Common Name5-aminolevulinate
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
Molecular FormulaC5H9NO3
Average Mass131.12990
Monoisotopic Mass131.05824
IUPAC Name5-amino-4-oxopentanoic acid
Traditional NameAminolevulinic acid
CAS Registry Number106-60-5
SMILES[NH3+]CC(=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
CHEBI IDCHEBI:356416
HMDB IDHMDB0001149
Pathways
NameSMPDB/PathBank
Glycine, serine and threonine metabolism
Porphyrin Metabolism
Dihydropyrimidine Dehydrogenase Deficiency (DHPD)
Non Ketotic Hyperglycinemia
Dimethylglycine Dehydrogenase Deficiency
Sarcosinemia
Hereditary Coproporphyria (HCP)
Acute Intermittent Porphyria
Congenital Erythropoietic Porphyria (CEP) or Gunther Disease
Porphyria Variegata (PV)
Dimethylglycine Dehydrogenase Deficiency
Hyperglycinemia, non-ketotic
3-Phosphoglycerate dehydrogenase deficiency
StateSolid
Water Solubility1.73e+02 g/l
logP-2.85
logS0.12
pKa (Strongest Acidic)4.05
pKa (Strongest Basic)7.84
Hydrogen Acceptor Count4
Hydrogen Donor Count2
Polar Surface Area80.39 Ų
Rotatable Bond Count4
Physiological Charge0
Formal Charge0
Refractivity30.45 m³·mol⁻¹
Polarizability12.62

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