3-Hydroxyanthranilate (BioCAD00000003554)

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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

Reviewed

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.

Entity Information

DBLinks

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

Metabolic Network
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
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Organism Source

Taxonomy Source

  1. Arthrobacter protophormiae [ncbi taxid: ]
  2. Brassica oleracea [ncbi taxid: 3712]
  3. Homo sapiens [ncbi taxid: 9606]
  4. Mus musculus [ncbi taxid: 10090]
  5. Saccharomyces cerevisiae [ncbi taxid: 4932]
  6. Streptomyces antibioticus [ncbi taxid: 1890]
  7. 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
View All Pathways