848:, and possibly carcinogenic based on animal data. It may cause adverse reproductive effects (fetotoxicity) and birth defects based on animal data. No human data as of 2008. It is listed as a potential skin, eye, and respiratory irritant, and users are warned not to ingest it. Protocols for ingestion, inhalation, and skin/eye exposure are standard for moderately poisonous compounds and include thorough rinsing in the case of skin and eyes, fresh air in the case of inhalation, and immediately contacting a physician in all cases to determine the best course of action and not to induce vomiting when of ingested. The
323:
228:
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35:
1418:
Kathrin I.; Jäger, Evelyn; Guevara, Carina
Ramallo; Sobeh, Mansour; Hielscher, Thomas; Poschet, Gernot; Reinhardt, Annekathrin; Hassel, Jessica C.; Zapatka, Marc; Hahn, Udo; von Deimling, Andreas; Hopf, Carsten; Schlichting, Rita; Escher, Beate I.; Burhenne, Jürgen; Haefeli, Walter E.; Ishaque, Naveed; Böhme, Alexander; Schäuble, Sascha; Thedieck, Kathrin; Trump, Saskia; Seiffert, Martina; Opitz, Christiane A. (2020-08-17).
480:
592:. A 2015 experiment showed that a high-tryptophan diet can decrease serum levels of IAA in mice, but that in humans, protein consumption has no reliably predictable effect on plasma IAA levels. Human cells have been known to produce IAA in vitro since the 1950s, and the critical biosynthesis gene IL4I1 has been identified.
1417:
Sadik, Ahmed; Somarribas
Patterson, Luis F.; Öztürk, Selcen; Mohapatra, Soumya R.; Panitz, Verena; Secker, Philipp F.; Pfänder, Pauline; Loth, Stefanie; Salem, Heba; Prentzell, Mirja Tamara; Berdel, Bianca; Iskar, Murat; Faessler, Erik; Reuter, Friederike; Kirst, Isabelle; Kalter, Verena; Foerster,
881:
in rats during the early stage of cerebral cortex development. IAA treatment of pregnant rats, at a dose of 1 gram per kg of body weight per day, decreased the locomotor activities of rat embryos/fetuses; treatment with IAA and analog 1(methyl)-IAA resulted in apoptosis of neuroepithelial cell and
861:. Humans typically have relatively high levels of IAA in their serum (~1 ÎĽM), but this can be increased further in certain disease conditions and can be a poor prognostic marker for cardiovascular health. Whether this IAA originates from endogenous biosynthesis via IL4I1 or gut
640:(ARF) proteins, forming a heterodimer, suppressing ARF activity. In 1997 it was described how ARFs bind to auxin-response gene elements in promoters of auxin regulated genes, generally activating transcription of that gene when an Aux/IAA protein is not bound.
2249:
Dou, Laetitia; Sallée, Marion; Cerini, Claire; Poitevin, Stéphane; Gondouin, Bertrand; Jourde-Chiche, Noemie; Fallague, Karim; Brunet, Philippe; Calaf, Raymond; Dussol, Bertrand; Mallet, Bernard; Dignat-George, Françoise; Burtey, Stephane (April 2015).
781:
Ltd. After 7 years of research he changed the direction of his study to try the same substances at high concentrations in order to stop plant growth. In 1940 he published his finding that IAA killed broadleaf plants within a cereal field.
2472:
Dalmazzo LF, Santana-Lemos BA, Jácomo RH, Garcia AB, Rego EM, da
Fonseca LM, FalcĂŁo RP (2011). "Antibody-targeted horseradish peroxidase associated with indole-3-acetic acid induces apoptosis in vitro in hematological malignancies".
1365:
Zhang, Xia; Gan, Min; Li, Jingyun; Li, Hui; Su, Meicheng; Tan, Dongfei; Wang, Shaolei; Jia, Man; Zhang, Liguo; Chen, Gang (2020-08-31). "An endogenous indole pyruvate pathway for tryptophan metabolism mediated by IL4I1".
929:(HRP) could be used in targeted cancer therapy. Radical-IAA molecules would attach to cells marked by HRP and HRP reactive cells would be selectively killed. In 2010 in vitro experiments proved this concept of IAA as an
801:
published their synthesis in 1941. When sprayed on broad-leaf dicot plants, they induce rapid, uncontrolled growth, eventually killing them. First introduced in 1946, these herbicides were in widespread use in
852:
health hazard rating for IAA is 2, which denotes a risk of temporary incapacitation with intense or prolonged, but not chronic exposure, and a possibility of residual injury. IAA is a direct ligand of the
699:
formation. The fungus uses a multidrug and toxic extrusion (MATE) transporter Mte1. Research into IAA-producing fungi to promote plant growth and protection in sustainable agriculture is underway.
2410:
Jeong YM, Oh MH, Kim SY, Li H, Yun HY, Baek KJ, Kwon NS, Kim WY, Kim DS (2010). "Indole-3-acetic acid/horseradish peroxidase induces apoptosis in TCCSUP human urinary bladder carcinoma cells".
608:
with all subsequent results for plant growth and development. On a larger scale, IAA serves as signaling molecule necessary for development of plant organs and coordination of growth.
2025:
Templeman W. G.; Marmoy C. J. (2008). "The effect upon the growth of plants of watering with solutions of plant-growth substances and of seed dressings containing these materials".
493:
1155:
Sugawara, Satoko; Hishiyama, Shojiro; Jikumaru, Yusuke; Hanada, Atsushi; Nishimura, Takeshi; Koshiba, Tomokazu; Zhao, Yunde; Kamiya, Yuji; Kasahara, Hiroyuki (2009).
1037:
Mashiguchi, Kiyoshi; Tanaka, Keita; Sakai, Tatsuya; Sugawara, Satoko; Kawaide, Hiroshi; Natsume, Masahiro; Hanada, Atsushi; Yaeno, Takashi; et al. (2011).
372:
2192:"Indole-3-Acetic Acid Alleviates Nonalcoholic Fatty Liver Disease in Mice via Attenuation of Hepatic Lipogenesis, and Oxidative and Inflammatory Stress"
1842:"Catabolic pathway for the production of skatole and indoleacetic acid by the acetogen Clostridium drakei, Clostridium scatologenes, and swine manure"
2575:
1096:
Won, Christina; Shen, Xiangling; Mashiguchi, Kiyoshi; Zheng, Zuyu; Dai, Xinhua; Cheng, Youfa; Kasahara, Hiroyuki; Kamiya, Yuji; et al. (2011).
1609:
Kerchev P, Muhlenbock P, Denecker J, Morreel K, Hoeberichts FA, van der Kelen K, Vandorpe M, Nguyen L, Audenaert D, van
Breusegem F (Feb 2015).
1650:
Patten CL, Blakney AJ, Coulson TJ (Nov 2013). "Activity, distribution and function of indole-3-acetic acid biosynthetic pathways in bacteria".
899:
1971:
Fox, Sidney W.; Bullock, Milon W. (1951). "Synthesis of
Indoleacetic Acid from Glutamic Acid and a Proposed Mechanism for the Conversion".
2309:"High-coverage metabolomics uncovers microbiota-driven biochemical landscape of interorgan transport and gut-brain communication in mice"
1222:
Howard Stibbs Henry; Richard Seed John (1975). "Short-Term
Metabolism of Tryptophan in Rats Infected with Trypanosoma brucei gambiense".
659:
IAA production is widespread among environmental bacteria that inhabit soils, waters, but also plant and animal hosts. Distribution and
531:
class. It is the best known of the auxins, and has been the subject of extensive studies by plant physiologists. IAA is a derivative of
1998:
Majima, RikĹŤ; Hoshino, Toshio (1925). "Synthetische
Versuche in der Indol-Gruppe, VI.: Eine neue Synthese von β-Indolyl-alkylaminen".
2437:
Wardman P (2002). "Indole-3-acetic acids and horseradish peroxidase: a new prodrug/enzyme combination for targeted cancer therapy".
858:
790:
337:
933:
when used in preclinical studies of targeted cancer therapy, as it induced apoptosis in bladder and in hematological malignancies.
2709:
833:
Little research has been conducted on the effects of IAA on humans and toxicity data are limited. No data on human carcinogenic,
1736:"Biosynthesis and Secretion of Indole-3-Acetic Acid and Its Morphological Effects on Tricholoma vaccinum-Spruce Ectomycorrhiza"
786:
1098:"Conversion of tryptophan to indole-3-acetic acid by TRYPTOPHAN AMINOTRANSFERASES OF ARABIDOPSIS and YUCCAs in Arabidopsis"
1318:"Formation of indole-3-acetic acid and tryptamine in animals: a method for estimation of indole-3-acetic acid in tissues"
561:, but there is also a biosynthetic pathway independent of tryptophan. Plants mainly produce IAA from tryptophan through
500:
2568:
919:
778:
621:
588:
280:
895:
617:
301:
785:
The search for an acid with a longer half life, i.e. a metabolically and environmentally more stable compound led to
2129:"Expression of the Human Aryl Hydrocarbon Receptor Complex in Yeast ACTIVATION OF TRANSCRIPTION BY INDOLE COMPOUNDS"
125:
865:
is unknown. A 2021 study found that normal mice had an average of 3.7 times as much IAA in their feces compared to
841:
2079:
1574:
Ulmasov, T; Hagen, G; Guilfoyle, TJ (1997). "ARF1, a transcription factor that binds to auxin response elements".
2694:
854:
903:
822:
747:
869:
mice, suggesting that the mammalian microbiome contributes significantly to the overall circulating amount.
535:, containing a carboxymethyl substituent. It is a colorless solid that is soluble in polar organic solvents.
2561:
769:
Many methods for its synthesis have been developed since its original synthesis from indole-3-acetonitrile.
1695:"Regulation of indole-3-acetic acid biosynthesis by branched-chain amino acids in Enterobacter cloacae UW5"
566:
562:
223:
2114:
926:
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2653:
818:
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660:
165:
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2320:
1853:
1793:"Indole-3-acetic acid: A widespread physiological code in interactions of fungi with other organisms"
1747:
1734:
Krause K, Henke C, Asiimwe T, Ulbricht A, Klemmer S, Schachtschabel D, Boland W, Kothe E (Oct 2015).
1270:
1168:
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557:. Plants can synthesize IAA by several independent biosynthetic pathways. Four of them start from
318:
91:
2633:
2498:
2166:
1675:
1507:
1457:
1399:
1186:
1899:"Microbial metabolites of tryptophan in the intestinal tract with special reference to skatole"
663:
of the involved enzymes suggests these pathways play a role beyond plant-microbe interactions.
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1420:"IL4I1 Is a Metabolic Immune Checkpoint that Activates the AHR and Promotes Tumor Progression"
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Registry of Toxic
Effects of Chemical Substances (RTECS). Page last updated:November 8, 2017.
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1001:
962:
866:
644:
625:
458:
395:
1157:"Biochemical analyses of indole-3-acetaldoxime-dependent auxin biosynthesis in Arabidopsis"
578:
In rats, IAA is a product of both endogenous and colonic microbial metabolism from dietary
289:
2689:
2605:
1259:"The Influence of Dietary Protein Intake on Mammalian Tryptophan and Phenolic Metabolites"
1005:
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2307:
Lai, Yunjia; Liu, Chih-Wei; Yang, Yifei; Hsiao, Yun-Chung; Ru, Hongyu; Lu, Kun (2021).
2284:
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1841:
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1735:
1611:"Activation of auxin signalling counteracts photorespiratory H2O2-dependent cell death"
1293:
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1199:
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1132:
1097:
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1038:
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989:
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and analogs of IAA. Robert
Pokorny an industrial chemist for the C.B. Dolge Company in
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17:
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1939:
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1436:
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significantly decreased brain sizes relative to body weight in embryonic rats.
616:
IAA enters the plant cell nucleus and binds to a protein complex composed of a
2368:"Effect of Indole-3-Acetic Acid Derivatives on Neuroepithelium in Rat Embryos"
1840:
Whitehead, T. R.; Price, N. P.; Drake, H. L.; Cotta, M. A. (25 January 2008).
862:
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696:
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2011:
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InChI=1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)
2658:
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2610:
1915:
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1711:
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1181:
1122:
1063:
915:
911:
907:
891:
857:, and IAA treatment of mice indicate liver-protective effects in a model of
629:
356:
InChI=1/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)
2544:
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1924:
1865:
1759:
849:
759:
648:
196:
2065:
2052:
Pokorny Robert (1941). "New
Compounds. Some Chlorophenoxyacetic Acids".
1984:
1190:
651:
mutants. This suggests a role for auxin signalling in stress tolerance.
205:
2384:
2367:
2208:
2190:
Ji, Yun; Gao, Yuan; Chen, Hong; Yin, Yue; Zhang, Weizhen (2019-09-03).
1542:
1316:
Weissbach, H.; King, W.; Sjoerdsma, A.; Udenfriend, S. (January 1959).
777:
William Gladstone Tempelman studied substances for growth promotion at
707:
677:
Fungi can form a fungal mantle around roots of perennial plants called
256:
1627:
1610:
2366:
Furukawa, Satoshi; Usuda, Koji; Abe, Masayoshi; Ogawa, Izumi (2005).
2252:"The cardiovascular effect of the uremic solute indole-3 acetic acid"
1527:"Aux/IAA proteins contain a potent transcriptional repression domain"
727:
692:
682:
532:
156:
1495:
470:
Except where otherwise noted, data are given for materials in their
950:
244:
2600:
810:
637:
633:
554:
544:
528:
136:
124:
114:
2553:
691:
was shown to produce IAA from tryptophan and excrete it from its
600:
As all auxins, IAA has many different effects, such as inducing
235:
2557:
2000:
Berichte der Deutschen Chemischen Gesellschaft (A and B Series)
669:
can produce IAA, from aromatic and branched-chain amino acids.
550:
306:
1791:
Fu SF, Wei JY, Chen HW, Liu YY, Lu HY, Chou JY (Aug 2015).
452:
168 to 170 °C (334 to 338 °F; 441 to 443 K)
1693:
Parsons CV, Harris DM, Patten CL, et al. (Sep 2015).
1477:"Function and regulation of cullin-RING ubiquitin ligases"
636:
proteins with increased speed. Aux/IAA proteins bind to
2509:
Wayne AS, Fitzgerald DJ, Kreitman RJ, Pastan I (2014).
925:
In 2002 it had been hypothesized that IAA coupled with
488:
990:"Auxin Biosynthesis and Its Role in Plant Development"
726:
Chemically, it can be synthesized by the reaction of
1039:"The main auxin biosynthesis pathway in Arabidopsis"
549:
IAA is predominantly produced in cells of the apex (
2115:"Indole-3-Acetic Acid: Material Safety Data Sheet."
746:Alternatively the compound has been synthesized by
695:. This induced branching in cultures, and enhanced
464:insoluble in water. Soluble in ethanol to 50mg/mL
268:
1938:Johnson, Herbert E.; Crosby, Donald G. (1964).
1257:Poesen R, Mutsaers HA, et al. (Oct 2015).
1161:Proceedings of the National Academy of Sciences
1102:Proceedings of the National Academy of Sciences
1043:Proceedings of the National Academy of Sciences
837:, or developmental effects have been created.
758:. Glutamic acid was converted to the necessary
565:. IAA is also produced from tryptophan through
100:
586:. This was first observed in rats infected by
2569:
2256:Journal of the American Society of Nephrology
951:"Why plants need more than one type of auxin"
894:-inducing ligand in mammals. As of 2010, the
8:
1525:Tiwari, SB; Hagen, G; Guilfoyle, TJ (2004).
2576:
2562:
2554:
2405:
2403:
1903:The American Journal of Clinical Nutrition
1368:Journal of Agricultural and Food Chemistry
647:-dependent cell death in photorespiratory
321:
226:
184:
26:
2534:
2383:
2342:
2332:
2283:
2225:
2207:
2144:
1914:
1873:
1816:
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1435:
1333:
1292:
1282:
1198:
1180:
1131:
1121:
1072:
1062:
1013:
710:, the odorant in feces, is produced from
523:) is the most common naturally occurring
288:
1973:Journal of the American Chemical Society
1897:Yokoyama, M. T.; Carlson, J. R. (1979).
734:in the presence of base at 250 °C:
941:
377:
342:
317:
204:
1846:Applied and Environmental Microbiology
217:
2372:The Journal of Toxicological Sciences
1006:10.1146/annurev-arplant-042809-112308
900:p38 mitogen-activated protein kinases
349:Key: SEOVTRFCIGRIMH-UHFFFAOYSA-N
164:
144:
7:
2080:"PGR Planofix - Crop Science India"
1322:The Journal of Biological Chemistry
949:Simon, Sibu; Petrášek, Jan (2011).
359:Key: SEOVTRFCIGRIMH-UHFFFAOYAT
259:
243:
2039:10.1111/j.1744-7348.1940.tb07517.x
898:are as follows: IAA/HRP activates
25:
2127:Miller, Charles A. (1997-12-26).
1475:Pekker, MD; Deshaies, RJ (2005).
859:non-alcoholic fatty liver disease
829:Mammalian toxicity/health effects
813:analogs on the market for use in
791:2,4,5-trichlorophenoxyacetic acid
738:
478:
413:
407:
33:
2133:Journal of Biological Chemistry
809:Other less expensive synthetic
474:(at 25 °C , 100 kPa).
994:Annual Review of Plant Biology
967:10.1016/j.plantsci.2010.12.007
787:2,4-dichlorophenoxyacetic acid
416:
401:
1:
2487:10.1016/j.leukres.2010.11.025
1809:10.1080/15592324.2015.1048052
1588:10.1126/science.276.5320.1865
1335:10.1016/S0021-9258(18)70339-6
773:History and synthetic analogs
553:) and very young leaves of a
2527:10.1182/blood-2014-01-492256
1664:10.3109/1040841X.2012.716819
1284:10.1371/journal.pone.0140820
920:poly(adp-ribose) polymerases
896:signal transduction pathways
806:by the middle of the 1950s.
779:Imperial Chemical Industries
622:ubiquitin-conjugating enzyme
589:Trypanosoma brucei gambiense
2511:"Immunotoxins for leukemia"
618:ubiquitin-activating enzyme
2726:
2334:10.1038/s41467-021-26209-8
1959:, vol. 5, p. 654
1437:10.1016/j.cell.2020.07.038
844:as mutagenic to mammalian
542:
2629:
2591:
2103:"1H-Indole-3-acetic acid"
2027:Annals of Applied Biology
855:aryl hydrocarbon receptor
468:
388:
368:
333:
84:
62:
46:
41:
32:
2451:10.2174/1381612023394610
2146:10.1074/jbc.272.52.32824
2084:www.cropscience.bayer.in
2012:10.1002/cber.19250580917
1380:10.1021/acs.jafc.0c03735
1236:10.1093/infdis/131.4.459
904:c-Jun N-terminal kinases
823:1-naphthaleneacetic acid
748:Fischer indole synthesis
718:gives the methylindole.
2710:Plant growth regulators
1182:10.1073/pnas.0811226106
1123:10.1073/pnas.1108436108
1064:10.1073/pnas.1108434108
714:via indoleacetic acid.
681:. A fungus specific to
56:-Indol-3-yl)acetic acid
2654:Plant peptide hormones
2268:10.1681/ASN.2013121283
1940:"Indole-3-acetic Acid"
1740:Appl Environ Microbiol
927:horseradish peroxidase
873:Developmental toxicity
73:-Indole-3-acetic acid,
2313:Nature Communications
1916:10.1093/ajcn/32.1.173
1712:10.1093/femsle/fnv153
840:IAA is listed in its
819:indole-3-butyric acid
799:Westport, Connecticut
661:substrate specificity
638:auxin response factor
612:Plant gene regulation
567:indole-3-acetaldoxime
563:indole-3-pyruvic acid
65:Indole-3-acetic acid,
28:Indole-3-acetic acid
1866:10.1128/AEM.02458-07
1760:10.1128/AEM.01991-15
1430:(5): 1252–1270.e34.
988:Zhao, Yunde (2010).
764:Strecker degradation
703:Skatole biosynthesis
666:Enterobacter cloacae
655:Bacterial physiology
628:(E3), resulting in
572:Arabidopsis thaliana
513:Indole-3-acetic acid
48:Preferred IUPAC name
2325:2021NatCo..12.6000L
2139:(52): 32824–32829.
2066:10.1021/ja01851a601
1985:10.1021/ja01150a094
1858:2008ApEnM..74.1950W
1752:2015ApEnM..81.7003K
1699:FEMS Microbiol Lett
1374:(39): 10678–10684.
1275:2015PLoSO..1040820P
1173:2009PNAS..106.5430S
1114:2011PNAS..10818518W
1055:2011PNAS..10818512M
914:, which results in
688:Tricholoma vaccinum
459:Solubility in water
434: g·mol
380:O=C(O)Cc1cc2ccccc12
67:indolylacetic acid,
29:
2634:24-Epibrassinolide
2385:10.2131/jts.30.165
2209:10.3390/nu11092062
1797:Plant Signal Behav
1652:Crit Rev Microbiol
1615:Plant Cell Environ
1543:10.1105/tpc.017384
795:phenoxy herbicides
596:Biological effects
501:Infobox references
75:indoleacetic acid,
27:
2677:
2676:
1957:Collected Volumes
1945:Organic Syntheses
1628:10.1111/pce.12250
1582:(5320): 1865–68.
643:IAA inhibits the
509:Chemical compound
507:
506:
302:CompTox Dashboard
126:Interactive image
18:Indoleacetic acid
16:(Redirected from
2717:
2695:Plant physiology
2606:Brassinosteroids
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2548:
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2439:Curr. Pharm. Des
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2054:J. Am. Chem. Soc
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2022:
2016:
2015:
1995:
1989:
1988:
1979:(6): 2754–2755.
1968:
1962:
1960:
1953:
1935:
1929:
1928:
1918:
1894:
1888:
1887:
1877:
1837:
1831:
1830:
1820:
1788:
1782:
1781:
1771:
1731:
1725:
1724:
1714:
1690:
1684:
1683:
1647:
1641:
1640:
1630:
1606:
1600:
1599:
1571:
1565:
1564:
1554:
1522:
1516:
1515:
1481:
1472:
1466:
1465:
1439:
1414:
1408:
1407:
1362:
1356:
1355:
1337:
1313:
1307:
1306:
1296:
1286:
1269:(10): e0140820.
1254:
1248:
1247:
1219:
1213:
1212:
1202:
1184:
1152:
1146:
1145:
1135:
1125:
1108:(45): 18518–23.
1093:
1087:
1086:
1076:
1066:
1034:
1028:
1027:
1017:
985:
979:
978:
946:
793:(2,4,5-T), both
742:
673:Fungal symbiosis
645:photorespiratory
626:ubiquitin ligase
491:
485:
482:
481:
433:
418:
415:
409:
403:
396:Chemical formula
326:
325:
310:
308:
292:
272:
261:
247:
230:
219:
208:
188:
168:
148:
128:
104:
37:
30:
21:
2725:
2724:
2720:
2719:
2718:
2716:
2715:
2714:
2680:
2679:
2678:
2673:
2625:
2587:
2582:
2552:
2508:
2471:
2470:
2466:
2445:(15): 1363–74.
2436:
2435:
2431:
2409:
2408:
2401:
2365:
2364:
2360:
2306:
2305:
2301:
2248:
2247:
2243:
2189:
2188:
2184:
2175:
2173:
2126:
2125:
2121:
2113:
2109:
2101:
2097:
2088:
2086:
2078:
2077:
2073:
2051:
2050:
2046:
2024:
2023:
2019:
1997:
1996:
1992:
1970:
1969:
1965:
1955:
1937:
1936:
1932:
1896:
1895:
1891:
1839:
1838:
1834:
1803:(8): e1048052.
1790:
1789:
1785:
1746:(20): 7003–11.
1733:
1732:
1728:
1692:
1691:
1687:
1649:
1648:
1644:
1608:
1607:
1603:
1573:
1572:
1568:
1524:
1523:
1519:
1496:10.1038/nrm1547
1479:
1474:
1473:
1469:
1416:
1415:
1411:
1364:
1363:
1359:
1315:
1314:
1310:
1256:
1255:
1251:
1221:
1220:
1216:
1154:
1153:
1149:
1095:
1094:
1090:
1049:(45): 18512–7.
1036:
1035:
1031:
987:
986:
982:
948:
947:
943:
939:
918:activation and
888:
875:
831:
775:
756:phenylhydrazine
724:
716:Decarboxylation
705:
675:
657:
614:
604:elongation and
598:
547:
541:
510:
503:
498:
497:
496: ?)
487:
483:
479:
475:
461:
431:
421:
412:
406:
398:
384:
381:
376:
375:
364:
361:
360:
357:
351:
350:
347:
341:
340:
329:
311:
304:
295:
275:
262:
250:
211:
191:
171:
151:
131:
118:
107:
94:
80:
78:
76:
74:
68:
66:
58:
57:
23:
22:
15:
12:
11:
5:
2723:
2721:
2713:
2712:
2707:
2702:
2697:
2692:
2682:
2681:
2675:
2674:
2672:
2671:
2669:Strigolactones
2666:
2664:Salicylic acid
2661:
2656:
2651:
2646:
2641:
2636:
2630:
2627:
2626:
2624:
2623:
2618:
2613:
2608:
2603:
2598:
2592:
2589:
2588:
2585:Plant hormones
2583:
2581:
2580:
2573:
2566:
2558:
2551:
2550:
2521:(16): 2470–7.
2464:
2429:
2399:
2358:
2319:(6000): 6000.
2299:
2262:(4): 876–887.
2241:
2182:
2119:
2117:November 2008.
2107:
2095:
2071:
2044:
2033:(4): 453–471.
2017:
1990:
1963:
1930:
1909:(1): 173–178.
1889:
1832:
1783:
1726:
1705:(18): fnv153.
1685:
1658:(4): 395–415.
1642:
1601:
1566:
1517:
1467:
1409:
1357:
1308:
1249:
1230:(4): 459–462.
1214:
1167:(13): 5430–5.
1147:
1088:
1029:
980:
940:
938:
935:
906:. It induces
887:
884:
874:
871:
830:
827:
774:
771:
744:
743:
723:
720:
704:
701:
679:ectomycorrhiza
674:
671:
656:
653:
630:ubiquitination
613:
610:
597:
594:
543:Main article:
540:
537:
508:
505:
504:
499:
477:
476:
472:standard state
469:
466:
465:
462:
457:
454:
453:
450:
444:
443:
440:
436:
435:
429:
423:
422:
419:
410:
404:
399:
394:
391:
390:
386:
385:
383:
382:
379:
371:
370:
369:
366:
365:
363:
362:
358:
355:
354:
352:
348:
345:
344:
336:
335:
334:
331:
330:
328:
327:
314:
312:
300:
297:
296:
294:
293:
285:
283:
277:
276:
274:
273:
265:
263:
255:
252:
251:
249:
248:
240:
238:
232:
231:
221:
213:
212:
210:
209:
201:
199:
193:
192:
190:
189:
181:
179:
173:
172:
170:
169:
161:
159:
153:
152:
150:
149:
141:
139:
133:
132:
130:
129:
121:
119:
112:
109:
108:
106:
105:
97:
95:
90:
87:
86:
82:
81:
64:
60:
59:
51:
50:
44:
43:
39:
38:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2722:
2711:
2708:
2706:
2703:
2701:
2698:
2696:
2693:
2691:
2688:
2687:
2685:
2670:
2667:
2665:
2662:
2660:
2657:
2655:
2652:
2650:
2647:
2645:
2642:
2640:
2637:
2635:
2632:
2631:
2628:
2622:
2619:
2617:
2614:
2612:
2609:
2607:
2604:
2602:
2599:
2597:
2596:Abscisic acid
2594:
2593:
2590:
2586:
2579:
2574:
2572:
2567:
2565:
2560:
2559:
2556:
2546:
2542:
2537:
2532:
2528:
2524:
2520:
2516:
2512:
2504:
2500:
2496:
2492:
2488:
2484:
2481:(5): 657–62.
2480:
2476:
2468:
2465:
2460:
2456:
2452:
2448:
2444:
2440:
2433:
2430:
2425:
2421:
2417:
2413:
2406:
2404:
2400:
2395:
2391:
2386:
2381:
2378:(3): 165–74.
2377:
2373:
2369:
2362:
2359:
2354:
2350:
2345:
2340:
2335:
2330:
2326:
2322:
2318:
2314:
2310:
2303:
2300:
2295:
2291:
2286:
2281:
2277:
2273:
2269:
2265:
2261:
2257:
2253:
2245:
2242:
2237:
2233:
2228:
2223:
2219:
2215:
2210:
2205:
2201:
2197:
2193:
2186:
2183:
2172:
2168:
2164:
2160:
2156:
2152:
2147:
2142:
2138:
2134:
2130:
2123:
2120:
2116:
2111:
2108:
2104:
2099:
2096:
2085:
2081:
2075:
2072:
2067:
2063:
2059:
2055:
2048:
2045:
2040:
2036:
2032:
2028:
2021:
2018:
2013:
2009:
2006:(9): 2042–6.
2005:
2001:
1994:
1991:
1986:
1982:
1978:
1974:
1967:
1964:
1958:
1951:
1947:
1946:
1941:
1934:
1931:
1926:
1922:
1917:
1912:
1908:
1904:
1900:
1893:
1890:
1885:
1881:
1876:
1871:
1867:
1863:
1859:
1855:
1852:(6): 1950–3.
1851:
1847:
1843:
1836:
1833:
1828:
1824:
1819:
1814:
1810:
1806:
1802:
1798:
1794:
1787:
1784:
1779:
1775:
1770:
1765:
1761:
1757:
1753:
1749:
1745:
1741:
1737:
1730:
1727:
1722:
1718:
1713:
1708:
1704:
1700:
1696:
1689:
1686:
1681:
1677:
1673:
1669:
1665:
1661:
1657:
1653:
1646:
1643:
1638:
1634:
1629:
1624:
1621:(2): 253–65.
1620:
1616:
1612:
1605:
1602:
1597:
1593:
1589:
1585:
1581:
1577:
1570:
1567:
1562:
1558:
1553:
1548:
1544:
1540:
1537:(2): 533–43.
1536:
1532:
1528:
1521:
1518:
1513:
1509:
1505:
1501:
1497:
1493:
1489:
1485:
1478:
1471:
1468:
1463:
1459:
1455:
1451:
1447:
1443:
1438:
1433:
1429:
1425:
1421:
1413:
1410:
1405:
1401:
1397:
1393:
1389:
1385:
1381:
1377:
1373:
1369:
1361:
1358:
1353:
1349:
1345:
1341:
1336:
1331:
1327:
1323:
1319:
1312:
1309:
1304:
1300:
1295:
1290:
1285:
1280:
1276:
1272:
1268:
1264:
1260:
1253:
1250:
1245:
1241:
1237:
1233:
1229:
1225:
1218:
1215:
1210:
1206:
1201:
1196:
1192:
1188:
1183:
1178:
1174:
1170:
1166:
1162:
1158:
1151:
1148:
1143:
1139:
1134:
1129:
1124:
1119:
1115:
1111:
1107:
1103:
1099:
1092:
1089:
1084:
1080:
1075:
1070:
1065:
1060:
1056:
1052:
1048:
1044:
1040:
1033:
1030:
1025:
1021:
1016:
1011:
1007:
1003:
999:
995:
991:
984:
981:
976:
972:
968:
964:
961:(3): 454–60.
960:
956:
955:Plant Science
952:
945:
942:
936:
934:
932:
928:
923:
921:
917:
913:
909:
905:
901:
897:
893:
885:
883:
880:
877:IAA produces
872:
870:
868:
864:
860:
856:
851:
847:
846:somatic cells
843:
838:
836:
828:
826:
824:
820:
816:
812:
807:
805:
800:
796:
792:
788:
783:
780:
772:
770:
767:
765:
761:
757:
753:
752:glutamic acid
749:
741:
737:
736:
735:
733:
732:glycolic acid
729:
721:
719:
717:
713:
709:
702:
700:
698:
694:
690:
689:
684:
680:
672:
670:
668:
667:
662:
654:
652:
650:
646:
641:
639:
635:
631:
627:
623:
619:
611:
609:
607:
606:cell division
603:
595:
593:
591:
590:
585:
581:
576:
574:
573:
568:
564:
560:
556:
552:
546:
538:
536:
534:
530:
526:
525:plant hormone
522:
518:
514:
502:
495:
490:
473:
467:
463:
460:
456:
455:
451:
449:
448:Melting point
446:
445:
441:
438:
437:
430:
428:
425:
424:
400:
397:
393:
392:
387:
378:
374:
367:
353:
343:
339:
332:
324:
320:
319:DTXSID5020738
316:
315:
313:
303:
299:
298:
291:
287:
286:
284:
282:
279:
278:
271:
267:
266:
264:
258:
254:
253:
246:
242:
241:
239:
237:
234:
233:
229:
225:
222:
220:
218:ECHA InfoCard
215:
214:
207:
203:
202:
200:
198:
195:
194:
187:
183:
182:
180:
178:
175:
174:
167:
163:
162:
160:
158:
155:
154:
147:
143:
142:
140:
138:
135:
134:
127:
123:
122:
120:
116:
111:
110:
103:
99:
98:
96:
93:
89:
88:
83:
72:
61:
55:
49:
45:
40:
36:
31:
19:
2700:Acetic acids
2621:Gibberellins
2518:
2514:
2478:
2474:
2467:
2442:
2438:
2432:
2418:(2): 122–6.
2415:
2411:
2375:
2371:
2361:
2316:
2312:
2302:
2259:
2255:
2244:
2199:
2195:
2185:
2174:. Retrieved
2136:
2132:
2122:
2110:
2098:
2087:. Retrieved
2083:
2074:
2057:
2053:
2047:
2030:
2026:
2020:
2003:
1999:
1993:
1976:
1972:
1966:
1956:
1949:
1943:
1933:
1906:
1902:
1892:
1849:
1845:
1835:
1800:
1796:
1786:
1743:
1739:
1729:
1702:
1698:
1688:
1655:
1651:
1645:
1618:
1614:
1604:
1579:
1575:
1569:
1534:
1530:
1520:
1487:
1483:
1470:
1427:
1423:
1412:
1371:
1367:
1360:
1328:(1): 81–86.
1325:
1321:
1311:
1266:
1262:
1252:
1227:
1224:J Infect Dis
1223:
1217:
1164:
1160:
1150:
1105:
1101:
1091:
1046:
1042:
1032:
997:
993:
983:
958:
954:
944:
924:
889:
879:microcephaly
876:
839:
832:
815:horticulture
808:
789:(2,4-D) and
784:
776:
768:
745:
725:
706:
686:
676:
664:
658:
642:
624:(E2), and a
615:
599:
587:
577:
570:
548:
539:Biosynthesis
520:
516:
512:
511:
442:White solid
85:Identifiers
77:heteroauxin,
70:
63:Other names
53:
2202:(9): 2062.
2060:(6): 1768.
1490:(1): 9–20.
931:immunotoxin
922:cleavage.
886:Immunotoxin
835:teratogenic
804:agriculture
582:along with
439:Appearance
389:Properties
224:100.001.590
166:ChEMBL82411
146:CHEBI:16411
2684:Categories
2644:Jasmonates
2611:Cytokinins
2507:cited in:
2176:2020-01-08
2089:2022-04-28
1531:Plant Cell
1484:Plant Cell
937:References
890:IAA is an
863:microbiota
821:(IBA) and
712:tryptophan
697:Hartig net
584:tryptophol
580:tryptophan
559:tryptophan
427:Molar mass
290:6U1S09C61L
177:ChemSpider
113:3D model (
92:CAS Number
2659:Polyamine
2649:Karrikins
2475:Leuk. Res
2412:Pharmazie
2276:1533-3450
2218:2072-6643
2196:Nutrients
2155:1083-351X
1462:221179265
1446:1097-4172
1404:221402986
1388:1520-5118
1344:0021-9258
1000:: 49–64.
916:caspase-3
912:caspase-9
908:caspase-8
892:apoptosis
867:germ-free
722:Synthesis
2639:Florigen
2616:Ethylene
2545:24578503
2503:32655907
2495:21168913
2459:12052213
2424:20225657
2394:16141651
2353:34667167
2294:25145928
2236:31484323
2171:45619222
1884:18223109
1827:26179718
1778:26231639
1721:26347301
1680:22123626
1672:22978761
1637:26317137
1561:14742873
1512:24159190
1504:15688063
1454:32818467
1396:32866000
1352:13610897
1303:26469515
1263:PLOS ONE
1209:19279202
1191:40455212
1142:22025721
1083:22025724
1024:20192736
975:21421392
850:NFPA 704
760:aldehyde
649:catalase
620:(E1), a
197:DrugBank
2705:Indoles
2536:3990911
2344:8526691
2321:Bibcode
2285:4378098
2227:6769627
2163:9407059
1875:2268313
1854:Bibcode
1818:4623019
1769:4579454
1748:Bibcode
1596:9188533
1576:Science
1294:4607412
1271:Bibcode
1244:1117200
1200:2664063
1169:Bibcode
1133:3215067
1110:Bibcode
1074:3215075
1051:Bibcode
1015:3070418
825:(NAA).
708:Skatole
685:called
634:Aux/IAA
527:of the
494:what is
492: (
432:175.187
257:PubChem
206:DB07950
102:87-51-4
2690:Auxins
2601:Auxins
2543:
2533:
2501:
2493:
2457:
2422:
2392:
2351:
2341:
2292:
2282:
2274:
2234:
2224:
2216:
2169:
2161:
2153:
1925:367144
1923:
1882:
1872:
1825:
1815:
1776:
1766:
1719:
1678:
1670:
1635:
1594:
1559:
1552:341922
1549:
1510:
1502:
1460:
1452:
1444:
1402:
1394:
1386:
1350:
1342:
1301:
1291:
1242:
1207:
1197:
1189:
1140:
1130:
1081:
1071:
1022:
1012:
973:
750:using
728:indole
693:hyphae
683:spruce
533:indole
489:verify
486:
373:SMILES
245:C00954
157:ChEMBL
42:Names
2515:Blood
2499:S2CID
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