D-Aminolevulinic acid

δ-Aminolevulinic acid

Clinical data
Pregnancy category	C
ATC code	L01XD04 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 5-amino-4-oxo-pentanoic acid
CAS Number	106-60-5 Y
PubChem CID	137
IUPHAR/BPS	4784
DrugBank	DB00855 Y
ChemSpider	134 Y
UNII	88755TAZ87
KEGG	D07567 Y
ChEBI	CHEBI:356416 Y
ChEMBL	CHEMBL601 Y
ECHA InfoCard	100.003.105
Chemical and physical data
Formula	C5H9NO3
Molar mass	131.13 g/mol
3D model (JSmol)	Interactive image
Melting point	118 °C (244 °F)
SMILES O=C(CN)CCC(=O)O
InChI InChI=1S/C5H9NO3/c6-3-4(7)1-2-5(8)9/h1-3,6H2,(H,8,9) Y Key:ZGXJTSGNIOSYLO-UHFFFAOYSA-N Y

δ-Aminolevulinic acid (also dALA, δ-ALA, 5ala or 5-aminolevulinic acid) is the first compound in the porphyrin synthesis pathway, the pathway that leads to heme in mammals and chlorophyll in plants.

In plants, production of δ-ALA is the step on which the speed of synthesis of chlorophyll is regulated. Plants that are fed by external δ-ALA accumulate toxic amounts of chlorophyll precursor, , indicating that the synthesis of this intermediate is not suppressed anywhere downwards in the chain of reaction. Protochlorophyllide is a strong photosensitizer in plants.

In non-photosynthetic eukaryotes such as animals, fungi, and protozoa, as well as the Alphaproteobacteria class of bacteria, it is produced by the enzyme ALA synthase, from glycine and succinyl CoA. This reaction is known as the Shemin pathway, which occurs in .

In plants, algae, bacteria (except for the α-proteobacteria group) and archaea, it is produced from glutamic acid via glutamyl-tRNA and glutamate-1-semialdehyde. The enzymes involved in this pathway are glutamyl-tRNA synthetase, glutamyl-tRNA reductase, and glutamate-1-semialdehyde 2,1-aminomutase. This pathway is known as the C5 or Beale pathway. In most plastid-containing species, glutamyl-tRNA is encoded by a plastid gene, and the transcription, as well as the following steps of C5 pathway, take place in plastids.