ChemFOnt: Showing chemical card for beta-Indole acetic acid (CFc000333464)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:13:35 UTC

Chemfont ID

CFc000333464

Molecule Identification

Common Name

beta-Indole acetic acid

Definition

Indoleacetic 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. Indoleacetic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). Indoleacetic acid is a mild, odorless, and sour tasting compound and can be found in a number of food items such as garlic, bilberry, chicory, and macadamia nut, which makes indoleacetic acid a potential biomarker for the consumption of these food products. Indoleacetic acid can be found primarily in most biofluids, including cerebrospinal fluid (CSF), urine, blood, and feces, as well as throughout most human tissues. Indoleacetic acid exists in all living organisms, ranging from bacteria to humans. In humans, indoleacetic acid is involved in the tryptophan metabolism. Moreover, indoleacetic acid is found to be associated with appendicitis and irritable bowel syndrome. Indoleacetic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Indole-3-acetic acid (IAA, 3-IAA) is the most common, naturally occurring, plant hormone of the auxin 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 indole, containing a carboxymethyl substituent. It is a colorless solid that is soluble in polar organic solvents . Chronic Exposure: Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(indol-3-yl)Acetate	ChEBI
(indol-3-yl)Acetic acid	ChEBI
2-(indol-3-yl)Ethanoic acid	ChEBI
3-Indolylessigsaeure	ChEBI
Heteroauxin	ChEBI
IAA	ChEBI
IES	ChEBI
Indole-3-acetic acid	Kegg
Indoleacetate	Kegg
(1H-indol-3-yl)Acetate	Kegg
2-(indol-3-yl)Ethanoate	Generator
Indole-3-acetate	Generator
(1H-indol-3-yl)Acetic acid	Generator
(1H-indol-3-yl)-Acetate	HMDB
(1H-indol-3-yl)-Acetic acid	HMDB
1H-indol-3-Ylacetate	HMDB
1H-indol-3-Ylacetic acid	HMDB
1H-Indole-3-acetate	HMDB
1H-Indole-3-acetic acid	HMDB
2-(1H-indol-3-yl)Acetate	HMDB
2-(1H-indol-3-yl)Acetic acid	HMDB
2-(3-Indolyl)acetate	HMDB
2-(3-Indolyl)acetic acid	HMDB
3-(Carboxymethyl)indole	HMDB
3-IAA	HMDB
3-Indole-acetic acid	HMDB
3-Indoleacetate	HMDB
3-Indoleacetic acid	HMDB
3-Indolylacetate	HMDB
3-Indolylacetic acid	HMDB
alpha-indol-3-yl-Acetic acid	HMDB
b-Indoleacetate	HMDB
b-Indoleacetic acid	HMDB
b-Indolylacetate	HMDB
b-Indolylacetic acid	HMDB
beta-Indole-3-acetic acid	HMDB
beta-Indoleacetate	HMDB
beta-Indoleacetic acid	HMDB
beta-Indolylacetate	HMDB
beta-Indolylacetic acid	HMDB
indol-3-Ylacetate	HMDB
indol-3-Ylacetic acid	HMDB
Indolyl-3-acetate	HMDB
Indolyl-3-acetic acid	HMDB
Indolylacetate	HMDB
Indolylacetic acid	HMDB
Kyselina 3-indolyloctova	HMDB
Rhizopin	HMDB
Rhizopon a	HMDB
Skatole carboxylate	HMDB
Skatole carboxylic acid	HMDB
Indoleacetic acid, calcium salt	HMDB
Indoleacetic acid, monopotassium salt	HMDB
Indoleacetic acid, monosodium salt	HMDB
IES CPD	HMDB
Indole acetic acid	HMDB
Indoleacetic acid, alpha-(14)C-labeled	HMDB
(R,R)-3,3'-Dithiobis(2-aminopropanoic acid)	HMDB
(R-(R,r))-3,3'-dithiobis(2-aminopropanoic acid)	HMDB
3,3'-Dithiobis-L-alanine	HMDB
beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulfide	HMDB
beta,Beta'-dithiodialanine	HMDB
Bis(beta-amino-beta-carboxyethyl) disulfide	HMDB
e921	HMDB
L-alpha-Diamino-beta-dithiolactic acid	HMDB
L-Dicysteine	HMDB
Oxidized L-cysteine	HMDB
(R,R)-3,3'-Dithiobis(2-aminopropanoate)	HMDB
(R-(R,r))-3,3'-dithiobis(2-aminopropanoate)	HMDB
b,Beta'-diamino-b,beta'-dicarboxydiethyl disulfide	HMDB
b,Beta'-diamino-b,beta'-dicarboxydiethyl disulphide	HMDB
beta,Beta'-diamino-beta,beta'-dicarboxydiethyl disulphide	HMDB
Β,beta'-diamino-β,beta'-dicarboxydiethyl disulfide	HMDB
Β,beta'-diamino-β,beta'-dicarboxydiethyl disulphide	HMDB
b,Beta'-dithiodialanine	HMDB
Β,beta'-dithiodialanine	HMDB
Bis(b-amino-b-carboxyethyl) disulfide	HMDB
Bis(b-amino-b-carboxyethyl) disulphide	HMDB
Bis(beta-amino-beta-carboxyethyl) disulphide	HMDB
Bis(β-amino-β-carboxyethyl) disulfide	HMDB
Bis(β-amino-β-carboxyethyl) disulphide	HMDB
L-a-Diamino-b-dithiolactate	HMDB
L-a-Diamino-b-dithiolactic acid	HMDB
L-alpha-Diamino-beta-dithiolactate	HMDB
L-Α-diamino-β-dithiolactate	HMDB
L-Α-diamino-β-dithiolactic acid	HMDB
(-)-Cystine	HMDB
(R-(R,r))-3,3'-dithiobis	HMDB
2-Amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoate	HMDB
2-Amino-3-(2-amino-2-carboxy-ethyl)disulfanyl-propanoic acid	HMDB
2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoate	HMDB
2-Amino-3-[(2-amino-2-carboxyethyl)dithio]propanoic acid	HMDB
3,3'-Dithiobis	HMDB
3,3'-Dithiobis[2-amino-[R-(r,r)]-propanoate	HMDB
3,3'-Dithiobis[2-amino-[R-(r,r)]-propanoic acid	HMDB
3,3'-Dithiodialanine	HMDB
b,B'-diamino-b,b'-dicarboxydiethyl disulfide	HMDB
b,B'-dithiodialanine	HMDB
beta,Beta'-dithiobisalanine	HMDB
Bis(b-amino-beta-carboxyethyl) disulfide	HMDB
Cysteine disulfide	HMDB
Cystin	HMDB
Cystine	HMDB
Cystine acid	HMDB
D(+)-3,3'-Dithiobis(2-aminopropanoate	HMDB
D(+)-3,3'-Dithiobis(2-aminopropanoic acid	HMDB
Dicysteine	HMDB
Gelucystine	HMDB
L-(-)-Cystine	HMDB
L-Cysteine disulfide	HMDB
L-Cystin	HMDB
[R-(R,r)]-3,3'-dithiobis	HMDB
L Cystine	HMDB
Copper cystinate	HMDB
(+)-Lactic acid	HMDB
(S)-(+)-Lactic acid	HMDB
(S)-2-Hydroxypropanoic acid	HMDB
(S)-2-Hydroxypropionic acid	HMDB
L-(+)-alpha-Hydroxypropionic acid	HMDB
L-(+)-Lactic acid	HMDB
L-Milchsaeure	HMDB
L-Lactate	HMDB
(+)-Lactate	HMDB
(S)-(+)-Lactate	HMDB
(S)-2-Hydroxypropanoate	HMDB
(S)-2-Hydroxypropionate	HMDB
L-(+)-a-Hydroxypropionate	HMDB
L-(+)-a-Hydroxypropionic acid	HMDB
L-(+)-alpha-Hydroxypropionate	HMDB
L-(+)-Α-hydroxypropionate	HMDB
L-(+)-Α-hydroxypropionic acid	HMDB
L-(+)-Lactate	HMDB
(alpha)-Lactate	HMDB
(alpha)-Lactic acid	HMDB
(S)-(+)-2-Hydroxypropanoate	HMDB
(S)-(+)-2-Hydroxypropanoic acid	HMDB
(S)-2-Hydroxy-propanoate	HMDB
(S)-2-Hydroxy-propanoic acid	HMDB
(S)-Lactate	HMDB
(S)-Lactic acid	HMDB
1-Hydroxyethane 1-carboxylate	HMDB
1-Hydroxyethane 1-carboxylic acid	HMDB
1-Hydroxyethanecarboxylate	HMDB
1-Hydroxyethanecarboxylic acid	HMDB
2-Hydroxypropanoate	HMDB
2-Hydroxypropanoic acid	HMDB
2-Hydroxypropionate	HMDB
a-Hydroxypropanoate	HMDB
a-Hydroxypropanoic acid	HMDB
a-Hydroxypropionate	HMDB
a-Hydroxypropionic acid	HMDB
alpha-Hydroxypropanoate	HMDB
alpha-Hydroxypropanoic acid	HMDB
alpha-Hydroxypropionate	HMDB
alpha-Hydroxypropionic acid	HMDB
L-(+)- Lactic acid	HMDB
L-2-Hydroxypropanoate	HMDB
L-2-Hydroxypropanoic acid	HMDB
Lactate	HMDB
Lactic acid	HMDB
Milk acid	HMDB
Sarcolactic acid	HMDB
2-Hydroxypropionic acid	HMDB
D-Lactic acid	HMDB
D Lactic acid	HMDB
Lactate, ammonium	HMDB
2 Hydroxypropanoic acid	HMDB
2 Hydroxypropionic acid	HMDB
Ammonium lactate	HMDB
L Lactic acid	HMDB
9-beta-D-Ribofuranosyl-9H-purin-6-ol	HMDB
9-beta-D-Ribofuranosylhypoxanthine	HMDB
Hypoxanthine D-riboside	HMDB
Hypoxanthosine	HMDB
i	HMDB
Inosin	HMDB
Inosina	HMDB
Inosinum	HMDB
Inotin	HMDB
9-b-D-Ribofuranosyl-9H-purin-6-ol	HMDB
9-Β-D-ribofuranosyl-9H-purin-6-ol	HMDB
9-b-D-Ribofuranosylhypoxanthine	HMDB
9-Β-D-ribofuranosylhypoxanthine	HMDB
(-)-Inosine	HMDB
1,9-Dihydro-9-b-D-ribofuranosyl-6H-purin-6-one	HMDB
1,9-Dihydro-9-beta-D-ribofuranosyl-6H-purin-6-one	HMDB
1,9-Dihydro-9-beta-delta-ribofuranosyl-6H-purin-6-one	HMDB
9-b-D-Ribofuranosyl-hypoxanthine	HMDB
9-beta-D-Ribofuranosyl-hypoxanthine	HMDB
9-beta-delta-Ribofuranosyl-hypoxanthine	HMDB
9-beta-delta-Ribofuranosylhypoxanthine	HMDB
9beta-D-Ribofuranosylhypoxanthine	HMDB
9beta-delta-Ribofuranosylhypoxanthine	HMDB
Atorel	HMDB
beta-D-Ribofuranoside hypoxanthine-9	HMDB
beta-delta-Ribofuranoside hypoxanthine-9	HMDB
beta-Inosine	HMDB
HXR	HMDB
Hypoxanthine 9-beta-D-ribofuranoside	HMDB
Hypoxanthine 9-beta-delta-ribofuranoside	HMDB
Hypoxanthine nucleoside	HMDB
Hypoxanthine ribonucleoside	HMDB
Hypoxanthine riboside	HMDB
Hypoxanthine-9 beta-D-ribofuranoside	HMDB
Hypoxanthine-9 beta-delta-ribofuranoside	HMDB
Hypoxanthine-9-beta-D-ribofuranoside	HMDB
Hypoxanthine-9-beta-delta-ribofuranoside	HMDB
Hypoxanthine-9-D-ribofuranoside	HMDB
Hypoxanthine-9-delta-ribofuranoside	HMDB
Hypoxanthine-ribose	HMDB
Indole-3-carboxaldehyde	HMDB
Ino	HMDB
Inosie	HMDB
Iso-prinosine	HMDB
Oxiamin	HMDB
Panholic-L	HMDB
Pantholic-L	HMDB
Ribonosine	HMDB
Selfer	HMDB
Trophicardyl	HMDB
(2S)-6-(Acetylamino)-2-aminohexanoic acid	HMDB
N(6)-ACETYLLYSINE	HMDB
N(zeta)-Acetyllysine	HMDB
N-epsilon-Acetyl-L-lysine	HMDB
N-Epsilon-Acetyllysine	HMDB
N(epsilon)-Acetyl-L-lysine	HMDB
N(zeta)-Acetyl-L-lysine	HMDB
(2S)-6-(Acetylamino)-2-aminohexanoate	HMDB
N(Z)-Acetyllysine	HMDB
N(Ζ)-acetyllysine	HMDB
N(Z)-Acetyl-L-lysine	HMDB
N(Ζ)-acetyl-L-lysine	HMDB
e-Acetyl-L-lysine	HMDB
e-N-Acetyl-L-lysine	HMDB
e-N-Acetyllysine	HMDB
epsilon-Acetyl-L-lysine	HMDB
epsilon-N-Acetyl-L-lysine	HMDB
epsilon-N-Acetyllysine	HMDB
L-e-N-Acetyllysine	HMDB
L-epsilon-N-Acetyllysine	HMDB
N-e-Acetyl-L-lysine	HMDB
N-e-Acetyllysine	HMDB
N6-Acetyllysine	HMDB
Ne-acetyl-L-lysine	HMDB
Ne-acetyllysine	HMDB
Omega-N-acetyl-L-lysine	HMDB
W-N-Acetyl-L-lysine	HMDB
N(6)-Acetyllsine	HMDB
Omega-acetyllsine	HMDB
beta-Alanyl-3-methyl-L-histidine	HMDB
beta-Alanyl-N(pai)-methyl-L-histidine	HMDB
b-Alanyl-3-methyl-L-histidine	HMDB
Β-alanyl-3-methyl-L-histidine	HMDB
b-Alanyl-N(pai)-methyl-L-histidine	HMDB
Β-alanyl-N(pai)-methyl-L-histidine	HMDB
L-Anserine	HMDB
L-N-b-Alanyl-3-methyl-histidine	HMDB
L-N-beta-Alanyl-3-methyl-histidine	HMDB
N-b-Alanyl-3-methyl-L-histidine	HMDB
N-beta-Alanyl-3-methyl-L-histidine	HMDB
Balanine	HMDB
Beta Alanyl 3 methylhistidine	HMDB
Beta-Alanyl-3-methylhistidine	HMDB
Ophidine	HMDB
Indoleacetic acid	ChEBI
3-(Carboxymethyl)-1H-indole	PhytoBank
3-Indolylmethylcarboxylic acid	PhytoBank
alpha-IAA	PhytoBank
α-IAA	PhytoBank
beta-IAA	PhytoBank
β-IAA	PhytoBank
β-Indoleacetic acid	PhytoBank

Chemical Formula

C₁₀H₉NO₂

Average Molecular Weight

175.184

Monoisotopic Molecular Weight

175.063328537

IUPAC Name

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

Traditional Name

β-indole-3-acetic acid

CAS Registry Number

87-51-4

SMILES

OC(=O)CC1=CNC2=CC=CC=C12

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

Chemical Taxonomy

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 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0000197)

Food

Vegetable

Root vegetable

Red beetroot (FooDB: FOOD00264)

Process

Not Available

Role

Not Available

Physical Properties

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