Hydroxymethylbilane

Hydroxymethylbilane, also known as preuroporphyrinogen, is an organic compound that occurs in living organisms during the synthesis of porphyrins, a group of critical substances that include haemoglobin, myoglobin, and chlorophyll. The name is often abbreviated as HMB.

Hydroxymethylbilane
Names
IUPAC name
3,3′,3′′,3′′′-[3,8,13,18-Tetrakis(carboxymethyl)-19-(hydroxymethyl)-5,10,15,22,23,24-hexahydro-21H-biline-2,7,12,17-tetrayl]tetrapropanoic acid
Systematic IUPAC name
3,3′,3′′,3′′′-[14,33,53,73-Tetrakis(carboxymethyl)-15-(hydroxymethyl)-11H,31H,51H,71H-1,7(2),3,5(2,5)-tetrapyrrolaheptaphane-13,34,54,74-tetrayl]tetrapropanoic acid
Identifiers
3D model (JSmol)
1209089
ChEBI
ChEMBL
ChemSpider
KEGG
MeSH hydroxymethylbilane
  • InChI=1S/C40H46N4O17/c45-17-32-25(12-40(60)61)21(4-8-36(52)53)29(44-32)15-31-24(11-39(58)59)20(3-7-35(50)51)28(43-31)14-30-23(10-38(56)57)19(2-6-34(48)49)27(42-30)13-26-22(9-37(54)55)18(16-41-26)1-5-33(46)47/h16,41-45H,1-15,17H2,(H,46,47)(H,48,49)(H,50,51)(H,52,53)(H,54,55)(H,56,57)(H,58,59)(H,60,61) checkY
    Key: WDFJYRZCZIUBPR-UHFFFAOYSA-N checkY
  • InChI=1/C40H46N4O17/c45-17-32-25(12-40(60)61)21(4-8-36(52)53)29(44-32)15-31-24(11-39(58)59)20(3-7-35(50)51)28(43-31)14-30-23(10-38(56)57)19(2-6-34(48)49)27(42-30)13-26-22(9-37(54)55)18(16-41-26)1-5-33(46)47/h16,41-45H,1-15,17H2,(H,46,47)(H,48,49)(H,50,51)(H,52,53)(H,54,55)(H,56,57)(H,58,59)(H,60,61)
    Key: WDFJYRZCZIUBPR-UHFFFAOYAI
  • O=C(O)Cc1c(c[nH]c1Cc2c(c(c([nH]2)Cc3[nH]c(c(c3CCC(=O)O)CC(=O)O)Cc4c(c(c([nH]4)CO)CC(=O)O)CCC(=O)O)CC(=O)O)CCC(=O)O)CCC(=O)O
Properties
C40H46N4O17
Molar mass 854.81 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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Infobox references

The compound is a substituted bilane, a chain of four pyrrole rings interconnected by methylene bridges −CH2−. The chain starts with a hydroxymethyl group −CH2−OH and ends with an hydrogen, in place of the respective methylene bridges. The other two carbon atoms of each pyrrole cycle are connected to an acetic acid group −CH2−COOH and a propionic acid group −CH2−CH2−COOH, in that order. [1]

The compound is generated from four molecules of porphobilinogen by the enzyme porphobilinogen deaminase:

Biosynthesis of pre-uroporphyrinogen from porphobilinogen

The enzyme uroporphyrinogen III synthase closes the chain to form a porphyrinogen a class of compounds with the hexahydroporphine macrocycle; specifically, uroporphyrinogen III. In the absence of the enzyme, the compound undergoes spontaneous cyclization and becomes uroporphyrinogen I.

References
  1. Paul R. Ortiz de Montellano (2008). "Hemes in Biology". Wiley Encyclopedia of Chemical Biology. John Wiley & Sons. doi:10.1002/9780470048672.wecb221. ISBN 978-0470048672.
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