Record Information
Version1.0
Creation date2010-04-08 22:04:57 UTC
Update date2019-11-26 02:56:27 UTC
Primary IDFDB001404
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIndole-3-butyric acid
Description3-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 Number133-32-4
Structure
Thumb
Synonyms
SynonymSource
1H-Indole-3-butanoic acidChEBI
3-Indolyl-gamma-butyric acidChEBI
4-(indol-3-yl)Butyric acidChEBI
4-indol-3-Ylbutyric acidChEBI
IBAChEBI
Indole-3-butanoic acidChEBI
Indolebutyric acidChEBI
SeradixChEBI
Indole-3-butyric acidKegg
1H-Indole-3-butanoateGenerator
3-Indolyl-g-butyrateGenerator
3-Indolyl-g-butyric acidGenerator
3-Indolyl-gamma-butyrateGenerator
3-Indolyl-γ-butyrateGenerator
3-Indolyl-γ-butyric acidGenerator
4-(indol-3-yl)ButyrateGenerator
4-indol-3-YlbutyrateGenerator
Indole-3-butanoateGenerator
IndolebutyrateGenerator
Indole-3-butyrateGenerator
3-IndolebutyrateGenerator
Indolebutyric acid, monoammonium saltMeSH
Indolebutyric acid, monopotassium saltMeSH
Indolebutyric acid, monosodium saltMeSH
1H-Indole-3-butyrateHMDB
1H-Indole-3-butyric acidHMDB
3-Indole butyrateHMDB
3-Indole butyric acidHMDB
3-Indolylbutyric acidHMDB
3-IodolebutyrateHMDB
4-(1H-indol-3-yl)-ButyrateHMDB
4-(1H-indol-3-yl)-Butyric acidHMDB
4-(1H-indol-3-yl)ButanoateHMDB
4-(1H-Indol-3-yl)butanoic acidHMDB
4-(3-1H-Indolyl)butyrateHMDB
4-(3-1H-Indolyl)butyric acidHMDB
4-(3-Indole)-butyrateHMDB
4-(3-Indole)-butyric acidHMDB
4-(3-Indolyl)butyrateHMDB
4-(3-Indolyl)butyric acidHMDB
4-(Indolyl)- butyrateHMDB
4-(Indolyl)- butyric acidHMDB
4-indol-3-Ylbutyric-acidHMDB
b-IndolebutyrateHMDB
b-Indolebutyric acidHMDB
beta-IndolebutyrateHMDB
beta-Indolebutyric acidHMDB
Indole 3-butyrateHMDB
Indole 3-butyric acidHMDB
Indole-3 butyrateHMDB
Indole-3 butyric acidHMDB
Indole-3-butrylateHMDB
Indole-3-butrylic acidHMDB
Indolyl-3-butyrateHMDB
Indolyl-3-butyric acidHMDB
3-Indolebutyric acidChEBI
4-(1H-Indol-3-yl)butyric acidHMDB
4-(3-Indolyl)butanoic acidHMDB
4-(Indol-3-yl)butanoateHMDB
[3-(3-Indolyl)propyl]carboxylic acidHMDB
beta-IBAHMDB
beta-Indolylbutyric acidHMDB
gamma-(Indol-3-yl)butyric acidHMDB
gamma-(Indole-3)-butyric acidHMDB
β-IBAHMDB
β-Indolebutyric acidHMDB
β-Indolylbutyric acidHMDB
γ-(Indol-3-yl)butyric acidHMDB
γ-(Indole-3)-butyric acidHMDB
β-indolebutyric acidbiospider
1H-Indole-3-butanoic acid (9CI)biospider
4-(1H-Indol-3-yl)-butyratebiospider
4-(1H-Indol-3-yl)-butyric acidbiospider
4-(1H-indol-3-yl)butanoatebiospider
4-(1H-indol-3-yl)butanoic acidbiospider
4-(Indol-3-yl)butyratebiospider
4-(Indol-3-yl)butyric acidbiospider
4-(indolyl)- butyratebiospider
4-(indolyl)- butyric acidbiospider
4-(Indolyl)butyric acidbiospider
4-indol-3-ylbutyratebiospider
4-Indol-3-ylbutyric-acidbiospider
B-indolebutyratebiospider
B-indolebutyric acidbiospider
Beta-ibabiospider
Beta-indolebutyratebiospider
Beta-indolebutyric acidbiospider
Beta-indolylbutyric acidbiospider
Butyric acid, 4-(indolyl)-biospider
Indol-3,4'-yl butyric acidbiospider
Indolbutyric acidbiospider
Indole butyric acidbiospider
Indole-3 Butyratebiospider
Indole-3 Butyric acidbiospider
Indole-3-Butrylatebiospider
Indole-3-Butrylic acidbiospider
Indole-3-butyric acid (8CI)biospider
Predicted Properties
PropertyValueSource
Water Solubility0.36 g/LALOGPS
logP2.38ALOGPS
logP2.6ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)4.86ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.65 m³·mol⁻¹ChemAxon
Polarizability22.03 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC12H13NO2
IUPAC name4-(1H-indol-3-yl)butanoic acid
InChI IdentifierInChI=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 KeyJTEDVYBZBROSJT-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CCCC1=CNC2=C1C=CC=C2
Average Molecular Weight203.2371
Monoisotopic Molecular Weight203.094628665
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point124.5 oC
Boiling PointNot Available
Experimental Water Solubility0.25 mg/mL at 20 oCTOMLIN,C (1994)
Experimental logP2.30HANSCH,C ET AL. (1995)
Experimental pKa4.7
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSIndole-3-butyric acid, 1 TMS, GC-MS Spectrumsplash10-000x-0910000000-7c2b4d74ecedb117caf3Spectrum
GC-MSIndole-3-butyric acid, 2 TMS, GC-MS Spectrumsplash10-0udi-0391000000-c62444bc1faa5f67d652Spectrum
GC-MSIndole-3-butyric acid, non-derivatized, GC-MS Spectrumsplash10-001i-0920000000-a53e6a97ea38d50751b7Spectrum
GC-MSIndole-3-butyric acid, non-derivatized, GC-MS Spectrumsplash10-000x-0910000000-7c2b4d74ecedb117caf3Spectrum
GC-MSIndole-3-butyric acid, non-derivatized, GC-MS Spectrumsplash10-0udi-0391000000-c62444bc1faa5f67d652Spectrum
Predicted GC-MSIndole-3-butyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-005c-2900000000-6403d086e6b2ec4ac0d3Spectrum
Predicted GC-MSIndole-3-butyric acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05j0-7920000000-fc57e474504223a4e838Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0f79-0970000000-7543d99fe8a1f2b0de25Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00lu-0900000000-b46d8f64c372b7348dbdSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00lu-2900000000-ccb02800c683b0a921eeSpectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-001i-0920000000-a53e6a97ea38d50751b7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0090000000-d6f784c6fec287fbd7c4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0590000000-22d2baa6bbf6262cb3cfSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-1900000000-21352951c1447c77df39Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-2900000000-184013bb3b879000bdf1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-2900000000-cd1951f573aa0d883a8cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0f79-1930000000-d04d53f6788d45ef881fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-002u-2900000000-e52b6e60b86d650a9c2eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0032-8900000000-f17437c2c96f7f7f4ed2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-017j-9500000000-8e79159a3b4ebf3488d8Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-5900000000-afb8479ad9268699e823Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-d6f784c6fec287fbd7c4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0590000000-22d2baa6bbf6262cb3cfSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-1900000000-21352951c1447c77df39Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-2900000000-184013bb3b879000bdf1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-2900000000-cd1951f573aa0d883a8cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0960000000-cbabcf60da67d36a7a52Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pbl-2910000000-66aadf35b92473e5d20eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-5900000000-3eb3c75b1c9c299f55b5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0290000000-534678e83a3a049ca362Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-1890000000-baeca4f8b84a743b76a0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9700000000-72990cf325b9dadb784aSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID8298
ChEMBL IDCHEMBL582878
KEGG Compound IDC11284
Pubchem Compound ID8617
Pubchem Substance IDNot Available
ChEBI ID33070
Phenol-Explorer IDNot Available
DrugBank IDDB02740
HMDB IDHMDB02096
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDINDOLE-3-BUTYRIC-ACID
BIGG IDNot Available
KNApSAcK IDC00000116
HET ID3IB
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDIndole-3-butyric_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
insulinase inhibitor23924 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
insulinotonicDUKE
Enzymes
NameGene NameUniProt ID
Beta-2-microglobulin precursor [Contains: Beta-2-microglobulin variant pI 5.3]B2MP61769
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot 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).