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Record Information
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2018-05-20 20:14:53 UTC
Secondary Accession Numbers
  • HMDB15127
Metabolite Identification
Common NameMethyl aminolevulinate
DescriptionMethyl aminolevulinate is only found in individuals that have used or taken this drug. It is a prodrug that is metabolised to Protoporphyrin IX (a photosensitizer) used in photodynamic therapy.Photosensitization following application of methyl aminolevulinate cream occurs through the metabolic conversion of methyl aminolevulinate (prodrug) to photoactive porphyrins (PAP), which accumulates in the skin lesions to which the cream has been applied. When exposed to light of appropriate wavelength and energy, the accumulated photoactive porphyrins produce a photodynamic reaction, resulting in a cytotoxic process dependent upon the simultaneous presence of oxygen. The absorption of light results in an excited state of porphyrin molecules, and subsequent spin transfer from photoactive porphyrins to molecular oxygen generates singlet oxygen, which can further react to form superoxide and hydroxyl radicals.
5-Aminolevulinic acid methyl esterChEBI
Aminolevulinic acid methyl esterChEBI
Methyl delta-aminolevulinateChEBI
5-Aminolevulinate methyl esterGenerator
Methyl aminolevulinic acidGenerator
Aminolevulinate methyl esterGenerator
Methyl delta-aminolevulinic acidGenerator
Methyl δ-aminolevulinateGenerator
Methyl δ-aminolevulinic acidGenerator
delta-Aminolevulinic acid methyl esterMeSH
Chemical FormulaC6H11NO3
Average Molecular Weight145.1564
Monoisotopic Molecular Weight145.073893223
IUPAC Namemethyl 5-amino-4-oxopentanoate
Traditional Namemethyl aminolevulinate
CAS Registry Number33320-16-0
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as delta amino acids and derivatives. These are compounds containing a carboxylic acid group and an amino group at the C5 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDelta amino acids and derivatives
Alternative Parents
  • Delta amino acid or derivatives
  • Gamma-keto acid
  • Fatty acid ester
  • Fatty acid methyl ester
  • Keto acid
  • Fatty acyl
  • Alpha-aminoketone
  • Methyl ester
  • Carboxylic acid ester
  • Ketone
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Amine
  • Organooxygen compound
  • Primary amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors

Biological location:


Industrial application:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility220 g/LNot Available
LogP-1.2Not Available
Predicted Properties
Water Solubility220 g/LALOGPS
pKa (Strongest Acidic)16.12ChemAxon
pKa (Strongest Basic)7.83ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area69.39 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity35.22 m³·mol⁻¹ChemAxon
Polarizability14.55 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-9000000000-3022d6725fb55c4c97adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-2900000000-650383912a456fb9097dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01xt-9700000000-e633d077d788d7da5aaeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-b7719cdec62b57f60bc2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-284ced4b4d42c8a36fe1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-8900000000-ff49e64ba3b4c3411930View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abd-9000000000-979ef83e0d13fbac6d92View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Normal Concentrations
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00992 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00992 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00992
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID138950
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl_Aminolevulinate
METLIN IDNot Available
PubChem Compound157922
PDB IDNot Available
ChEBI ID724125
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Smits T, Moor AC: New aspects in photodynamic therapy of actinic keratoses. J Photochem Photobiol B. 2009 Sep 4;96(3):159-69. doi: 10.1016/j.jphotobiol.2009.06.003. Epub 2009 Jun 13. [PubMed:19592269 ]
  2. MEDSAFE [Link]