AFCDB: 1H-Indole-3-acetic acid (FDB000933)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:46 UTC

Update date

2024-11-29 22:27:21 UTC

Primary ID

FDB000933

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

1H-Indole-3-acetic acid

Description

Widely distributed in higher plants Indole-3-acetic acid, also known as IAA, is a heterocyclic compound that is a phytohormone called auxin. This colourless solid is probably the most important plant auxin. The molecule is derived from indole, containing a carboxymethyl group (acetic acid). 1H-Indole-3-acetic acid is found in many foods, some of which are lettuce, cherry tomato, chinese bayberry, and okra.

CAS Number

87-51-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	1.38 g/L	ALOGPS
logP	1.87	ALOGPS
logP	1.71	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	4.66	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.09 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	48.45 m³·mol⁻¹	ChemAxon
Polarizability	17.74 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H9NO2

IUPAC name

2-(1H-indol-3-yl)acetic acid

InChI Identifier

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)

InChI Key

SEOVTRFCIGRIMH-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)CC1=CNC2=C1C=CC=C2

Average Molecular Weight

175.184

Monoisotopic Molecular Weight

175.063328537

Classification

Description

Belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indole-3-acetic acid derivatives

Alternative Parents

Substituents

Indole-3-acetic acid derivative
3-alkylindole
Indole
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrole
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Carbonyl group
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:16411 )
indole-3-acetic acids (CHEBI:16411 )
Indole alkaloids (C00954 )
Auxins (C00954 )

Ontology

Whole grain cereal products

Nuts and legumes:

Nuts

Legumes:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	1.41	HANSCH,C ET AL. (1995)
Experimental pKa	pKa2 16.9 (NH)	DFC
Experimental Water Solubility	1.5 mg/mL at 20 oC	SHIU,WY et al. (1990)
Isoelectric point	Not Available
Mass Composition	C 68.56%; H 5.18%; N 8.00%; O 18.27%	DFC
Melting Point	Mp 164-165°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-001i-1900000000-3ffc47eb6c977956ad93	2014-09-20	View Spectrum
GC-MS	1H-Indole-3-acetic acid, 2 TMS, GC-MS Spectrum	splash10-0udi-0391000000-7581f14fe5be5b2b2954	Spectrum
GC-MS	1H-Indole-3-acetic acid, 2 TMS, GC-MS Spectrum	splash10-0udi-0691000000-de9ac4f748d50db109ea	Spectrum
GC-MS	1H-Indole-3-acetic acid, 2 TMS, GC-MS Spectrum	splash10-0udi-0591000000-9687f83d1372abe23c3c	Spectrum
GC-MS	1H-Indole-3-acetic acid, 2 TMS, GC-MS Spectrum	splash10-0udi-1793100000-7c78003038436ec5a902	Spectrum
GC-MS	1H-Indole-3-acetic acid, 1 TMS, GC-MS Spectrum	splash10-00ai-7910000000-4aa7b8244f32048c76bc	Spectrum
GC-MS	1H-Indole-3-acetic acid, 2 TMS, GC-MS Spectrum	splash10-0fk9-9250000000-a5f931fc3292056dba65	Spectrum
GC-MS	1H-Indole-3-acetic acid, 1 TMS, GC-MS Spectrum	splash10-001i-1920000000-f0ecee61454a589493af	Spectrum
GC-MS	1H-Indole-3-acetic acid, 2 TMS, GC-MS Spectrum	splash10-0udi-1692000000-ce863a1ca2a657cb41d5	Spectrum
GC-MS	1H-Indole-3-acetic acid, non-derivatized, GC-MS Spectrum	splash10-003r-0900000000-1edcb4977a52155bc130	Spectrum
GC-MS	1H-Indole-3-acetic acid, non-derivatized, GC-MS Spectrum	splash10-0udi-0391000000-7581f14fe5be5b2b2954	Spectrum
GC-MS	1H-Indole-3-acetic acid, non-derivatized, GC-MS Spectrum	splash10-0udi-0691000000-de9ac4f748d50db109ea	Spectrum
GC-MS	1H-Indole-3-acetic acid, non-derivatized, GC-MS Spectrum	splash10-0udi-0591000000-9687f83d1372abe23c3c	Spectrum
GC-MS	1H-Indole-3-acetic acid, non-derivatized, GC-MS Spectrum	splash10-0udi-1793100000-7c78003038436ec5a902	Spectrum
GC-MS	1H-Indole-3-acetic acid, non-derivatized, GC-MS Spectrum	splash10-00ai-7910000000-4aa7b8244f32048c76bc	Spectrum
GC-MS	1H-Indole-3-acetic acid, non-derivatized, GC-MS Spectrum	splash10-0fk9-9250000000-a5f931fc3292056dba65	Spectrum
GC-MS	1H-Indole-3-acetic acid, non-derivatized, GC-MS Spectrum	splash10-001i-1920000000-f0ecee61454a589493af	Spectrum
GC-MS	1H-Indole-3-acetic acid, non-derivatized, GC-MS Spectrum	splash10-0udi-1692000000-ce863a1ca2a657cb41d5	Spectrum
GC-MS	1H-Indole-3-acetic acid, non-derivatized, GC-MS Spectrum	splash10-0udi-0691000000-f6073f8f35a6930b5aac	Spectrum
Predicted GC-MS	1H-Indole-3-acetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0059-1900000000-ab74ec83b16ac0b97d12	Spectrum
Predicted GC-MS	1H-Indole-3-acetic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-7920000000-8dab2ad22251c9fbd21c	Spectrum
Predicted GC-MS	1H-Indole-3-acetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1H-Indole-3-acetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1H-Indole-3-acetic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1H-Indole-3-acetic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	1H-Indole-3-acetic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-0900000000-f6dbb01a35af3042d126	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-0900000000-2ae231b7d0e2cd50aed8	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-6900000000-9eae14faa16b8f8259da	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-003r-0900000000-1edcb4977a52155bc130	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00e9-0900000000-187b48f2258823cbc6a2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-001i-0900000000-30b7a73fa446d0e3c8d3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-0900000000-bbe0fb5a48f89ea6e383	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-0900000000-97850f400d80de278334	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-0900000000-600545759ef108827b9e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0kxr-5900000000-ba2eed29832f9ee48921	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-004l-5900000000-a0b30710f83e53b6f3db	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-001i-9500000000-146ac0a20f9d53e76291	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-053r-9600000000-d9258b3c6b5c6f748f6e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-004i-9300000000-b59628beb41b424daf4a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (UPLC Waters, Quattro Ultima Pt Micromass) , Positive (Annotated)	splash10-004i-0900000000-755373c9248cfb6425fc	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-004i-0900000000-2b3df7a1dd85faea6705	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-003r-0900000000-9522ab089ab89b64f96a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-001i-0900000000-b735e95cb23091491c2e	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-2a3dd24f136523e6ce1e	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-053r-0900000000-77436493836245345cb8	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00lr-1900000000-4e0b6f24d03c0b25800f	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00e9-0900000000-1d045a56f3669a1c9391	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05ai-0900000000-518778c36bacbf77b901	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a5c-3900000000-323fc64084836756be30	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-2a3dd24f136523e6ce1e	2015-05-27	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, DMSO-d6, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16411

Phenol-Explorer ID

Not Available

DrugBank ID

DB07950

HMDB ID

HMDB00197

CRC / DFC (Dictionary of Food Compounds) ID

BNC14-M:BNC14-M

EAFUS ID

Not Available

Dr. Duke ID

INDOLE-ACETIC-ACID|BETA-INDOLACETIC-ACID|INDOLE-3-ACETIC-ACID

BIGG ID

1485312

KNApSAcK ID

C00000100

HET ID

IAC

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1251501

SuperScent ID

Not Available

Wikipedia ID

Indole-3-acetic_acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Show entries

Search:

Food	Content Range	Average	Reference

Carrot	Expected but not quantified	Not Available	DUKE
Common pea	Expected but not quantified	Not Available	DUKE, KNAPSACK
Green bean	Expected but not quantified	Not Available	KNAPSACK
Spinach	Expected but not quantified	Not Available	DUKE
Yellow wax bean	Expected but not quantified	Not Available	KNAPSACK
Barley	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Broccoli	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Cucumber	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Dill	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis
Eggplant	Expected but not quantified	Not Available	Inferred by geno/metabolomic analysis

Showing 1 to 10 of 41 entries

Biological Effects and Interactions

Health Effects / Bioactivities

Show entries

Search:

Descriptor	ID	Definition	Reference
allelochemic			DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
herbicide	24527	A substance used to destroy plant pests.	DUKE
hormone	24621	Originally referring to an endogenous compound that is formed in specialized organ or group of cells and carried to another organ or group of cells, in the same organism, upon which it has a specific regulatory function, the term is now commonly used to include non-endogenous, semi-synthetic and fully synthetic analogues of such compounds.	DUKE
hypoglycemic	35526	A drug which lowers the blood glucose level.	DUKE
insulinase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
insulinotonic			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE

Showing 1 to 8 of 8 entries

Enzymes

Not Available

Pathways

Show entries

Search:

Name	SMPDB Link	KEGG Link
Metabolism and Physiological Effects of Indole Acetic Acid	SMP0123235	Not Available
Metabolism and Physiological Effects of Indolelacetyl glutamine	SMP0126755	Not Available
Metabolism and Physiological Effects of Indolelactic Acid	SMP0126749	Not Available
Tryptophan Metabolism	SMP00063	map00380

Showing 1 to 4 of 4 entries

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Show entries

Search:

Flavor	Citations
mild	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
odorless	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sour	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Showing 1 to 3 of 3 entries

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

1H-Indole-3-acetic acid (FDB000933)

Structure for FDB000933 (1H-Indole-3-acetic acid)