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Protoporphyrin IX information


Protoporphyrin IX
Identifiers
CAS Number
  • 553-12-8 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:15430 checkY
ChEMBL
  • ChEMBL267548 checkY
ChemSpider
  • 10469486 checkY
ECHA InfoCard 100.008.213 Edit this at Wikidata
EC Number
  • 209-033-7
Gmelin Reference
251232
KEGG
  • C02191
PubChem CID
  • 4971
UNII
  • C2K325S808 checkY
CompTox Dashboard (EPA)
  • DTXSID4048353 Edit this at Wikidata
InChI
  • InChI=1S/C34H34N4O4/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25/h7-8,13-16,35,38H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16- checkY
    Key: KSFOVUSSGSKXFI-UJJXFSCMSA-N checkY
SMILES
  • CC\1=C(/C/2=C/C3=N/C(=C\C4=C(C(=C(N4)/C=C\5/C(=C(C(=N5)/C=C1\N2)C=C)C)C=C)C)/C(=C3CCC(=O)O)C)CCC(=O)O
Properties
Chemical formula
C34H34N4O4
Molar mass 562.658 g/mol
Density 1.27 g/cm3
Hazards
GHS labelling:[1]
Pictograms
GHS07: Exclamation mark
Signal word
Warning
Hazard statements
H315, H319, H335
Precautionary statements
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Protoporphyrin IX is an organic compound, classified as a porphyrin, that plays an important role in living organisms as a precursor to other critical compounds like heme (hemoglobin) and chlorophyll. It is a deeply colored solid that is not soluble in water. The name is often abbreviated as PPIX.

Protoporphyrin IX contains a porphine core, a tetrapyrrole macrocycle with a marked aromatic character. Protoporphyrin IX is essentially planar, except for the N-H bonds that are bent out of the plane of the rings, in opposite (trans) directions.[2]

  1. ^ "protoporphyrin IX". pubchem.ncbi.nlm.nih.gov.
  2. ^ Winslow S. Caughey; James A. Ibers (1977). "Crystal and Molecular Structure of the Free Base Porphyrin, Protoporphyrin IX Dimethyl Ester". J. Am. Chem. Soc. 99 (20): 6639–6645. doi:10.1021/ja00462a027. PMID 19518.

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Protoporphyrin IX

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Protoporphyrin IX is an organic compound, classified as a porphyrin, that plays an important role in living organisms as a precursor to other critical...

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Zinc protoporphyrin

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Zinc protoporphyrin (ZPP) refers to coordination complexes of zinc and protoporphyrin IX. It is a red-purple solid that is soluble in water. The complex...

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Magnesium protoporphyrin IX methyltransferase

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In enzymology, a magnesium protoporphyrin IX methyltransferase (EC 2.1.1.11) is an enzyme that catalyzes the chemical reaction S-adenosyl-L-methionine...

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Aminolevulinic acid

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in the cytosol and finally gets converted to Protoporphyrin IX inside the mitochondria. This protoporphyrin molecule chelates with iron in presence of enzyme...

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Chlorophyllide

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and protoporphyrinogen IX, which is oxidised to the fully aromatic protoporphyrin IX. Insertion of iron into protoporphyrin IX in for example mammals...

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Ferrochelatase

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biosynthesis of heme, converting protoporphyrin IX into heme B. It catalyses the reaction: protoheme + 2 H+ = protoporphyrin + Fe2+ Ferrochelatase catalyzes...

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Protoporphyrinogen oxidase

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Protoporphyrinogen oxidase is responsible for the seventh step in biosynthesis of protoporphyrin IX. This porphyrin is the precursor to hemoglobin, the oxygen carrier...

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Magnesium chelatase

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three-component enzyme (EC 6.6.1.1) that catalyses the insertion of Mg2+ into protoporphyrin IX. This is the first unique step in the synthesis of chlorophyll and...

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Porphyrin

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Derivatives of protoporphyrin IX are common in nature, the precursor to hemes. Octaethylporphyrin (H2OEP) is a synthetic analogue of protoporphyrin IX. Unlike...

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Protoporphyrinogen IX

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that include hemoglobin and chlorophyll. It is a direct precursor of protoporphyrin IX. The compound is a porphyrinogen, meaning that it has a non-aromatic...

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Porphine

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Derivatives of protoporphyrin IX are common in nature, the precursor to hemes. Octaethylporphyrin (H2OEP) is a synthetic analogue of protoporphyrin IX. Unlike...

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Heme

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cytotoxic, most probably due to the iron atom contained within its protoporphyrin IX ring, which can act as a Fenton's reagent to catalyze in an unfettered...

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Heme oxygenase

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structure by indicating its parent molecule was protoporphyrin IX cleaved at the alpha position (see protoporphyrin IX for further information on the Fischer nomenclature...

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Chlorophyll b

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porphobilinogen (PBG), and four molecules of PBG are coupled, forming protoporphyrin IX. Chlorophyll synthase is the enzyme that completes the biosynthesis...

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Chlorophyll a

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porphobilinogen (PBG), and four molecules of PBG are coupled, forming protoporphyrin IX. Chlorophyll synthase is the enzyme that completes the biosynthesis...

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Erythropoietic porphyria

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severe itching and burning sensation of the skin due to the buildup of protoporphyrin IX. One possible treatment was discovered when treating an individual...

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Hematoporphyrin

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Sensibion) is a porphyrin prepared from hemin. It is a derivative of protoporphyrin IX, where the two vinyl groups have been hydrated (converted to alcohols)...

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Hemoprotein

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probably evolved to incorporate the iron atom contained within the protoporphyrin IX ring of heme into proteins. As it makes hemeproteins responsive to...

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Chlorophyll

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PMID 7842850. Willows RD (June 2003). "Biosynthesis of chlorophylls from protoporphyrin IX". Natural Product Reports. 20 (3): 327–41. doi:10.1039/B110549N. PMID 12828371...

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Hexaminolevulinate

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of heme), and is internalized and processed into the photoactive protoporphyrin IX at a high rate by tumor cells. After exposure to 360-450 nm light...

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Crop desiccation

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complex. PPO inhibitors poison that enzyme, causing a build up of Protoporphyrin IX (Proto). Normally Proto is present in very low amounts, but when there...

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Phytochrome

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Chlorophyll and haem (Heme) share a common precursor in the form of Protoporphyrin IX, and share the same characteristic closed tetrapyrrole ring structure...

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Liquid biopsy

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studied to detect or monitor other diseases. For example, isolation of protoporphyrin IX from blood samples can be used as a diagnostic tool for atherosclerosis...

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Hemoglobin A

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where it reacts with protoporphyrin-III oxidase to produce protoporphyrin IX. Iron is then enzymatically inserted into protoporphyrin via ferrochelatase...

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Porphyria

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by a deficiency in ferrochelatase, leading to the accumulation of protoporphyrin IX in red blood cells, plasma, and tissues. Patients with EPP experience...

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Hemin

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such as heme B found in the hemoglobin of human blood. Hemin is protoporphyrin IX containing a ferric iron (Fe3+) ion with a coordinating chloride ligand...

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Bilirubin

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means the bilin's parent compound was protoporphyrin IX cleaved at the alpha-methine bridge (see protoporphyrin IX nomenclature). Origins pertaining to...

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Methyl aminolevulinate

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sensitizer in photodynamic therapy. It is a prodrug that is metabolized to protoporphyrin IX. It is marketed as Metvix. Metvix cream is applied topically and some...

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Myeloperoxidase

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The light chains are glycosylated and contain the modified iron protoporphyrin IX active site. Together, the light and heavy chains form two identical...

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