Indole-3-acetate (BioCAD00000012405)

blood cerebrospinal fluid (csf) feces saliva urine brain fibroblasts kidney liver placenta platelet

Metabolite Card

Formula: C10H9NO2 (175.0633)
SMILES: OC(=O)CC1=CNC2=C1C=CC=C2

Synonyms [en]

indoleacetic acid; indole-3-acetic acid; heteroauxin; 3-indoleacetic acid; (indol-3-yl)acetate; Indole-3-acetate

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Indole-3-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: BioCAD00000012405). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Indoleacetic acid (IAA) is a breakdown product of tryptophan metabolism and is often produced by the action of bacteria in the mammalian gut. Higher levels of IAA are associated with bacteria from Clostridium species including C. stricklandii, C. lituseburense, C. subterminale, and C. putrefaciens (PMID: 12173102). IAA can be found in Agrobacterium, Azospirillum, Bacillus, Bradyrhizobium, Clostridium, Enterobacter, Pantoea, Pseudomonas, Rhizobium (PMID: 12173102, PMID: 17555270, PMID: 12147474, PMID: 19400643, PMID: 9450337, PMID: 21397014) (https://link.springer.com/chapter/10.1007/978-1-4612-3084-7_7) (https://escholarship.org/uc/item/1bf1b5m3). Some endogenous production of IAA in mammalian tissues also occurs. It may be produced by the decarboxylation of tryptamine or the oxidative deamination of tryptophan. IAA frequently occurs at low levels in urine and has been found in elevated levels in the urine of patients with phenylketonuria (PMID: 13610897). IAA has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). Using material extracted from human urine, it was discovered by Kogl in 1933 that indoleacetic acid is also an important plant hormone (PMID: 13610897). Specifically, IAA is a member of the group of phytohormones called auxins. IAA is generally considered to be the most important native auxin. Plant cells synthesize IAA from tryptophan (Wikipedia). IAA and some derivatives can be oxidized by horseradish peroxidase (HRP) into cytotoxic species. IAA is only toxic after oxidative decarboxylation; the effect of IAA/HRP is thought to be due in part to the formation of methylene-oxindole, which may conjugate with DNA bases and protein thiols. IAA/HRP could be used as the basis for targeted cancer, a potential new role for plant auxins in cancer therapy (PMID: 11163327).

Cytoplasm Mitochondria
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 6505-45-9
  • CAS Registry Number: 87-51-4
  • PubChem: 4205
  • PubChem: 802
  • ChEBI: ChEBI:16411
  • HMDB: HMDB0000197
  • HMDB: HMDB00197
  • KEGG: C00954
  • NCBI MeSH: indoleacetic acid
  • Wikipedia: Indole-3-acetic acid
  • Wikipedia: Indole-3-acetic_acid
  • DrugBank: DB07950
  • RefMet: RM0135909
  • MoNA: AU279601
  • MoNA: AU279603
  • MoNA: AU279604
  • MoNA: AU279605
  • MoNA: AU279606
  • MoNA: BAF_UVA_POS000603
  • MoNA: BAF_UVA_POS000604
  • MoNA: BAF_UVA_POS000865
  • MoNA: BAF_UVA_POS000866
  • MoNA: BAF_UVA_POS000867
  • MoNA: CCMSLIB00000578058
  • MoNA: CCMSLIB00005464240
  • MoNA: CCMSLIB00005464241
  • MoNA: CCMSLIB00005464251
  • MoNA: CCMSLIB00005464252
  • MoNA: CCMSLIB00005720197
  • MoNA: CCMSLIB00005720507
  • MoNA: CCMSLIB00005720541
  • MoNA: CCMSLIB00005720802
  • MoNA: CCMSLIB00005720836
  • MoNA: CCMSLIB00005724307
  • MoNA: CCMSLIB00005724329
  • MoNA: EMBL-MCF_spec79775
  • MoNA: FiehnHILIC000080
  • MoNA: FiehnHILIC000965
  • MoNA: FiehnHILIC001662
  • MoNA: FiehnHILIC002762
  • MoNA: HMDB0000197_c_ms_1670
  • MoNA: HMDB0000197_c_ms_1705
  • MoNA: HMDB0000197_ms_ms_319
  • MoNA: HMDB0000197_ms_ms_320
  • MoNA: HMDB0000197_ms_ms_321
  • MoNA: JP001408
  • MoNA: KO001226
  • MoNA: KO001227
  • MoNA: KO001228
  • MoNA: KO001229
  • MoNA: KO001230
  • MoNA: KO003212
  • MoNA: KO003213
  • MoNA: KO003214
  • MoNA: KO003215
  • MoNA: KO003216
  • MoNA: KZ000036
  • MoNA: KZ000142
  • MoNA: KZ000143
  • MoNA: KZ000144
  • MoNA: LU019051
  • MoNA: LU019052
  • MoNA: LU019053
  • MoNA: LU019054
  • MoNA: LU019055
  • MoNA: LU019056
  • MoNA: MoNA010017
  • MoNA: MoNA010018
  • MoNA: MoNA010019
  • MoNA: MoNA010020
  • MoNA: MoNA010021
  • MoNA: MoNA010022
  • MoNA: MoNA016719
  • MoNA: MoNA016720
  • MoNA: MoNA023914
  • MoNA: MoNA023919
  • MoNA: MoNA032896
  • MoNA: MoNA032897
  • MoNA: MoNA032898
  • MoNA: MoNA033699
  • MoNA: MoNA033700
  • MoNA: MoNA033702
  • MoNA: MoNA034425
  • MoNA: MoNA034426
  • MoNA: MoNA035080
  • MoNA: MoNA035083
  • MoNA: MoNA035805
  • MoNA: MoNA035807
  • MoNA: MoNA036601
  • MoNA: MoNA036602
  • MoNA: MoNA036604
  • MoNA: MoNA037009
  • MoNA: MoNA037010
  • MoNA: MoNA037012
  • MoNA: MoNA037280
  • MoNA: MoNA037427
  • MoNA: MoNA037718
  • MoNA: MoNA038009
  • MoNA: MoNA038179
  • MoNA: MoNA038455
  • MoNA: MoNA038645
  • MoNA: MoNA038745
  • MoNA: MoNA038906
  • MoNA: MT000032
  • MoNA: PB000510
  • MoNA: PB000511
  • MoNA: PB000512
  • MoNA: PB000513
  • MoNA: PB000514
  • MoNA: PR010197
  • MoNA: PR010198
  • MoNA: PR020128
  • MoNA: PR100148
  • MoNA: PR100149
  • MoNA: PR100570
  • MoNA: PS025501
  • MoNA: PS025502
  • MoNA: PS025503
  • MoNA: PS025504
  • MoNA: PS025505
  • MoNA: PT102550
  • MoNA: PT102553
  • MoNA: PT202550
  • MoNA: RP016601
  • MoNA: RP016602
  • MoNA: RP016603
  • MoNA: RP016611
  • MoNA: RP016612
  • Metlin: METLIN_70
  • Coconut NaturalProduct: CNP0284198.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02678 1.2.1.3 indole-3-acetaldehyde:NAD+ oxidoreductase
KEGG:R02681 1.2.3.7 indole-3-acetaldehyde:oxygen oxidoreductase
KEGG:R03092 C00954 + C00007<=>C05834 + C00011
KEGG:R03093 3.5.5.1 3-indoleacetonitrile aminohydrolase
KEGG:R03094 2.4.1.121 UDPglucose:indole-3-acetate beta-D-glucosyltransferase
KEGG:R03095 6.3.2.20 indoleacetate:L-lysine ligase (ADP-forming)
KEGG:R03096 3.5.1.4 indole-3-acetamide amidohydrolase
KEGG:R03097 1.13.11.- C00954 + C00007<=>C05835
KEGG:R08609 2.5.1.- C00463<=>C00954
KEGG:R10181 1.14.13.168 indole-3-pyruvate,NADPH:oxygen oxidoreductase (1-hydroxylating, decarboxylating)
KEGG:R10452 2.1.1.278 S-adenosyl-L-methionine:(indol-3-yl)acetate O-methyltransferase
KEGG:R11730 1.14.13.235 (indol-3-yl)acetate,NADH:oxygen oxidoreductase (2-hydroxylating)
KEGG:R12303 4.1.1.115 (1H-indol-3-yl)acetate carboxy-lyase (skatole-forming)
KEGG:R12501 1.14.11.- C00954 + C00026 + C00007<=>C22202 + C00042 + C00011
KEGG:R12513 3.5.1.134 (indol-3-yl)acetyl-L-aspartate amidohydrolase
KEGG:R12968 6.2.1.75 (indol-3-yl)acetate:CoA ligase (AMP-forming)
View More
Organism Source

Taxonomy Source

  1. Aconitum heterophyllum [ncbi taxid: 279769]
  2. Alcea rosea [ncbi taxid: 65557]
  3. Alcyonium utinomii [ncbi taxid: ]
  4. Aldisa sanguinea [ncbi taxid: 2049529]
  5. Aloe africana [ncbi taxid: 1080010]
  6. Aloe ferox [ncbi taxid: 117798]
  7. Aloe spicata [ncbi taxid: 992642]
  8. Aloe vera [ncbi taxid: 34199]
  9. Alpinia blepharocalyx [ncbi taxid: 105668]
  10. Anabaena cylindrica [ncbi taxid: 1165]
  11. Anguilla japonica [ncbi taxid: 7937]
  12. Aonidiella aurantii [ncbi taxid: 30082]
  13. Aplysina archeri [ncbi taxid: 289390]
  14. Arabidopsis thaliana [ncbi taxid: 3702]
  15. Araiostegiella perdurans [ncbi taxid: ]
  16. Artemisia gilvescens [ncbi taxid: 2044567]
  17. Aspergillus carneus [ncbi taxid: 41282]
  18. Aspergillus fumigatus [ncbi taxid: 746128]
  19. Aspergillus striatus [ncbi taxid: 469280]
  20. Balanops australiana [ncbi taxid: 1118758]
  21. Billbergia buchholtzii [ncbi taxid: ]
  22. Brassica oleracea [ncbi taxid: 3712]
  23. Brassica oxyrrhina [ncbi taxid: 180534]
  24. Bryophyllum calycinum [ncbi taxid: ]
  25. Carapichea ipecacuanha [ncbi taxid: 77880]
  26. Castanea crenata [ncbi taxid: 103480]
  27. Ceratocystis fimbriata [ncbi taxid: 5158]
  28. Chamaebatia foliolosa [ncbi taxid: 140996]
  29. Chamaecyparis lawsoniana [ncbi taxid: 58030]
  30. Cheilanthes chusana [ncbi taxid: ]
  31. Chlorobaculum tepidum [ncbi taxid: 1097]
  32. Citrullus lanatus [ncbi taxid: 3654]
  33. Citrus sinensis [ncbi taxid: 2711]
  34. Citrus unshiu [ncbi taxid: 55188]
  35. Cleome hassleriana [ncbi taxid: ]
  36. Cortinarius odoratus [ncbi taxid: ]
  37. Corylus avellana [ncbi taxid: 13451]
  38. Cotinus coggygria [ncbi taxid: 269719]
  39. Dalbergia dolichopetala [ncbi taxid: ]
  40. Datura stramonium [ncbi taxid: 4076]
  41. Diospyros kaki [ncbi taxid: 35925]
  42. Dolichos lablab [ncbi taxid: ]
  43. Ecklonia kurome [ncbi taxid: ]
  44. Eleutherobia albiflora [ncbi taxid: ]
  45. epichloë festucae [ncbi taxid: ]
  46. Eucalyptus jenseni [ncbi taxid: ]
  47. Euonymus tingens [ncbi taxid: 1089406]
  48. Euphorbia cornigera [ncbi taxid: 2510634]
  49. Euphorbia escula [ncbi taxid: ]
  50. Glycine soja [ncbi taxid: 3848]
  51. Guatteria dielsiana [ncbi taxid: ]
  52. Gymnopus confluens [ncbi taxid: ]
  53. Homo sapiens [ncbi taxid: 9606]
  54. Hordeum vulgare [ncbi taxid: 4513]
  55. Hylocomium splendens [ncbi taxid: 53007]
  56. Isatis tinctoria [ncbi taxid: 161756]
  57. Kokoona reflexa [ncbi taxid: 1504447]
  58. Lathyrus maritimus [ncbi taxid: ]
  59. Lycopersicon esculentum [ncbi taxid: ]
  60. Lygodium flexuosum [ncbi taxid: 85330]
  61. Macrolepiota neomastoidea [ncbi taxid: ]
  62. Maesa ramentacea [ncbi taxid: 1526298]
  63. Malus pumila [ncbi taxid: 283210]
  64. Melolontha melolontha [ncbi taxid: 7061]
  65. Millettia laurentii [ncbi taxid: 2747815]
  66. Monodora tenuifolia [ncbi taxid: 306973]
  67. Mus musculus [ncbi taxid: 10090]
  68. Nicotiana tabacum [ncbi taxid: 4097]
  69. Nototodarus sloanii [ncbi taxid: 215440]
  70. Ocimum tenuiflorum [ncbi taxid: 204149]
  71. Oenanthe fistulosa [ncbi taxid: 254046]
  72. Olea europaea subsp. cuspidata [ncbi taxid: 129566]
  73. Panax ginseng [ncbi taxid: 4054]
  74. Peltigera dolichorrhiza [ncbi taxid: 176453]
  75. Penicillium janczewskii [ncbi taxid: 121612]
  76. Persea lingue [ncbi taxid: 128683]
  77. Persicaria tinctoria [ncbi taxid: 96455]
  78. Phaseolus mungo [ncbi taxid: ]
  79. Phaseolus vulgaris [ncbi taxid: 3885]
  80. Picea abies [ncbi taxid: 3329]
  81. Picea sitchensis [ncbi taxid: 3332]
  82. Picris evae [ncbi taxid: 379638]
  83. Pinus contorta [ncbi taxid: 3339]
  84. Pinus slyvestris [ncbi taxid: ]
  85. Pinus strobus [ncbi taxid: 3348]
  86. Pinus sylvestris [ncbi taxid: 3349]
  87. Pisum sativum [ncbi taxid: ]
  88. Pluchea odorata [ncbi taxid: 1548633]
  89. Prunus cerasus [ncbi taxid: 140311]
  90. Prunus domestica [ncbi taxid: 3758]
  91. Pseudoplexaura flagellosa [ncbi taxid: 287903]
  92. Pseudotsuga menziesii [ncbi taxid: 3357]
  93. Pycnarrhena ozantha [ncbi taxid: 2812727]
  94. Quercus robur [ncbi taxid: 38942]
  95. Raphanus sativus [ncbi taxid: 3726]
  96. Rhizopus suinus [ncbi taxid: ]
  97. Ricinus communis [ncbi taxid: 3988]
  98. Russula delica [ncbi taxid: 111140]
  99. Saccharina japonica [ncbi taxid: 88149]
  100. Saccharomyces cerevisiae [ncbi taxid: 4932]
  101. Salacia lehmbachii [ncbi taxid: 213839]
  102. Salvia yosgadensis [ncbi taxid: 1933769]
  103. Sideritis brevibracteata [ncbi taxid: ]
  104. Sideroxylon cubense [ncbi taxid: 362723]
  105. Streptomyces 195-02 [ncbi taxid: ]
  106. Streptomyces CRF14 [ncbi taxid: ]
  107. Streptomyces En-1 [ncbi taxid: ]
  108. Streptomyces fradiae NKZ-259 [ncbi taxid: ]
  109. Streptomyces griseoincarnatus SCF18 [ncbi taxid: ]
  110. Streptomyces matansis BG5 [ncbi taxid: ]
  111. Streptomyces pulcher CRF17 [ncbi taxid: ]
  112. Streptomyces RSF17 [ncbi taxid: ]
  113. Streptomyces sp. KLBMP S0051 [ncbi taxid: 1691592]
  114. Streptomyces sp. NEAU-S7GS2 [ncbi taxid: 2202000]
  115. Streptomyces sp. OC1610.4 [ncbi taxid: ]
  116. Streptomyces vinaceus CRF2 [ncbi taxid: ]
  117. Swartschewskia papyracea [ncbi taxid: 75886]
  118. Taiwanofungus camphoratus [ncbi taxid: 2696576]
  119. Vicia amurensis [ncbi taxid: 154495]
  120. Vigna unguiculata var. sesquipedalis [ncbi taxid: ]
  121. Viguiera decurrens [ncbi taxid: 1048926]
  122. Vitis vinifera [ncbi taxid: 29760]
  123. Zea mays [ncbi taxid: 4577]

Pathway Synthetic

pathway id name
BioCyc:LEISH_PWY-581 IAA biosynthesis I
Plant Reactome:R-OSA-9826798 Gravitropism under normal or artificial gravity environments
Plant Reactome:R-OSA-9030557 Lateral root initiation
Plant Reactome:R-OSA-9030693 Lateral root development
Plant Reactome:R-OSA-9928372 Root gravitropism
Plant Reactome:R-HVU-9030769 Growth and developmental processes
Plant Reactome:R-HVU-9035605 Regulation of seed size
Plant Reactome:R-OAU-9030769 Growth and developmental processes
Plant Reactome:R-OAU-9035605 Regulation of seed size
Plant Reactome:R-OAU-2744345 Metabolism and regulation
Plant Reactome:R-OAU-1119388 IAA biosynthesis VI (via indole-3-acetamide)
Plant Reactome:R-TAE-1119486 IAA biosynthesis I
Plant Reactome:R-TAE-5608118 Auxin signalling
Plant Reactome:R-FVE-5608118 Auxin signalling
Plant Reactome:R-FVE-1119388 IAA biosynthesis VI (via indole-3-acetamide)
Plant Reactome:R-MES-5608118 Auxin signalling
Plant Reactome:R-MES-2744345 Metabolism and regulation
Plant Reactome:R-MES-2744341 Hormone signaling, transport, and metabolism
Plant Reactome:R-MES-8868860 Auxin transport
Plant Reactome:R-TDI-2744345 Metabolism and regulation
View All Pathways