<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4494</id>
  <title>T3D4440</title>
  <common-name>Protoporphyrin IX</common-name>
  <description>Protoporphyrins are tetrapyrroles containing 4 methyl, 2 propionic and 2 vinyl side chains. Protopophyrin is produced by oxidation of the methylene bridge of protoporphyrinogen. Protoporphyrin IX is the only naturally occurring isomer; it is an intermediate in heme biosynthesis, combining with ferrous iron to form protoheme IX, the heme prosthetic group of hemoglobin. Protoporphyrin IX is created by the enzyme protoporphyrinogen oxidase. The enzyme ferrochelatase converts it into heme. Protoporphyrin IX naturally occurs in small amounts in feces. It is accumulated and excreted excessively in the feces in protoporphyria and variegate porphyria. Protoporphyrin IX is also responsible for the brown pigment (Ooporphyrin) of birds' eggs Protoporphyrin IX is used as a branch point in the biosynthetic pathway leading to Heme (by insertion of iron) and chlorophylls (by insertion of Mg and further side-chain transformation). Protoporphyrin IX can be used to treat liver disorders, mainly as the sodium salt. Shows anti-HIV activity.</description>
  <cas>553-12-8</cas>
  <pubchem-id>4971</pubchem-id>
  <chemical-formula>C34H34N4O4</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>300°C</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility>0.169 mg/mL at 25°C</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <target nil="true"/>
  <mechanism-of-toxicity nil="true"/>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Chronically high levels of porophyrins are associated with porphyrias such as Porphyria variegate, Acute Intermittent Porphyria and Hereditary Coproporphyria (HCP).</health-effects>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-29T06:51:17Z</created-at>
  <updated-at type="dateTime">2026-05-14T17:33:28Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Protoporphyrin IX</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C02191</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>15430</chebi-id>
  <biocyc-id>PROTOPORPHYRIN_IX</biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB02285</drugbank-id>
  <pdb-id>PP9</pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(C=C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C=C)=C4C)/C(C)=C3CCC(O)=O</moldb-smiles>
  <moldb-formula>C34H34N4O4</moldb-formula>
  <moldb-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-</moldb-inchi>
  <moldb-inchikey>KSFOVUSSGSKXFI-UJJXFSCMSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">562.6582</moldb-average-mass>
  <moldb-mono-mass type="decimal">562.258005596</moldb-mono-mass>
  <origin>Endogenous</origin>
  <state>Solid</state>
  <logp>6.58</logp>
  <hmdb-id>HMDB00241</hmdb-id>
  <chembl-id>CHEMBL1325592</chembl-id>
  <chemspider-id>10469486</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;Elaine A. Best, Charles Lee Hershberger, Christopher Carl Frye, &amp;#8220;Methods of reducing the levels of protoporphyrin IX in recombinant hemoglobin preparations.&amp;#8221; U.S. Patent US6136565, issued April, 1998.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003400</chemdb-id>
  <dsstox-id>DTXSID4048353</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id nil="true"/>
  <iupac>3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid</iupac>
  <moldb-polar-surface-area>131.96</moldb-polar-surface-area>
  <moldb-refractivity>163.81120000000004</moldb-refractivity>
  <moldb-polarizability>66.03349029270831</moldb-polarizability>
  <moldb-rotatable-bond-count>8</moldb-rotatable-bond-count>
  <moldb-acceptor-count>6</moldb-acceptor-count>
  <moldb-donor-count>4</moldb-donor-count>
  <moldb-pka-strongest-acidic>3.684359896427431</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>4.958835229373015</moldb-pka-strongest-basic>
  <moldb-physiological-charge>-2</moldb-physiological-charge>
  <moldb-number-of-rings>5</moldb-number-of-rings>
  <moldb-alogps-logp>4.40</moldb-alogps-logp>
  <moldb-alogps-logs>-4.41</moldb-alogps-logs>
  <moldb-alogps-solubility>2.17e-02 g/l</moldb-alogps-solubility>
</compound>
