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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
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
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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference