Protoporphyrin IX

Protoporphyrin IX
	200px
Identifiers
CAS Number	553-12-8
ChEBI	CHEBI:15430
ChEMBL	ChEMBL267548
ChemSpider	10469486
Jmol 3D model	Interactive image
PubChem	4971
	InChI InChI=1S/C34H34N4O4/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25/h7-8,13-16,35,38H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16- Key: KSFOVUSSGSKXFI-UJJXFSCMSA-N ; InChI=1/C34H34N4O4/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25/h7-8,13-16,35,38H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16- Key: KSFOVUSSGSKXFI-UJJXFSCMBK ;
	SMILES CC\1=C(/C/2=C/C3=N/C(=C\C4=C(C(=C(N4)/C=C\5/C(=C(C(=N5)/C=C1\N2)C=C)C)C=C)C)/C(=C3CCC(=O)O)C)CCC(=O)O ;
Properties
Chemical formula	C34H34N4O4
Molar mass	562.658 g/mol
Vapor pressure	{{{value}}}
	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

Protoporphyrin IX, in the metabolism of porphyrin, is created by the enzyme protoporphyrinogen oxidase.

Protoporphyrin IX biosynthesis

Protoporphyrin IX is an important precursor to biologically essential prosthetic groups such as heme, cytochrome c, and chlorophylls. As a result, a number of organisms are able to synthesize this tetrapyrrole from basic precursors such as glycine and succinyl CoA, or glutamate. Despite the wide range of organisms that synthesize protoporphyrin IX the process is largely conserved from bacteria to mammals with a few distinct exceptions in higher plants.^[1]^[2]^[3]

Protoporphyrin IX Biosynthetic pathway

Heme b biosynthesis

In heme biosynthesis, the enzyme ferrochelatase converts it into heme b (i.e. Fe-protoporphyrin IX or protoheme IX).

Heme synthesis - note that some reactions occur in the cytoplasm and some in the mitochondrion (yellow)

Chlorophyll biosynthesis

In chlorophyll biosynthesis, the enzyme magnesium chelatase converts it into Mg-protoporphyrin IX.

Protoporphyrin IX

Contents