CHEBI:17549 - 5-aminolevulinic acid

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ChEBI Name 5-aminolevulinic acid
ChEBI ID CHEBI:17549
Definition The simplest δ-amino acid in which the hydrogens at the γ position are replaced by an oxo group. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin. Used (in the form of the hydrochloride salt)in combination with blue light illumination for the treatment of minimally to moderately thick actinic keratosis of the face or scalp.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:20547, CHEBI:2034
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Formula C5H9NO3
Net Charge 0
Average Mass 131.12990
Monoisotopic Mass 131.058
InChI InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)
InChIKey ZGXJTSGNIOSYLO-UHFFFAOYSA-N
SMILES NCC(=O)CCC(O)=O
Metabolite of Species Details
Mus musculus (NCBI:10090) Source: BioModels - MODEL1507180067 See: PubMed
Saccharomyces cerevisiae (NCBI:4932) Source: yeast.sf.net See: PubMed
Escherichia coli (NCBI:562) See: PubMed
Homo sapiens (NCBI:9606) See: DOI
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
Saccharomyces cerevisiae metabolite
Any fungal metabolite produced during a metabolic reaction in Baker's yeast (Saccharomyces cerevisiae ).
Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
Application(s): 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.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
dermatologic drug
A drug used to treat or prevent skin disorders or for the routine care of skin.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 5-aminolevulinic acid (CHEBI:17549) has functional parent 4-oxopentanoic acid (CHEBI:45630)
5-aminolevulinic acid (CHEBI:17549) has role Escherichia coli metabolite (CHEBI:76971)
5-aminolevulinic acid (CHEBI:17549) has role Saccharomyces cerevisiae metabolite (CHEBI:75772)
5-aminolevulinic acid (CHEBI:17549) has role antineoplastic agent (CHEBI:35610)
5-aminolevulinic acid (CHEBI:17549) has role dermatologic drug (CHEBI:50177)
5-aminolevulinic acid (CHEBI:17549) has role human metabolite (CHEBI:77746)
5-aminolevulinic acid (CHEBI:17549) has role mouse metabolite (CHEBI:75771)
5-aminolevulinic acid (CHEBI:17549) has role photosensitizing agent (CHEBI:47868)
5-aminolevulinic acid (CHEBI:17549) has role plant metabolite (CHEBI:76924)
5-aminolevulinic acid (CHEBI:17549) has role prodrug (CHEBI:50266)
5-aminolevulinic acid (CHEBI:17549) is a δ-amino acid (CHEBI:35931)
5-aminolevulinic acid (CHEBI:17549) is a 4-oxo monocarboxylic acid (CHEBI:35950)
5-aminolevulinic acid (CHEBI:17549) is conjugate acid of 5-aminolevulinate (CHEBI:12109)
5-aminolevulinic acid (CHEBI:17549) is conjugate base of 5-ammoniolevulinic acid (CHEBI:132970)
5-aminolevulinic acid (CHEBI:17549) is tautomer of 5-ammoniolevulinate (CHEBI:356416)
Incoming methyl 5-aminolevulinate (CHEBI:724125) has functional parent 5-aminolevulinic acid (CHEBI:17549)
5-ammoniolevulinic acid (CHEBI:132970) is conjugate acid of 5-aminolevulinic acid (CHEBI:17549)
5-aminolevulinate (CHEBI:12109) is conjugate base of 5-aminolevulinic acid (CHEBI:17549)
5-ammoniolevulinate (CHEBI:356416) is tautomer of 5-aminolevulinic acid (CHEBI:17549)
IUPAC Name
5-amino-4-oxopentanoic acid
Synonyms Sources
5-ALA ChEBI
5-Amino-4-oxopentanoate KEGG COMPOUND
5-Amino-4-oxovaleric acid KEGG COMPOUND
5-Aminolevulinate KEGG COMPOUND
aminolevulinic acid ChemIDplus
dALA ChEBI
δ-ALA ChEBI
δ-aminolevulinic acid ChemIDplus
Database Links Databases
166 DrugCentral
Aminolevulinic_acid Wikipedia
C00007378 KNApSAcK
C00430 KEGG COMPOUND
D07567 KEGG DRUG
DB00855 DrugBank
HMDB0001149 HMDB
LSM-5677 LINCS
View more database links
Registry Numbers Types Sources
106-60-5 CAS Registry Number KEGG COMPOUND
106-60-5 CAS Registry Number ChemIDplus
1759139 Reaxys Registry Number Reaxys
1759139 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
11303952 PubMed citation Europe PMC
15756058 PubMed citation Europe PMC
15996585 PubMed citation Europe PMC
18982627 PubMed citation Europe PMC
19378778 PubMed citation Europe PMC
22378066 PubMed citation Europe PMC
22700502 PubMed citation Europe PMC
23242333 PubMed citation Europe PMC
23291627 PubMed citation Europe PMC
23299429 PubMed citation Europe PMC
23307195 PubMed citation Europe PMC
23339045 PubMed citation Europe PMC
23360321 PubMed citation Europe PMC
7890117 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2010-12-14 A naturally occurring amino acid produced from succinyl-CoA and glycine, 5-aminolevulinic acid is the first compound in the biosynthetic pathway leading to heme. It is metabolised in the body to protoporphyrin IX, a photosensitiser, and is used in the photodynamic treatment of actinic keratoses and non-melanoma skin cancer, including basal cell carcinoma. Topical application is followed 14-18 hours later by illumination with blue light, resulting in the generation of toxic singlet oxygen that destroys cell membranes and thereby kills the tumour cells.