Showing metabocard for Porphobilinogen (BMDB0000245)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:27:19 UTC
Update Date2020-05-19 22:01:32 UTC
BMDB IDBMDB0000245
Secondary Accession Numbers
  • BMDB00245
Metabolite Identification
Common 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 possibly soluble (in water) and 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. In cattle, porphobilinogen is involved in the metabolic pathway called the porphyrin metabolism pathway. Porphobilinogen is a potentially toxic compound.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5-(Aminomethyl)-4-(carboxymethyl)-pyrrole-3-propionateHMDB
5-(Aminomethyl)-4-(carboxymethyl)-pyrrole-3-propionic acidHMDB
PBGHMDB
PorphobilinogenHMDB
Chemical FormulaC10H14N2O4
Average Molecular Weight226.2292
Monoisotopic Molecular Weight226.095356946
IUPAC Name3-[5-(aminomethyl)-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid
Traditional Nameporphobilinogen
CAS Registry Number487-90-1
SMILES
NCC1=C(CC(O)=O)C(CCC(O)=O)=CN1
InChI Identifier
InChI=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
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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.4ALOGPS
logP-2.7ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.66ChemAxon
pKa (Strongest Basic)8.78ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.41 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity56.38 m³·mol⁻¹ChemAxon
Polarizability22.56 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Erythrocyte
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
ErythrocyteExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000245
DrugBank IDDB02272
Phenol Explorer Compound IDNot Available
FooDB IDFDB021916
KNApSAcK IDC00007339
Chemspider ID995
KEGG Compound IDC00931
BioCyc IDPORPHOBILINOGEN
BiGG IDNot Available
Wikipedia LinkPorphobilinogen
METLIN IDNot Available
PubChem Compound1021
PDB IDNot Available
ChEBI ID17381
References
Synthesis ReferenceFrydman, Benjamin; Despuy, Maria E.; Rapoport, Henry. Pyrroles from azaindoles. A synthesis of porphobilinogen. Journal of the American Chemical Society (1965), 87(15), 3530-1.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Porphobilinogen deaminase
General function:
Coenzyme transport and metabolism
Specific function:
Tetrapolymerization of the monopyrrole PBG into the hydroxymethylbilane pre-uroporphyrinogen in several discrete steps.
Gene Name:
HMBS
Uniprot ID:
Q2KIN5
Molecular weight:
39515.0
Reactions
4 Porphobilinogen + Water → Hydroxymethylbilane +4 Ammoniadetails
Enzyme Details
2. Delta-aminolevulinic acid dehydratase
General function:
Coenzyme transport and metabolism
Specific function:
Not Available
Gene Name:
ALAD
Uniprot ID:
Q2KIL3
Molecular weight:
36126.0
Enzyme Details
3. Delta-aminolevulinic acid dehydratase
General function:
Coenzyme transport and metabolism
Specific function:
Catalyzes an early step in the biosynthesis of tetrapyrroles. Binds two molecules of 5-aminolevulinate per subunit, each at a distinct site, and catalyzes their condensation to form porphobilinogen (By similarity).
Gene Name:
ALAD
Uniprot ID:
Q58DK5
Molecular weight:
36081.0
Reactions
5-Aminolevulinic acid → Porphobilinogen +2 Waterdetails