Molecule

indole-3-acetate

AlkaPlorer ID: AK001638

Synonym: 'Indole-3-acetic acid', '3-indoleacetate', '(Indol-3-yl)acetate', 'heteroauxin', '3-Indoleacetate', 'IAA', '(indol-3-yl)acetic acid', '(indol-3-yl)acetate', 'MLS001331664', '2338-19-4', 'MLS001332400', 'MLS001332399', '3-Indolylessigsaeure', 'MLS001066408', 'Indoleacetic acid', 'IES', '2-(indol-3-yl)ethanoic acid', '2-(indol-3-yl)ethanoate', 'MLSMR', 'SMR000471855', '3-Indoleacetic acid', '87-51-4', 'indole-3-acetic acid'

IUPAC Name: 2-(1H-indol-3-yl)acetate

Structure

SMILES: O=C([O-])CC1=CNC2=CC=CC=C12

InChI: 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)/p-1

InChIKey: SEOVTRFCIGRIMH-UHFFFAOYSA-M

Reference

Identification and quantification of three active auxins in different tissues of <i>Tropaeolum majus</i>

PubChem CID: 801

CAS: 87-51-4

LOTUS: LTS0250222

COCONUT: CNP0284198

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Hordeum vulgare	Hordeum	Poaceae	Poales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Saccharina japonica	Saccharina	Laminariaceae	Laminariales	Phaeophyceae	None	None	Eukaryota
Carapichea ipecacuanha	Carapichea	Rubiaceae	Gentianales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Persicaria tinctoria	Persicaria	Polygonaceae	Caryophyllales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Aloe spicata	Aloe	Asphodelaceae	Asparagales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Aloe ferox	Aloe	Asphodelaceae	Asparagales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
Aloe africana	Aloe	Asphodelaceae	Asparagales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota

Properties Information

Molecule Weight: 174.179

TPSA？: 55.92

MolLogP？: 0.4602999999999991

Number of H-Donors: 1

Number of H-Acceptors: 2

RingCount: 2

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Arabidopsis thaliana	Peptide deformylase 1A, chloroplastic	IC50	1000000.0	nM	10.1021/jm060910c
Aspergillus fumigatus	Brevianamide F prenyltransferase	Activity	0.6	%	10.1021/np800501m
Aspergillus fumigatus	Brevianamide F prenyltransferase	Activity	2.8	%	10.1021/np800501m
Avena sativa	Avena sativa	Activity	nan	None	10.1584/jpestics.26.266
Avena sativa	Avena sativa	GI	nan	None	10.1584/jpestics.26.266
Bacillus subtilis	Bacillus subtilis	MIC	nan	None	10.1021/jm060910c
Cricetulus griseus	V79	Surviving fraction	0.01	None	10.1016/s0960-894x(02)00505-x
Cryphonectria parasitica	Cryphonectria parasitica	IZ	12.0	mm	10.1021/jf990685q
Cryphonectria parasitica	Cryphonectria parasitica	IZ	14.0	mm	10.1021/jf990685q
Cryphonectria parasitica	Cryphonectria parasitica	IZ	16.0	mm	10.1021/jf990685q
Cryphonectria parasitica	Cryphonectria parasitica	IZ	21.0	mm	10.1021/jf990685q
Cucumis sativus	Cucumis sativus	Activity	150.0	%	10.1016/j.bmcl.2009.04.048
Electrophorus electricus	Acetylcholinesterase	Inhibition	2.98	%	10.1016/j.bmc.2012.09.040
Equus caballus	Cholinesterase	Inhibition	-7.42	%	10.1016/j.bmc.2012.09.040
Escherichia coli	Escherichia coli	MIC	nan	None	10.1021/jm060910c
Escherichia coli	Peptide deformylase	IC50	1000000.0	nM	10.1021/jm060910c
Fuchsia	Fuchsia	Ratio	0.0	None	10.1021/jf010991f
Fusarium culmorum	Fusarium culmorum	IC50	420.0	ug.mL-1	10.1584/jpestics.G09-66
Globisporangium debaryanum	Globisporangium debaryanum	IC50	301.0	ug.mL-1	10.1584/jpestics.G09-66
Homo sapiens	Kynurenine--oxoglutarate transaminase I	Activity	nan	None	10.1021/jm9000874
Homo sapiens	Peptide deformylase mitochondrial	IC50	nan	None	10.1021/jm060910c
Homo sapiens	Serum albumin	logKA	0.102	None	10.1016/j.bmc.2007.04.005
Homo sapiens	Tyrosine-protein kinase receptor FLT3	Inhibition	nan	%	10.1021/acs.jmedchem.8b01714
Lactuca sativa	Lactuca sativa	Activity	nan	None	10.1021/np040178p
Laetisaria fuciformis	Laetisaria fuciformis	GI	nan	None	10.1021/jf990685q
Macrophomina phaseolina	Macrophomina phaseolina	IC50	807.0	ug.mL-1	10.1584/jpestics.G09-66
Magnaporthiopsis poae	Magnaporthiopsis poae	GI	nan	None	10.1021/jf990685q
Oryza sativa	Oryza sativa	Activity	5.28	mM	10.1016/j.bmcl.2007.06.025
Oryza sativa	Oryza sativa	Activity	7.66	mM	10.1016/j.bmcl.2007.06.025
Oryza sativa	Oryza sativa	Activity	8.72	mM	10.1016/j.bmcl.2007.06.025
Oryza sativa	Oryza sativa	Activity	9.25	mM	10.1016/j.bmcl.2007.06.025
Oryza sativa	Oryza sativa	Activity	9.81	mM	10.1016/j.bmcl.2007.06.025
Oryza sativa	Oryza sativa	Activity	10.6	mM	10.1016/j.bmcl.2007.06.025
Oryza sativa	Oryza sativa	Activity	11.72	mM	10.1016/j.bmcl.2007.06.025
Oryza sativa	Oryza sativa	Activity	14.45	mM	10.1016/j.bmcl.2007.06.025
Oryza sativa	Oryza sativa	Activity	15.61	mM	10.1016/j.bmcl.2007.06.025
Oryza sativa	Oryza sativa	Activity	17.62	mM	10.1016/j.bmcl.2007.06.025
Oryza sativa	Oryza sativa	Activity	18.73	mM	10.1016/j.bmcl.2007.06.025
Oryza sativa	Oryza sativa	Activity	20.26	mM	10.1016/j.bmcl.2007.06.025
Rattus norvegicus	Liver microsomes	Activity	nan	None	10.1021/np970150w
Rhizoctonia solani	Rhizoctonia solani	GI	nan	None	10.1021/jf990685q
Rhizoctonia solani	Rhizoctonia solani	IC50	1009.0	ug.mL-1	10.1584/jpestics.G09-66
Saccharomyces cerevisiae	Saccharomyces cerevisiae	EC50	300000.0	nM	10.1016/j.ejmech.2022.114845
Staphylococcus aureus (strain NCTC 8325)	ATP-dependent Clp protease proteolytic subunit	Inhibition	nan	%	10.1021/acs.jmedchem.9b01746
Vigna mungo	Vigna mungo	Activity	36.0	%	10.1271/bbb.80138
Vigna mungo	Vigna mungo	Activity	nan	None	10.1271/bbb.80138
None	ADMET	LogP app	-6.4	None	10.1016/j.bmc.2007.03.040
None	Molecular identity unknown	Rate constant (k)	3.8	Ie3 M-1 s-1	10.1016/s0960-894x(02)00505-x
None	No relevant target	log K	1.42	None	10.1016/j.bmc.2007.04.005
None	No relevant target	LogP	1.41	None	10.1016/j.bmc.2007.03.040
None	Unchecked	Activity	1.7	%	10.1021/np800501m
None	Unchecked	Activity	45.3	%	10.1021/np800501m
None	Unchecked	IC50	42980.0	nM	10.1039/C7MD00390K
None	Unchecked	IC50	500000.0	nM	10.1021/jm401432c
None	Unchecked	IC50	1000000.0	nM	10.1021/jm060910c
None	Unchecked	IC50	1000000.0	nM	10.1021/jm900823s
None	Unchecked	Inhibition	8.6	%	10.1016/j.ejmech.2018.10.027

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT000788	*OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O.O=C(O)Cc1c[nH]c2ccccc12>>O=C(O)Cc1cn([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c2ccccc12	RXN-9076
AKRT004115	CC(=O)O.c1ccc2[nH]ccc2c1>>O=C(O)Cc1c[nH]c2ccccc12	MNXR176713
AKRT005269	CC(C)=CCOP(=O)(O)OP(=O)(O)O.O=C(O)Cc1c[nH]c2ccccc12>>CC(C)=CCc1cccc2[nH]cc(CC(=O)O)c12	enzymemap_40444
AKRT005270	CC(C)=CCOP(=O)(O)OP(=O)(O)O.O=C(O)Cc1c[nH]c2ccccc12>>CC(C)=CCc1cccc2c(CC(=O)O)c[nH]c12	enzymemap_41296
AKRT005804	CC(C)C[C@H](N)C(=O)O.O=C(O)Cc1c[nH]c2ccccc12>>CC(C)C[C@H](NC(=O)Cc1c[nH]c2ccccc12)C(=O)O	RXN-2945
AKRT005886	CC(C)C[C@H](NC(=O)Cc1c[nH]c2ccccc12)C(=O)O>>O=C(O)Cc1c[nH]c2ccccc12	RXN-2982
AKRT006310	CC(C)[C@H](N)C(=O)O.O=C(O)Cc1c[nH]c2ccccc12>>CC(C)[C@H](NC(=O)Cc1c[nH]c2ccccc12)C(=O)O	RXN-9083
AKRT010007	CC[C@H](C)[C@H](N)C(=O)O.O=C(O)Cc1c[nH]c2ccccc12>>CC[C@H](C)[C@H](NC(=O)Cc1c[nH]c2ccccc12)C(=O)O	RXN-10430
AKRT011043	COC(=O)Cc1c[nH]c2ccccc12>>O=C(O)Cc1c[nH]c2ccccc12	RXN-10711
AKRT012420	CSCC[C@H](N)C(=O)O.O=C(O)Cc1c[nH]c2ccccc12>>CSCC[C@H](NC(=O)Cc1c[nH]c2ccccc12)C(=O)O	RXN-10431
AKRT012660	C[33S].O=C(O)Cc1c[nH]c2ccccc12>>COC(=O)Cc1c[nH]c2ccccc12	None
AKRT013621	C[C@H](N)C(=O)O.O=C(O)Cc1c[nH]c2ccccc12>>C[C@H](NC(=O)Cc1c[nH]c2ccccc12)C(=O)O	RXN-2944
AKRT013725	C[C@H](NC(=O)Cc1c[nH]c2ccccc12)C(=O)O>>O=C(O)Cc1c[nH]c2ccccc12	RXN-2981
AKRT014723	C[SAH].O=C(O)Cc1c[nH]c2ccccc12>>COC(=O)Cc1c[nH]c2ccccc12	RXN-9825
AKRT014724	C[SAH].O=C(O)Cc1c[nH]c2ccccc12>>Cc1[nH]c2ccccc2c1CC(=O)O	enzymemap_26812
AKRT015650	N#CCc1c[nH]c2ccccc12>>O=C(O)Cc1c[nH]c2ccccc12	RXN-1404
AKRT016889	NC(=O)CC[C@H](N)C(=O)O.O=C(O)Cc1c[nH]c2ccccc12>>NC(=O)CC[C@H](NC(=O)Cc1c[nH]c2ccccc12)C(=O)O	RXN-2948
AKRT016988	NC(=O)Cc1c[nH]c2ccccc12>>O=C(O)Cc1c[nH]c2ccccc12	RXNN-404
AKRT017701	NCC(=O)O.O=C(O)Cc1c[nH]c2ccccc12>>O=C(O)CNC(=O)Cc1c[nH]c2ccccc12	RXN-10429
AKRT018112	NCCCC[C@H](N)C(=O)O.O=C(O)Cc1c[nH]c2ccccc12>>N[C@@H](CCCCNC(=O)Cc1c[nH]c2ccccc12)C(=O)O	INDOLEACETATE--LYSINE-LIGASE-RXN
AKRT018698	N[C@@H](CC(=O)O)C(=O)O.O=C(O)Cc1c[nH]c2ccccc12>>O=C(O)C[C@H](NC(=O)Cc1c[nH]c2ccccc12)C(=O)O	RXN-2946
AKRT019200	N[C@@H](CCC(=O)O)C(=O)O.O=C(O)Cc1c[nH]c2ccccc12>>O=C(O)CC[C@H](NC(=O)Cc1c[nH]c2ccccc12)C(=O)O	RXN-2947
AKRT019769	N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O.O=C(O)Cc1c[nH]c2ccccc12>>O=C(Cc1c[nH]c2ccccc12)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)O	RXN-10433
AKRT019949	N[C@@H](Cc1ccc(O)cc1)C(=O)O.O=C(O)Cc1c[nH]c2ccccc12>>O=C(Cc1c[nH]c2ccccc12)N[C@@H](Cc1ccc(O)cc1)C(=O)O	RXN-10432
AKRT020074	N[C@@H](Cc1ccccc1)C(=O)O.O=C(O)Cc1c[nH]c2ccccc12>>O=C(Cc1c[nH]c2ccccc12)N[C@@H](Cc1ccccc1)C(=O)O	RXN-9084
AKRT021954	Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O.O=C(O)Cc1c[nH]c2ccccc12>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OC(=O)Cc2c[nH]c3ccccc23)[C@@H](O)[C@H]1O	69719
AKRT022426	O=C(Cc1c[nH]c2ccccc12)OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O>>O=C(O)Cc1c[nH]c2ccccc12	RXN-3163
AKRT022433	O=C(Cc1c[nH]c2ccccc12)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O>>O=C(O)Cc1c[nH]c2ccccc12	RXN-3165
AKRT022436	O=C(Cc1c[nH]c2ccccc12)O[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O>>O=C(O)Cc1c[nH]c2ccccc12	RXN-3164
AKRT022446	O=C(Cc1c[nH]c2ccccc12)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O>>O=C(O)Cc1c[nH]c2ccccc12	RXN-3166
AKRT022590	O=C(O)C(=O)Cc1c[nH]c2ccccc12>>O=C(O)Cc1c[nH]c2ccccc12	RXNDQC-2
AKRT022591	O=C(O)C(=O)Cc1c[nH]c2ccccc12>>O=C(O)Cc1c[nH]c2ccccc12.O=C=O	None
AKRT022629	O=C(O)C(O)c1c[nH]c2ccccc12>>O=C(O)Cc1c[nH]c2ccccc12	MNXR176881
AKRT022755	O=C(O)CCC(=O)[CoA].O=C(O)Cc1c[nH]c2ccccc12>>O=C([CoA])Cc1c[nH]c2ccccc12	enzymemap_50894
AKRT022926	O=C(O)C[C@H](NC(=O)Cc1c[nH]c2ccccc12)C(=O)O>>N[C@@H](CC(=O)O)C(=O)O.O=C(O)Cc1c[nH]c2ccccc12	None
AKRT022928	O=C(O)C[C@H](NC(=O)Cc1c[nH]c2ccccc12)C(=O)O>>O=C(O)Cc1c[nH]c2ccccc12	60428
AKRT022948	O=C(O)Cc1c[nH]c2ccccc12.O=C(O)[C@@H]1CCCN1>>O=C(O)[C@@H]1CCCN1C(=O)Cc1c[nH]c2ccccc12	RXN-10434
AKRT022949	O=C(O)Cc1c[nH]c2ccccc12.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O)c(=O)[nH]1>>O=C(Cc1c[nH]c2ccccc12)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O	2.4.1.121-RXN
AKRT022950	O=C(O)Cc1c[nH]c2ccccc12.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O)c(=O)[nH]1>>O=C(Cc1c[nH]c2ccccc12)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1	None
AKRT022951	O=C(O)Cc1c[nH]c2ccccc12.OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O>>O=C(Cc1c[nH]c2ccccc12)OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O	MNXR176767
AKRT022952	O=C(O)Cc1c[nH]c2ccccc12.OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O>>O=C(Cc1c[nH]c2ccccc12)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O	MNXR176769
AKRT022953	O=C(O)Cc1c[nH]c2ccccc12.OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O>>O=C(Cc1c[nH]c2ccccc12)O[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O	MNXR176768
AKRT022954	O=C(O)Cc1c[nH]c2ccccc12>>CC1(O)C(=O)Nc2ccccc21	R03092
AKRT022955	O=C(O)Cc1c[nH]c2ccccc12>>Cc1c[nH]c2ccccc12	R12303
AKRT022956	O=C(O)Cc1c[nH]c2ccccc12>>Cc1c[nH]c2ccccc12.O=C=O	None
AKRT022957	O=C(O)Cc1c[nH]c2ccccc12>>O=C(O)/C=C1\C=Nc2ccccc21	RXN-21806
AKRT022958	O=C(O)Cc1c[nH]c2ccccc12>>O=C(O)CC1(O)C(=O)Nc2ccccc21	MNXR176784
AKRT022959	O=C(O)Cc1c[nH]c2ccccc12>>O=C(O)CC1C(=O)Nc2ccccc21	RXN-3181
AKRT022960	O=C(O)Cc1c[nH]c2ccccc12>>O=C(O)Cc1c(O)[nH]c2ccccc12	RXN-14711
AKRT022961	O=C(O)Cc1c[nH]c2ccccc12>>O=C(O)Cc1c[nH]c2ccc(O)cc12	enzymemap_12393
AKRT022962	O=C(O)Cc1c[nH]c2ccccc12>>O=C(O)[C@H](O)c1c[nH]c2ccccc12	RXN-5421
AKRT022963	O=C(O)Cc1c[nH]c2ccccc12>>O=C([CoA])Cc1c[nH]c2ccccc12	69715
AKRT022964	O=C(O)Cc1c[nH]c2ccccc12>>O=C=O	R03092
AKRT022965	O=C(O)Cc1c[nH]c2ccccc12>>O=CNc1ccccc1C(=O)CC(=O)O	R03097
AKRT022966	O=C(O)Cc1c[nH]c2ccccc12>>c1ccc2[nH]ccc2c1	RXN-1408
AKRT023453	O=C([CoA])Cc1c[nH]c2ccccc12>>O=C(O)Cc1c[nH]c2ccccc12	enzymemap_89521
AKRT023689	O=CCc1c[nH]c2ccccc12>>O=C(O)Cc1c[nH]c2ccccc12	RXN-10715
AKRT024534	O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O)c(=O)[nH]1.O=C(O)Cc1c[nH]c2ccccc12>>O=C(Cc1c[nH]c2ccccc12)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O	enzymemap_33959