Porphobilinogen

 Porphobilinogen (PBG) is an organic compound that occurs in living organisms as an intermediate in the biosynthesis of porphyrins, which include critical substances like hemoglobin and chlorophyll.^[1]

Porphobilinogen

Names
IUPAC name 3-[5-(Aminomethyl)-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid
Identifiers
CAS Number	487-90-1
3D model (JSmol)	Interactive image
ChemSpider	995
DrugBank	DB02272
ECHA InfoCard	100.006.970
EC Number	207-666-3
MeSH	Porphobilinogen
PubChem CID	1021
UNII	74KHC72QXK
CompTox Dashboard (EPA)	DTXSID4060070
InChI 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)  Key: QSHWIQZFGQKFMA-UHFFFAOYSA-N  InChI=1/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) Key: QSHWIQZFGQKFMA-UHFFFAOYAF
SMILES C1=C(C(=C(N1)CN)CC(=O)O)CCC(=O)O
Properties
Chemical formula	C10H14N2O4
Molar mass	226.229
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

The structure of the molecule can be described as molecule of pyrrole with sidechains substituted for hydrogen atoms at positions 2, 3 and 4 in the ring (1 being the nitrogen atom); respectively, an aminomethyl group −CH
2−NH
2, an acetic acid (carboxymethyl) group −CH
2−COOH, and a propionic acid (carboxyethyl) group −CH
2−CH
2−COOH.

BiosynthesisEdit

In the first step of the porphyrin biosynthesis pathway, porphobilinogen is generated from aminolevulinate (ALA) by the enzyme ALA dehydratase.

MetabolismEdit

In the typical porphyrin biosynthesis pathway, four molecules of porphobilinogen are concatenated by carbons 2 and 5 of the pyrrole ring (adjacent to the nitrogen atom) into hydroxymethyl bilane by the enzyme porphobilinogen deaminase, also known as hydroxymethylbilane synthase.

PathologiesEdit

Acute intermittent porphyria causes an increase in urinary porphobilinogen.^[2]

This article uses material from the Wikipedia article  Metasyntactic variable, which is released under the  Creative Commons Attribution-ShareAlike 3.0 Unported License.