<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4327</id>
  <title>T3D4273</title>
  <common-name>5-Aminolevulinic acid</common-name>
  <description>5-Aminolevulinic acid is an intermediate in heme synthesis. This is the first compound in the porphyrin synthesis pathway. It is produced by the enzyme ALA synthase, from glycine and succinyl CoA. This reaction is known as the Shemin pathway. Aminolevulinic acid plus blue light illumination using a blue light photodynamic therapy illuminator is indicated for the treatment of minimally to moderately thick actinic keratoses of the face or scalp.</description>
  <cas>106-60-5</cas>
  <pubchem-id>137</pubchem-id>
  <chemical-formula>C5H9NO3</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>156-158°C</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility>Very soluble</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral bioavailability is 50-60%.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>According to the presumed mechanism of action, photosensitization following application of aminolevulinic acid (ALA) topical solution occurs through the metabolic conversion of ALA to protoporphyrin IX (PpIX), which accumulates in the skin to which aminolevulinic acid has been applied. When exposed to light of appropriate wavelength and energy, the accumulated PpIX produces a photodynamic reaction, a cytotoxic process dependent upon the simultaneous presence of light and oxygen. The absorption of light results in an excited state of the porphyrin molecule, and subsequent spin transfer from PpIX to molecular oxygen generates singlet oxygen, which can further react to form superoxide and hydroxyl radicals. Photosensitization of actinic (solar) keratosis lesions using aminolevulinic acid, plus illumination with the BLU-UTM Blue Light Photodynamic Therapy Illuminator (BLU-U), is the basis for aminolevulinic acid photodynamic therapy (PDT).</mechanism-of-toxicity>
  <metabolism>Following topical administration, synthesis into protoporphyrin IX takes place in situ in the skin.Half Life: Mean half-life is 0.70 &amp;plusmn; 0.18 h after the oral dose and 0.83 &amp;plusmn; 0.05 h after the intravenous dose.</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Aminolevulinic acid plus blue light illumination using a blue light photodynamic therapy illuminator is indicated for the treatment of minimally to moderately thick actinic keratoses of the face or scalp.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-29T06:11:37Z</created-at>
  <updated-at type="dateTime">2026-03-26T19:58:36Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Aminolevulinic_acid</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C00430</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>17549</chebi-id>
  <biocyc-id>5-AMINO-LEVULINATE</biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB00855</drugbank-id>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>NCC(=O)CCC(O)=O</moldb-smiles>
  <moldb-formula>C5H9NO3</moldb-formula>
  <moldb-inchi>InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)</moldb-inchi>
  <moldb-inchikey>ZGXJTSGNIOSYLO-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">131.1299</moldb-average-mass>
  <moldb-mono-mass type="decimal">131.058243159</moldb-mono-mass>
  <origin>Endogenous</origin>
  <state>Solid</state>
  <logp>-1.5</logp>
  <hmdb-id>HMDB01149</hmdb-id>
  <chembl-id>CHEMBL601</chembl-id>
  <chemspider-id>134</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;Takashi Ebata, Hiroshi Kawakami, Katsuya Matsumoto, Koshi Koseki, Hajime Matsushita, &amp;#8220;Method of preparing an acid additional salt of delta-aminolevulinic acid.&amp;#8221; U.S. Patent US5284973, issued July, 1974.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003233</chemdb-id>
  <dsstox-id>DTXSID8048490</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id nil="true"/>
  <iupac>5-amino-4-oxopentanoic acid</iupac>
</compound>
