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 is a weakly acidic compound (based on its pKa). 3-Indolebutyric Acid has been detected, but not quantified in, a few different foods, such as common pea, corns, and potato. This could make 3-indolebutyric Acid a potential biomarker for the consumption of these foods.
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, monosodium saltMeSH
Indolebutyric acid, monopotassium saltMeSH
Indolebutyric acid, monoammonium 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
DHIChEBI
Dopamine lutineChEBI
AminochromeHMDB
DopaminochromeHMDB
[3-(3-Indolyl)propyl]carboxylic acidbiospider
β-indolebutyric acidbiospider
1H-Indole-3-butanoic acid (9CI)biospider
3-Indolebutyric acidbiospider
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-(1H-Indol-3-yl)butyric acidbiospider
4-(3-Indolyl)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
gamma-(Indol-3-yl)butyric acidbiospider
gamma-(Indole-3)-butyric acidbiospider
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-000x-0910000000-7c2b4d74ecedb117caf3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-0391000000-c62444bc1faa5f67d652JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-0920000000-a53e6a97ea38d50751b7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000x-0910000000-7c2b4d74ecedb117caf3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-0391000000-c62444bc1faa5f67d652JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-005c-2900000000-6403d086e6b2ec4ac0d3JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05j0-7920000000-fc57e474504223a4e838JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0f79-0970000000-7543d99fe8a1f2b0de25JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00lu-0900000000-b46d8f64c372b7348dbdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00lu-2900000000-ccb02800c683b0a921eeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-001i-0920000000-a53e6a97ea38d50751b7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0090000000-d6f784c6fec287fbd7c4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0590000000-22d2baa6bbf6262cb3cfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-1900000000-21352951c1447c77df39JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-2900000000-184013bb3b879000bdf1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-2900000000-cd1951f573aa0d883a8cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0f79-1930000000-d04d53f6788d45ef881fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-002u-2900000000-e52b6e60b86d650a9c2eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0032-8900000000-f17437c2c96f7f7f4ed2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-017j-9500000000-8e79159a3b4ebf3488d8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-5900000000-afb8479ad9268699e823JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0090000000-d6f784c6fec287fbd7c4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0590000000-22d2baa6bbf6262cb3cfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-1900000000-21352951c1447c77df39JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-2900000000-184013bb3b879000bdf1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-2900000000-cd1951f573aa0d883a8cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0960000000-cbabcf60da67d36a7a52JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pbl-2910000000-66aadf35b92473e5d20eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-5900000000-3eb3c75b1c9c299f55b5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0290000000-534678e83a3a049ca362JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-1890000000-baeca4f8b84a743b76a0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9700000000-72990cf325b9dadb784aJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
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).