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Porphobilinogen information


Porphobilinogen
Names
Preferred IUPAC name
3-[5-(Aminomethyl)-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid
Identifiers
CAS Number
  • 487-90-1 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 995 ☒N
DrugBank
  • DB02272 checkY
ECHA InfoCard 100.006.970 Edit this at Wikidata
EC Number
  • 207-666-3
MeSH Porphobilinogen
PubChem CID
  • 1021
UNII
  • 74KHC72QXK ☒N
CompTox Dashboard (EPA)
  • DTXSID4060070 Edit this at Wikidata
InChI
  • InChI=1S/C10H14N2O4/c11-4-8-7(3-10(15)16)6(5-12-8)1-2-9(13)14/h5,12H,1-4,11H2,(H,13,14)(H,15,16) ☒N
    Key: QSHWIQZFGQKFMA-UHFFFAOYSA-N ☒N
  • InChI=1/C10H14N2O4/c11-4-8-7(3-10(15)16)6(5-12-8)1-2-9(13)14/h5,12H,1-4,11H2,(H,13,14)(H,15,16)
    Key: QSHWIQZFGQKFMA-UHFFFAOYAF
SMILES
  • C1=C(C(=C(N1)CN)CC(=O)O)CCC(=O)O
Properties
Chemical formula
C10H14N2O4
Molar mass 226.229
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

Porphobilinogen (PBG) is an organic compound that occurs in living organisms as an intermediate in the biosynthesis of porphyrins, which include critical substances like hemoglobin and chlorophyll.[1]

The structure of the molecule can be described as molecule of pyrrole with sidechains substituted for hydrogen atoms at positions 2, 3 and 4 in the ring (1 being the nitrogen atom); respectively, an aminomethyl group −CH2−NH2, an acetic acid (carboxymethyl) group −CH2−COOH, and a propionic acid (carboxyethyl) group −CH2−CH2−COOH.

  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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Porphobilinogen

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Porphobilinogen (PBG) is an organic compound that occurs in living organisms as an intermediate in the biosynthesis of porphyrins, which include critical...

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Porphobilinogen deaminase

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Porphobilinogen deaminase (hydroxymethylbilane synthase, or uroporphyrinogen I synthase) is an enzyme (EC 2.5.1.61) that in humans is encoded by the HMBS...

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Acute intermittent porphyria

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affecting the production of heme resulting from a deficiency of the enzyme porphobilinogen deaminase. It is the most common of the acute porphyrias. The clinical...

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Porphyrin

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pathway. Two molecules of dALA are then combined by porphobilinogen synthase to give porphobilinogen (PBG), which contains a pyrrole ring. Four PBGs are...

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Pyrrole

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derivatives are also called pyrroles, e.g., N-methylpyrrole, C4H4NCH3. Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural...

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Phycocyanobilin

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undergo a condensation reaction catalyzed by Porphobilinogen (PBG) Synthase to yield a molecule of Porphobilinogen (PBG) (not shown). Four molecules of PBG...

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Lone pair

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enzymes, such as zinc cations in the ALAD enzyme, which is also known as porphobilinogen synthase, and is important in the synthesis of heme, a key component...

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Porphyria

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analysis of blood, urine, and stool. In general, urine estimation of porphobilinogen (PBG) is the first step if acute porphyria is suspected. As a result...

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Chlorophyll b

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5-aminolevulinic acid (ALA); two molecules of ALA are then reduced to porphobilinogen (PBG), and four molecules of PBG are coupled, forming protoporphyrin...

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Hydroxymethylbilane

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that order. HMB is generated from four molecules of porphobilinogen by the enzyme porphobilinogen deaminase: The enzyme uroporphyrinogen III synthase...

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PBG

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power connector The Pepsi Bottling Group (NYSE:PBG), a US company Porphobilinogen Plattsburgh International Airport in Plattsburgh, New York (IATA Code:...

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Chlorophyll a

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5-aminolevulinic acid (ALA); two molecules of ALA are then reduced to porphobilinogen (PBG), and four molecules of PBG are coupled, forming protoporphyrin...

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Stacy Warner

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various failed attempts to diagnose Mark, House tests Mark's urine for porphobilinogen. The test is positive, and Mark is diagnosed with acute intermittent...

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Lead poisoning

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(January 2001). "The molecular mechanism of lead inhibition of human porphobilinogen synthase". The Journal of Biological Chemistry. 276 (2): 1531–7. doi:10...

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Lead

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growth. In the human body, lead inhibits porphobilinogen synthase and ferrochelatase, preventing both porphobilinogen formation and the incorporation of iron...

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Hereditary coproporphyria

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measurement of urine porphobilinogen is recommended as a screening test for patients suspected of having an acute porphyria. Elevated porphobilinogen is indicative...

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Protoporphyrin IX

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compound is synthesized from acyclic precursors via a mono-pyrrole (porphobilinogen) then a tetrapyrrole (a porphyrinogen, specifically uroporphyrinogen...

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Vitamin B12

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deaminase and cosynthetase which transform aminolevulinic acid via porphobilinogen and hydroxymethylbilane to uroporphyrinogen III. The latter is the...

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Aminolevulinic acid dehydratase deficiency porphyria

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obtaining biomarkers in the urine or blood. These biomarkers include urine porphobilinogen (PBG), aminolevulinic acid (ALA), and porphyrins found in blood and...

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Urine test strip

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substances interfere with the Ehrlich reaction on the Multistix strip: porphobilinogen, indican, p-amino salicylic acid, sulphonamide, methyldopa, procaine...

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Allosteric regulation

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model for allosteric regulation from the classic MWC and KNF models. Porphobilinogen synthase (PBGS) is the prototype morpheein. Ensemble models of allosteric...

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Gunther disease

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congenital erythropoietic porphyria, urine aminolavulanic acid and porphobilinogen are typically normal. However, uroporphyrin and coproporphyrin tend...

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RNA interference

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neurovisceral attacks and AHP disease) such as aminolevulinic acid (ALA) and porphobilinogen (PBG) from accumulating. To facilitate entry into the cytoplasm, givosiran...

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C10H14N2O4

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226.23 g/mol, exact mass: 226.0954 u) may refer to: Carbidopa 2C-N Porphobilinogen Proxibarbital Valofane This set index page lists chemical structure...

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Small interfering RNA

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porphyria (AHP). The disease is caused due to the accumulation of toxic porphobilinogen (PBG) molecules which are formed during the production of heme. These...

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Phenylalanine hydroxylase

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Many studies suggest that mammalian PAH shows behavior comparable to porphobilinogen synthase (PBGS), wherein a variety of factors such as pH and ligand...

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