CHEBI:724125 - methyl 5-aminolevulinate

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ChEBI Name methyl 5-aminolevulinate
ChEBI ID CHEBI:724125
Definition The methyl ester of 5-aminolevulinic acid. A prodrug, it is metabolised to protoporphyrin IX, a photosensitizer, and is used in the photodynamic treatment of non-melanoma skin cancer (including basal cell carcinoma). Topical application (often as the hydrochloride salt) results in an accumulation of protoporphyrin IX in the skin lesions to which the cream has been applied. Subsequent illumination with red light results in the generation of toxic singlet oxygen that destroys cell membranes and thereby kills the tumour cells.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C6H11NO3
Net Charge 0
Average Mass 145.15640
Monoisotopic Mass 145.074
InChI InChI=1S/C6H11NO3/c1-10-6(9)3-2-5(8)4-7/h2-4,7H2,1H3
InChIKey YUUAYBAIHCDHHD-UHFFFAOYSA-N
SMILES COC(=O)CCC(=O)CN
Roles Classification
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
photosensitizing agent
A chemical compound that can be excited by light of a specific wavelength and subsequently transfer energy to a chosen reactant. This is commonly molecular oxygen within a cancer tissue, which is converted to (highly rective) singlet state oxygen. This rapidly reacts with any nearby biomolecules, ultimately killing the cancer cells.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
dermatologic drug
A drug used to treat or prevent skin disorders or for the routine care of skin.
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ChEBI Ontology
Outgoing methyl 5-aminolevulinate (CHEBI:724125) has functional parent 5-aminolevulinic acid (CHEBI:17549)
methyl 5-aminolevulinate (CHEBI:724125) has role antineoplastic agent (CHEBI:35610)
methyl 5-aminolevulinate (CHEBI:724125) has role dermatologic drug (CHEBI:50177)
methyl 5-aminolevulinate (CHEBI:724125) has role photosensitizing agent (CHEBI:47868)
methyl 5-aminolevulinate (CHEBI:724125) has role prodrug (CHEBI:50266)
methyl 5-aminolevulinate (CHEBI:724125) is a δ-amino acid ester (CHEBI:60638)
Incoming methyl 5-aminolevulinate hydrochloride (CHEBI:60641) has part methyl 5-aminolevulinate (CHEBI:724125)
IUPAC Name
methyl 5-amino-4-oxopentanoate
Synonyms Sources
5-aminolevulinic acid methyl ester ChemIDplus
aminolevulinic acid methyl ester ChemIDplus
Methyl aminolevulinate ChEMBL
methyl δ-aminolevulinate ChEBI
Manual Xrefs Databases
168 DrugCentral
D08204 KEGG DRUG
DB00992 DrugBank
Methyl_Aminolevulinate Wikipedia
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Registry Numbers Types Sources
33320-16-0 CAS Registry Number ChemIDplus
33320-16-0 CAS Registry Number KEGG DRUG
5921212 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017