Metabolite Card
Formula: C7H7NO3 (153.0426)
SMILES: NC1=C(O)C=CC=C1C(O)=O
Synonyms [en]
3-hydroxyanthranilate; 3-Hydroxyanthranilic acid; 3-Ohaa; 3-Oxyanthranilic acid; 2-Amino-3-hydroxybenzoic acid; 2-AMINO-3-HYDROXY-BENZOIC ACID
Last reviewed on 2024-06-28.
Cite this Page
3-Hydroxyanthranilate. 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: BioCAD00000003554). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
3-Hydroxyanthranilic acid, also known as 2-amino-3-hydroxy-benzoate or 3-ohaa, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3-Hydroxyanthranilic acid is a drug. 3-Hydroxyanthranilic acid exists in all living species, ranging from bacteria to humans. Within humans, 3-hydroxyanthranilic acid participates in a number of enzymatic reactions. In particular, 3-hydroxyanthranilic acid and L-alanine can be biosynthesized from L-3-hydroxykynurenine through the action of the enzyme kynureninase. In addition, 3-hydroxyanthranilic acid can be converted into cinnavalininate through the action of the enzyme catalase. 3-Hydroxyanthranilic acid is an intermediate in the metabolism of tryptophan. In humans, 3-hydroxyanthranilic acid is involved in tryptophan metabolism. Outside of the human body, 3-hydroxyanthranilic acid has been detected, but not quantified in brassicas. This could make 3-hydroxyanthranilic acid a potential biomarker for the consumption of these foods. It is new antioxidant isolated from methanol extract of tempeh. It is effective in preventing autoxidation of soybean oil and powder, while antioxidant 6,7,4'-trihydroxyisoflavone is not.
DBLinks
- CAS Registry Number: 548-93-6
- PubChem CID: 86
- ChEBI: 15793
- HMDB: HMDB0001476
- LipidMaps:
- KEGG: C00632
- BioCyc: 3-HYDROXY-ANTHRANILATE
- NCBI MeSH: 3-Hydroxyanthranilic Acid
- Wikipedia: 3-hydroxyanthranilic_acid
Other DBLinks
- CAS Registry Number: 548-93-6
- PubChem: 3905
- PubChem: 86
- ChEBI: ChEBI:15793
- HMDB: HMDB0001476
- KEGG: C00632
- BioCyc: 3-HYDROXY-ANTHRANILATE
- NCBI MeSH: 3-Hydroxyanthranilic Acid
- Wikipedia: 3-Hydroxyanthranilic_acid
- DrugBank: DB03644
- RefMet: RM0136103
- MoNA: BAF_UVA_POS000072
- MoNA: BAF_UVA_POS000073
- MoNA: BAF_UVA_POS000074
- MoNA: BAF_UVA_POS001235
- MoNA: CCMSLIB00000578325
- MoNA: CCMSLIB00005464068
- MoNA: CCMSLIB00005464082
- MoNA: CCMSLIB00005464083
- MoNA: CCMSLIB00005720524
- MoNA: CCMSLIB00005720819
- MoNA: EMBL-MCF_spec75927
- MoNA: FiehnHILIC000073
- MoNA: FiehnHILIC000955
- MoNA: FiehnHILIC001657
- MoNA: FiehnHILIC002499
- MoNA: FiehnLib000268
- MoNA: FIO00668
- MoNA: FIO00669
- MoNA: FIO00670
- MoNA: FIO00671
- MoNA: FIO00672
- MoNA: FIO00673
- MoNA: FIO00674
- MoNA: FIO00675
- MoNA: MoNA010137
- MoNA: MoNA010138
- MoNA: MoNA010139
- MoNA: MoNA010140
- MoNA: MoNA010141
- MoNA: MoNA010142
- MoNA: MoNA010823
- MoNA: MoNA010824
- MoNA: MoNA010825
- MoNA: MoNA023863
- MoNA: MoNA023884
- MoNA: MoNA032378
- MoNA: MoNA032379
- MoNA: MoNA032380
- MoNA: MoNA033472
- MoNA: MoNA033474
- MoNA: MoNA033475
- MoNA: MoNA034409
- MoNA: MoNA034413
- MoNA: MoNA034414
- MoNA: MoNA035610
- MoNA: MoNA035611
- MoNA: MoNA035613
- MoNA: MoNA036889
- MoNA: MoNA036890
- MoNA: MoNA036895
- MoNA: MoNA037276
- MoNA: MoNA037651
- MoNA: MoNA038006
- MoNA: MoNA038391
- MoNA: MoNA038643
- MoNA: MoNA038864
- MoNA: OUF00049
- MoNA: PS057301
- MoNA: PS057302
- MoNA: PS057303
- MoNA: PS057304
- MoNA: PS057305
- MoNA: PS057306
- Coconut NaturalProduct: CNP0324729.0
Class / Ontology
- WishartLab ClassyFire: [Benzoic acids and derivatives] Benzoic acids and derivatives
- RefMet: [Hydroxybenzoic acids] Hydroxybenzoic acids
- ChEBI: [CHEBI:15793] 3-hydroxyanthranilic acid
- Coconut NaturalProduct: [Aminoacids] Aminoacids
| ID | EC Number | Name |
|---|---|---|
| KEGG:R02665 | 1.13.11.6 | 3-hydroxyanthranilate:oxygen 3,4-oxidoreductase (decyclizing) |
| KEGG:R02666 | 1.10.3.5 | 3-hydroxyanthranilate:oxygen oxidoreductase |
| KEGG:R02667 | 2.1.1.97 | S-adenosyl-L-methionine:3-hydroxyanthranilate 4-C-methyltransferase |
| KEGG:R02668 | 3.7.1.3 | 3-hydroxy-L-kynurenine hydrolase |
| KEGG:R02669 | 4.1.1.- | C00632<=>C01987 + C00011 |
| KEGG:R02670 | 1.11.1.6 | 2 C00632 + 4 C00007<=>C05640 + 2 C00704 + 2 C00027 + 2 C00080 |
| KEGG:R02671 | 2.1.1.- | C00632 + C00019<=>C05831 + C00021 |
| KEGG:R07730 | 5.4.99.- | C16235<=>C00632 |
| KEGG:R09517 | 1.14.14.8 | anthranilate,FAD:oxygen oxidoreductase (3-hydroxylating) |
| BioCyc:3-HYDROXY-KYNURENINASE-RXN | 3.7.1.3 | 3-HYDROXY-L-KYNURENINE + WATER --> PROTON + 3-HYDROXY-ANTHRANILATE + L-ALPHA-ALANINE |
| BioCyc:RXN-10724 | 1.14.14.8 | ANTHRANILATE + OXYGEN-MOLECULE + FADH2 --> PROTON + 3-HYDROXY-ANTHRANILATE + WATER + FAD |
| BioCyc:3-HYDROXYANTHRANILATE-OXIDASE-RXN | 1.10.3.5 | OXYGEN-MOLECULE + 3-HYDROXY-ANTHRANILATE --> HYDROGEN-PEROXIDE + CPD-386 |
| BioCyc:2.1.1.97-RXN | 2.1.1.97 | S-ADENOSYLMETHIONINE + 3-HYDROXY-ANTHRANILATE --> PROTON + ADENOSYL-HOMO-CYS + CPD-403 |
| BioCyc:1.13.11.6-RXN | 1.13.11.6 | 3-HYDROXY-ANTHRANILATE + OXYGEN-MOLECULE --> 2-AMINO-3-3-OXOPROP-2-ENYL-BUT-2-ENEDI |
| BioCyc:RXN-8846 | CPD-9169 --> 3-HYDROXY-ANTHRANILATE |
Taxonomy Source
- Arthrobacter protophormiae [ncbi taxid: ]
- Brassica oleracea [ncbi taxid: 3712]
- Homo sapiens [ncbi taxid: 9606]
- Mus musculus [ncbi taxid: 10090]
- Saccharomyces cerevisiae [ncbi taxid: 4932]
- Streptomyces antibioticus [ncbi taxid: 1890]
- Streptomyces chartreusis NRRL 3882 [ncbi taxid: 1079985]
Pathway Synthetic
| pathway id | name |
|---|---|
| BioCyc:CALBI_TRYPTOPHAN-DEGRADATION-1 | tryptophan degradation via kynurenine |
| BioCyc:CALBI_NADSYN-PWY | NAD biosynthesis (from tryptophan) |
| WikiPathways:WP3228 | NAD biosynthesis II from tryptophan |
| WikiPathways:WP3604 | Biochemical pathways: part I |
| WikiPathways:WP5044 | Kynurenine pathway and links to cell senescence |
| WikiPathways:WP2485 | NAD biosynthesis II (from tryptophan) |
| WikiPathways:WP3645 | NAD+ biosynthetic pathways |
| PathBank:SMP0002353 | Tryptophan Metabolism |
| PathBank:SMP0087330 | Tryptophan Metabolism |
| PathBank:SMP0087237 | Tryptophan Metabolism |
| PathBank:SMP0063693 | Tryptophan Metabolism |
| PathBank:SMP0000063 | Tryptophan Metabolism |
| PathBank:SMP0002338 | NAD Metabolism |
| PathBank:SMP0087451 | Tryptophan Metabolism |