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
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.
DBLinks
- CAS Registry Number: 106-60-5
- PubChem CID: 137
- ChEBI: 17549
- HMDB: HMDB0001149
- LipidMaps: LMFA01100055
- KEGG: C00430
- BioCyc: 5-AMINO-LEVULINATE
- NCBI MeSH: Aminolevulinic Acid
- Wikipedia: Aminolevulinic_acid
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
- WishartLab ClassyFire: [Amino acids, peptides, and analogues] Amino acids, peptides, and analogues
- RefMet: [Amino FA] Amino FA
- LipidMaps: [Amino fatty acids [FA0110]] Amino fatty acids [FA0110]
- ChEBI: [CHEBI:17549] 5-aminolevulinic acid
- Coconut NaturalProduct: [Aminoacids] Aminoacids
| 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 |
Taxonomy Source
- A new engineered strain of Pichia pastoris [n.a.] [ncbi taxid: ]
- Arabidopsis thaliana [ncbi taxid: 3702]
- Citrullus lanatus [ncbi taxid: 3654]
- Escherichia coli [ncbi taxid: 562]
- Escherichia coli HH 31-LFT [fdhCbopt] [ncbi taxid: ]
- Homo sapiens [ncbi taxid: 9606]
- Mus musculus [ncbi taxid: 10090]
- Rhodobacter sphaeroides [ncbi taxid: ]
- Saccharomyces cerevisiae [ncbi taxid: 4932]
- Saccharomyces cerevisiae ò-carotenogenic strain SM14-ÃÂURA3 [YAH1; ARH1] [ncbi taxid: ]
- Serratia marcescens SK68 [rcsB] [ncbi taxid: ]
- Streptomyces hygrospinosus OaniF [aniF] [ncbi taxid: ]
- 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 |