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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:36 UTC
Update Date2021-10-13 04:37:29 UTC
HMDB IDHMDB0002096
Secondary Accession Numbers
  • HMDB02096
Metabolite Identification
Common Name3-Indolebutyric acid
Description3-Indolebutyric acid is an indolic tryptophan metabolite occasionally found in human urine. (PMID:7130309 ). 3-Indolebutyric acid is a plasma and urinary tryptophan-related metabolite related to metabolic and skin diseases. (PMID:15206797 ). Plasma levels of tryptophan metabolites in the umbilical vein and artery are significantly higher than those in the maternal vein. (PMID:1506727 ). 3-Indolebutyric acid has been shown to accelerated glucose uptake in the rat diaphragm. (PMID:6025019 ). 3-Indolebutyric acid is also a microbial netabolite, urinary indole-3-butyrate is produced by Clostridia sp. (PMID:6630445 ).
Structure
Data?1595010390
Synonyms
ValueSource
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
Chemical FormulaC12H13NO2
Average Molecular Weight203.2371
Monoisotopic Molecular Weight203.094628665
IUPAC Name4-(1H-indol-3-yl)butanoic acid
Traditional Name3-indolebutyric acid
CAS Registry Number133-32-4
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 KeyJTEDVYBZBROSJT-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.
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
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point124.5 °CNot Available
Boiling Point426.56 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.25 mg/mL at 20 °CNot Available
LogP2.30HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.36 g/LALOGPS
logP10(2.38) g/LALOGPS
logP10(2.6) g/LChemAxon
logS10(-2.8) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+146.66331661259
DarkChem[M-H]-145.74831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Indolebutyric acidOC(=O)CCCC1=CNC2=C1C=CC=C23428.6Standard polar33892256
3-Indolebutyric acidOC(=O)CCCC1=CNC2=C1C=CC=C21900.3Standard non polar33892256
3-Indolebutyric acidOC(=O)CCCC1=CNC2=C1C=CC=C22091.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Indolebutyric acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCCC1=C[NH]C2=CC=CC=C122140.6Semi standard non polar33892256
3-Indolebutyric acid,1TMS,isomer #2C[Si](C)(C)N1C=C(CCCC(=O)O)C2=CC=CC=C212196.4Semi standard non polar33892256
3-Indolebutyric acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCCC1=CN([Si](C)(C)C)C2=CC=CC=C122168.8Semi standard non polar33892256
3-Indolebutyric acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCCC1=CN([Si](C)(C)C)C2=CC=CC=C122114.8Standard non polar33892256
3-Indolebutyric acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCCC1=CN([Si](C)(C)C)C2=CC=CC=C122343.5Standard polar33892256
3-Indolebutyric acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCC1=C[NH]C2=CC=CC=C122393.6Semi standard non polar33892256
3-Indolebutyric acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=C(CCCC(=O)O)C2=CC=CC=C212435.6Semi standard non polar33892256
3-Indolebutyric acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122617.8Semi standard non polar33892256
3-Indolebutyric acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122557.0Standard non polar33892256
3-Indolebutyric acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122559.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-Indolebutyric acid GC-MS (1 TMS)splash10-000x-0910000000-7c2b4d74ecedb117caf32014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Indolebutyric acid GC-MS (2 TMS)splash10-0udi-0391000000-c62444bc1faa5f67d6522014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Indolebutyric acid EI-B (Non-derivatized)splash10-001i-0920000000-a53e6a97ea38d50751b72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Indolebutyric acid GC-MS (Non-derivatized)splash10-000x-0910000000-7c2b4d74ecedb117caf32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Indolebutyric acid GC-MS (Non-derivatized)splash10-0udi-0391000000-c62444bc1faa5f67d6522017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Indolebutyric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-005c-2900000000-6403d086e6b2ec4ac0d32017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Indolebutyric acid GC-MS (1 TMS) - 70eV, Positivesplash10-05j0-7920000000-fc57e474504223a4e8382017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Indolebutyric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indolebutyric acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0f79-0970000000-7543d99fe8a1f2b0de252012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indolebutyric acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00lu-0900000000-b46d8f64c372b7348dbd2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indolebutyric acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-00lu-2900000000-ccb02800c683b0a921ee2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indolebutyric acid EI-B (HITACHI M-68) , Positive-QTOFsplash10-001i-0920000000-a53e6a97ea38d50751b72012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-0udi-0090000000-d6f784c6fec287fbd7c42012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-0udi-0590000000-22d2baa6bbf6262cb3cf2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-014i-1900000000-21352951c1447c77df392012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-014i-2900000000-184013bb3b879000bdf12012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-014i-2900000000-cd1951f573aa0d883a8c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOFsplash10-0f79-1930000000-d04d53f6788d45ef881f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOFsplash10-002u-2900000000-e52b6e60b86d650a9c2e2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOFsplash10-0032-8900000000-f17437c2c96f7f7f4ed22012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOFsplash10-017j-9500000000-8e79159a3b4ebf3488d82012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOFsplash10-014i-5900000000-afb8479ad9268699e8232012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ , negative-QTOFsplash10-0udi-0090000000-d6f784c6fec287fbd7c42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ , negative-QTOFsplash10-0udi-0590000000-22d2baa6bbf6262cb3cf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ , negative-QTOFsplash10-014i-1900000000-21352951c1447c77df392017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ , negative-QTOFsplash10-014i-2900000000-184013bb3b879000bdf12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Indolebutyric acid LC-ESI-QQ , negative-QTOFsplash10-014i-2900000000-cd1951f573aa0d883a8c2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Indolebutyric acid 10V, Positive-QTOFsplash10-0udr-0960000000-cbabcf60da67d36a7a522017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Indolebutyric acid 20V, Positive-QTOFsplash10-0pbl-2910000000-66aadf35b92473e5d20e2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Indolebutyric acid 40V, Positive-QTOFsplash10-0006-5900000000-3eb3c75b1c9c299f55b52017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Indolebutyric acid 10V, Negative-QTOFsplash10-0udi-0290000000-534678e83a3a049ca3622017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Indolebutyric acid 20V, Negative-QTOFsplash10-0zfr-1890000000-baeca4f8b84a743b76a02017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Indolebutyric acid 40V, Negative-QTOFsplash10-0a4l-9700000000-72990cf325b9dadb784a2017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, Methanol, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue Locations
  • Neuron
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Schizophrenia
details
Associated Disorders and Diseases
Disease References
Schizophrenia
  1. Cai HL, Li HD, Yan XZ, Sun B, Zhang Q, Yan M, Zhang WY, Jiang P, Zhu RH, Liu YP, Fang PF, Xu P, Yuan HY, Zhang XH, Hu L, Yang W, Ye HS: Metabolomic analysis of biochemical changes in the plasma and urine of first-episode neuroleptic-naive schizophrenia patients after treatment with risperidone. J Proteome Res. 2012 Aug 3;11(8):4338-50. doi: 10.1021/pr300459d. Epub 2012 Jul 26. [PubMed:22800120 ]
Associated OMIM IDs
DrugBank IDDB02740
Phenol Explorer Compound IDNot Available
FooDB IDFDB001404
KNApSAcK IDC00000116
Chemspider ID8298
KEGG Compound IDC11284
BioCyc IDCPD-10507
BiGG IDNot Available
Wikipedia LinkIndole-3-butyric_acid
METLIN ID6485
PubChem Compound8617
PDB IDNot Available
ChEBI ID33070
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1190841
References
Synthesis ReferencePolaczkowa, W.; Porowska, N. 3-Indolebutyric acid. Przemysl Chemiczny (1950), 6 340-3.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Merle M, Gilbert A, Fredenucci JF, Petry D, Foliguet B, Mosnier M: Experimental and clinical study of the effect of naftidrofuryl on the recovery from peripheral nerve lesions. Microsurgery. 1994;15(3):179-86. [PubMed:8015423 ]
  2. Hirsch JL, Bensoussan JJ, Mosnier M, Lehert P: [Evaluation of the efficacy and tolerance of naftidrofuryl in patients presenting with exertional angina. Multicenter double-blind versus placebo study]. Ann Cardiol Angeiol (Paris). 1999 Feb;48(2):137-45. [PubMed:12555338 ]
  3. Meininger V, Chaineau E, Soudiere B: [Effect of naftidrofuryl (LS129) on axonal growth]. Rev Neurol (Paris). 1994;150(2):115-22. [PubMed:7863151 ]
  4. Eguchi K, Kamimura S, Yonezawa M, Mitsui Y, Mizutani Y, Kudo T: [Tryptophan and its metabolite concentrations in human plasma during the perinatal period]. Nihon Sanka Fujinka Gakkai Zasshi. 1992 Jun;44(6):663-8. [PubMed:1506727 ]
  5. Tonelli D, Gattavecchia E, Gandolfi M: Thin-layer chromatographic determination of indolic tryptophan metabolites in human urine using Sep-Pak C18 extraction. J Chromatogr. 1982 Sep 10;231(2):283-9. [PubMed:7130309 ]
  6. Marklova E, Albahri Z, Nozickova M: HPLC profiling of Trp-related metabolites in humans. Adv Exp Med Biol. 2003;527:739-44. [PubMed:15206797 ]
  7. Silverstein MN, Wakim KG, Bahn RC: The influence of tryptophan metabolites on tissue uptake of glucose. Metabolism. 1967 May;16(5):410-2. [PubMed:6025019 ]
  8. Lombard GL, Dowell VR Jr: Comparison of three reagents for detecting indole production by anaerobic bacteria in microtest systems. J Clin Microbiol. 1983 Sep;18(3):609-13. [PubMed:6630445 ]

Enzymes

General function:
Not Available
Specific function:
Beta-2-microglobulin is the beta-chain of major histocompatibility complex class I molecules
Gene Name:
B2M
Uniprot ID:
P61769
Molecular weight:
13715.0
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]