| 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 propenspanyopents. 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 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(4E)2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo–21H-biline-8,12-dipropanoic acidChEBI
(4E)2,17-Diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo–21H-biline-8,12-dipropanoateGenerator
(4E,15Z)-Bilirubin ixaHMDB
| Chemical Formlia |
C33H36N4O6
| Average Molecliar Weight |
584.6621
| Monoisotopic Molecliar 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 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)=CC1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(N2)C=C2NC(=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 |
| Description |
This compound belongs to the class of chemical entities known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organoheterocyclic compounds
| Sub Class |
Tetrapyrroles and derivatives
| Direct Parent |
Bilirubins
| Alternative Parents |
Substituted pyrroles
Dicarboxylic acids and derivatives
Pyrrolines
Heteroaromatic compounds
Secondary carboxylic acid amides
Lactams
Carboxylic acids
Azacyclic compounds
Organopnictogen compounds
Organonitrogen compounds
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| 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
| Molecliar Framework |
Aromatic heteromonocyclic compounds
| External Descriptors |
dicarboxylic acid (CHEBI:72719 )
biladienes (CHEBI:72719 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
| Biofunction |
Waste products, Heme catabolism
| Application |
Not Available
| Cellliar locations |
Cytoplasm
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.0096 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity168.9 m3·mol-1ChemAxon
Polarizability65.39 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar 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
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite 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
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00488
| Metagene Link |
HMDB00488
| METLIN ID |
5475
| PubChem Compound |
21252250
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: Dehydrocorydaline (chloride)
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 |
- Kunikata T, Itoh S, Ozaki T, Kondo M, Isobe K, Onishi S: Formation of propentdyopents and biliverdin, oxidized metabolites of bilirubin, in infants receiving oxygen therapy. Pediatr Int. 2000 Aug;42(4):331-6. [PubMed:10986860 ]
|
PMID: 26454020