You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Showing metabocard for Bilirubin (HMDB0000054)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (26)transporters (2) Show 28 proteinsXML
enzymes (26)transporters (2) Show 28 proteins
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:24:00 UTC
HMDB IDHMDB0000054
Secondary Accession Numbers
  • HMDB00054
Metabolite Identification
Common NameBilirubin
DescriptionBilirubin 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
Data?1582752109
MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000054 (Bilirubin)


  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
Download

3D MOL for HMDB0000054 (Bilirubin)

Download
3D SDF for HMDB0000054 (Bilirubin)

  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>
HMDB0000054

> <DATABASE_NAME>
hmdb

> <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

$$$$

Download
3D-SDF for HMDB0000054 (Bilirubin)
https://cactus.nci.nih.gov/chemical/structure/CC1=C(C=C)%5CC(NC1=O)=C%5CC1=C(...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:78})
 79 82  0  0  0  0  0  0  0  0999 V2000
    8.4662   -0.0581   -0.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0349    0.2874   -0.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3270    1.3749   -0.7916 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8215    2.4050   -1.7222 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9193    3.0945   -1.4281 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9881    1.2899   -0.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9808    0.1585    0.6084 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1849   -0.4344    0.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4945   -1.4512    1.1482 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417    2.1608   -0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6658    1.8690    0.1229 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6103    2.7575    0.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6091    4.2124   -0.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5477    2.0496    0.8230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8128    2.6072    1.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7388    2.4407   -0.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0993    2.9983    0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0804    2.9604   -0.6386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3071    3.4795    1.3654 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9560    0.7721    1.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1191   -0.3320    1.6158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7113   -0.9701    0.5320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2985   -1.9620   -0.2959 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0610   -2.6122   -0.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0470   -3.8161    0.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4066   -4.4663    0.6584 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6300   -5.5487    1.4201 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2954   -4.0133   -0.0232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3550   -2.2753   -1.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3479   -3.3201   -2.2391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4130   -1.4433   -0.8160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9957   -0.6489    0.2302 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6824   -1.4181   -1.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7691   -0.9033   -0.7451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7987   -0.5937    0.6103 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0168   -0.1149    0.9277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3802    0.2518    2.0320 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8258   -0.1134   -0.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2259    0.3292   -0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8779    0.7836    0.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0176   -0.6034   -1.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4118   -0.7872   -2.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2395    0.6475    0.5963 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1270    0.4267    0.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6002   -1.1385   -0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7066    0.2877   -1.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2921    2.5997   -2.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2385    3.9015   -2.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4919    2.8478   -0.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2256   -0.1545    1.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0967    3.0671   -0.9733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769    4.3096   -1.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9325    4.7643    0.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6170    4.6158   -0.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2280    2.0710    2.0065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7221    3.6654    1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3236    2.9769   -0.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8295    1.3825   -0.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9360    3.3301   -0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7713   -1.0822    2.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5379    0.0810    2.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3088   -2.9441   -1.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8064   -1.8930    0.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992   -3.4843    1.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3017   -4.5353    0.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5179   -5.9308    1.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6835   -4.2726   -1.8291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0181   -3.0138   -3.0423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3369   -3.4294   -2.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5285    0.0301    0.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8063   -1.8008   -2.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0597   -0.7052    1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7221    0.2841   -1.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3817    0.8287    1.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9039    1.1079    0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4468   -0.4737   -2.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7626   -0.1832   -3.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3113   -1.8376   -3.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7697   -0.1643    0.6263 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 44  1  0  0  0  0
  1 45  1  0  0  0  0
  1 46  1  0  0  0  0
  2  3  2  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  4  5  2  0  0  0  0
  4 47  1  0  0  0  0
  5 48  1  0  0  0  0
  5 49  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  2  0  0  0  0
  7  8  1  0  0  0  0
  7 50  1  0  0  0  0
  8  9  2  0  0  0  0
 10 11  1  0  0  0  0
 10 51  1  0  0  0  0
 11 12  2  0  0  0  0
 11 43  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 52  1  0  0  0  0
 13 53  1  0  0  0  0
 13 54  1  0  0  0  0
 14 15  1  0  0  0  0
 14 20  2  0  0  0  0
 15 16  1  0  0  0  0
 15 55  1  0  0  0  0
 15 56  1  0  0  0  0
 16 17  1  0  0  0  0
 16 57  1  0  0  0  0
 16 58  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 18 59  1  0  0  0  0
 20 21  1  0  0  0  0
 20 43  1  0  0  0  0
 21 22  1  0  0  0  0
 21 60  1  0  0  0  0
 21 61  1  0  0  0  0
 22 23  2  0  0  0  0
 22 32  1  0  0  0  0
 23 24  1  0  0  0  0
 23 29  1  0  0  0  0
 24 25  1  0  0  0  0
 24 62  1  0  0  0  0
 24 63  1  0  0  0  0
 25 26  1  0  0  0  0
 25 64  1  0  0  0  0
 25 65  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 27 66  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 30 67  1  0  0  0  0
 30 68  1  0  0  0  0
 30 69  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 32 70  1  0  0  0  0
 33 34  2  0  0  0  0
 33 71  1  0  0  0  0
 34 35  1  0  0  0  0
 34 41  1  0  0  0  0
 35 36  1  0  0  0  0
 35 72  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 41  2  0  0  0  0
 39 40  2  0  0  0  0
 39 73  1  0  0  0  0
 40 74  1  0  0  0  0
 40 75  1  0  0  0  0
 41 42  1  0  0  0  0
 42 76  1  0  0  0  0
 42 77  1  0  0  0  0
 42 78  1  0  0  0  0
 43 79  1  0  0  0  0
M  END
$$$$

Download
PDB for HMDB0000054 (Bilirubin)
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

Download
3D PDB for HMDB0000054 (Bilirubin)
COMPND    https://cactus.nci.nih.gov/chemical/structure/CC1=C(C=C)%5CC(NC1=O)=C%5CC1=C(... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNL     1       8.466  -0.058  -0.618  1.00  0.00           C  
HETATM    2  C   UNL     1       7.035   0.287  -0.296  1.00  0.00           C  
HETATM    3  C   UNL     1       6.327   1.375  -0.792  1.00  0.00           C  
HETATM    4  C   UNL     1       6.822   2.405  -1.722  1.00  0.00           C  
HETATM    5  C   UNL     1       7.919   3.095  -1.428  1.00  0.00           C  
HETATM    6  C   UNL     1       4.988   1.290  -0.201  1.00  0.00           C  
HETATM    7  N   UNL     1       4.981   0.159   0.608  1.00  0.00           N  
HETATM    8  C   UNL     1       6.185  -0.434   0.548  1.00  0.00           C  
HETATM    9  O   UNL     1       6.495  -1.451   1.148  1.00  0.00           O  
HETATM   10  C   UNL     1       3.942   2.161  -0.407  1.00  0.00           C  
HETATM   11  C   UNL     1       2.666   1.869   0.123  1.00  0.00           C  
HETATM   12  C   UNL     1       1.610   2.757   0.257  1.00  0.00           C  
HETATM   13  C   UNL     1       1.609   4.212  -0.136  1.00  0.00           C  
HETATM   14  C   UNL     1       0.548   2.050   0.823  1.00  0.00           C  
HETATM   15  C   UNL     1      -0.813   2.607   1.153  1.00  0.00           C  
HETATM   16  C   UNL     1      -1.739   2.441  -0.053  1.00  0.00           C  
HETATM   17  C   UNL     1      -3.099   2.998   0.277  1.00  0.00           C  
HETATM   18  O   UNL     1      -4.080   2.960  -0.639  1.00  0.00           O  
HETATM   19  O   UNL     1      -3.307   3.479   1.365  1.00  0.00           O  
HETATM   20  C   UNL     1       0.956   0.772   1.023  1.00  0.00           C  
HETATM   21  C   UNL     1       0.119  -0.332   1.616  1.00  0.00           C  
HETATM   22  C   UNL     1      -0.711  -0.970   0.532  1.00  0.00           C  
HETATM   23  C   UNL     1      -0.298  -1.962  -0.296  1.00  0.00           C  
HETATM   24  C   UNL     1       1.061  -2.612  -0.291  1.00  0.00           C  
HETATM   25  C   UNL     1       1.047  -3.816   0.653  1.00  0.00           C  
HETATM   26  C   UNL     1       2.407  -4.466   0.658  1.00  0.00           C  
HETATM   27  O   UNL     1       2.630  -5.549   1.420  1.00  0.00           O  
HETATM   28  O   UNL     1       3.295  -4.013  -0.023  1.00  0.00           O  
HETATM   29  C   UNL     1      -1.355  -2.275  -1.153  1.00  0.00           C  
HETATM   30  C   UNL     1      -1.348  -3.320  -2.239  1.00  0.00           C  
HETATM   31  C   UNL     1      -2.413  -1.443  -0.816  1.00  0.00           C  
HETATM   32  N   UNL     1      -1.996  -0.649   0.230  1.00  0.00           N  
HETATM   33  C   UNL     1      -3.682  -1.418  -1.428  1.00  0.00           C  
HETATM   34  C   UNL     1      -4.769  -0.903  -0.745  1.00  0.00           C  
HETATM   35  N   UNL     1      -4.799  -0.594   0.610  1.00  0.00           N  
HETATM   36  C   UNL     1      -6.017  -0.115   0.928  1.00  0.00           C  
HETATM   37  O   UNL     1      -6.380   0.252   2.032  1.00  0.00           O  
HETATM   38  C   UNL     1      -6.826  -0.113  -0.293  1.00  0.00           C  
HETATM   39  C   UNL     1      -8.226   0.329  -0.419  1.00  0.00           C  
HETATM   40  C   UNL     1      -8.878   0.784   0.646  1.00  0.00           C  
HETATM   41  C   UNL     1      -6.018  -0.603  -1.309  1.00  0.00           C  
HETATM   42  C   UNL     1      -6.412  -0.787  -2.751  1.00  0.00           C  
HETATM   43  N   UNL     1       2.240   0.647   0.596  1.00  0.00           N  
HETATM   44  H   UNL     1       9.127   0.427   0.101  1.00  0.00           H  
HETATM   45  H   UNL     1       8.600  -1.139  -0.563  1.00  0.00           H  
HETATM   46  H   UNL     1       8.707   0.288  -1.623  1.00  0.00           H  
HETATM   47  H   UNL     1       6.292   2.600  -2.643  1.00  0.00           H  
HETATM   48  H   UNL     1       8.239   3.901  -2.071  1.00  0.00           H  
HETATM   49  H   UNL     1       8.492   2.848  -0.546  1.00  0.00           H  
HETATM   50  H   UNL     1       4.226  -0.154   1.131  1.00  0.00           H  
HETATM   51  H   UNL     1       4.097   3.067  -0.973  1.00  0.00           H  
HETATM   52  H   UNL     1       1.277   4.310  -1.170  1.00  0.00           H  
HETATM   53  H   UNL     1       0.932   4.764   0.516  1.00  0.00           H  
HETATM   54  H   UNL     1       2.617   4.616  -0.039  1.00  0.00           H  
HETATM   55  H   UNL     1      -1.228   2.071   2.006  1.00  0.00           H  
HETATM   56  H   UNL     1      -0.722   3.665   1.398  1.00  0.00           H  
HETATM   57  H   UNL     1      -1.324   2.977  -0.907  1.00  0.00           H  
HETATM   58  H   UNL     1      -1.829   1.383  -0.298  1.00  0.00           H  
HETATM   59  H   UNL     1      -4.936   3.330  -0.381  1.00  0.00           H  
HETATM   60  H   UNL     1       0.771  -1.082   2.063  1.00  0.00           H  
HETATM   61  H   UNL     1      -0.538   0.081   2.381  1.00  0.00           H  
HETATM   62  H   UNL     1       1.309  -2.944  -1.299  1.00  0.00           H  
HETATM   63  H   UNL     1       1.806  -1.893   0.049  1.00  0.00           H  
HETATM   64  H   UNL     1       0.799  -3.484   1.661  1.00  0.00           H  
HETATM   65  H   UNL     1       0.302  -4.535   0.314  1.00  0.00           H  
HETATM   66  H   UNL     1       3.518  -5.931   1.390  1.00  0.00           H  
HETATM   67  H   UNL     1      -1.683  -4.273  -1.829  1.00  0.00           H  
HETATM   68  H   UNL     1      -2.018  -3.014  -3.042  1.00  0.00           H  
HETATM   69  H   UNL     1      -0.337  -3.429  -2.631  1.00  0.00           H  
HETATM   70  H   UNL     1      -2.529   0.030   0.673  1.00  0.00           H  
HETATM   71  H   UNL     1      -3.806  -1.801  -2.430  1.00  0.00           H  
HETATM   72  H   UNL     1      -4.060  -0.705   1.229  1.00  0.00           H  
HETATM   73  H   UNL     1      -8.722   0.284  -1.377  1.00  0.00           H  
HETATM   74  H   UNL     1      -8.382   0.829   1.604  1.00  0.00           H  
HETATM   75  H   UNL     1      -9.904   1.108   0.553  1.00  0.00           H  
HETATM   76  H   UNL     1      -7.447  -0.474  -2.888  1.00  0.00           H  
HETATM   77  H   UNL     1      -5.763  -0.183  -3.385  1.00  0.00           H  
HETATM   78  H   UNL     1      -6.311  -1.838  -3.025  1.00  0.00           H  
HETATM   79  H   UNL     1       2.770  -0.164   0.626  1.00  0.00           H  
CONECT    1    2   44   45   46                                       
CONECT    2    1    3    3    8                                       
CONECT    3    2    2    4    6                                       
CONECT    4    3    5    5   47                                       
CONECT    5    4    4   48   49                                       
CONECT    6    3    7   10   10                                       
CONECT    7    6    8   50                                            
CONECT    8    7    2    9    9                                       
CONECT    9    8    8                                                 
CONECT   10    6    6   11   51                                       
CONECT   11   10   12   12   43                                       
CONECT   12   11   11   13   14                                       
CONECT   13   12   52   53   54                                       
CONECT   14   12   15   20   20                                       
CONECT   15   14   16   55   56                                       
CONECT   16   15   17   57   58                                       
CONECT   17   16   18   19   19                                       
CONECT   18   17   59                                                 
CONECT   19   17   17                                                 
CONECT   20   14   14   21   43                                       
CONECT   21   20   22   60   61                                       
CONECT   22   21   23   23   32                                       
CONECT   23   22   22   24   29                                       
CONECT   24   23   25   62   63                                       
CONECT   25   24   26   64   65                                       
CONECT   26   25   27   28   28                                       
CONECT   27   26   66                                                 
CONECT   28   26   26                                                 
CONECT   29   23   30   31   31                                       
CONECT   30   29   67   68   69                                       
CONECT   31   29   29   32   33                                       
CONECT   32   31   22   70                                            
CONECT   33   31   34   34   71                                       
CONECT   34   33   33   35   41                                       
CONECT   35   34   36   72                                            
CONECT   36   35   37   37   38                                       
CONECT   37   36   36                                                 
CONECT   38   36   39   41   41                                       
CONECT   39   38   40   40   73                                       
CONECT   40   39   39   74   75                                       
CONECT   41   38   38   34   42                                       
CONECT   42   41   76   77   78                                       
CONECT   43   20   11   79                                            
CONECT   44    1                                                      
CONECT   45    1                                                      
CONECT   46    1                                                      
CONECT   47    4                                                      
CONECT   48    5                                                      
CONECT   49    5                                                      
CONECT   50    7                                                      
CONECT   51   10                                                      
CONECT   52   13                                                      
CONECT   53   13                                                      
CONECT   54   13                                                      
CONECT   55   15                                                      
CONECT   56   15                                                      
CONECT   57   16                                                      
CONECT   58   16                                                      
CONECT   59   18                                                      
CONECT   60   21                                                      
CONECT   61   21                                                      
CONECT   62   24                                                      
CONECT   63   24                                                      
CONECT   64   25                                                      
CONECT   65   25                                                      
CONECT   66   27                                                      
CONECT   67   30                                                      
CONECT   68   30                                                      
CONECT   69   30                                                      
CONECT   70   32                                                      
CONECT   71   33                                                      
CONECT   72   35                                                      
CONECT   73   39                                                      
CONECT   74   40                                                      
CONECT   75   40                                                      
CONECT   76   42                                                      
CONECT   77   42                                                      
CONECT   78   42                                                      
CONECT   79   43                                                      
MASTER        0    0    0    0    0    0    0    0   79    0   79    0
END

Download
SMILES for HMDB0000054 (Bilirubin)
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
Download
INCHI for HMDB0000054 (Bilirubin)
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-
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionic acidChEBI
2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acidChEBI
2,7,13,17-Tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoic acidChEBI
8,12-Bis(2-carboxyethyl)-2,7,13,17-tetramethyl-3,18-divinylbiladiene-ac-1,19(21H,24H)-dioneChEBI
Bilirubin(Z,Z)ChEBI
Bilirubin-ixalphaChEBI
1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionateGenerator
2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoateGenerator
2,7,13,17-Tetramethyl-1,19-dioxo-3,18-divinyl-1,10,19,22,23,24-hexahydro-21H-biline-8,12-dipropanoateGenerator
Bilirubin ixalphaHMDB
(4Z,15Z)-Bilirubin ixaHMDB
(Z,Z)-Bilirubin ixaHMDB
1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-biline-8,12-dipropionateHMDB
1,10,19,22,23,24-Hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-biline-8,12-dipropionic acidHMDB
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)propanoateHMDB
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 acidHMDB
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-ylideneHMDB
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]propanoateHMDB
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 acidHMDB
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]propanoateHMDB
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 acidHMDB
Bilirubin IX-alphaHMDB
CholerythrinHMDB
HematoidinHMDB
Bilirubin IX alphaHMDB
Chemical FormulaC33H36N4O6
Average Molecular Weight584.6621
Monoisotopic Molecular Weight584.263484904
IUPAC Name3-(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 Namebilirubin
CAS Registry Number635-65-4
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 KeyBPYKTIZUTYGOLE-IFADSCNNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassTetrapyrroles and derivatives  
Sub ClassBilirubins  
Direct ParentBilirubins  
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 FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect:
Disposition
Route of exposure:
Source:
Biological location:
Process
Naturally occurring process:
Role
Biological role:
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.009 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0096 g/LALOGPS
logP3.22ALOGPS
logP3.12ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)4.03ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area164.38 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity168.9 m³·mol⁻¹ChemAxon
Polarizability66.16 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties
Collision Cross Sections
NameAdductTypeData SourceValueReference
DeepCCS[M-H]-ExperimentalMetCCS_train_neg247.18230932474  
AllCCS[M-H]-ExperimentalNot Available247.182http://allccs.zhulab.cn/database/detail?ID=AllCCS00000314  
DarkChem[M+H]+PredictedNot Available31661259  
DarkChem[M-H]-PredictedNot Available31661259  
AllCCS[M+H]+PredictedNot Available242.83632859911  
AllCCS[M-H]-PredictedNot Available241.45332859911  
Retention Indices
Underivatized
Not Available
Derivatized
DerivativeValueReference
Bilirubin,1TMS,#15322.767Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,1TMS,#25322.9185Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,1TMS,#35164.133Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,1TMS,#45376.3794Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,1TMS,#55155.9834Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,1TMS,#65379.954Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TMS,#15144.0757Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TMS,#25201.1377Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TMS,#35204.276Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TMS,#45018.058Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TMS,#55010.2344Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TMS,#65199.9526Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TMS,#75203.813Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TMS,#85017.7427Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TMS,#95010.387Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TMS,#105090.5337Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TMS,#115101.729Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TMS,#124880.3745Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TMS,#135298.9756Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TMS,#145087.6743Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TMS,#155077.786Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,1TBDMS,#15517.6484Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,1TBDMS,#25517.384Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,1TBDMS,#35397.603Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,1TBDMS,#45504.499Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,1TBDMS,#55396.052Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,1TBDMS,#65507.715Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TBDMS,#15501.0747Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TBDMS,#25512.161Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TBDMS,#35511.2812Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TBDMS,#45394.4087Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TBDMS,#55397.7227Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TBDMS,#65510.5083Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TBDMS,#75512.2007Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TBDMS,#85394.284Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TBDMS,#95398.1304Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TBDMS,#105443.728Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TBDMS,#115454.0986Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TBDMS,#125279.248Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TBDMS,#135578.0303Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TBDMS,#145448.2295Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Bilirubin,2TBDMS,#155435.017Lange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Spectra
GC-MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00vr-0100090000-d19585e898437e8be1d52017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01vn-3100069000-c39a7113e7f8eb3fa22a2017-10-06View Spectrum
LC-MS/MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-000i-0090000000-50ff729317f07f6120b52017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  30V, Positivesplash10-0002-0090000000-83d0d13757dcbce356042021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  40V, Positivesplash10-0002-0090000000-491b2676042d627277842021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  40V, Negativesplash10-01p9-1090000000-1d547122826037e04cfb2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  30V, Negativesplash10-000i-1090000000-30f7fa38dcf8706b38c62021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  10V, Negativesplash10-001i-1030090000-dea3b39afc072d2855c52021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  20V, Negativesplash10-000i-1090010000-369d79a300efec3a6c782021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  10V, Positivesplash10-0002-0091050000-78e3736d034dec9b8fa92021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  30V, Positivesplash10-0002-0091000000-cc507e875cc295800fa02021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  20V, Positivesplash10-0002-0090000000-679d7d93f8aeb5b1c0d12021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  10V, Positivesplash10-0002-0090020000-ea54f49e76225d2519902021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  30V, Positivesplash10-0002-0091000000-24657f467af3adfa1e8c2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  0V, Positivesplash10-000i-0020090000-5bcce058438671178ee42021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  10V, Positivesplash10-0002-0092030000-24054054aef5b235a8502021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum -  0V, Positivesplash10-000i-0030090000-b525a9b7bb66406e6afc2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-00ks-0000090000-ddf9acb7f968b90797642016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-00g0-0110290000-ae6f323e9f5e9e26199c2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-0uml-1102910000-df5146b3612e4fb4ce5e2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-001i-0000090000-6deb1aed1a9c3839e2a92016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-053i-1010190000-7435a4388bade8e83d102016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-052f-9010240000-cc90fff0581c6bcefd0d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-001i-0010090000-467141ca1354a02b0aef2021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-00s9-0030390000-ecd6322d5a093ef12c522021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-000f-0090400000-57eee3679925f2fa12ee2021-09-07View Spectrum
NMR
Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, C, experimental)2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, DMSO, experimental)2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, DMSO, experimental)2016-10-22View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, 100%_DMSO, predicted)2012-12-04View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
    • 

  • Extracellular
    • 

  • Membrane (predicted from logP)
    • 

  • Endoplasmic reticulum
Biospecimen Locations
  • Bile
    • 

  • Blood
    • 

  • Cerebrospinal Fluid (CSF)
    • 

  • Feces
    • 

  • Urine
Tissue Locations
  • Bile
    • 

  • Bone Marrow
    • 

  • Brain
    • 

  • Epidermis
    • 

  • Erythrocyte
    • 

  • Fibroblasts
    • 

  • Intestine
    • 

  • Kidney
    • 

  • Liver
    • 

  • Neuron
    • 

  • Pancreas
    • 

  • Placenta
    • 

  • Platelet
    • 

  • Skeletal Muscle
    • 

  • Spleen
    • 

  • Thyroid Gland
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified13.0 (5.0-21.0) uMAdult (>18 years old)Both
 
Normal
    • McPherson, Richar...
    •  Louise M. Malark...
  details
BloodDetected and Quantified15.2 +/- 2.0 uMAdult (>18 years old)BothNormal  details
BloodDetected and Quantified<12.828 uMAdult (>18 years old)Both
 
Normal		  details
BloodDetected and Quantified<12 uMNewborn (0-30 days old)Not Specified
 
Normal		  details
BloodDetected and Quantified<3.4 uMChildren (1-13 years old)Not Specified
 
Normal		  details
BloodDetected and Quantified3-21 uMNewborn (0-30 days old)Not Specified
 
Normal		  details
BloodDetected and Quantified<20 uMChildren (1-13 years old)Not Specified
 
Normal		  details
BloodDetected and Quantified8.0 +/- 0.9 uMAdult (>18 years old)BothNormal  details
BloodDetected and Quantified310.265 +/- 65.850 uMNewborn (0-30 days old)Not SpecifiedNormal  details
BloodDetected and Quantified6.842-20.525 uMChildren (1-13 years old)Not Specified
 
Normal		  details
BloodDetected and Quantified5.131-17.104 uMAdult (>18 years old)BothNormal  details
BloodDetected and Quantified5.10-18.0 uMAdult (>18 years old)BothNormal  details
BloodDetected and Quantified<17 uMChildren (1 - 13 years old)Not AvailableNormal
    • Hereditary Jaundi...
  details
BloodDetected and Quantified8.500 +/- 4 uMAdult (>18 years old)Not SpecifiedNormal
    • Geigy Scientific ...
  details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
 
Normal		  details
Cerebrospinal Fluid (CSF)Detected and Quantified0 - 0.2 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
  details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
 
Normal		  details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
 
Normal		  details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
 
Normal		  details
UrineDetected and Quantified< 0.1 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Tietz Clinical Gu...
  details
UrineDetected and Quantified0.032 (0.0019-0.21) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
  details
UrineDetected and Quantified0.51-5.13 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
  details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BileDetected and Quantified5000 (4300-5700) uMAdult (>18 years old)BothCrohn's disease  details
BileDetected and Quantified2600 (2400-2800) uMAdult (>18 years old)BothGallstone disease  details
BileDetected and Quantified4600 (3900-5300) uMAdult (>18 years old)Both
 
Crohn's disease		  details
BileDetected and Quantified5900 (4300-7500) uMAdult (>18 years old)Both
 
Crohn's disease		  details
BloodDetected and Quantified14.6 +/- 2.5 uMAdult (>18 years old)Both
 
Growth hormone deficiency		  details
BloodDetected and Quantified650 uMAdolescent (13-18 years old)MaleCrigler-Najjar syndrome Type I  details
BloodDetected and Quantified25.656-78.678 uMAdult (>18 years old)Both
 
Anemia, congenital dyserythropoietic, type II		  details
BloodDetected and Quantified28.7-170 uMChildren (1-13 years old)Both
 
Infantile Liver Failure Syndrome 2		  details
BloodDetected and Quantified22-41 uMNewborn (0-30 days old)Both
 
Citrullinemia type II, neonatal-onset		  details
BloodDetected and Quantified46.9-233 uMChildren (1-13 years old)Both
 
Infantile Liver Failure Syndrome 2		  details
BloodDetected and Quantified41-101 uMNewborn (0-30 days old)Both
 
Citrullinemia type II, neonatal-onset		  details
BloodDetected and Quantified73.1-85.0 uMInfant (0-1 year old)Female
 
Infantile Liver Failure Syndrome 2		  details
BloodDetected and Quantified41(6-381) uMChildren (1-13 years old)BothCholestasis, progressive familial intrahepatic, 1  details
BloodDetected and Quantified59.2 uMInfant (0-1 year old)Female
 
Wolcott-Rallison syndrome
    • Neonatal diabetes...
  details
BloodDetected and Quantified106 uMInfant (0-1 year old)FemaleBile Acid Synthesis Defect, Congenital, 1  details
BloodDetected and Quantified24.5 uMAdult (>18 years old)FemaleLecithin:cholesterol Acyltransferase Deficiency  details
BloodDetected and Quantified8.80 +/- 1.22 uMAdult (>18 years old)Both
 
Growth hormone deficiency		  details
BloodDetected and Quantified573.0 (291.0-855.0) uMChildren (1-13 years old)BothCrigler-Najjar syndrome Type I
    • MetaGene: Metabol...
  details
BloodDetected and Quantified29.59 uMNewborn (0-30 days old)Male
 
Lathosterolosis		  details
BloodDetected and Quantified380.733 +/- 142.989 uMNewborn (0-30 days old)Both
 
Glucose-6-phosphate dehydrogenase deficiency		  details
BloodDetected and Quantified6.842-20.525 uMAdult (>18 years old)Male
 
Primary Hypomagnesemia		  details
BloodDetected and Quantified18.814-518.248 uMAdult (>18 years old)Male
 
Cholestasis, progressive familial intrahepatic, 1		  details
BloodDetected and Quantified42.247 uMNewborn (0-30 days old)Male
 
Lathosterolosis		  details
BloodDetected and Quantified42.760-141.962 uMChildren (1-13 years old)Female
 
Cholestasis, progressive familial intrahepatic, 1		  details
BloodDetected and Quantified78.678 uMNewborn (0-30 days old)MaleDonohue Syndrome  details
BloodDetected and Quantified111.175 uMNewborn (0-30 days old)MaleDonohue Syndrome  details
Cerebrospinal Fluid (CSF)Detected and Quantified17.3 +/- 12.4 uMAdult (>18 years old)Both
 
Cerebral Vasospasm		  details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
 
Colorectal cancer		  details
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Not Specified
 
Premature neonates		  details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer  details
Associated Disorders and Diseases
Disease References
Crohn's disease
  1. 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  ] 
Gallbladder disease
  1. 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  ] 
Growth hormone deficiency
  1. Darzy KH, Murray RD, Gleeson HK, Pezzoli SS, Thorner MO, Shalet SM: The impact of short-term fasting on the dynamics of 24-hour growth hormone (GH) secretion in patients with severe radiation-induced GH deficiency. J Clin Endocrinol Metab. 2006 Mar;91(3):987-94. Epub 2005 Dec 29. [PubMed:16384844  ] 
Crigler-Najjar syndrome type I
  1. Farrell GC, Gollan JL, Stevens SM, Grierson JM: Crigler-Najjar Type 1 syndrome: absence of hepatic bilirubin UDP-glucuronyl transferase activity and therapeutic responses to light. Aust N Z J Med. 1982 Aug;12(4):280-5. [PubMed:6814411  ] 
  2. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium. 
Primary hypomagnesemia
  1. Jin-no Y, Kamiya Y, Okada M, Hirako M, Takada N, Kawaguchi M: Primary hypomagnesemia caused by isolated magnesium malabsorption: atypical case in adult. Intern Med. 1999 Mar;38(3):261-5. [PubMed:10337938  ] 
Anemia, congenital dyserythropoietic, type II
  1. Bianchi P, Fermo E, Vercellati C, Boschetti C, Barcellini W, Iurlo A, Marcello AP, Righetti PG, Zanella A: Congenital dyserythropoietic anemia type II (CDAII) is caused by mutations in the SEC23B gene. Hum Mutat. 2009 Sep;30(9):1292-8. doi: 10.1002/humu.21077. [PubMed:19621418  ] 
Lathosterolosis
  1. Brunetti-Pierri N, Corso G, Rossi M, Ferrari P, Balli F, Rivasi F, Annunziata I, Ballabio A, Russo AD, Andria G, Parenti G: Lathosterolosis, a novel multiple-malformation/mental retardation syndrome due to deficiency of 3beta-hydroxysteroid-delta5-desaturase. Am J Hum Genet. 2002 Oct;71(4):952-8. Epub 2002 Aug 20. [PubMed:12189593  ] 
Glucose-6-phosphate dehydrogenase deficiency
  1. Iranpour R, Akbar MR, Haghshenas I: Glucose-6-phosphate dehydrogenase deficiency in neonates. Indian J Pediatr. 2003 Nov;70(11):855-7. [PubMed:14703221  ] 
Cholestasis, progressive familial intrahepatic, 1
  1. Nagasaka H, Yorifuji T, Kosugiyama K, Egawa H, Kawai M, Murayama K, Hasegawa M, Sumazaki R, Tsubaki J, Kikuta H, Matsui A, Tanaka K, Matsuura N, Kobayashi K: Resistance to parathyroid hormone in two patients with familial intrahepatic cholestasis: possible involvement of the ATP8B1 gene in calcium regulation via parathyroid hormone. J Pediatr Gastroenterol Nutr. 2004 Oct;39(4):404-9. [PubMed:15448432  ] 
  2. Schukfeh N, Metzelder ML, Petersen C, Reismann M, Pfister ED, Ure BM, Kuebler JF: Normalization of serum bile acids after partial external biliary diversion indicates an excellent long-term outcome in children with progressive familial intrahepatic cholestasis. J Pediatr Surg. 2012 Mar;47(3):501-5. doi: 10.1016/j.jpedsurg.2011.08.010. [PubMed:22424345  ] 
Donohue Syndrome
  1. Nijim Y, Awni Y, Adawi A, Bowirrat A: Classic Case Report of Donohue Syndrome (Leprechaunism; OMIM *246200): The Impact of Consanguineous Mating. Medicine (Baltimore). 2016 Feb;95(6):e2710. doi: 10.1097/MD.0000000000002710. [PubMed:26871809  ] 
Citrullinemia type II, neonatal-onset
  1. Ohura T, Kobayashi K, Tazawa Y, Nishi I, Abukawa D, Sakamoto O, Iinuma K, Saheki T: Neonatal presentation of adult-onset type II citrullinemia. Hum Genet. 2001 Feb;108(2):87-90. [PubMed:11281457  ] 
Infantile Liver Failure Syndrome 2
  1. Staufner C, Haack TB, Kopke MG, Straub BK, Kolker S, Thiel C, Freisinger P, Baric I, McKiernan PJ, Dikow N, Harting I, Beisse F, Burgard P, Kotzaeridou U, Lenz D, Kuhr J, Himbert U, Taylor RW, Distelmaier F, Vockley J, Ghaloul-Gonzalez L, Ozolek JA, Zschocke J, Kuster A, Dick A, Das AM, Wieland T, Terrile C, Strom TM, Meitinger T, Prokisch H, Hoffmann GF: Recurrent acute liver failure due to NBAS deficiency: phenotypic spectrum, disease mechanisms, and therapeutic concepts. J Inherit Metab Dis. 2016 Jan;39(1):3-16. doi: 10.1007/s10545-015-9896-7. Epub 2015 Nov 5. [PubMed:26541327  ] 
Bile Acid Synthesis Defect, Congenital, 1
  1. Huang HY, Zhou H, Wang H, Chen YX, Fang F: Novel Mutations in the 3beta-hydroxy-5-C27-steroid Dehydrogenase Gene (HSD3B7) in a Patient with Neonatal Cholestasis. Chin Med J (Engl). 2016 Jan 5;129(1):98-100. doi: 10.4103/0366-6999.172603. [PubMed:26712441  ] 
Lecithin:cholesterol Acyltransferase Deficiency
  1. Idzior-Walus B, Sieradzki J, Kostner G, Malecki MT, Klupa T, Wesolowska T, Rostworowski W, Hartwich J, Walus M, Kiec AD, Naruszewicz M: Familial lecithin-cholesterol acyltransferase deficiency: biochemical characteristics and molecular analysis of a new LCAT mutation in a Polish family. Atherosclerosis. 2006 Apr;185(2):413-20. Epub 2005 Jul 26. [PubMed:16051254  ] 
Wolcott-Rallison syndrome
  1. Can Thi Bich Ngoc, Vu Chi Dung, Sarah Flanagan and Sian Ellard (2013). Neonatal diabetes in Wolcott-Rallison syndrome: a case report. International Journal of Pediatric Endocrinology. 
Cerebral vasospasm
  1. Pyne-Geithman GJ, Morgan CJ, Wagner K, Dulaney EM, Carrozzella J, Kanter DS, Zuccarello M, Clark JF: Bilirubin production and oxidation in CSF of patients with cerebral vasospasm after subarachnoid hemorrhage. J Cereb Blood Flow Metab. 2005 Aug;25(8):1070-7. [PubMed:15789034  ] 
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383  ] 
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050  ] 
Associated OMIM IDs
  • 266600   (Crohn's disease)
    • 

  • 139250   (Growth hormone deficiency)
    • 

  • 218800   (Crigler-Najjar syndrome type I)
    • 

  • 248250   (Primary hypomagnesemia)
    • 

  • 224100   (Anemia, congenital dyserythropoietic, type II)
    • 

  • 607330   (Lathosterolosis)
    • 

  • 300908   (Glucose-6-phosphate dehydrogenase deficiency)
    • 

  • 211600   (Cholestasis, progressive familial intrahepatic, 1)
    • 

  • 246200   (Donohue Syndrome)
    • 

  • 605814   (Citrullinemia type II, neonatal-onset)
    • 

  • 616483   (Infantile Liver Failure Syndrome 2)
    • 

  • 607765   (Bile Acid Synthesis Defect, Congenital, 1)
    • 

  • 245900   (Lecithin:cholesterol Acyltransferase Deficiency)
    • 

  • 226980   (Wolcott-Rallison syndrome)
    • 

  • 114500   (Colorectal cancer)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021886  
KNApSAcK IDC00029828  
Chemspider ID4444055  
KEGG Compound IDC00486  
BioCyc IDBILIRUBIN  
BiGG ID35117  
Wikipedia LinkBilirubin  
METLIN ID81  
PubChem Compound5280352  
PDB IDNot Available
ChEBI ID16990  
Food Biomarker OntologyNot Available
VMH IDBILIRUB  
MarkerDB IDMDB00000027  
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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  ] 
  2. 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  ] 
  3. 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  ] 
  4. 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  ] 
  5. 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  ] 
  6. 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  ] 
  7. 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  ] 
  8. 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  ] 
  9. 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  ] 
  10. 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  ] 
  11. 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  ] 
  12. 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  ] 
  13. 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  ] 
  14. 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  ] 
  15. 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  ] 
  16. 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  ] 
  17. 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  ] 
  18. 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  ] 
  19. 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  ] 
  20. 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  ] 
  21. 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  ] 
  22. 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  ] 
  23. 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  ] 
  Only showing the first  10 proteins. There  are 28 proteins in total. 
Show all enzymes and transporters
Enzymes
  Enzyme Details
1. Heme oxygenase 1
General function:
Involved in heme oxygenase (decyclizing) activity
Specific function:
Heme oxygenase cleaves the heme ring at the alpha methene bridge to form biliverdin. Biliverdin is subsequently converted to bilirubin by biliverdin reductase. Under physiological conditions, the activity of heme oxygenase is highest in the spleen, where senescent erythrocytes are sequestrated and destroyed.

Gene Name:
HMOX1
Uniprot ID:
P09601  
Molecular weight:
32818.345
References
  1. Matsuoka Y, Masuda H, Yokoyama M, Kihara K: Protective effects of bilirubin against cyclophosphamide induced hemorrhagic cystitis in rats. J Urol. 2008 Mar;179(3):1160-6. doi: 10.1016/j.juro.2007.10.031. [PubMed:18206168  ] 
  Enzyme Details
2. UDP-glucuronosyltransferase 2B28
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.

Gene Name:
UGT2B28
Uniprot ID:
Q9BY64  
Molecular weight:
38742.9
Reactions
Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
  Enzyme Details
3. UDP-glucuronosyltransferase 2B4
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.

Gene Name:
UGT2B4
Uniprot ID:
P06133  
Molecular weight:
60512.035
Reactions
Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
  Enzyme Details
4. UDP-glucuronosyltransferase 1-4
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.

Gene Name:
UGT1A4
Uniprot ID:
P22310  
Molecular weight:
60024.535
Reactions
Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
  Enzyme Details
5. UDP-glucuronosyltransferase 2B10
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.

Gene Name:
UGT2B10
Uniprot ID:
P36537  
Molecular weight:
60773.485
Reactions
Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
  Enzyme Details
6. UDP-glucuronosyltransferase 2B7
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).

Gene Name:
UGT2B7
Uniprot ID:
P16662  
Molecular weight:
60720.15
Reactions
Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
  Enzyme Details
7. UDP-glucuronosyltransferase 2B15
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.

Gene Name:
UGT2B15
Uniprot ID:
P54855  
Molecular weight:
61035.815
Reactions
Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
  Enzyme Details
8. UDP-glucuronosyltransferase 2A1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.

Gene Name:
UGT2A1
Uniprot ID:
Q9Y4X1  
Molecular weight:
60771.605
Reactions
Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
  Enzyme Details
9. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.

Gene Name:
UGT1A1
Uniprot ID:
P22309  
Molecular weight:
59590.91
Reactions
Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
  Enzyme Details
10. UDP-glucuronosyltransferase 1-9
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.

Gene Name:
UGT1A9
Uniprot ID:
O60656  
Molecular weight:
59940.495
Reactions
Uridine diphosphate glucuronic acid + Bilirubin → Uridine 5'-diphosphate + Bilirubin diglucuronidedetails
Transporters
  Enzyme Details
1. Solute carrier organic anion transporter family member 1B1
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6  
Molecular weight:
76448.0
References
  1. Zhang W, He YJ, Gan Z, Fan L, Li Q, Wang A, Liu ZQ, Deng S, Huang YF, Xu LY, Zhou HH: OATP1B1 polymorphism is a major determinant of serum bilirubin level but not associated with rifampicin-mediated bilirubin elevation. Clin Exp Pharmacol Physiol. 2007 Dec;34(12):1240-4. [PubMed:17973861  ] 
  Enzyme Details
2. Canalicular multispecific organic anion transporter 1
General function:
Involved in ATP binding
Specific function:
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:
ABCC2
Uniprot ID:
Q92887  
Molecular weight:
174205.6
References
  1. Watanabe N, Takashimizu S, Kojima S, Kagawa T, Nishizaki Y, Mine T, Matsuzaki S: Clinical and pathological features of a prolonged type of acute intrahepatic cholestasis. Hepatol Res. 2007 Aug;37(8):598-607. Epub 2007 May 22. [PubMed:17517076  ] 
  Only showing the first  10 proteins. There  are 28 proteins in total. 
Show all enzymes and transporters