5-Aminolevulinate (BioCAD00000004744)

blood urine bladder epidermis fibroblasts kidney spleen testis

Metabolite Card

Formula: C5H9NO3 (131.0582)
SMILES: NCC(=O)CCC(O)=O

Synonyms [en]

5-Aminolevulinate; 5-Amino-4-oxopentanoate; 5-Amino-4-oxopentanoic acid; 5-Aminolevulinic acid; 5-amino-levulinic acid; delta-aminolevulinic acid

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

5-Aminolevulinate. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000004744). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

5-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.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 106-60-5
  • CAS Registry Number: 5451-09-2
  • CAS Registry Number: 9/2/51
  • PubChem: 137
  • ChEBI: ChEBI:17549
  • ChEBI: ChEBI:356416
  • HMDB: HMDB0001149
  • HMDB: HMDB01149
  • LipidMaps: LMFA01100055
  • KEGG: C00430
  • BioCyc: 5-AMINO-LEVULINATE
  • NCBI MeSH: Aminolevulinic Acid
  • Wikipedia: Aminolevulinic_acid
  • DrugBank: DB00855
  • RefMet: RM0153225
  • MoNA: BAF_UVA_POS001060
  • MoNA: BAF_UVA_POS001061
  • MoNA: BAF_UVA_POS001062
  • MoNA: BAF_UVA_POS001063
  • MoNA: BAF_UVA_POS001064
  • MoNA: CCMSLIB00005463957
  • MoNA: CCMSLIB00005463958
  • MoNA: CCMSLIB00005464052
  • MoNA: CCMSLIB00005720430
  • MoNA: CCMSLIB00005720729
  • MoNA: EMBL-MCF_spec121141
  • MoNA: EMBL-MCF_spec273191
  • MoNA: EMBL-MCF_spec273200
  • MoNA: EMBL-MCF_spec273210
  • MoNA: EMBL-MCF_spec273231
  • MoNA: EMBL_MCF_2_0_HRMS_Library000485
  • MoNA: EMBL_MCF_2_0_HRMS_Library000486
  • MoNA: HMDB0001149_c_ms_1427
  • MoNA: HMDB0001149_c_ms_1457
  • MoNA: HMDB0001149_ms_ms_1433
  • MoNA: HMDB0001149_ms_ms_1434
  • MoNA: HMDB0001149_ms_ms_1435
  • MoNA: KO002153
  • MoNA: KO002154
  • MoNA: KO002155
  • MoNA: KO002156
  • MoNA: KO002157
  • MoNA: KZ000181
  • MoNA: KZ000182
  • MoNA: MoNA001950
  • MoNA: MoNA001951
  • MoNA: MoNA001952
  • MoNA: MoNA010850
  • MoNA: MoNA010851
  • MoNA: MoNA010852
  • MoNA: MoNA010853
  • MoNA: MoNA024103
  • MoNA: MoNA032125
  • MoNA: MoNA032126
  • MoNA: MoNA032129
  • MoNA: MoNA034078
  • MoNA: MoNA034080
  • MoNA: MoNA034083
  • MoNA: MoNA036054
  • MoNA: MoNA036057
  • MoNA: MoNA036059
  • MoNA: MoNA036581
  • MoNA: MoNA036582
  • MoNA: MoNA036583
  • MoNA: MoNA037172
  • MoNA: MoNA038565
  • MoNA: MoNA038730
  • MoNA: MoNA_0006906
  • MoNA: MoNA_0006907
  • MoNA: MoNA_0006908
  • MoNA: MoNA_0006909
  • MoNA: MoNA_0006910
  • MoNA: MoNA_0006911
  • MoNA: MoNA_0007162
  • MoNA: MoNA_0007163
  • MoNA: MoNA_0007164
  • MoNA: MoNA_0008621
  • MoNA: MoNA_0008622
  • MoNA: MoNA_0008623
  • MoNA: MoNA_0008624
  • MoNA: MoNA_0008625
  • MoNA: MoNA_0008626
  • MoNA: MoNA_0008894
  • MoNA: MoNA_0009302
  • MoNA: MoNA_0009941
  • MoNA: MoNA_0009942
  • MoNA: MoNA_0009943
  • MoNA: MoNA_0009944
  • MoNA: MoNA_0009945
  • MoNA: MoNA_0009946
  • MoNA: OUF00070
  • MoNA: OUF00071
  • MoNA: PM000921
  • MoNA: PM000979
  • MoNA: PR010216
  • MoNA: PR010217
  • MoNA: PR100221
  • MoNA: PR100633
  • MoNA: PS039101
  • MoNA: PS039102
  • Metlin: METLIN_74883
  • Metlin: METLIN_75
  • Coconut NaturalProduct: CNP0153451.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R00036 4.2.1.24 5-aminolevulinate hydro-lyase (adding 5-aminolevulinate and cyclizing; porphobilinogen-forming)
KEGG:R00830 2.3.1.37 succinyl-CoA:glycine C-succinyltransferase (decarboxylating)
KEGG:R02271 2.6.1.43 5-aminolevulinate:pyruvate aminotransferase
KEGG:R02272 5.4.3.8 (S)-4-amino-5-oxopentanoate 4,5-aminomutase
BioCyc:PORPHOBILSYNTH-RXN 4.2.1.24 2 5-AMINO-LEVULINATE --> PROTON + 2 WATER + PORPHOBILINOGEN
BioCyc:GSAAMINOTRANS-RXN 5.4.3.8 GLUTAMATE-1-SEMIALDEHYDE --> 5-AMINO-LEVULINATE
BioCyc:AMINOLEVULINATE-AMINOTRANSFERASE-RXN 2.6.1.43 PYRUVATE + 5-AMINO-LEVULINATE<=>L-ALPHA-ALANINE + CPD-473
BioCyc:RXN-15714 6.2.1.- 5-aminolevulinyl-CoA synthase
BioCyc:5-AMINOLEVULINIC-ACID-SYNTHASE-RXN 2.3.1.37 PROTON + GLY + SUC-COA --> CARBON-DIOXIDE + CO-A + 5-AMINO-LEVULINATE
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Organism Source

Taxonomy Source

  1. A new engineered strain of Pichia pastoris [n.a.] [ncbi taxid: ]
  2. Arabidopsis thaliana [ncbi taxid: 3702]
  3. Citrullus lanatus [ncbi taxid: 3654]
  4. Escherichia coli [ncbi taxid: 562]
  5. Escherichia coli HH 31-LFT [fdhCbopt] [ncbi taxid: ]
  6. Homo sapiens [ncbi taxid: 9606]
  7. Mus musculus [ncbi taxid: 10090]
  8. Rhodobacter sphaeroides [ncbi taxid: ]
  9. Saccharomyces cerevisiae [ncbi taxid: 4932]
  10. Saccharomyces cerevisiae ò-carotenogenic strain SM14-ÃÂURA3 [YAH1; ARH1] [ncbi taxid: ]
  11. Serratia marcescens SK68 [rcsB] [ncbi taxid: ]
  12. Streptomyces hygrospinosus OaniF [aniF] [ncbi taxid: ]
  13. Trichoderma sp. AYA 20-1 [n.a.] [ncbi taxid: ]

Pathway Synthetic

pathway id name
BioCyc:CAULONA1000_PWY-5189 tetrapyrrole biosynthesis II
BioCyc:CAULONA1000_PWY-5188 tetrapyrrole biosynthesis I
BioCyc:CALBI_PWY3B3-2 tetrapyrrole biosynthesis
PathBank:SMP0000953 Porphyrin Metabolism
WikiPathways:WP3604 Biochemical pathways: part I
WikiPathways:WP5169 Hemesynthesis defects and porphyrias
WikiPathways:WP269 Heme biosynthesis
WikiPathways:WP4506 Tyrosine metabolism and related disorders
PathBank:SMP0120694 Dihydropyrimidine Dehydrogenase Deficiency (DHPD)
PathBank:SMP0120754 Non-Ketotic Hyperglycinemia
PathBank:SMP0120770 Hyperglycinemia, Non-Ketotic
PathBank:SMP0120492 Hereditary Coproporphyria (HCP)
PathBank:SMP0120544 Porphyria Variegata (PV)
PathBank:SMP0000024 Porphyrin Metabolism
PathBank:SMP0000242 Dimethylglycine Dehydrogenase Deficiency
PathBank:SMP0000223 Non-Ketotic Hyperglycinemia
PathBank:SMP0000484 Dimethylglycine Dehydrogenase Deficiency
PathBank:SMP0087338 Glycine and Serine Metabolism
PathBank:SMP0087466 Glycine and Serine Metabolism
PathBank:SMP0120653 3-Phosphoglycerate Dehydrogenase Deficiency
View All Pathways