Record Information
Version1.0
Creation date2011-09-21 00:12:50 UTC
Update date2015-07-21 06:57:10 UTC
Primary IDFDB022366
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBiliverdin
DescriptionBiliverdin is a green pigment formed as a byproduct of hemoglobin breakdown. It consists of four linearly connected pyrrole rings (a tetrapyrrole). Biliverdin is formed when the heme group in hemoglobin is cleaved at its alpha-methene bridge. The resulting biliverdin is then reduced to bilirubin, a yellow pigment, by the enzyme biliverdin reductase. The changing color of a bruise from deep purple to yellow over time is a graphical indicator of this reaction. Biosynthesized from hemoglobin as a precursor of bilirubin. Occurs in the bile of amphibia and of birds, but not in normal human bile or serum. [HMDB]
CAS Number114-25-0
Structure
Thumb
Synonyms
SynonymSource
1,3,6,7-Tetramethyl-4,5-dicarboxyethyl-2,8-divinylbilenonehmdb
Biliverdin IXhmdb
Biliverdin IX alphahmdb
Biliverdinehmdb
Dehydrobilirubinhmdb
Protobiliverdin IXhmdb
Uteroverdinehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP3.77ALOGPS
logP3.17ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)3.96ChemAxon
pKa (Strongest Basic)0.44ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area160.95 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity169.16 m³·mol⁻¹ChemAxon
Polarizability64.98 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC33H34N4O6
IUPAC name3-(2-{[3-(2-carboxyethyl)-5-[(3-ethenyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-ylidene)methyl]-4-methyl-1H-pyrrol-2-yl]methylidene}-5-[(3-ethenyl-4-methyl-2-oxo-2H-pyrrol-5-yl)methylidene]-4-methyl-2,5-dihydro-1H-pyrrol-3-yl)propanoic acid
InChI IdentifierInChI=1S/C33H34N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-15,34-35H,1-2,9-12H2,3-6H3,(H,37,42)(H,38,39)(H,40,41)
InChI KeyRCNSAJSGRJSBKK-UHFFFAOYSA-N
Isomeric SMILESCC1=C(C=C)C(NC1=O)=CC1=C(C)C(CCC(O)=O)=C(N1)C=C1NC(=CC2=NC(=O)C(C=C)=C2C)C(C)=C1CCC(O)=O
Average Molecular Weight582.6463
Monoisotopic Molecular Weight582.24783484
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
  • Dipyrrin
  • Dicarboxylic acid or derivatives
  • Substituted pyrrole
  • Pyrrole
  • Pyrroline
  • Heteroaromatic compound
  • Carboxamide group
  • Lactam
  • N-acylimine
  • Secondary carboxylic acid amide
  • Azacycle
  • Organic 1,3-dipolar compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
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
SpectraNot Available
ChemSpider ID4510089
ChEMBL IDNot Available
KEGG Compound IDC00500
Pubchem Compound ID5353439
Pubchem Substance IDNot Available
ChEBI ID17033
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01008
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID35167
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDBiliverdin
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
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Porphyrin MetabolismSMP00024 map00860
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference