Marvin  11151010102D          

 10  9  0  0  0  0            999 V2000
    5.6259   -4.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9115   -4.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1971   -4.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3405   -4.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0548   -4.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9115   -5.2859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4826   -4.4609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0548   -3.2234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7693   -4.4609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4886   -4.0455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  2  6  2  0  0  0  0
  2  3  1  0  0  0  0
  3  7  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <ID>
CHEBI:724125

> <NAME>
methyl 5-aminolevulinate

> <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.

> <STAR>
3

> <SYNONYM>
methyl delta-aminolevulinate; Methyl aminolevulinate; aminolevulinic acid methyl ester; 5-aminolevulinic acid methyl ester

> <IUPAC_NAME>
methyl 5-amino-4-oxopentanoate

> <FORMULA>
C6H11NO3

> <MASS>
145.15640

> <MONOISOTOPIC_MASS>
145.07389

> <CHARGE>
0

> <SMILES>
COC(=O)CCC(=O)CN

> <INCHI>
InChI=1S/C6H11NO3/c1-10-6(9)3-2-5(8)4-7/h2-4,7H2,1H3

> <INCHIKEY>
YUUAYBAIHCDHHD-UHFFFAOYSA-N

> <CAS_REGISTRY_NUMBER>
33320-16-0

> <REAXYS_REGISTRY_NUMBER>
5921212

> <CHEMIDPLUS>
33320-16-0

> <DRUGBANK_ACCESSION>
DB00992

> <KEGG_DRUG_ACCESSION>
D08204

> <WIKIPEDIA_ACCESSION>
Methyl_Aminolevulinate

> <PUBMED_CITATION>
21197524; 21254852; 21978711; 22582911; 22785615; 22949035; 22971196; 23046014; 23212624

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