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Showing Compound Bilirubin (FDB021886)

Record Information
Version1.0
Creation date2011-09-21 00:04:32 UTC
Update date2019-11-26 03:21:00 UTC
Primary IDFDB021886
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBilirubin
DescriptionBilirubin is a bile pigment that is a degradation product of heme. In particular, bilirubin is a yellow breakdown product of normal heme catabolism. Its levels are elevated in certain diseases and it is responsible for the yellow color of bruises. Bilirubin is an excretion product, and the body does not control levels. Bilirubin levels reflect the balance between production and excretion. Thus, there is no "normal" level of bilirubin. Bilirubin consists of an open chain of four pyrroles (tetrapyrrole); by contrast, the heme molecule is a closed ring of four pyrroles, called porphyrin. -- Wikipedia [HMDB]. Bilirubin is found in many foods, some of which are barley, mustard spinach, other bread, and sesbania flower.
CAS Number635-65-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
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
(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
1,10,19,22,23,24-hexahydro-2,7,13,17-Tetramethyl-1,19-dioxo-3,18-divinylbiline-8,12-dipropionateGenerator
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-dipropanoatehmdb
2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-Biline-8,12-dipropanoic 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)-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
Bilirubinhmdb
Predicted 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
Chemical FormulaC33H36N4O6
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
InChI IdentifierInChI=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
Isomeric SMILESCC1=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
Average Molecular Weight584.6621
Monoisotopic Molecular Weight584.263484904
Classification
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:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSBilirubin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00vr-0100090000-d19585e898437e8be1d5Spectrum
Predicted GC-MSBilirubin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01vn-3100069000-c39a7113e7f8eb3fa22aSpectrum
Predicted GC-MSBilirubin, "Bilirubin,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TMS_2_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBilirubin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-000i-0090000000-50ff729317f07f6120b52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0002-0090000000-83d0d13757dcbce356042021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0002-0090000000-491b2676042d627277842021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-01p9-1090000000-1d547122826037e04cfb2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-000i-1090000000-30f7fa38dcf8706b38c62021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-1030090000-dea3b39afc072d2855c52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-1090010000-369d79a300efec3a6c782021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0091050000-78e3736d034dec9b8fa92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0002-0091000000-cc507e875cc295800fa02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-679d7d93f8aeb5b1c0d12021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090020000-ea54f49e76225d2519902021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0002-0091000000-24657f467af3adfa1e8c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-000i-0020090000-5bcce058438671178ee42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0092030000-24054054aef5b235a8502021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-000i-0030090000-b525a9b7bb66406e6afc2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ks-0000090000-ddf9acb7f968b90797642016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00g0-0110290000-ae6f323e9f5e9e26199c2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uml-1102910000-df5146b3612e4fb4ce5e2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0000090000-6deb1aed1a9c3839e2a92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053i-1010190000-7435a4388bade8e83d102016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9010240000-cc90fff0581c6bcefd0d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0010090000-d21be2c11a0dfd17c6e92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0030190000-749f82b203e182b3e46f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kac-0291230000-962a583eff6dd8d5cf732021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0010090000-467141ca1354a02b0aef2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, C, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, DMSO, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, DMSO, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Spectrum
ChemSpider ID4444055
ChEMBL IDCHEMBL501680
KEGG Compound IDC00486
Pubchem Compound ID5280352
Pubchem Substance IDNot Available
ChEBI ID16990
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00054
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID35117
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDBilirubin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
UDP-glucuronosyltransferase 2B28UGT2B28Q9BY64
UDP-glucuronosyltransferase 2B4UGT2B4P06133
UDP-glucuronosyltransferase 1-4UGT1A4P22310
UDP-glucuronosyltransferase 2B10UGT2B10P36537
UDP-glucuronosyltransferase 2B7UGT2B7P16662
UDP-glucuronosyltransferase 2B15UGT2B15P54855
UDP-glucuronosyltransferase 2A1UGT2A1Q9Y4X1
UDP-glucuronosyltransferase 1-1UGT1A1P22309
UDP-glucuronosyltransferase 1-9UGT1A9O60656
UDP-glucuronosyltransferase 1-8UGT1A8Q9HAW9
UDP-glucuronosyltransferase 1-3UGT1A3P35503
UDP-glucuronosyltransferase 1-10UGT1A10Q9HAW8
UDP-glucuronosyltransferase 2B17UGT2B17O75795
UDP-glucuronosyltransferase 1-6UGT1A6P19224
UDP-glucuronosyltransferase 1-5UGT1A5P35504
UDP-glucuronosyltransferase 2B11UGT2B11O75310
UDP-glucuronosyltransferase 1-7UGT1A7Q9HAW7
UDP-glucuronosyltransferase 2A3UGT2A3Q6UWM9
Pathways
NameSMPDB LinkKEGG Link
Porphyrin MetabolismSMP00024 map00860
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference