5-Methoxyindoleacetate (BioCAD00000004872)
Metabolite Card
Formula: C11H11NO3 (205.0739)
SMILES: COC1=CC2=C(NC=C2CC(O)=O)C=C1
Synonyms [en]
5-Methoxyindoleacetate; 5-methoxyindole-3-acetic acid; 5-methoxyindoleacetic acid; 5-Methoxyindol-3-ylacetic acid; 2-(5-methoxy-1H-indol-3-yl)acetic acid; 5-Methoxy-3-indoleacetic acid
Last reviewed on 2024-06-28.
Cite this Page
5-Methoxyindoleacetate. 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: BioCAD00000004872). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
5-Methoxyindoleacetate, also known as 5-methoxy-IAA or 5-MIAA, belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. 5-Methoxyindoleacetic acid is formed through oxidative deamination. It is identified in the urine, and the concentration is determined to be 1.3 µg/mL using GC-MS (PMID: 12908946). An increase in urinary 5-MIAA excretion was shown in patients with cancer of the stomach, rectum, and lung (PMID: 2446428).
DBLinks
- CAS Registry Number: 3471-31-6
- PubChem CID: 18986
- ChEBI: 28281
- HMDB: HMDB0004096
- LipidMaps:
- KEGG: C05660
- BioCyc: CPD-12020
- NCBI MeSH: 5-methoxyindoleacetic acid
- Wikipedia:
Other DBLinks
- CAS Registry Number: 142396-09-6
- CAS Registry Number: 3471-31-6
- PubChem: 18986
- PubChem: 7971
- ChEBI: ChEBI:28281
- HMDB: HMDB0004096
- HMDB: HMDB04096
- KEGG: C05660
- BioCyc: CPD-12020
- NCBI MeSH: 5-methoxyindoleacetic acid
- RefMet: RM0028464
- MoNA: FiehnHILIC000127
- MoNA: FiehnHILIC001019
- MoNA: FiehnHILIC001706
- MoNA: FiehnHILIC002553
- MoNA: FiehnLib000908
- MoNA: HMDB0004096_c_ms_1846
- MoNA: KO001452
- MoNA: KO001453
- MoNA: KO001454
- MoNA: KO001455
- MoNA: KO001456
- MoNA: KO003477
- MoNA: KO003478
- MoNA: KO003479
- MoNA: KO003480
- MoNA: KO003481
- MoNA: KO009067
- MoNA: KO009068
- MoNA: MoNA033500
- MoNA: MoNA033501
- MoNA: MoNA033503
- MoNA: MoNA035624
- MoNA: MoNA035626
- MoNA: MoNA035627
- MoNA: MoNA036910
- MoNA: MoNA036912
- MoNA: MoNA036913
- MoNA: MoNA037657
- MoNA: MoNA038395
- MoNA: MoNA038875
- Metlin: METLIN_7016
- Coconut NaturalProduct: CNP0036942.1
- Coconut NaturalProduct: CNP0036942.2
- Coconut NaturalProduct: CNP0267742.0
- Coconut NaturalProduct: CNP0323085.1
Class / Ontology
- WishartLab ClassyFire: [Indolyl carboxylic acids and derivatives] Indolyl carboxylic acids and derivatives
- RefMet: [Indoleacetic acids] Indoleacetic acids
- ChEBI: [CHEBI:28281] 5-methoxyindole-3-acetic acid
- Coconut NaturalProduct: [Dipeptides] Dipeptides
- Coconut NaturalProduct: [Simple indole alkaloids] Simple indole alkaloids
| ID | EC Number | Name |
|---|---|---|
| KEGG:R04905 | 2.1.1.4 | S-adenosyl-L-methionine:N-acetylserotonin O-methyltransferase |
| BioCyc:RXN-11068 | 5-methoxyindoleacetaldehyde dehydrogenase |
Taxonomy Source
Pathway Synthetic
| pathway id | name |
|---|---|
| BioCyc:HUMAN_PWY66-401 | superpathway of tryptophan utilization |
| BioCyc:HUMAN_PWY-6402 | superpathway of melatonin degradation |
| BioCyc:META_PWY-6399 | melatonin degradation II |
| BioCyc:HUMAN_PWY-6399 | melatonin degradation II |
| BioCyc:META_PWY-6402 | superpathway of melatonin degradation |
| WikiPathways:WP79 | Tryptophan metabolism |
| PathBank:SMP0087330 | Tryptophan Metabolism |
| PathBank:SMP0087237 | Tryptophan Metabolism |
| PathBank:SMP0063693 | Tryptophan Metabolism |
| PathBank:SMP0000063 | Tryptophan Metabolism |
| PathBank:SMP0087451 | Tryptophan Metabolism |