Hmdb loader
Show more...Show more...Show more...Show more...Show more...Show more...Show more...
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:29 UTC
HMDB IDHMDB0001149
Secondary Accession Numbers
  • HMDB01149
Metabolite Identification
Common Name5-Aminolevulinic acid
Description5-Aminolevulinic acid, also known as 5-aminolevulinate or 5-amino-4-oxopentanoate, 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. 5-Aminolevulinic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 5-Aminolevulinic acid exists in all living species, ranging from bacteria to humans. 5-aminolevulinic acid can be biosynthesized from glycine and succinyl-CoA by the enzyme 5-aminolevulinate synthase. The simplest delta-amino acid in which the hydrogens at the gamma position are replaced by an oxo group. In humans, 5-aminolevulinic acid is involved in the metabolic disorder called the dimethylglycine dehydrogenase deficiency pathway. Outside of the human body, 5-Aminolevulinic acid has been detected, but not quantified in several different foods, such as american butterfish, vaccinium (blueberry, cranberry, huckleberry), amaranths, purple mangosteens, and garden cress. 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. It is metabolised to protoporphyrin IX, a photoactive compound which accumulates in the skin.
Structure
Thumb
Synonyms
Chemical FormulaC5H9NO3
Average Molecular Weight131.1299
Monoisotopic Molecular Weight131.058243159
IUPAC Name5-amino-4-oxopentanoic acid
Traditional Nameaminolevulinic acid
CAS Registry Number106-60-5
SMILES
NCC(=O)CCC(O)=O
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point156 - 158 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available130.7http://allccs.zhulab.cn/database/detail?ID=AllCCS00002158
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Mitochondria
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Bladder
  • Epidermis
  • Fibroblasts
  • Kidney
  • Spleen
  • Testis
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Acute intermittent porphyria
  1. Marsden JT, Rees DC: Urinary excretion of porphyrins, porphobilinogen and delta-aminolaevulinic acid following an attack of acute intermittent porphyria. J Clin Pathol. 2014 Jan;67(1):60-5. doi: 10.1136/jclinpath-2012-201367. Epub 2013 Aug 1. [PubMed:23908454 ]
Protoporphyria, Erythropoietic
  1. MAGNUS IA, JARRETT A, PRANKERD TA, RIMINGTON C: Erythropoietic protoporphyria. A new porphyria syndrome with solar urticaria due to protoporphyrinaemia. Lancet. 1961 Aug 26;2(7200):448-51. [PubMed:13765301 ]
Associated OMIM IDs
  • 610247 (Eosinophilic esophagitis)
  • 176000 (Acute intermittent porphyria)
  • 177000 (Protoporphyria, Erythropoietic)
DrugBank IDDB00855
Phenol Explorer Compound IDNot Available
FooDB IDFDB022452
KNApSAcK IDC00007378
Chemspider ID134
KEGG Compound IDC00430
BioCyc ID5-AMINO-LEVULINATE
BiGG ID34963
Wikipedia LinkAminolevulinic_acid
METLIN ID6037
PubChem Compound137
PDB IDNot Available
ChEBI ID17549
Food Biomarker OntologyNot Available
VMH ID5AOP
MarkerDB IDMDB00000303
Good Scents IDNot Available
References
Synthesis ReferenceGoli?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.
Material Safety Data Sheet (MSDS)Not Available
General References

Enzymes

General function:
Involved in 5-aminolevulinate synthase activity
Specific function:
Not Available
Gene Name:
ALAS2
Uniprot ID:
P22557
Molecular weight:
64632.86
Reactions
Succinyl-CoA + Glycine → 5-Aminolevulinic acid + Coenzyme A + CO(2)details
Succinyl-CoA + Glycine → 5-Aminolevulinic acid + Coenzyme A + Carbon dioxidedetails
General function:
Involved in 5-aminolevulinate synthase activity
Specific function:
Not Available
Gene Name:
ALAS1
Uniprot ID:
P13196
Molecular weight:
70580.325
Reactions
Succinyl-CoA + Glycine → 5-Aminolevulinic acid + Coenzyme A + CO(2)details
Succinyl-CoA + Glycine → 5-Aminolevulinic acid + Coenzyme A + Carbon dioxidedetails
General function:
Involved in porphobilinogen synthase activity
Specific function:
Catalyzes an early step in the biosynthesis of tetrapyrroles. Binds two molecules of 5-aminolevulinate per subunit, each at a distinct site, and catalyzes their condensation to form porphobilinogen.
Gene Name:
ALAD
Uniprot ID:
P13716
Molecular weight:
36294.485
Reactions
5-Aminolevulinic acid → Porphobilinogen + Waterdetails