Coproporphyrinogen III

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Coproporphyrinogen III
Names
IUPAC name
3-[8,12,17-tris(2-carboxyethyl)-3,7,13,18-tetramethyl-5,10,15,20,21,22, 23,24-octahydroporphyrin-2-yl]propanoic acid
Identifiers
3D model (JSmol)
ChemSpider
MeSH Coproporphyrinogen+III
  • InChI=1S/C36H44N4O8/c1-17-21(5-9-33(41)42)29-14-27-19(3)22(6-10-34(43)44)30(39-27)15-28-20(4)24(8-12-36(47)48)32(40-28)16-31-23(7-11-35(45)46)18(2)26(38-31)13-25(17)37-29/h37-40H,5-16H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48) ☒N
    Key: NIUVHXTXUXOFEB-UHFFFAOYSA-N ☒N
  • InChI=1/C36H44N4O8/c1-17-21(5-9-33(41)42)29-14-27-19(3)22(6-10-34(43)44)30(39-27)15-28-20(4)24(8-12-36(47)48)32(40-28)16-31-23(7-11-35(45)46)18(2)26(38-31)13-25(17)37-29/h37-40H,5-16H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)
    Key: NIUVHXTXUXOFEB-UHFFFAOYAI
  • Cc1c2[nH]c(c1CCC(=O)O)Cc3c(c(c([nH]3)Cc4c(c(c([nH]4)Cc5c(c(c([nH]5)C2)C)CCC(=O)O)CCC(=O)O)C)CCC(=O)O)C
Properties
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).
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Coproporphyrinogen III in an intermediate in the biosynthesis of natural porphyrins. It is produced from uroporphyrinogen III by the enzyme uroporphyrinogen III decarboxylase. In this process, four carboxymethyl groups (-CH2CO2H) are converted to methyl groups (CH3).

Subsequently coproporphyrinogen III oxidase converts coproporphyrinogen III into protoporphyrinogen IX.[1]

Heme synthesis—note that some reactions occur in the cytoplasm and some in the mitochondrion (yellow)
  1. ^ Paul R. Ortiz de Montellano (2008). "Hemes in Biology". Wiley Encyclopedia of Chemical Biology. John Wiley & Sons. doi:10.1002/9780470048672.wecb221.