Bovine Metabolome Database: Showing metabocard for 3-Indolebutyric acid (BMDB0002096)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:51:10 UTC

Update Date

2020-05-11 20:45:10 UTC

BMDB ID

BMDB0002096

Secondary Accession Numbers

BMDB02096

Metabolite Identification

Common Name

3-Indolebutyric 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. Based on a literature review a significant number of articles have been published on 3-Indolebutyric acid.

Structure

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

Synonyms

Value	Source
1H-Indole-3-butanoic acid	ChEBI
3-Indolyl-gamma-butyric acid	ChEBI
4-(indol-3-yl)Butyric acid	ChEBI
4-indol-3-Ylbutyric acid	ChEBI
IBA	ChEBI
Indole-3-butanoic acid	ChEBI
Indolebutyric acid	ChEBI
Seradix	ChEBI
Indole-3-butyric acid	Kegg
1H-Indole-3-butanoate	Generator
3-Indolyl-g-butyrate	Generator
3-Indolyl-g-butyric acid	Generator
3-Indolyl-gamma-butyrate	Generator
3-Indolyl-γ-butyrate	Generator
3-Indolyl-γ-butyric acid	Generator
4-(indol-3-yl)Butyrate	Generator
4-indol-3-Ylbutyrate	Generator
Indole-3-butanoate	Generator
Indolebutyrate	Generator
Indole-3-butyrate	Generator
3-Indolebutyrate	Generator
Indolebutyric acid, monoammonium salt	MeSH
Indolebutyric acid, monopotassium salt	MeSH
Indolebutyric acid, monosodium salt	MeSH
1H-Indole-3-butyrate	HMDB
1H-Indole-3-butyric acid	HMDB
3-Indole butyrate	HMDB
3-Indole butyric acid	HMDB
3-Indolylbutyric acid	HMDB
3-Iodolebutyrate	HMDB
4-(1H-indol-3-yl)-Butyrate	HMDB
4-(1H-indol-3-yl)-Butyric acid	HMDB
4-(1H-indol-3-yl)Butanoate	HMDB
4-(1H-Indol-3-yl)butanoic acid	HMDB
4-(3-1H-Indolyl)butyrate	HMDB
4-(3-1H-Indolyl)butyric acid	HMDB
4-(3-Indole)-butyrate	HMDB
4-(3-Indole)-butyric acid	HMDB
4-(3-Indolyl)butyrate	HMDB
4-(3-Indolyl)butyric acid	HMDB
4-(Indolyl)- butyrate	HMDB
4-(Indolyl)- butyric acid	HMDB
4-indol-3-Ylbutyric-acid	HMDB
b-Indolebutyrate	HMDB
b-Indolebutyric acid	HMDB
beta-Indolebutyrate	HMDB
beta-Indolebutyric acid	HMDB
Indole 3-butyrate	HMDB
Indole 3-butyric acid	HMDB
Indole-3 butyrate	HMDB
Indole-3 butyric acid	HMDB
Indole-3-butrylate	HMDB
Indole-3-butrylic acid	HMDB
Indolyl-3-butyrate	HMDB
Indolyl-3-butyric acid	HMDB
3-Indolebutyric acid	ChEBI
4-(1H-Indol-3-yl)butyric acid	HMDB
4-(3-Indolyl)butanoic acid	HMDB
4-(Indol-3-yl)butanoate	HMDB
[3-(3-Indolyl)propyl]carboxylic acid	HMDB
beta-IBA	HMDB
beta-Indolylbutyric acid	HMDB
gamma-(Indol-3-yl)butyric acid	HMDB
gamma-(Indole-3)-butyric acid	HMDB
β-IBA	HMDB
β-Indolebutyric acid	HMDB
β-Indolylbutyric acid	HMDB
γ-(Indol-3-yl)butyric acid	HMDB
γ-(Indole-3)-butyric acid	HMDB

Chemical Formula

C₁₂H₁₃NO₂

Average Molecular Weight

203.2371

Monoisotopic Molecular Weight

203.094628665

IUPAC Name

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

Traditional Name

3-indolebutyric acid

CAS Registry Number

133-32-4

SMILES

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

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

Chemical Taxonomy

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

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	124.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.25 mg/mL at 20 °C	Not Available
LogP	2.3	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-000x-0910000000-7c2b4d74ecedb117caf3	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0udi-0391000000-c62444bc1faa5f67d652	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-0920000000-a53e6a97ea38d50751b7	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000x-0910000000-7c2b4d74ecedb117caf3	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-0391000000-c62444bc1faa5f67d652	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-005c-2900000000-6403d086e6b2ec4ac0d3	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05j0-7920000000-fc57e474504223a4e838	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0f79-0970000000-7543d99fe8a1f2b0de25	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00lu-0900000000-b46d8f64c372b7348dbd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00lu-2900000000-ccb02800c683b0a921ee	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positive	splash10-001i-0920000000-a53e6a97ea38d50751b7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0090000000-d6f784c6fec287fbd7c4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udi-0590000000-22d2baa6bbf6262cb3cf	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-014i-1900000000-21352951c1447c77df39	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-014i-2900000000-184013bb3b879000bdf1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-014i-2900000000-cd1951f573aa0d883a8c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0f79-1930000000-d04d53f6788d45ef881f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-002u-2900000000-e52b6e60b86d650a9c2e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0032-8900000000-f17437c2c96f7f7f4ed2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-017j-9500000000-8e79159a3b4ebf3488d8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-014i-5900000000-afb8479ad9268699e823	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0090000000-d6f784c6fec287fbd7c4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0590000000-22d2baa6bbf6262cb3cf	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-1900000000-21352951c1447c77df39	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-2900000000-184013bb3b879000bdf1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-2900000000-cd1951f573aa0d883a8c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-0960000000-cbabcf60da67d36a7a52	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pbl-2910000000-66aadf35b92473e5d20e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-5900000000-3eb3c75b1c9c299f55b5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0290000000-534678e83a3a049ca362	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-1890000000-baeca4f8b84a743b76a0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9700000000-72990cf325b9dadb784a	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Membrane

Biospecimen Locations

Neuron
Platelet

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Platelet	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details