Showing Compound indole-3-acetate (FDB030920)

Record Information

Version

1.0

Creation date

2015-05-07 20:31:38 UTC

Update date

2019-11-26 03:21:57 UTC

Primary ID

FDB030920

Secondary Accession Numbers

FDB000933
FDB004267

Chemical Information

FooDB Name

indole-3-acetate

Description

1h-indol-3-ylacetic acid, also known as (indol-3-yl)acetate or heteroauxin, belongs to indole-3-acetic acid derivatives class of compounds. Those are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. 1h-indol-3-ylacetic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 1h-indol-3-ylacetic acid is a mild, odorless, and sour tasting compound and can be found in a number of food items such as sweet bay, chinese bayberry, winter squash, and linden, which makes 1h-indol-3-ylacetic acid a potential biomarker for the consumption of these food products. 1h-indol-3-ylacetic acid can be found primarily in most biofluids, including blood, feces, saliva, and urine, as well as throughout most human tissues. 1h-indol-3-ylacetic acid exists in all living species, ranging from bacteria to humans. In humans, 1h-indol-3-ylacetic acid is involved in the tryptophan metabolism. Moreover, 1h-indol-3-ylacetic acid is found to be associated with appendicitis and irritable bowel syndrome. 1h-indol-3-ylacetic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Chronic Exposure: Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(+)-Lactate	HMDB
(+)-Lactic acid	HMDB
(-)-Cystine	HMDB
(-)-Inosine	HMDB
(1H-indol-3-yl)-Acetate	HMDB
(1H-indol-3-yl)-Acetic acid	HMDB
(1H-indol-3-yl)Acetate	Kegg
(1H-indol-3-yl)Acetic acid	Generator
(2S)-6-(Acetylamino)-2-aminohexanoate	HMDB
(2S)-6-(Acetylamino)-2-aminohexanoic acid	HMDB

Showing 1 to 10 of 272 entries

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

Dermal

Enteral:

Ingestion

Source:

Biological location:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
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

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ChEMBL ID

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KEGG Compound ID

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Pubchem Compound ID

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Pubchem Substance ID

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ChEBI ID

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Phenol-Explorer ID

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DrugBank ID

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HMDB ID

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CRC / DFC (Dictionary of Food Compounds) ID

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EAFUS ID

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Dr. Duke ID

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BIGG ID

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KNApSAcK ID

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HET ID

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Food Biomarker Ontology

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VMH ID

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Flavornet ID

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GoodScent ID

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SuperScent ID

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Wikipedia ID

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Phenol-Explorer Metabolite ID

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Duplicate IDS

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Biological Effects and Interactions

Health Effects / Bioactivities

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Enzymes

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Content Reference

Showing Compound indole-3-acetate (FDB030920)

Structure for FDB030920 (indole-3-acetate)