course. Adv Physiol Educ. 2005 Mar;29(1):40-50. [PubMed:15718382 ]
Slusher TM, Angyo IA, Bode-Thomas F, Akor F, Pam SD, Adetunji AA, McLaren DW, Wong RJ, Vreman HJ, Stevenson DK: Transcutaneous bilirubin measurements and serum total bilirubin levels in indigenous African infants. Pediatrics. 2004 Jun;113(6):1636-41. [PubMed:15173484 ]
Ciszowski K, Gomolka E, Jenner B: [The influence of the dose, time since ingestion and concentration of the xenobiotic on the clinical state and severity of liver damage with patients intoxicated with paracetamol]. Przegl Lek. 2005;62(6):456-61. [PubMed:16225094 ]
Sando M, Sato Y, Iwata S, Akita H, Sunakawa K: In vitro protein binding of teicoplanin to neonatal serum. J Infect Chemother. 2004 Oct;10(5):280-3. [PubMed:16163462 ]
Danko I, Jia Z, Zhang G: Nonviral gene transfer into liver and muscle for treatment of hyperbilirubinemia in the gunn rat. Hum Gene Ther. 2004 Dec;15(12):1279-86. [PubMed:15684703 ]
Kotal P, Van der Veere CN, Sinaasappel M, Elferink RO, Vitek L, Brodanova M, Jansen PL, Fevery J: Intestinal excretion of unconjugated bilirubin in man and rats with inherited unconjugated hyperbilirubinemia. Pediatr Res. 1997 Aug;42(2):195-200. [PubMed:9262222 ]
Ochenashko OV, Volkova NA, Mazur SP, Somov AY, Fuller BJ, Petrenko AY: Cryopreserved fetal liver cell transplants support the chronic failing liver in rats with CCl4-induced cirrhosis. Cell Transplant. 2006;15(1):23-33. [PubMed:16700327 ]
Lapidus A, Akerlund JE, Einarsson C: Gallbladder bile composition in patients with Crohn 's disease. World J Gastroenterol. 2006 Jan 7;12(1):70-4. [PubMed:16440420 ]
Sikkel E, Pasman SA, Oepkes D, Kanhai HH, Vandenbussche FP: On the origin of amniotic fluid bilirubin. Placenta. 2004 May;25(5):463-8. [PubMed:15081641 ]
Schmidt CM, Powell ES, Yiannoutsos CT, Howard TJ, Wiebke EA, Wiesenauer CA, Baumgardner JA, Cummings OW, Jacobson LE, Broadie TA, Canal DF, Goulet RJ Jr, Curie EA, Cardenes H, Watkins JM, Loehrer PJ, Lillemoe KD, Madura JA: Pancreaticoduodenectomy: a 20-year experience in 516 patients. Arch Surg. 2004 Jul;139(7):718-25; discussion 725-7. [PubMed:15249403 ]
Nanjundaswamy S, Petrova A, Mehta R, Hegyi T: Transcutaneous bilirubinometry in preterm infants receiving phototherapy. Am J Perinatol. 2005 Apr;22(3):127-31. [PubMed:15838745 ]
Dwarka D, Thaver V, Naidu M, Baijnath H: NEW INSIGHTS INTO THE PRESENCE OF BILIRUBIN IN A PLANT SPECIES STRELITZIA NICOLAI (STRELITZIACEAE). Afr J Tradit Complement Altern Med. 2017 Jan 13;14(2):253-262. doi: 10.21010/ajtcam.v14i2.27. eCollection 2017. [PubMed:28573242 ]
Vasavda C, Kothari R, Malla AP, Tokhunts R, Lin A, Ji M, Ricco C, Xu R, Saavedra HG, Sbodio JI, Snowman AM, Albacarys L, Hester L, Sedlak TW, Paul BD, Snyder SH: Bilirubin Links Heme Metabolism to Neuroprotection by Scavenging Superoxide. Cell Chem Biol. 2019 Oct 17;26(10):1450-1460.e7. doi: 10.1016/j.chembiol.2019.07.006. Epub 2019 Jul 25. [PubMed:31353321 ]

Showing NP-Card for Bilirubin (NP0000301)

MOL for NP0000301 (Bilirubin)

3D MOL for NP0000301 (Bilirubin)

3D SDF for NP0000301 (Bilirubin)

3D-SDF for NP0000301 (Bilirubin)

PDB for NP0000301 (Bilirubin)

3D PDB for NP0000301 (Bilirubin)

SMILES for NP0000301 (Bilirubin)

INCHI for NP0000301 (Bilirubin)

Structure for NP0000301 (Bilirubin)

3D Structure for NP0000301 (Bilirubin)