AFCDB: Indole-3-butyric acid (FDB001404)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:57 UTC

Update date

2019-11-26 02:56:27 UTC

Primary ID

FDB001404

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Indole-3-butyric acid

Description

3-Indolebutyric acid, also known as 1H-indole-3-butanoate or 4-(indol-3-yl)butyrate, belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. 3-Indolebutyric acid has been detected, but not quantified in, several different foods, such as chickens (Gallus gallus), common peas (Pisum sativum), potatos (Solanum tuberosum), corns (Zea mays), and domestic pigs (Sus scrofa domestica). This could make 3-indolebutyric acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3-Indolebutyric acid.

CAS Number

133-32-4

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.36 g/L	ALOGPS
logP	2.38	ALOGPS
logP	2.6	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.86	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	4	ChemAxon
Refractivity	57.65 m³·mol⁻¹	ChemAxon
Polarizability	22.03 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

C12H13NO2

IUPAC name

4-(1H-indol-3-yl)butanoic acid

InChI Identifier

InChI=1S/C12H13NO2/c14-12(15)7-3-4-9-8-13-11-6-2-1-5-10(9)11/h1-2,5-6,8,13H,3-4,7H2,(H,14,15)

InChI Key

JTEDVYBZBROSJT-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)CCCC1=CNC2=C1C=CC=C2

Average Molecular Weight

203.2371

Monoisotopic Molecular Weight

203.094628665

Classification

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indol-3-yl carboxylic acid (CHEBI:33070 )

Ontology

Physiological effect

Health effect:

Health condition:

Schizophrenia

Disposition

Route of exposure:

Enteral:

Ingestion

Clostridium

Biological location:

Cell and elements:

Cell:

Nerve cell

Element:

Platelet

Subcellular:

Biofluid and excreta:

Blood

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	124.5 oC
Boiling Point	Not Available
Experimental Water Solubility	0.25 mg/mL at 20 oC	TOMLIN,C (1994)
Experimental logP	2.30	HANSCH,C ET AL. (1995)
Experimental pKa	4.7
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Indole-3-butyric acid, 1 TMS, GC-MS Spectrum	splash10-000x-0910000000-7c2b4d74ecedb117caf3	Spectrum
GC-MS	Indole-3-butyric acid, 2 TMS, GC-MS Spectrum	splash10-0udi-0391000000-c62444bc1faa5f67d652	Spectrum
GC-MS	Indole-3-butyric acid, non-derivatized, GC-MS Spectrum	splash10-001i-0920000000-a53e6a97ea38d50751b7	Spectrum
GC-MS	Indole-3-butyric acid, non-derivatized, GC-MS Spectrum	splash10-000x-0910000000-7c2b4d74ecedb117caf3	Spectrum
GC-MS	Indole-3-butyric acid, non-derivatized, GC-MS Spectrum	splash10-0udi-0391000000-c62444bc1faa5f67d652	Spectrum
Predicted GC-MS	Indole-3-butyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-005c-2900000000-6403d086e6b2ec4ac0d3	Spectrum
Predicted GC-MS	Indole-3-butyric acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05j0-7920000000-fc57e474504223a4e838	Spectrum
Predicted GC-MS	Indole-3-butyric acid, non-derivatized, 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)	splash10-0f79-0970000000-7543d99fe8a1f2b0de25	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00lu-0900000000-b46d8f64c372b7348dbd	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00lu-2900000000-ccb02800c683b0a921ee	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positive	splash10-001i-0920000000-a53e6a97ea38d50751b7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0090000000-d6f784c6fec287fbd7c4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udi-0590000000-22d2baa6bbf6262cb3cf	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-014i-1900000000-21352951c1447c77df39	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-014i-2900000000-184013bb3b879000bdf1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-014i-2900000000-cd1951f573aa0d883a8c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0f79-1930000000-d04d53f6788d45ef881f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-002u-2900000000-e52b6e60b86d650a9c2e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0032-8900000000-f17437c2c96f7f7f4ed2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-017j-9500000000-8e79159a3b4ebf3488d8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-5900000000-afb8479ad9268699e823	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0090000000-d6f784c6fec287fbd7c4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0590000000-22d2baa6bbf6262cb3cf	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-1900000000-21352951c1447c77df39	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-2900000000-184013bb3b879000bdf1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-2900000000-cd1951f573aa0d883a8c	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-0960000000-cbabcf60da67d36a7a52	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pbl-2910000000-66aadf35b92473e5d20e	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-5900000000-3eb3c75b1c9c299f55b5	2017-07-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0290000000-534678e83a3a049ca362	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-1890000000-baeca4f8b84a743b76a0	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9700000000-72990cf325b9dadb784a	2017-07-26	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

33070

Phenol-Explorer ID

Not Available

DrugBank ID

DB02740

HMDB ID

HMDB02096

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

INDOLE-3-BUTYRIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00000116

HET ID

3IB

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Indole-3-butyric_acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
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

Enzymes

Name	Gene Name	UniProt ID
Beta-2-microglobulin precursor [Contains: Beta-2-microglobulin variant pI 5.3]	B2M	P61769

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

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).

Indole-3-butyric acid (FDB001404)

Structure for FDB001404 (Indole-3-butyric acid)