methyl 5-aminolevulinate (CHEBI:724125)

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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

Average Mass

145.15640

Monoisotopic Mass

145.07389

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.

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

Last Modified

22 February 2017