Imidazole-4-acetate (BioCAD00000012367)
Metabolite Card
Formula: C5H6N2O2 (126.0429)
SMILES: OC(=O)CC1=CN=CN1
Synonyms [en]
imidazoleacetic acid; Imidazole-4-acetate; 4-Imidazoleacetate; imidazol-4-ylacetic acid; imidazole-4-acetic acid; 4(5)-Imidazoleacetate
Last reviewed on 2024-06-28.
Cite this Page
Imidazole-4-acetate. 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: BioCAD00000012367). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
Imidazol-4-ylacetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by an imidazol-4-yl group. It has a role as a mouse metabolite. It is a monocarboxylic acid and a member of imidazoles. It derives from an acetic acid. It is a conjugate acid of an imidazol-4-ylacetate. It is a tautomer of an imidazol-5-ylacetic acid and a 2H-imidazol-4-ylacetic acid. Imidazoleacetic acid, also known as 4(5)-imidazoleacetate or IAA, belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring. Imidazoleacetic acid exists in all living organisms, ranging from bacteria to humans. imidazoleacetic acid can be biosynthesized from imidazole-4-acetaldehyde through its interaction with the enzyme aldehyde dehydrogenase, mitochondrial. In humans, imidazoleacetic acid is involved in histidine metabolism. Outside of the human body, Imidazoleacetic acid has been detected, but not quantified in several different foods, such as chinese cinnamons, jostaberries, vanilla, butternut squash, and red rices. Imidazoleacetic acid is a potentially toxic compound. Imidazoleacetic acid is a metabolite product of Histamine metabolism.
DBLinks
- CAS Registry Number: 645-65-8
- PubChem CID: 96215
- ChEBI: 16974
- HMDB: HMDB0002024
- LipidMaps:
- KEGG: C02835
- BioCyc: 4-IMIDAZOLEACETATE
- NCBI MeSH: imidazoleacetic acid
- Wikipedia:
Other DBLinks
- CAS Registry Number: 3251-69-2
- CAS Registry Number: 645-65-8
- PubChem: 96215
- ChEBI: ChEBI:16974
- ChEBI: ChEBI:70804
- HMDB: HMDB0002024
- HMDB: HMDB02024
- KEGG: C02835
- BioCyc: 4-IMIDAZOLEACETATE
- NCBI MeSH: imidazoleacetic acid
- RefMet: RM0009104
- MoNA: BAF_UVA_POS000354
- MoNA: BAF_UVA_POS000355
- MoNA: BAF_UVA_POS001553
- MoNA: BAF_UVA_POS001554
- MoNA: CCMSLIB00000578275
- MoNA: CCMSLIB00005464081
- MoNA: CCMSLIB00005720471
- MoNA: EMBL-MCF_spec129382
- MoNA: EMBL-MCF_spec129383
- MoNA: EMBL-MCF_spec129421
- MoNA: EMBL-MCF_spec61043
- MoNA: HMDB0002024_c_ms_1241
- MoNA: HMDB0002024_c_ms_1319
- MoNA: HMDB0002024_ms_ms_1950
- MoNA: HMDB0002024_ms_ms_1951
- MoNA: HMDB0002024_ms_ms_1952
- MoNA: KO003182
- MoNA: KO003183
- MoNA: KO003184
- MoNA: KO003185
- MoNA: KO003186
- MoNA: MoNA002082
- MoNA: MoNA002083
- MoNA: MoNA002085
- MoNA: MoNA016726
- MoNA: MoNA017910
- MoNA: MoNA017911
- MoNA: MoNA024027
- MoNA: MoNA032240
- MoNA: MoNA032241
- MoNA: MoNA032243
- MoNA: MoNA034217
- MoNA: MoNA034218
- MoNA: MoNA034219
- MoNA: MoNA036148
- MoNA: MoNA036150
- MoNA: MoNA036151
- MoNA: MoNA037219
- MoNA: MoNA037934
- MoNA: MoNA038597
- MoNA: MoNA_0006942
- MoNA: MoNA_0006943
- MoNA: MoNA_0006944
- MoNA: MoNA_0006945
- MoNA: MoNA_0006946
- MoNA: MoNA_0006947
- MoNA: MoNA_0008663
- MoNA: MoNA_0008664
- MoNA: MoNA_0008665
- MoNA: MoNA_0008666
- MoNA: MoNA_0008667
- MoNA: MoNA_0008668
- MoNA: MoNA_0008931
- MoNA: MoNA_0009336
- MoNA: MoNA_0009337
- MoNA: MoNA_0009338
- Metlin: METLIN_6445
- Coconut NaturalProduct: CNP0253943.0
- Coconut NaturalProduct: CNP0530503.0
Class / Ontology
- WishartLab ClassyFire: [Imidazoles] Imidazoles
- RefMet: [Imidazole alkaloids] Imidazole alkaloids
- ChEBI: [CHEBI:16974] imidazol-4-ylacetic acid
- ChEBI: [CHEBI:70804] imidazol-5-ylacetic acid
- Coconut NaturalProduct: [Imidazole alkaloids] Imidazole alkaloids
- Coconut NaturalProduct: [Aminoacids] Aminoacids
| ID | EC Number | Name |
|---|---|---|
| KEGG:R04065 | 1.2.1.3 | imidazole acetaldehyde:NAD+ oxidoreductase |
| KEGG:R04066 | 1.14.13.5 | imidazole-4-acetate,NADH:oxygen oxidoreductase (5-hydroxylating) |
| KEGG:R04068 | 6.3.4.8 | imidazole-4-acetate:5-phosphoribosyl-diphosphate ligase (ADP- and pyrophosphate- forming) |
| BioCyc:6.3.4.8-RXN | 6.3.4.8 | PRPP + 4-IMIDAZOLEACETATE + ATP + WATER --> Pi + PPI + 1-5-PHOSPHORIBOSYLIMIDAZOLE-4-ACETATE + ADP + PROTON |
| BioCyc:IMIDAZOLEACETATE-4-MONOOXYGENASE-RXN | 1.14.13.5 | 4-IMIDAZOLEACETATE + NADH + OXYGEN-MOLECULE --> 5-HYDROXY-4-IMIDAZOLEACETATE + NAD + WATER |
| BioCyc:RXN-10089 | 1.2.1.3 | imidazole acetaldehyde reductase |
Taxonomy Source
- Astragalus oxyphysus [ncbi taxid: 90201]
- Centaurea glastifolia [ncbi taxid: 75647]
- Clavaria pyxidata [ncbi taxid: ]
- Cucumaria okhotensis [ncbi taxid: ]
- Cuscuta reflexa [ncbi taxid: 4129]
- Euphorbia armena [ncbi taxid: ]
- Galanthus nivalis [ncbi taxid: 4670]
- Grindelia havardii [ncbi taxid: 1114740]
- Homo sapiens [ncbi taxid: 9606]
- Hydrodictyon reticulatum [ncbi taxid: 3107]
- Mus musculus [ncbi taxid: 10090]
- Nephelium maingayi [ncbi taxid: 1277290]
- Oenanthe phellandrium [ncbi taxid: ]
- Plantago depressa [ncbi taxid: 411227]
- Polyscias scutellaria [ncbi taxid: 150539]
- Prunus dulcis [ncbi taxid: 3755]
- Pyrus pyraster [ncbi taxid: 356590]
- Senecio candollei [ncbi taxid: 462509]
Pathway Synthetic
| pathway id | name |
|---|---|
| WikiPathways:WP1581 | Histidine metabolism |