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Human Metabolome Database Version 3.5

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Showing metabocard for D-Urobilin (HMDB04161)

Record Information
Version 3.5
Creation Date 2006-08-13 07:20:04 -0600
Update Date 2013-02-08 17:13:04 -0700
HMDB ID HMDB04161
Secondary Accession Numbers None
Metabolite Identification
Common Name D-Urobilin
Description Urobilin is one of the final by-products of hemoglobin breakdown. Urobilin is excreted in both the urine and feces from many mammals, particularly humans. It is primarily responsible for the yellow color of urine. The breakdown of hemoglobin to biliverdin is common to most animals, while the next step, the conversion of biliverdin to bilirubin, and subsequently to the urobilinogens (urobilin is one particular oxidized chemical form of urobilinogen) is unique to mammals. (PMID: 16604237 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Urobilin
Chemical Formula C33H40N4O6
Average Molecular Weight 588.6939
Monoisotopic Molecular Weight 588.294785032
IUPAC Name 3-(2-{[(2Z)-3-(2-carboxyethyl)-5-[(4-ethenyl-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 IUPAC Name 3-(2-{[(2Z)-3-(2-carboxyethyl)-5-[(4-ethenyl-3-methyl-5-oxo-1,2-dihydropyrrol-2-yl)methyl]-4-methylpyrrol-2-ylidene]methyl}-5-[(3-ethyl-4-methyl-5-oxo-1,2-dihydropyrrol-2-yl)methyl]-4-methyl-1H-pyrrol-3-yl)propanoic acid
CAS Registry Number 3947-38-4
SMILES CCC1=C(C)C(=O)NC1CC1=C(C)C(CCC(O)=O)=C(N1)\C=C1/N=C(CC2NC(=O)C(C=C)=C2C)C(C)=C1CCC(O)=O
InChI Identifier InChI=1S/C33H40N4O6/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/h8,15,26-27,35H,2,7,9-14H2,1,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b28-15-
InChI Key DOKCNDVEPDZOJQ-MBTHVWNTSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Tetrapyrroles and Derivatives
Sub Class N/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • Carboxamide Group
  • Carboxylic Acid
  • Dicarboxylic Acid Derivative
  • Dipyrrin
  • Lactam
  • Pyrrole
  • Pyrroline
  • Secondary Carboxylic Acid Amide
Direct Parent Tetrapyrroles and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
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 1.409 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.03 g/L ALOGPS
LogP 2.88 ALOGPS
LogP 0.94 ChemAxon
LogS -4.30 ALOGPS
pKa (strongest acidic) 3.88 ChemAxon
pKa (strongest basic) 5.96 ChemAxon
Hydrogen Acceptor Count 7 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 160.95 A2 ChemAxon
Rotatable Bond Count 13 ChemAxon
Refractivity 166.3 ChemAxon
Polarizability 66.05 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
Article_icon
3.36-15.13 umol/mmol creatinine Adult (>18 years old) Both Normal by ICP-MS
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 FDB023326
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID C05795 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04161 Link_out
Metagene Link HMDB04161 Link_out
METLIN ID Not Available
PubChem Compound 6276321 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Watson, 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 Not Available