Showing metabocard for Mesobilirubinogen (BMDB0001898)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:48:47 UTC
Update Date2020-04-22 15:09:03 UTC
BMDB IDBMDB0001898
Secondary Accession Numbers
  • BMDB01898
Metabolite Identification
Common NameMesobilirubinogen
DescriptionMesobilirubinogen, also known as i-urobilinogen or urobilinogen ixalpha, belongs to the class of organic compounds known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative. Based on a literature review a significant number of articles have been published on Mesobilirubinogen.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,17-Diethyl-1,4,5,10,15,16,19,22,23,24-decahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acidChEBI
8,12-Bis(2-carboxyethyl)-3,18-diethyl-2,7,13,17-tetramethylbilane-1,19(4H,16H)-dioneChEBI
I-urobilinogenChEBI
Mesobilirubinogen ixalphaChEBI
Urobilinogen ixalphaChEBI
UrobilinogenKegg
2,17-Diethyl-1,4,5,10,15,16,19,22,23,24-decahydro-3,7,13,18-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoateGenerator
2,17-Diethyl-1,4,5,10,15,16,19,22,23,24-decahydro-3,7,13,18-tetramethyl-1,19-dioxo-biline-8,12-dipropionic acidHMDB
MesobilirubinogenChEBI
Mesobilirubinogen IXαHMDB
Urobilinogen IXαHMDB
Chemical FormulaC33H44N4O6
Average Molecular Weight592.7257
Monoisotopic Molecular Weight592.32608516
IUPAC Name3-(2-{[3-(2-carboxyethyl)-5-[(4-ethyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-2-yl]methyl}-5-[(3-ethyl-4-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-3-yl)propanoic acid
Traditional Nameurobilinogen
CAS Registry Number14684-37-8
SMILES
CCC1=C(C)C(=O)NC1CC1=C(C)C(CCC(O)=O)=C(CC2=C(CCC(O)=O)C(C)=C(CC3NC(=O)C(CC)=C3C)N2)N1
InChI Identifier
InChI=1S/C33H44N4O6/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/h26-27,34-35H,7-15H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)
InChI KeyOBHRVMZSZIDDEK-UHFFFAOYSA-N
Chemical Taxonomy
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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP1.969Not Available
Predicted Properties
PropertyValueSource
logP3.11ALOGPS
logP3.77ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)4.06ChemAxon
pKa (Strongest Basic)-0.018ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area164.38 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity166.04 m³·mol⁻¹ChemAxon
Polarizability67.38 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001898
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022727
KNApSAcK IDNot Available
Chemspider ID24980
KEGG Compound IDC05790
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkUrobilinogen
METLIN IDNot Available
PubChem Compound26818
PDB IDNot Available
ChEBI ID29026
References
Synthesis ReferenceWatson, C. J.; Lightner, D. A.; Moscowitz, A.; Davis, E.; Petryka, Z. J.; Weimer, M. A natural crystalline urobilinogen composed of d- and l-components of differing molecular weight. Proceedings of the National Academy of Sciences of the United States of America (1968), 61(1), 223-8
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available