Record Information
Version1.0
Creation date2011-09-21 00:05:06 UTC
Update date2020-09-17 15:38:31 UTC
Primary IDFDB021916
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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
Synonyms
SynonymSource
5-(Aminomethyl)-4-(carboxymethyl)-pyrrole-3-propionateHMDB
5-(Aminomethyl)-4-(carboxymethyl)-pyrrole-3-propionic acidHMDB
PBGHMDB
PorphobilinogenHMDB
5-(aminomethyl)-4-(carboxymethyl)-Pyrrole-3-propionatehmdb
5-(aminomethyl)-4-(carboxymethyl)-Pyrrole-3-propionic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility2.72 g/LALOGPS
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Indirect biological role:

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSPorphobilinogen, 4 TMS, GC-MS Spectrumsplash10-001j-1923000000-70c31b91868484322655Spectrum
GC-MSPorphobilinogen, non-derivatized, GC-MS Spectrumsplash10-001j-1923000000-70c31b91868484322655Spectrum
Predicted GC-MSPorphobilinogen, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-3920000000-d4006159f28f6672d3a5Spectrum
Predicted GC-MSPorphobilinogen, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0080-9071000000-ad88926555e7416fedb3Spectrum
Predicted GC-MSPorphobilinogen, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPorphobilinogen, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPorphobilinogen, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPorphobilinogen, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPorphobilinogen, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPorphobilinogen, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPorphobilinogen, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPorphobilinogen, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPorphobilinogen, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPorphobilinogen, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPorphobilinogen, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPorphobilinogen, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPorphobilinogen, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPorphobilinogen, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPorphobilinogen, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPorphobilinogen, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPorphobilinogen, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPorphobilinogen, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPorphobilinogen, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPorphobilinogen, TBDMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPorphobilinogen, TBDMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0090000000-912aa953bdd13d6d18caSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00dl-1900000000-8a87960bb63c4915db22Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-006x-9500000000-c934217374e64d6edee3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-1910000000-4a59655d524261d288a0Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-0a4i-9000000000-5a7fed67c4a8909b6d89Spectrum
MS/MSLC-MS/MS Spectrum - n/a 15V, negativesplash10-00xr-0910000000-79d39f97cef0385e0978Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0fb9-0790000000-a3976589df77175b4e7bSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0fb9-0890000000-8659c76eb4cd3bbc050aSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0ui0-0970000000-ace836f5bc7c40d838f3Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-0ufr-0970000000-34b54c13783e56f913edSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0udi-0920000000-ab742bdbcc6ad44ca7adSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-0udi-0900000000-d9086599996dff3ecc2bSpectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-0udi-1900000000-ca027f0ab39ba0260c42Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-0zfr-4900000000-c5f999c0aa9c0e985528Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, negativesplash10-0a4i-9700000000-c39abc4f07f6ba584489Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-0a4i-9400000000-6eece2186d7d8e426696Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 18V, negativesplash10-0a4i-9200000000-4b1d1515941d17b58cd8Spectrum
MS/MSLC-MS/MS Spectrum - n/a 15V, negativesplash10-0udi-0900000000-4211fc4d53d78720f632Spectrum
MS/MSLC-MS/MS Spectrum - n/a 15V, negativesplash10-0a4i-0900000000-3b3b751b5b26d5ba4273Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0980000000-423d28b762ba4c07586bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-0910000000-31575764ba8bd8d50279Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-074r-0900000000-9d96bd59f1a4371a8df4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0790000000-2cc911a67c1aa8e35d99Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06ur-0940000000-2c3da60da6ab9523fbf3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-4900000000-cf52dffb4284f9eeaa5dSpectrum
NMRNot Available
ChemSpider ID995
ChEMBL IDNot Available
KEGG Compound IDC00931
Pubchem Compound ID1021
Pubchem Substance IDNot Available
ChEBI ID17381
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00245
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID36404
KNApSAcK IDNot Available
HET IDPBG
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPorphobilinogen
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Porphyrin MetabolismSMP00024 map00860
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference