(Indol-3-yl)acetamide (BioCAD00000000769)

blood urine

Metabolite Card

Formula: C10H10N2O (174.0793)
SMILES: NC(=O)CC1=CNC2=C1C=CC=C2

Synonyms [en]

indole-3-acetamide; (indol-3-yl)acetamide; 1H-Indole-3-acetamide; indoleacetamide; 2-(1H-Indol-3-yl)acetamide; 3-Indoleacetamide

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

(Indol-3-yl)acetamide. 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: BioCAD00000000769). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Indole-3-acetamide, also known as 2-(3-indolyl)acetamide or IAM, belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Indole-3-acetamide has been detected, but not quantified, in several different foods, such as Alaska wild rhubarbs, lingonberries, butternut squash, pineapples, and agaves. Indole-3-acetamide is also found in the common pea and has been isolated from the etiolated seedlings of the black gram (Phaseolus mungo).

Cytoplasm Extracellular
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 879-06-1
  • CAS Registry Number: 879-37-8
  • PubChem: 397
  • ChEBI: ChEBI:16031
  • HMDB: HMDB0029739
  • KEGG: C02693
  • BioCyc: CPD-237
  • NCBI MeSH: indoleacetamide
  • DrugBank: DB08652
  • RefMet: RM0042324
  • MoNA: BAF_UVA_POS000281
  • MoNA: BAF_UVA_POS000282
  • MoNA: BAF_UVA_POS000283
  • MoNA: BAF_UVA_POS000284
  • MoNA: CCMSLIB00000578068
  • MoNA: CCMSLIB00000578326
  • MoNA: CCMSLIB00005464177
  • MoNA: CCMSLIB00005464178
  • MoNA: CCMSLIB00005464179
  • MoNA: CCMSLIB00005720196
  • MoNA: CCMSLIB00005720527
  • MoNA: CCMSLIB00005720822
  • MoNA: EMBL-MCF_spec143466
  • MoNA: EMBL-MCF_spec143467
  • MoNA: EMBL-MCF_spec143510
  • MoNA: EMBL-MCF_spec75212
  • MoNA: EMBL_MCF_2_0_HRMS_Library000200
  • MoNA: EMBL_MCF_2_0_HRMS_Library000201
  • MoNA: EMBL_MCF_2_0_HRMS_Library000247
  • MoNA: FiehnHILIC000436
  • MoNA: FiehnHILIC001260
  • MoNA: FiehnHILIC002008
  • MoNA: FiehnHILIC002761
  • MoNA: FiehnLib000936
  • MoNA: FiehnLib000937
  • MoNA: FiehnLib000938
  • MoNA: FiehnLib000939
  • MoNA: HMDB0029739_c_ms_1759
  • MoNA: HMDB0029739_c_ms_1805
  • MoNA: KO001221
  • MoNA: KO001222
  • MoNA: KO001223
  • MoNA: KO001224
  • MoNA: KO001225
  • MoNA: MoNA016727
  • MoNA: MoNA016886
  • MoNA: MoNA023867
  • MoNA: MoNA023888
  • MoNA: MoNA033636
  • MoNA: MoNA033637
  • MoNA: MoNA033638
  • MoNA: MoNA035757
  • MoNA: MoNA035761
  • MoNA: MoNA035762
  • MoNA: MoNA037701
  • MoNA: MoNA038441
  • MoNA: MoNA038888
  • Metlin: METLIN_3302
  • Coconut NaturalProduct: CNP0131710.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R00679 1.13.12.3 L-tryptophan:oxygen 2-oxidoreductase (decarboxylating)
KEGG:R03096 3.5.1.4 indole-3-acetamide amidohydrolase
KEGG:R04020 4.2.1.84 indole-3-acetamide hydro-lyase
Rhea:RHEA:16166 1.13.12.3 L-tryptophan + O2 => indole-3-acetamide + CO2 + H2O
Rhea:RHEA:16167 1.13.12.3 indole-3-acetamide + CO2 + H2O => L-tryptophan + O2
Rhea:RHEA:16168 1.13.12.3 L-tryptophan + O2 <=> indole-3-acetamide + CO2 + H2O
Rhea:RHEA:34372 3.5.1.4 indole-3-acetamide + H2O => (indol-3-yl)acetate + NH4+
Rhea:RHEA:34373 3.5.1.4 (indol-3-yl)acetate + NH4+ => indole-3-acetamide + H2O
Rhea:RHEA:34374 3.5.1.4 indole-3-acetamide + H2O <=> (indol-3-yl)acetate + NH4+
BioCyc:RXN-7567 4.2.1.84 indole-3-acetonitrile hydratase
BioCyc:RXNN-404 3.5.1.4 CPD-237 + WATER --> INDOLE_ACETATE_AUXIN + AMMONIUM
BioCyc:TRYPTOPHAN-2-MONOOXYGENASE-RXN 1.13.12.3 OXYGEN-MOLECULE + TRP --> CPD-237 + WATER + CARBON-DIOXIDE
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Organism Source

Taxonomy Source

  1. Aldrovanda vesiculosa [ncbi taxid: 173386]
  2. Anabaena cylindrica [ncbi taxid: 1165]
  3. Chamaebatia foliolosa [ncbi taxid: 140996]
  4. Chlorobaculum tepidum [ncbi taxid: 1097]
  5. Citrullus lanatus [ncbi taxid: 3654]
  6. Citrus unshiu [ncbi taxid: 55188]
  7. Dryocosmus kuriphilus [ncbi taxid: 310278]
  8. Dysidea etheria [ncbi taxid: 283597]
  9. Euphorbia escula [ncbi taxid: ]
  10. Guatteria dielsiana [ncbi taxid: ]
  11. Olea europaea subsp. cuspidata [ncbi taxid: 129566]
  12. Peltigera dolichorrhiza [ncbi taxid: 176453]
  13. Persea lingue [ncbi taxid: 128683]
  14. Phaseolus mungo [ncbi taxid: ]
  15. Pisum sativum [ncbi taxid: ]
  16. Pseudomonas savastanoi [ncbi taxid: 29438]
  17. Pycnarrhena ozantha [ncbi taxid: 2812727]
  18. Streptomyces atroolivaceus [ncbi taxid: 66869]
  19. Streptomyces mutabilis [ncbi taxid: 67332]
  20. Swartschewskia papyracea [ncbi taxid: 75886]
  21. Taiwanofungus camphoratus [ncbi taxid: 2696576]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-5025 indole-3-acetate biosynthesis IV (bacteria)
BioCyc:META_PWY-581 indole-3-acetate biosynthesis II
BioCyc:AGRO_PWY-5025 indole-3-acetate biosynthesis IV (bacteria)
BioCyc:META_PWY-3161 indole-3-acetate biosynthesis III (bacteria)
BioCyc:LEISH_PWY-581 IAA biosynthesis I
BioCyc:THAPS_PWY-581 IAA biosynthesis I
BioCyc:ARA_PWY-581 indole-3-acetate biosynthesis II
BioCyc:AGRO_PWY-3161 indole-3-acetate biosynthesis III (bacteria)
BioCyc:AURANTIMONAS_PWY-5025 indole-3-acetate biosynthesis IV (bacteria)
Plant Reactome:R-OAU-2744345 Metabolism and regulation
Plant Reactome:R-OAU-1119388 IAA biosynthesis VI (via indole-3-acetamide)
Plant Reactome:R-FVE-1119388 IAA biosynthesis VI (via indole-3-acetamide)
Plant Reactome:R-MES-2744345 Metabolism and regulation
Plant Reactome:R-MES-2744341 Hormone signaling, transport, and metabolism
Plant Reactome:R-TDI-2744345 Metabolism and regulation
Plant Reactome:R-TDI-1119388 IAA biosynthesis VI (via indole-3-acetamide)
Plant Reactome:R-DRO-2744345 Metabolism and regulation
Plant Reactome:R-OGU-2744341 Hormone signaling, transport, and metabolism
Plant Reactome:R-PTI-2744345 Metabolism and regulation
Plant Reactome:R-PTI-2744341 Hormone signaling, transport, and metabolism
View All Pathways