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Record Information
Version4.0
Creation Date2006-08-13 13:17:12 UTC
Update Date2017-09-27 08:24:27 UTC
HMDB IDHMDB0004158
Secondary Accession Numbers
  • HMDB04158
Metabolite Identification
Common NameD-Urobilinogen
DescriptionUrobilinogen is a colourless product of bilirubin reduction. It is formed in the intestines by bacterial action. Some urobilinogen is reabsorbed, taken up by the hepatocytes into the circulation and excreted by the kidney. This constitutes the normal "intrahepatic urobilinogen cycle". Increased amounts of bilirubin are formed in haemolysis which generates increased urobilinogen in the gut. In liver disease (such as hepatitis) the intrahepatic urobilinogen cycle is inhibited also increasing urobilinogen levels. Urobilinogen is converted to the yellow pigmented urobilin apparent in urine. The urobilinogen remaining in the intestine (stercobilinogen) is oxidized to brown stercobilin which gives the feces their characteristic color. In biliary obstruction, below normal amounts of conjugated bilirubin reach the intestine for conversion to urobilinogen. With limited urobilinogen available for reabsorption and excretion, the amount of urobilin found in the urine is low.
Structure
Thumb
Synonyms
ValueSource
UrobilinogenHMDB
Chemical FormulaC33H42N4O6
Average Molecular Weight590.7098
Monoisotopic Molecular Weight590.310435096
IUPAC Name3-(2-{[3-(2-carboxyethyl)-5-[(4-ethenyl-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 Name3-(2-{[3-(2-carboxyethyl)-5-[(4-ethenyl-3-methyl-5-oxo-1,2-dihydropyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-2-yl]methyl}-5-[(3-ethyl-4-methyl-5-oxo-1,2-dihydropyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-3-yl)propanoic acid
CAS Registry Number17208-65-0
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(C=C)=C3C)N2)N1
InChI Identifier
InChI=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/h8,26-27,34-35H,2,7,9-15H2,1,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)
InChI KeyKSQFFJKKJAEKTB-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as bilirubins. These are organic compounds containing a dicarboxylic acyclic tetrapyrrole derivative.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassTetrapyrroles and derivatives
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
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.021 g/LALOGPS
logP2.77ALOGPS
logP3.46ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)4.06ChemAxon
pKa (Strongest Basic)2.07ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area164.38 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity166.09 m³·mol⁻¹ChemAxon
Polarizability65.82 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-0009110000-22201ddfa15f4e8ab99fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000090000-e7d752494982063db039View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-0200290000-a50512ce586c48b2dd77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-2000920000-82cae0801f5ae06ee29dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0079-0000090000-c473bc91332a49995cbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ds-1100090000-63230997999368b5e280View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9010220000-1e3be1cd0f823364b481View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Acute Intermittent PorphyriaPw000174Pw000174 greyscalePw000174 simpleNot Available
Congenital Erythropoietic Porphyria (CEP) or Gunther DiseasePw000176Pw000176 greyscalePw000176 simpleNot Available
Hereditary Coproporphyria (HCP)Pw000211Pw000211 greyscalePw000211 simpleNot Available
Porphyria Variegata (PV)Pw000175Pw000175 greyscalePw000175 simpleNot Available
Porphyrin MetabolismPw000158Pw000158 greyscalePw000158 simpleMap00860
Displaying all 5 entries
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)BothNormal details
    UrineDetected and Quantified0.000-2.878 umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified0.00-2.88 umol/mmol creatinineAdult (>18 years old)BothNormal
      • David F. Putnam C...
    details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB023323
    KNApSAcK IDNot Available
    Chemspider ID389649
    KEGG Compound IDC05791
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkUrobilinogen
    METLIN ID7021
    PubChem Compound440784
    PDB IDNot Available
    ChEBI IDNot Available
    References
    Synthesis ReferenceWatson, C. J.; Lowry, P. T. A further study of crystalline d-urobilin. Journal of Biological Chemistry (1956), 218 633-9.
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Binder L, Smith D, Kupka T, Nelson B, Glass B, Wainscott M, Haynes J: Failure of prediction of liver function test abnormalities with the urine urobilinogen and urine bilirubin assays. Arch Pathol Lab Med. 1989 Jan;113(1):73-6. [PubMed:2642693 ]

    Enzymes

    General function:
    Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
    Specific function:
    Plays an important role in the degradation of dermatan and keratan sulfates.
    Gene Name:
    GUSB
    Uniprot ID:
    P08236
    Molecular weight:
    74731.46
    Reactions
    Bilirubin diglucuronide + Water + Reduced acceptor → D-Urobilinogen + D-Glucuronic acid + Acceptordetails