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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2021-10-13 05:48:31 UTC
HMDB IDHMDB0015127
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.
Structure
Data?1582753261
Synonyms
ValueSource
5-Aminolevulinic acid methyl esterChEBI
Aminolevulinic acid methyl esterChEBI
Methyl delta-aminolevulinateChEBI
5-Aminolevulinate methyl esterGenerator
Aminolevulinate methyl esterGenerator
Methyl delta-aminolevulinic acidGenerator
Methyl δ-aminolevulinateGenerator
Methyl δ-aminolevulinic acidGenerator
Methyl aminolevulinic acidGenerator
delta-Aminolevulinic acid methyl esterHMDB
ALA-meHMDB
Methyl 5-aminolevulinic acidHMDB
Methyl aminolevulinateChEBI
Chemical FormulaC6H11NO3
Average Molecular Weight145.1564
Monoisotopic Molecular Weight145.073893223
IUPAC Namemethyl 5-amino-4-oxopentanoate
Traditional Namemethyl aminolevulinate
CAS Registry Number33320-16-0
SMILES
COC(=O)CCC(=O)CN
InChI Identifier
InChI=1S/C6H11NO3/c1-10-6(9)3-2-5(8)4-7/h2-4,7H2,1H3
InChI KeyYUUAYBAIHCDHHD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as delta amino acids and derivatives. Delta amino acids and derivatives 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
Substituents
  • 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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point228.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility220 g/LNot Available
LogP-1.2Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility220 g/LALOGPS
logP10(-1.3) g/LALOGPS
logP10(-0.85) g/LChemAxon
logS10(0.18) 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+132.39131661259
DarkChem[M-H]-128.00231661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Methyl aminolevulinateCOC(=O)CCC(=O)CN1894.5Standard polar33892256
Methyl aminolevulinateCOC(=O)CCC(=O)CN1215.8Standard non polar33892256
Methyl aminolevulinateCOC(=O)CCC(=O)CN1226.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Methyl aminolevulinate,1TMS,isomer #1COC(=O)CCC(=CN)O[Si](C)(C)C1429.8Semi standard non polar33892256
Methyl aminolevulinate,1TMS,isomer #1COC(=O)CCC(=CN)O[Si](C)(C)C1366.1Standard non polar33892256
Methyl aminolevulinate,1TMS,isomer #1COC(=O)CCC(=CN)O[Si](C)(C)C2316.1Standard polar33892256
Methyl aminolevulinate,1TMS,isomer #2COC(=O)CC=C(CN)O[Si](C)(C)C1396.7Semi standard non polar33892256
Methyl aminolevulinate,1TMS,isomer #2COC(=O)CC=C(CN)O[Si](C)(C)C1456.2Standard non polar33892256
Methyl aminolevulinate,1TMS,isomer #2COC(=O)CC=C(CN)O[Si](C)(C)C2327.4Standard polar33892256
Methyl aminolevulinate,1TMS,isomer #3COC(=O)CCC(=O)CN[Si](C)(C)C1406.5Semi standard non polar33892256
Methyl aminolevulinate,1TMS,isomer #3COC(=O)CCC(=O)CN[Si](C)(C)C1427.3Standard non polar33892256
Methyl aminolevulinate,1TMS,isomer #3COC(=O)CCC(=O)CN[Si](C)(C)C2013.7Standard polar33892256
Methyl aminolevulinate,2TMS,isomer #1COC(=O)CCC(=CN[Si](C)(C)C)O[Si](C)(C)C1603.0Semi standard non polar33892256
Methyl aminolevulinate,2TMS,isomer #1COC(=O)CCC(=CN[Si](C)(C)C)O[Si](C)(C)C1571.7Standard non polar33892256
Methyl aminolevulinate,2TMS,isomer #1COC(=O)CCC(=CN[Si](C)(C)C)O[Si](C)(C)C1832.5Standard polar33892256
Methyl aminolevulinate,2TMS,isomer #2COC(=O)CC=C(CN[Si](C)(C)C)O[Si](C)(C)C1543.3Semi standard non polar33892256
Methyl aminolevulinate,2TMS,isomer #2COC(=O)CC=C(CN[Si](C)(C)C)O[Si](C)(C)C1615.4Standard non polar33892256
Methyl aminolevulinate,2TMS,isomer #2COC(=O)CC=C(CN[Si](C)(C)C)O[Si](C)(C)C1772.6Standard polar33892256
Methyl aminolevulinate,2TMS,isomer #3COC(=O)CCC(=O)CN([Si](C)(C)C)[Si](C)(C)C1625.1Semi standard non polar33892256
Methyl aminolevulinate,2TMS,isomer #3COC(=O)CCC(=O)CN([Si](C)(C)C)[Si](C)(C)C1615.3Standard non polar33892256
Methyl aminolevulinate,2TMS,isomer #3COC(=O)CCC(=O)CN([Si](C)(C)C)[Si](C)(C)C1836.8Standard polar33892256
Methyl aminolevulinate,3TMS,isomer #1COC(=O)CCC(=CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C1769.4Semi standard non polar33892256
Methyl aminolevulinate,3TMS,isomer #1COC(=O)CCC(=CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C1625.4Standard non polar33892256
Methyl aminolevulinate,3TMS,isomer #1COC(=O)CCC(=CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C1784.8Standard polar33892256
Methyl aminolevulinate,3TMS,isomer #2COC(=O)CC=C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C1731.8Semi standard non polar33892256
Methyl aminolevulinate,3TMS,isomer #2COC(=O)CC=C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C1728.8Standard non polar33892256
Methyl aminolevulinate,3TMS,isomer #2COC(=O)CC=C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C1718.7Standard polar33892256
Methyl aminolevulinate,1TBDMS,isomer #1COC(=O)CCC(=CN)O[Si](C)(C)C(C)(C)C1646.7Semi standard non polar33892256
Methyl aminolevulinate,1TBDMS,isomer #1COC(=O)CCC(=CN)O[Si](C)(C)C(C)(C)C1587.0Standard non polar33892256
Methyl aminolevulinate,1TBDMS,isomer #1COC(=O)CCC(=CN)O[Si](C)(C)C(C)(C)C2397.2Standard polar33892256
Methyl aminolevulinate,1TBDMS,isomer #2COC(=O)CC=C(CN)O[Si](C)(C)C(C)(C)C1611.2Semi standard non polar33892256
Methyl aminolevulinate,1TBDMS,isomer #2COC(=O)CC=C(CN)O[Si](C)(C)C(C)(C)C1646.1Standard non polar33892256
Methyl aminolevulinate,1TBDMS,isomer #2COC(=O)CC=C(CN)O[Si](C)(C)C(C)(C)C2374.9Standard polar33892256
Methyl aminolevulinate,1TBDMS,isomer #3COC(=O)CCC(=O)CN[Si](C)(C)C(C)(C)C1626.0Semi standard non polar33892256
Methyl aminolevulinate,1TBDMS,isomer #3COC(=O)CCC(=O)CN[Si](C)(C)C(C)(C)C1658.2Standard non polar33892256
Methyl aminolevulinate,1TBDMS,isomer #3COC(=O)CCC(=O)CN[Si](C)(C)C(C)(C)C2058.7Standard polar33892256
Methyl aminolevulinate,2TBDMS,isomer #1COC(=O)CCC(=CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2020.8Semi standard non polar33892256
Methyl aminolevulinate,2TBDMS,isomer #1COC(=O)CCC(=CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1981.1Standard non polar33892256
Methyl aminolevulinate,2TBDMS,isomer #1COC(=O)CCC(=CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2050.9Standard polar33892256
Methyl aminolevulinate,2TBDMS,isomer #2COC(=O)CC=C(CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1969.9Semi standard non polar33892256
Methyl aminolevulinate,2TBDMS,isomer #2COC(=O)CC=C(CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2001.3Standard non polar33892256
Methyl aminolevulinate,2TBDMS,isomer #2COC(=O)CC=C(CN[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C1999.9Standard polar33892256
Methyl aminolevulinate,2TBDMS,isomer #3COC(=O)CCC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2030.3Semi standard non polar33892256
Methyl aminolevulinate,2TBDMS,isomer #3COC(=O)CCC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2016.3Standard non polar33892256
Methyl aminolevulinate,2TBDMS,isomer #3COC(=O)CCC(=O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2009.3Standard polar33892256
Methyl aminolevulinate,3TBDMS,isomer #1COC(=O)CCC(=CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2374.2Semi standard non polar33892256
Methyl aminolevulinate,3TBDMS,isomer #1COC(=O)CCC(=CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2213.5Standard non polar33892256
Methyl aminolevulinate,3TBDMS,isomer #1COC(=O)CCC(=CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2114.5Standard polar33892256
Methyl aminolevulinate,3TBDMS,isomer #2COC(=O)CC=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2359.9Semi standard non polar33892256
Methyl aminolevulinate,3TBDMS,isomer #2COC(=O)CC=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2305.4Standard non polar33892256
Methyl aminolevulinate,3TBDMS,isomer #2COC(=O)CC=C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2063.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methyl aminolevulinate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-9000000000-3022d6725fb55c4c97ad2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl aminolevulinate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl aminolevulinate 10V, Positive-QTOFsplash10-01ot-2900000000-650383912a456fb9097d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl aminolevulinate 20V, Positive-QTOFsplash10-01xt-9700000000-e633d077d788d7da5aae2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl aminolevulinate 40V, Positive-QTOFsplash10-0a4i-9000000000-b7719cdec62b57f60bc22016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl aminolevulinate 10V, Negative-QTOFsplash10-0006-1900000000-284ced4b4d42c8a36fe12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl aminolevulinate 20V, Negative-QTOFsplash10-01ox-8900000000-ff49e64ba3b4c34119302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl aminolevulinate 40V, Negative-QTOFsplash10-0abd-9000000000-979ef83e0d13fbac6d922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl aminolevulinate 10V, Positive-QTOFsplash10-03ds-8900000000-f33383bd50764c860dcd2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl aminolevulinate 20V, Positive-QTOFsplash10-0a4v-9100000000-4d3bd966083ee3a6cb742021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl aminolevulinate 40V, Positive-QTOFsplash10-0a4i-9000000000-f959af592dec9c76c0832021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl aminolevulinate 10V, Negative-QTOFsplash10-03di-5900000000-a4e49e408520259affc72021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl aminolevulinate 20V, Negative-QTOFsplash10-0a4l-9100000000-122fee87748ea05791072021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl aminolevulinate 40V, Negative-QTOFsplash10-00dl-9000000000-1fd2185d0aeb194b2cd02021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00992 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1698161
References
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]