I-Urobilin (CHEM035646)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:57:16 UTC
Update Date2016-11-09 01:21:21 UTC
Accession NumberCHEM035646
Identification
Common NameI-Urobilin
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3,18-Diethyl-1,4,5,15,16,19,22,24-octahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoic acidChEBI
3,18-Diethyl-1,4,5,15,16,19,22,24-octahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropionic acidChEBI
8,12-Bis(2-carboxyethyl)-3,18-diethyl-2,7,13,17-tetramethylbilene-b-1,19(4H,16H)-dioneChEBI
I-urobilinChEBI
3,18-Diethyl-1,4,5,15,16,19,22,24-octahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropanoateGenerator
3,18-Diethyl-1,4,5,15,16,19,22,24-octahydro-2,7,13,17-tetramethyl-1,19-dioxo-21H-biline-8,12-dipropionateGenerator
(-)-UrobilinHMDB
3,18-Diethyl-1,4,5,15,16,19,22,24-octahydro-2,7,13,17-tetramethyl-1,19-dioxo-biline-8,12-dipropionic acidHMDB
Urobilin ixαHMDB
Urobilin ixalphaHMDB
UrobilinHMDB
Chemical FormulaC33H42N4O6
Average Molecular Mass590.710 g/mol
Monoisotopic Mass590.310 g/mol
CAS Registry Number1856-98-0
IUPAC Name3-(2-{[3-(2-carboxyethyl)-5-[(4-ethyl-3-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)methyl]-4-methyl-2H-pyrrol-2-ylidene]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 Nameurobilin
SMILESCCC1=C(C)C(=O)NC1CC1=C(C)C(CCC(O)=O)=C(N1)\C=C1/N=C(CC2NC(=O)C(CC)=C2C)C(C)=C1CCC(O)=O
InChI IdentifierInChI=1S/C33H42N4O6/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/h15,26-27,35H,7-14H2,1-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b28-15-
InChI KeyKDCCOOGTVSRCHX-MBTHVWNTSA-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
  • Dipyrrin
  • Dicarboxylic acid or derivatives
  • Substituted pyrrole
  • Pyrrole
  • Pyrroline
  • Heteroaromatic compound
  • Carboxamide group
  • Ketimine
  • Lactam
  • Secondary carboxylic acid amide
  • Azacycle
  • Organic 1,3-dipolar compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Imine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.048 g/LALOGPS
logP3.04ALOGPS
logP1.23ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.88ChemAxon
pKa (Strongest Basic)5.98ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area160.95 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity166.26 m³·mol⁻¹ChemAxon
Polarizability66.89 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000090000-d85b5fa954be28328eeaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-059i-1230980000-7aaa425dbac6f050567bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-1590620000-21469cd955bcda852e04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0200390000-89bfa93324aa87bfd8feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00el-1600590000-81d90b579c77efab02b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-3302950000-7625ffaca4872cd8837eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004160
FooDB IDFDB111639
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkUrobilin
Chemspider ID389650
ChEBI ID36378
PubChem Compound ID440785
Kegg Compound IDC05794
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Watson, C. J.; Weimer, Mary; Hawkinson, Violet E. Differences in the formation of mesobiliviolin and glaucobilin from d- and i-urobilins. Journal of Biological Chemistry (1960), 235 787-94.
2. Watson, C. J.; Weimer, Mary; Hawkinson, Violet E. Differences in the formation of mesobiliviolin and glaucobilin from d- and i-urobilins. Journal of Biological Chemistry (1960), 235 787-94.
3. Treem WR, Malet PF, Gourley GR, Hyams JS: Bile and stone analysis in two infants with brown pigment gallstones and infected bile. Gastroenterology. 1989 Feb;96(2 Pt 1):519-23.
4. Jones-Lepp TL: Chemical markers of human waste contamination: analysis of urobilin and pharmaceuticals in source waters. J Environ Monit. 2006 Apr;8(4):472-8. Epub 2006 Mar 10.