Showing Compound Porphobilinogen (FDB021916)

Record Information

Version

1.0

Creation date

2011-09-21 00:05:06 UTC

Update date

2020-09-17 15:38:31 UTC

Primary ID

FDB021916

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Porphobilinogen

Description

Porphobilinogen, 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 Number

487-90-1

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Show entries

Search:

Synonym	Source
5-(Aminomethyl)-4-(carboxymethyl)-pyrrole-3-propionate	HMDB
5-(aminomethyl)-4-(carboxymethyl)-Pyrrole-3-propionate	hmdb
5-(Aminomethyl)-4-(carboxymethyl)-pyrrole-3-propionic acid	HMDB
5-(aminomethyl)-4-(carboxymethyl)-Pyrrole-3-propionic acid	hmdb
PBG	HMDB
Porphobilinogen	HMDB

Showing 1 to 6 of 6 entries

Predicted Properties

Property	Value	Source
Water Solubility	2.72 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-2.7	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	3.66	ChemAxon
pKa (Strongest Basic)	8.78	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.41 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	56.38 m³·mol⁻¹	ChemAxon
Polarizability	22.56 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H14N2O4

IUPAC name

3-[5-(aminomethyl)-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid

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 Key

QSHWIQZFGQKFMA-UHFFFAOYSA-N

Isomeric SMILES

NCC1=C(CC(O)=O)C(CCC(O)=O)=CN1

Average Molecular Weight

226.2292

Monoisotopic Molecular Weight

226.095356946

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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Aralkylamines

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:17381 )
pyrroles (CHEBI:17381 )
aralkylamino compound (CHEBI:17381 )

Ontology

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Organ and components:

Liver

Biofluid and excreta:

Subcellular:

Cytoplasm

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Acute intermittent porphyria

Role

Indirect biological role:

Biological role:

Metabolite

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Porphobilinogen, 4 TMS, GC-MS Spectrum	splash10-001j-1923000000-70c31b91868484322655	Spectrum
GC-MS	Porphobilinogen, non-derivatized, GC-MS Spectrum	splash10-001j-1923000000-70c31b91868484322655	Spectrum
Predicted GC-MS	Porphobilinogen, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-3920000000-d4006159f28f6672d3a5	Spectrum
Predicted GC-MS	Porphobilinogen, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0080-9071000000-ad88926555e7416fedb3	Spectrum
Predicted GC-MS	Porphobilinogen, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Porphobilinogen, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Porphobilinogen, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Porphobilinogen, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Porphobilinogen, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Porphobilinogen, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Porphobilinogen, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Porphobilinogen, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Porphobilinogen, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Porphobilinogen, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Porphobilinogen, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Porphobilinogen, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Porphobilinogen, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Porphobilinogen, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Porphobilinogen, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Porphobilinogen, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Porphobilinogen, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Porphobilinogen, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Porphobilinogen, TBDMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Porphobilinogen, TBDMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Porphobilinogen, TBDMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-0090000000-912aa953bdd13d6d18ca	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00dl-1900000000-8a87960bb63c4915db22	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-006x-9500000000-c934217374e64d6edee3	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0udi-1910000000-4a59655d524261d288a0	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, negative	splash10-0a4i-9000000000-5a7fed67c4a8909b6d89	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 15V, negative	splash10-00xr-0910000000-79d39f97cef0385e0978	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, negative	splash10-0fb9-0790000000-a3976589df77175b4e7b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-0fb9-0890000000-8659c76eb4cd3bbc050a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0ui0-0970000000-ace836f5bc7c40d838f3	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-0ufr-0970000000-34b54c13783e56f913ed	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-0udi-0920000000-ab742bdbcc6ad44ca7ad	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, negative	splash10-0udi-0900000000-d9086599996dff3ecc2b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, negative	splash10-0udi-1900000000-ca027f0ab39ba0260c42	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, negative	splash10-0zfr-4900000000-c5f999c0aa9c0e985528	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 13V, negative	splash10-0a4i-9700000000-c39abc4f07f6ba584489	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, negative	splash10-0a4i-9400000000-6eece2186d7d8e426696	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 18V, negative	splash10-0a4i-9200000000-4b1d1515941d17b58cd8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 15V, negative	splash10-0udi-0900000000-4211fc4d53d78720f632	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 15V, negative	splash10-0a4i-0900000000-3b3b751b5b26d5ba4273	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4l-0980000000-423d28b762ba4c07586b	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dl-0910000000-31575764ba8bd8d50279	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-074r-0900000000-9d96bd59f1a4371a8df4	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0059-0790000000-2cc911a67c1aa8e35d99	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06ur-0940000000-2c3da60da6ab9523fbf3	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bt9-4900000000-cf52dffb4284f9eeaa5d	2015-05-27	View Spectrum