Record Information
Version1.0
Created at2020-04-17 18:41:16 UTC
Updated at2020-12-07 19:11:03 UTC
CannabisDB IDCDB004831
Secondary Accession NumbersNot Available
Cannabis Compound 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 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. Porphobilinogen is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
5-(Aminomethyl)-4-(carboxymethyl)-pyrrole-3-propionateHMDB
5-(Aminomethyl)-4-(carboxymethyl)-pyrrole-3-propionic acidHMDB
PBGHMDB
PorphobilinogenHMDB
Chemical FormulaC10H14N2O4
Average Molecular Weight226.23
Monoisotopic Molecular Weight226.0954
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Biological role:

Industrial application:

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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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-0090000000-912aa953bdd13d6d18ca2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00dl-1900000000-8a87960bb63c4915db222012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-006x-9500000000-c934217374e64d6edee32012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0udi-1910000000-4a59655d524261d288a02020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-0a4i-9000000000-5a7fed67c4a8909b6d892020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 15V, negativesplash10-00xr-0910000000-79d39f97cef0385e09782020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-0fb9-0790000000-a3976589df77175b4e7b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-0fb9-0890000000-8659c76eb4cd3bbc050a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-0ui0-0970000000-ace836f5bc7c40d838f32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-0ufr-0970000000-34b54c13783e56f913ed2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0udi-0920000000-ab742bdbcc6ad44ca7ad2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, negativesplash10-0udi-0900000000-d9086599996dff3ecc2b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, negativesplash10-0udi-1900000000-ca027f0ab39ba0260c422020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, negativesplash10-0zfr-4900000000-c5f999c0aa9c0e9855282020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, negativesplash10-0a4i-9700000000-c39abc4f07f6ba5844892020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 14V, negativesplash10-0a4i-9400000000-6eece2186d7d8e4266962020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 18V, negativesplash10-0a4i-9200000000-4b1d1515941d17b58cd82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 15V, negativesplash10-0udi-0900000000-4211fc4d53d78720f6322020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 15V, negativesplash10-0a4i-0900000000-3b3b751b5b26d5ba42732020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4l-0980000000-423d28b762ba4c07586b2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-0910000000-31575764ba8bd8d502792015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-074r-0900000000-9d96bd59f1a4371a8df42015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0790000000-2cc911a67c1aa8e35d992015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06ur-0940000000-2c3da60da6ab9523fbf32015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-4900000000-cf52dffb4284f9eeaa5d2015-05-27View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Porphobilinogen deaminaseHMBS11q23.3P08397 details
Delta-aminolevulinic acid dehydrataseALAD9q33.1P13716 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Delta-aminolevulinic acid dehydrataseALAD9q33.1P13716 details
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000245
DrugBank IDDB02272
Phenol Explorer Compound IDNot Available
FoodDB 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
General ReferencesNot Available

Enzymes

General function:
Involved in hydroxymethylbilane synthase activity
Specific function:
Tetrapolymerization of the monopyrrole PBG into the hydroxymethylbilane pre-uroporphyrinogen in several discrete steps.
Gene Name:
HMBS
Uniprot ID:
P08397
Molecular weight:
39329.74
General function:
Involved in porphobilinogen synthase activity
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.
Gene Name:
ALAD
Uniprot ID:
P13716
Molecular weight:
36294.485