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Porphobilinogen (PC000382)

Record Information
Version1.0
Creation date2015-10-09 22:30:22 UTC
Update date2017-01-19 02:36:21 UTC
FoodComEx IDPC000382
FoodDB RecordFDB021916
Chemical Information
NamePorphobilinogen
DescriptionPorphobilinogen, also known as PBG, belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. Porphobilinogen is a very strong basic compound (based on its pKa). Porphobilinogen exists in all living species, ranging from bacteria to humans. porphobilinogen can be biosynthesized from 5-aminolevulinic acid through its interaction with the enzyme Delta-aminolevulinic acid dehydratase. A dicarboxylic acid that is pyrole bearing aminomethyl, carboxymethyl and 2-carboxyethyl substituents at positions 2, 3 and 4 respectively. In humans, porphobilinogen is involved in the metabolic disorder called congenital erythropoietic porphyria (cep) or gunther disease pathway. Outside of the human body, Porphobilinogen has been detected, but not quantified in, several different foods, such as endives, acerola, muscadine grapes, asian pears, and hard wheats. This could make porphobilinogen a potential biomarker for the consumption of these foods. Porphobilinogen is a potentially toxic compound.
CAS Number487-90-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
5-(aminomethyl)-4-(carboxymethyl)-Pyrrole-3-propionatehmdb
5-(aminomethyl)-4-(carboxymethyl)-Pyrrole-3-propionic acidhmdb
PBGhmdb
Porphobilinogenhmdb
Chemical FormulaC10H14N2O4
IUPAC name3-[5-(aminomethyl)-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid
InChI IdentifierInChI=1S/C10H14N2O4/c11-4-8-7(3-10(15)16)6(5-12-8)1-2-9(13)14/h5,12H,1-4,11H2,(H,13,14)(H,15,16)
InChI KeyQSHWIQZFGQKFMA-UHFFFAOYSA-N
Isomeric SMILESNCC1=C(CC(O)=O)C(CCC(O)=O)=CN1
Average Molecular Weight226.2292
Monoisotopic Molecular Weight226.095356946
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Dicarboxylic acid or derivatives
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Amino acid
  • Amino acid or derivatives
  • Carboxylic acid derivative
  • Azacycle
  • Carboxylic acid
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 5 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Toronto Research Chemicals P689500