Indole-3-methyl acetate (BioCAD00000027382)

blood feces urine plant natural products microbial natural products

Metabolite Card

Formula: C11H11NO2 (189.079)
SMILES: COC(=O)CC1=CNC2=C1C=CC=C2

Synonyms [en]

Indole-3-methyl acetate; IAA methyl ester; Methyl indole-3-acetate; Methyl 2-(1H-indol-3-yl)acetate; Methyl iaa; Meiaa

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Indole-3-methyl 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: BioCAD00000027382). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Indole-3-methyl acetate, also known as methyl indole-3-acetate (methyl-IAA), is a catabolite of tryptophan converted by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine (PMID: 30120222). Pediatric enthesitis-related arthritis (ERA) patients (i.e. spondyloarthropathy associated with inflammatory bowel disease) have intestinal inflammation and decreased gut microbial diversity. Such alterations in the gut microbiota resulted in the reduction of tryptophan metabolism and several tryptophan metabolites in pediatric ERA fecal samples, including indole-3-methyl acetate (PMID: 27786174). Indole-3-methyl acetate is found in apple, and has been isolated from immature seeds of beach pea (Lathyrus maritimus), Vicia amurensis, wild soybean (Glycine soja), lobiya (Vigna catiang var. sinensis) and hyacinth bean (Dolichos lablab).

Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 1912-33-0
  • PubChem: 74706
  • ChEBI: ChEBI:72782
  • HMDB: HMDB0029738
  • HMDB: HMDB29738
  • BioCyc: CPD-10546
  • RefMet: RM0136624
  • MoNA: BAF_UVA_POS000392
  • MoNA: BAF_UVA_POS000747
  • MoNA: BAF_UVA_POS000748
  • MoNA: CCMSLIB00000578352
  • MoNA: CCMSLIB00005463613
  • MoNA: CCMSLIB00005463614
  • MoNA: CCMSLIB00005720547
  • MoNA: MoNA016725
  • MoNA: MoNA016884
  • MoNA: MoNA023838
  • MoNA: MoNA032476
  • MoNA: MoNA032477
  • MoNA: MoNA032479
  • MoNA: MoNA034553
  • MoNA: MoNA034554
  • MoNA: MoNA034555
  • MoNA: MoNA036328
  • MoNA: MoNA036329
  • MoNA: MoNA036331
  • MoNA: MoNA037316
  • MoNA: MoNA038054
  • MoNA: MoNA038663
  • Metlin: METLIN_86457
  • Coconut NaturalProduct: CNP0134536.0
  • Coconut NaturalProduct: CNP0185625.0
  • Coconut NaturalProduct: CNP0242770.0

Class / Ontology

Metabolic Network
ID EC Number Name
BioCyc:RXN-9825 2.1.1.278 S-ADENOSYLMETHIONINE + INDOLE_ACETATE_AUXIN --> CPD-10546 + ADENOSYL-HOMO-CYS
BioCyc:RXN-10711 3.1.1.1 CPD-10546 + WATER --> PROTON + INDOLE_ACETATE_AUXIN + METOH
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Organism Source

Taxonomy Source

  1. Brassica oleracea [ncbi taxid: 3712]
  2. Castanea crenata [ncbi taxid: 103480]
  3. Chamaecyparis lawsoniana [ncbi taxid: 58030]
  4. Citrullus lanatus [ncbi taxid: 3654]
  5. Citrus sinensis [ncbi taxid: 2711]
  6. Citrus unshiu [ncbi taxid: 55188]
  7. Corylus avellana [ncbi taxid: 13451]
  8. Cotinus coggygria [ncbi taxid: 269719]
  9. Dalbergia dolichopetala [ncbi taxid: ]
  10. Diospyros kaki [ncbi taxid: 35925]
  11. Dolichos lablab [ncbi taxid: ]
  12. Euphorbia escula [ncbi taxid: ]
  13. Glycine soja [ncbi taxid: 3848]
  14. Homo sapiens [ncbi taxid: 9606]
  15. Isatis tinctoria [ncbi taxid: 161756]
  16. Lathyrus maritimus [ncbi taxid: ]
  17. Lycopersicon esculentum [ncbi taxid: ]
  18. Lygodium flexuosum [ncbi taxid: 85330]
  19. Malus pumila [ncbi taxid: 283210]
  20. Nicotiana tabacum [ncbi taxid: 4097]
  21. Panax ginseng [ncbi taxid: 4054]
  22. Persicaria tinctoria [ncbi taxid: 96455]
  23. Phaseolus mungo [ncbi taxid: ]
  24. Phaseolus vulgaris [ncbi taxid: 3885]
  25. Picea abies [ncbi taxid: 3329]
  26. Picea sitchensis [ncbi taxid: 3332]
  27. Pinus contorta [ncbi taxid: 3339]
  28. Pinus slyvestris [ncbi taxid: ]
  29. Pisum sativum [ncbi taxid: ]
  30. Prunus cerasus [ncbi taxid: 140311]
  31. Prunus domestica [ncbi taxid: 3758]
  32. Pseudomonas amygdali [ncbi taxid: 47877]
  33. Pseudotsuga menziesii [ncbi taxid: 3357]
  34. Quercus robur [ncbi taxid: 38942]
  35. Raphanus sativus [ncbi taxid: 3726]
  36. Rhizopus suinus [ncbi taxid: ]
  37. Ricinus communis [ncbi taxid: 3988]
  38. Saccharomyces cerevisiae [ncbi taxid: 4932]
  39. Sarcotragus sp. [ncbi taxid: ]
  40. Streptomyces mutabilis sp. MII [ncbi taxid: ]
  41. Vicia amurensis [ncbi taxid: 154495]
  42. Vigna unguiculata var. sesquipedalis [ncbi taxid: ]
  43. Vitis vinifera [ncbi taxid: 29760]
  44. Zea mays [ncbi taxid: 4577]

Pathway Synthetic

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