ContaminantDB: Methyl aminolevulinate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 18:24:13 UTC

Update Date

2016-11-09 01:17:27 UTC

Accession Number

CHEM022216

Identification

Common Name

Methyl aminolevulinate

Class

Small Molecule

Description

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.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-Aminolevulinic acid methyl ester	ChEBI
Aminolevulinic acid methyl ester	ChEBI
Methyl delta-aminolevulinate	ChEBI
5-Aminolevulinate methyl ester	Generator
Aminolevulinate methyl ester	Generator
Methyl delta-aminolevulinic acid	Generator
Methyl δ-aminolevulinate	Generator
Methyl δ-aminolevulinic acid	Generator
Methyl aminolevulinic acid	Generator
delta-Aminolevulinic acid methyl ester	HMDB
ALA-me	HMDB
Methyl 5-aminolevulinic acid	HMDB
Methyl aminolevulinate	ChEBI

Chemical Formula

C₆H₁₁NO₃

Average Molecular Mass

145.156 g/mol

Monoisotopic Mass

145.074 g/mol

CAS Registry Number

33320-16-0

IUPAC Name

methyl 5-amino-4-oxopentanoate

Traditional Name

methyl aminolevulinate

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 Key

YUUAYBAIHCDHHD-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Delta 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 Framework

Aliphatic acyclic compounds

External Descriptors

delta-amino acid ester (CHEBI:724125 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	220 g/L	ALOGPS
logP	-1.3	ALOGPS
logP	-0.85	ChemAxon
logS	0.18	ALOGPS
pKa (Strongest Acidic)	16.12	ChemAxon
pKa (Strongest Basic)	7.83	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.39 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	35.22 m³·mol⁻¹	ChemAxon
Polarizability	14.55 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-9000000000-3022d6725fb55c4c97ad	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ot-2900000000-650383912a456fb9097d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01xt-9700000000-e633d077d788d7da5aae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-b7719cdec62b57f60bc2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1900000000-284ced4b4d42c8a36fe1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ox-8900000000-ff49e64ba3b4c3411930	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0abd-9000000000-979ef83e0d13fbac6d92	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03ds-8900000000-f33383bd50764c860dcd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4v-9100000000-4d3bd966083ee3a6cb74	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-f959af592dec9c76c083	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-5900000000-a4e49e408520259affc7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4l-9100000000-122fee87748ea0579107	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00dl-9000000000-1fd2185d0aeb194b2cd0	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum