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 |
PubChem
CID
|
|
CompTox Dashboard (
EPA)
|
|
| |
| |
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).
|
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.
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]
HMB is generated from four molecules of porphobilinogen by the enzyme porphobilinogen deaminase: [2]
The enzyme uroporphyrinogen III synthase closes the chain to form uroporphyrinogen III: [2]
Uroporphyrinogen III is a
porphyrinogen, which is a class of compounds with the
hexahydroporphine
macrocycle. In the absence of the enzyme, the compound undergoes spontaneous cyclization and becomes
uroporphyrinogen I.
[3]
[4]
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 |
PubChem
CID
|
|
CompTox Dashboard (
EPA)
|
|
| |
| |
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).
|
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.
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]
HMB is generated from four molecules of porphobilinogen by the enzyme porphobilinogen deaminase: [2]
The enzyme uroporphyrinogen III synthase closes the chain to form uroporphyrinogen III: [2]
Uroporphyrinogen III is a
porphyrinogen, which is a class of compounds with the
hexahydroporphine
macrocycle. In the absence of the enzyme, the compound undergoes spontaneous cyclization and becomes
uroporphyrinogen I.
[3]
[4]