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Human Metabolome Database Version 3.5

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Showing metabocard for 4E,15Z-Bilirubin IXa (HMDB00488)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:40 -0700
HMDB ID HMDB00488
Secondary Accession Numbers None
Metabolite Identification
Common Name 4E,15Z-Bilirubin IXa
Description 4E,15Z-Bilirubin IXa is an isomer of bilirubin, which has antioxidative effects. When bilirubin reacts with reactive oxygen species, oxidized metabolites of bilirubin are formed, such as biliverdin and propentdyopents. A decrease in serum bilirubin concentration and an increase in serum and urinary oxidized metabolites of bilirubin may indicate the protective action of bilirubin against reactive oxygen species. (PMID 10986860 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (4E)2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo--21H-Biline-8,12-dipropanoate
  2. (4E)2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo--21H-Biline-8,12-dipropanoic acid
  3. (4E,15Z)-Bilirubin Ixa
  4. 4E,15Z-Bilirubin IXa
Chemical Formula C33H36N4O6
Average Molecular Weight 584.6621
Monoisotopic Molecular Weight 584.263484904
IUPAC Name 3-(2-{[3-(2-carboxyethyl)-5-{[(2E)-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 IUPAC Name 3-(2-{[3-(2-carboxyethyl)-5-{[(2E)-4-ethenyl-3-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-2-yl]methyl}-5-{[(2Z)-3-ethenyl-4-methyl-5-oxo-1H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid
CAS Registry Number 69853-43-6
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-KDUUSRDASA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Tetrapyrroles and Derivatives
Sub Class Bilirubins
Other Descriptors
  • Organic Compounds
Substituents
  • Carboxylic Acid
  • Dicarboxylic Acid Derivative
  • Dipyrrin
  • Pyrrole
Direct Parent Bilirubins
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Waste products, Heme catabolism
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0096 g/L ALOGPS
LogP 3.22 ALOGPS
LogP 3.12 ChemAxon
LogS -4.78 ALOGPS
pKa (strongest acidic) 4.03 ChemAxon
pKa (strongest basic) -2.8 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 164.38 A2 ChemAxon
Rotatable Bond Count 12 ChemAxon
Refractivity 168.9 ChemAxon
Polarizability 65.39 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022070
KNApSAcK ID Not Available
Chemspider ID 13628097 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00488 Link_out
Metagene Link HMDB00488 Link_out
METLIN ID 5475 Link_out
PubChem Compound 21252250 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference McDonagh, Antony F.; Lightner, David A.; Wooldridge, Timothy A. Geometric isomerization of bilirubin-IXa and its dimethyl ester. Journal of the Chemical Society, Chemical Communications (1979), (3), 110-12.
Material Safety Data Sheet (MSDS) Not Available
General References Not Available