Coproporphyrinogen I

Coproporphyrinogen I

Names
IUPAC name 3-[7,12,17-tris(2-carboxyethyl)-3,8,13,18-tetramethyl-5,10,15,20,21,22, 23,24-octahydroporphyrin-2-yl]propanoic acid
Identifiers
CAS Number	31110-56-2
3D model (JSmol)	Interactive image
ChemSpider	389645
PubChem CID	440776
InChI InChI=1/C36H44N4O8/c1-17-21(5-9-33(41)42)29-14-26-19(3)23(7-11-35(45)46)31(39-26)16-28-20(4)24(8-12-36(47)48)32(40-28)15-27-18(2)22(6-10-34(43)44)30(38-27)13-25(17)37-29/h37-40H,5-16H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48) Key: WIUGGJKHYQIGNH-UHFFFAOYAR
SMILES O=C(O)CCc1c(c5[nH]c1Cc2[nH]c(c(c2C)CCC(=O)O)Cc3c(c(c([nH]3)Cc4c(c(c([nH]4)C5)CCC(=O)O)C)CCC(=O)O)C)C
Properties
Chemical formula	C36H44N4O8
Molar mass	660.757 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Coproporphyrinogen I is an isomer of coproporphyrinogen III, a metabolic intermediate in the normal biosynthesis of heme. Coproporphyrinogen I is produced in lesser quantities in acute intermittent porphyria.

Biosynthetic context

The tetrapyrrole called hydroxymethylbilane is normally converted by the action of uroporphyrinogen-III synthase to uroporphyrinogen III.^[1] Uroporphyrinogen III is subsequently converted into coproporphyrinogen III by the action of uroporphyrinogen III decarboxylase, and then on to heme. If, however, no uroporphyrinogen-III synthase is present, hydroxymethylbilane will spontaneously cyclise into uroporphyrinogen I, which is then converted into coproporphyrinogen I, also by uroporphyrinogen III decarboxylase.

The difference between coproporphyrinogen I and III is the arrangements of the four carboxyethyl ("P" groups) and the four methyl groups ("Me" groups). Coproporphyrinogen I has the sequence MeP-MeP-MeP-MeP, whereas in coproporphyrinogen III one MeP-group is reversed and hence an MeP-MeP-MeP-PMe arrangement.

References