Biotripyrrin-b (CHEM035509)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:49:59 UTC
Update Date2016-11-09 01:21:19 UTC
Accession NumberCHEM035509
Identification
Common NameBiotripyrrin-b
ClassSmall Molecule
DescriptionBiotripyrrin-a and biotripyrrin-b, bilirubin metabolites, are novel tripyrrole biocompounds and belong to a third group of bile pigments following biliverdin and bilirubin. They are regioisomers of each other. -- Yamaguchi T et al., J Biochem (Tokyo). 1994 Aug;116(2):298-303. PMID 7822247. These metabolites are recognized by an anti-bilirubin monoclonal antibody, 24G7, but are neg. in the diazo reaction. (PubMed ID 9836731 ).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-(2-{[(2Z)-3-(2-carboxyethyl)-5-hydroxy-4-methyl-2H-pyrrol-2-ylidene]methyl}-5-{[(2E)-4-ethenyl-5-hydroxy-3-methyl-2H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoateGenerator
Chemical FormulaC25H27N3O6
Average Molecular Mass465.506 g/mol
Monoisotopic Mass465.190 g/mol
CAS Registry Number158598-18-6
IUPAC Name3-(2-{[(2Z)-3-(2-carboxyethyl)-5-hydroxy-4-methyl-2H-pyrrol-2-ylidene]methyl}-5-{[(2E)-4-ethenyl-5-hydroxy-3-methyl-2H-pyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid
Traditional Name3-(2-{[(2Z)-3-(2-carboxyethyl)-5-hydroxy-4-methylpyrrol-2-ylidene]methyl}-5-{[(2E)-4-ethenyl-5-hydroxy-3-methylpyrrol-2-ylidene]methyl}-4-methyl-1H-pyrrol-3-yl)propanoic acid
SMILES[H]\C(C1=C(C)C(CCC(O)=O)=C(N1)C(\[H])=C1/N=C(O)C(C)=C1CCC(O)=O)=C1/N=C(O)C(C=C)=C1C
InChI IdentifierInChI=1S/C25H27N3O6/c1-5-15-12(2)19(27-25(15)34)10-18-13(3)16(6-8-22(29)30)20(26-18)11-21-17(7-9-23(31)32)14(4)24(33)28-21/h5,10-11,26H,1,6-9H2,2-4H3,(H,27,34)(H,28,33)(H,29,30)(H,31,32)/b19-10+,21-11-
InChI KeyPMIYFUGIVLGYIZ-YDSWVFJZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dipyrrins. Dipyrrins are compounds containing two pyrrole rings fused via a methine (-C=) group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrroles
Sub ClassSubstituted pyrroles
Direct ParentDipyrrins
Alternative Parents
Substituents
  • Dipyrrin
  • Dicarboxylic acid or derivatives
  • Cyclic carboximidic acid
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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 Solubility0.034 g/LALOGPS
logP1.61ALOGPS
logP1.38ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.37ChemAxon
pKa (Strongest Basic)5.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.57 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity130.7 m³·mol⁻¹ChemAxon
Polarizability51.13 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fs-1101900000-daa980a0c938fb4cb683Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-4000089000-40408d789d1d180c48aaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000900000-5e80fb254cbaf8344286Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-0104900000-176df8158ba5be158957Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0200-2938400000-cb8a899917a3bc026213Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-0000900000-cbc81b481d5b63227affSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gvk-1000900000-cfee32983a52516212fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9111300000-7470247fc7b58a28209cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0000900000-7bcc33eefe4e1afd19f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w90-0107900000-8ec823c438652d0ba4cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0umi-0309700000-c889b9e40f77166ce88fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0001900000-2c1dbc370e9cbbd65841Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-0007900000-4b3d779ab9df1ccaa0b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0009000000-4a4ad2287a6d4545b3bbSpectrum
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 IDHMDB0003324
FooDB IDFDB023139
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID59696712
ChEBI IDNot Available
PubChem Compound ID131750328
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yamaguchi T, Shioji I, Sugimoto A, Komoda Y, Nakajima H: Chemical structure of a new family of bile pigments from human urine. J Biochem. 1994 Aug;116(2):298-303.
2. Yamaguchi T, Hashizume T, Tanaka M, Nakayama M, Sugimoto A, Ikeda S, Nakajima H, Horio F: Bilirubin oxidation provoked by endotoxin treatment is suppressed by feeding ascorbic acid in a rat mutant unable to synthesize ascorbic acid. Eur J Biochem. 1997 Apr 15;245(2):233-40.
3. Shimoharada K, Inoue S, Nakahara M, Kanzaki N, Shimizu S, Kang D, Hamasaki N, Kinoshita S: Urine concentration of biopyrrins: a new marker for oxidative stress in vivo. Clin Chem. 1998 Dec;44(12):2554-5.
4. Yamaguchi T, Terakado M, Horio F, Aoki K, Tanaka M, Nakajima H: Role of bilirubin as an antioxidant in an ischemia-reperfusion of rat liver and induction of heme oxygenase. Biochem Biophys Res Commun. 1996 Jun 5;223(1):129-35.
5. Yamaguchi T, Horio F, Hashizume T, Tanaka M, Ikeda S, Kakinuma A, Nakajima H: Bilirubin is oxidized in rats treated with endotoxin and acts as a physiological antioxidant synergistically with ascorbic acid in vivo. Biochem Biophys Res Commun. 1995 Sep 5;214(1):11-9.