5-Aminolevulinic acid (CHEM003233)

Record Information
Version1.0
Creation Date2014-08-29 06:11:37 UTC
Update Date2026-05-14 16:50:50 UTC
Accession NumberCHEM003233
Identification
Common Name5-Aminolevulinic acid
ClassSmall Molecule
Description
5-Aminolevulinic acid is an intermediate in heme synthesis. This is the first compound in the porphyrin synthesis pathway. It is produced by the enzyme ALA synthase, from glycine and succinyl CoA. This reaction is known as the Shemin pathway. Aminolevulinic acid plus blue light illumination using a blue light photodynamic therapy illuminator is indicated for the treatment of minimally to moderately thick actinic keratoses of the face or scalp.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amine
  • Animal Toxin
  • Drug
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Photosensitizing Agent
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5-ALAChEBI
5-Amino-4-oxopentanoateChEBI
5-Amino-4-oxovaleric acidChEBI
5-AminolevulinateChEBI
Aminolevulinic acidChEBI
DALAChEBI
delta-ALAChEBI
delta-Aminolevulinic acidChEBI
5-Amino-4-oxopentanoic acidGenerator
5-Amino-4-oxovalerateGenerator
AminolevulinateGenerator
Δ-alaGenerator
delta-AminolevulinateGenerator
Δ-aminolevulinateGenerator
Δ-aminolevulinic acidGenerator
5-Amino-4-oxo-pentanoateHMDB
5-Amino-4-oxo-pentanoic acidHMDB
5-Amino-levulinateHMDB
5-Amino-levulinic acidHMDB
5-AminolaevulinateHMDB
5-Aminolaevulinic acidHMDB
AladermHMDB
Amino-levulinic acidHMDB
KerastickHMDB
5 AminolevulinateHMDB
Acid, Delta-aminolevulinicHMDB
LevulanHMDB
5 AminolaevulinateHMDB
Acid hydrochloride, aminolevulinicHMDB
Bertek brand OF aminolevulinic acid hydrochlorideHMDB
Hydrochloride, aminolevulinic acidHMDB
Acid, aminolevulinicHMDB
Aminolevulinic acid hydrochlorideHMDB
Delta Aminolevulinic acidHMDB
Chemical FormulaC5H9NO3
Average Molecular Mass131.130 g/mol
Monoisotopic Mass131.058 g/mol
CAS Registry Number106-60-5
IUPAC Name5-amino-4-oxopentanoic acid
Traditional Nameaminolevulinic acid
SMILESNCC(=O)CCC(O)=O
InChI IdentifierInChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9)
InChI KeyZGXJTSGNIOSYLO-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
  • Short-chain keto acid
  • Keto acid
  • Alpha-aminoketone
  • Amino acid
  • Ketone
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organooxygen compound
  • Primary amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Membrane
  • Mitochondria
Biofluid LocationsNot Available
Tissue Locations
  • Bladder
  • Fibroblasts
  • Kidney
  • Skin
  • Spleen
  • Stratum Corneum
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Glycine and Serine MetabolismSMP00004 map00260
Porphyrin MetabolismSMP00024 map00860
Acute Intermittent PorphyriaSMP00344 Not Available
Hereditary Coproporphyria (HCP)SMP00342 Not Available
Porphyria Variegata (PV)SMP00346 Not Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point156-158°C
Boiling PointNot Available
SolubilityVery soluble
Predicted Properties
PropertyValueSource
Water Solubility173 g/LALOGPS
logP-2.8ALOGPS
logP-3.3ChemAxon
logS0.12ALOGPS
pKa (Strongest Acidic)4.05ChemAxon
pKa (Strongest Basic)7.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.45 m³·mol⁻¹ChemAxon
Polarizability12.55 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral bioavailability is 50-60%.
Mechanism of ToxicityAccording to the presumed mechanism of action, photosensitization following application of aminolevulinic acid (ALA) topical solution occurs through the metabolic conversion of ALA to protoporphyrin IX (PpIX), which accumulates in the skin to which aminolevulinic acid has been applied. When exposed to light of appropriate wavelength and energy, the accumulated PpIX produces a photodynamic reaction, a cytotoxic process dependent upon the simultaneous presence of light and oxygen. The absorption of light results in an excited state of the porphyrin molecule, and subsequent spin transfer from PpIX to molecular oxygen generates singlet oxygen, which can further react to form superoxide and hydroxyl radicals. Photosensitization of actinic (solar) keratosis lesions using aminolevulinic acid, plus illumination with the BLU-UTM Blue Light Photodynamic Therapy Illuminator (BLU-U), is the basis for aminolevulinic acid photodynamic therapy (PDT).
MetabolismFollowing topical administration, synthesis into protoporphyrin IX takes place in situ in the skin. Half Life: Mean half-life is 0.70 ± 0.18 h after the oral dose and 0.83 ± 0.05 h after the intravenous dose.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesAminolevulinic acid plus blue light illumination using a blue light photodynamic therapy illuminator is indicated for the treatment of minimally to moderately thick actinic keratoses of the face or scalp.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00855
HMDB IDHMDB0001149
FooDB IDFDB022452
Phenol Explorer IDNot Available
KNApSAcK IDC00007378
BiGG ID34963
BioCyc ID5-AMINO-LEVULINATE
METLIN ID6037
PDB IDNot Available
Wikipedia LinkAminolevulinic_acid
Chemspider ID134
ChEBI ID17549
PubChem Compound ID137
Kegg Compound IDC00430
YMDB IDYMDB00083
ECMDB IDECMDB01149
References
Synthesis Reference

Takashi Ebata, Hiroshi Kawakami, Katsuya Matsumoto, Koshi Koseki, Hajime Matsushita, “Method of preparing an acid additional salt of delta-aminolevulinic acid.” U.S. Patent US5284973, issued July, 1974.

MSDSLink
General References
1. Goli?ski J., D?browski Z., Obukowicz B., Kami?ski J., Be?dowicz M., Kwa?ny M.: "Synthesis of 5-aminolevulinic acid (5-ALA)", ICRI Annual Report '99, 2000, 119-122.
2. Goli?ski J., D?browski Z., Obukowicz B., Kami?ski J., Be?dowicz M., Kwa?ny M.: "Synthesis of 5-aminolevulinic acid (5-ALA)", ICRI Annual Report '99, 2000, 119-122.
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11. Zareba G, Chmielnicka J: Disturbances in heme biosynthesis in rabbits after administration per os of low doses of tin or lead. Biol Trace Elem Res. 1992 Aug;34(2):115-22.
12. Srivastava G, Borthwick IA, Maguire DJ, Elferink CJ, Bawden MJ, Mercer JF, May BK: Regulation of 5-aminolevulinate synthase mRNA in different rat tissues. J Biol Chem. 1988 Apr 15;263(11):5202-9.
13. Maines MD, Mayer RD: Inhibition of testicular cytochrome P-450-dependent steroid biosynthesis by cis-platinum. Reversal by human chorionic gonadotropin. J Biol Chem. 1985 May 25;260(10):6063-8.
14. Santos MA, Belo VG, Santos G: Effectiveness of photodynamic therapy with topical 5-aminolevulinic acid and intense pulsed light versus intense pulsed light alone in the treatment of acne vulgaris: comparative study. Dermatol Surg. 2005 Aug;31(8 Pt 1):910-5.
15. Gederaas OA, Rasch MH, Berg K, Lagerberg JW, Dubbelman TM: Photodynamically induced effects in colon carcinoma cells (WiDr) by endogenous photosensitizers generated by incubation with 5-aminolaevulinic acid. J Photochem Photobiol B. 1999 Apr;49(2-3):162-70.
16. Lee S, Kollias N, McAuliffe DJ, Flotte TJ, Doukas AG: Topical drug delivery in humans with a single photomechanical wave. Pharm Res. 1999 Nov;16(11):1717-21.
17. van den Akker JT, Boot K, Vernon DI, Brown SB, Groenendijk L, van Rhoon GC, Sterenborg HJ: Effect of elevating the skin temperature during topical ALA application on in vitro ALA penetration through mouse skin and in vivo PpIX production in human skin. Photochem Photobiol Sci. 2004 Mar;3(3):263-7. Epub 2004 Feb 13.
18. Lerda D: Study of sperm characteristics in persons occupationally exposed to lead. Am J Ind Med. 1992;22(4):567-71.
19. Winkler A, Muller-Goymann CC: Comparative permeation studies for delta-aminolevulinic acid and its n-butylester through stratum corneum and artificial skin constructs. Eur J Pharm Biopharm. 2002 May;53(3):281-7.
20. Authors unspecified: Hexyl aminolevulinate: 5-ALA hexylester, 5-ALA hexylesther, aminolevulinic acid hexyl ester, hexaminolevulinate, hexyl 5-aminolevulinate, P 1206. Drugs R D. 2005;6(4):235-8.
21. Collaud S, Jichlinski P, Marti A, Aymon D, Gurny R, Lange N: An open pharmacokinetic study of hexylaminolevulinate-induced photodiagnosis after intravesical administration. Drugs R D. 2006;7(3):173-86.
22. Fritsch C, Batz J, Bolsen K, Schulte KW, Zumdick M, Ruzicka T, Goerz G: Ex vivo application of delta-aminolevulinic acid induces high and specific porphyrin levels in human skin tumors: possible basis for selective photodynamic therapy. Photochem Photobiol. 1997 Jul;66(1):114-8.
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