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Record Information
Version3.6
Creation Date2006-05-22 14:17:36 UTC
Update Date2016-02-11 01:05:17 UTC
HMDB IDHMDB02096
Secondary Accession NumbersNone
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 ).
Structure
Thumb
Synonyms
ValueSource
Indole-3-butyric acidKegg
IBAKegg
Indole-3-butyrateGenerator
3-IndolebutyrateGenerator
1H-Indole-3-butanoateHMDB
1H-Indole-3-butanoic acidHMDB
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-(indol-3-yl)ButyrateHMDB
4-(indol-3-yl)Butyric acidHMDB
4-(Indolyl)- butyrateHMDB
4-(Indolyl)- butyric acidHMDB
4-indol-3-YlbutyrateHMDB
4-indol-3-Ylbutyric 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-butanoateHMDB
Indole-3-butanoic acidHMDB
Indole-3-butrylateHMDB
Indole-3-butrylic acidHMDB
IndolebutyrateHMDB
Indolebutyric acidHMDB
Indolyl-3-butyrateHMDB
Indolyl-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=CC=CC=C12
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 KeyInChIKey=JTEDVYBZBROSJT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indoles. These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct ParentIndoles
Alternative Parents
Substituents
  • Indole
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point124.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.25 mg/mL at 20 °CNot Available
LogP2.30HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.36 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.65 m3·mol-1ChemAxon
Polarizability22.03 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-000x-0910000000-7c2b4d74ecedb117caf3View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-0391000000-c62444bc1faa5f67d652View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0f79-0970000000-7543d99fe8a1f2b0de25View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00lu-0900000000-b46d8f64c372b7348dbdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00lu-2900000000-ccb02800c683b0a921eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-001i-0920000000-a53e6a97ea38d50751b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0090000000-d6f784c6fec287fbd7c4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0590000000-22d2baa6bbf6262cb3cfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-1900000000-21352951c1447c77df39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014i-2900000000-184013bb3b879000bdf1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-2900000000-cd1951f573aa0d883a8cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0f79-1930000000-d04d53f6788d45ef881fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-002u-2900000000-e52b6e60b86d650a9c2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0032-8900000000-f17437c2c96f7f7f4ed2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-017j-9500000000-8e79159a3b4ebf3488d8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-5900000000-afb8479ad9268699e823View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Nerve Cells
  • Platelet
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02740
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001404
KNApSAcK IDC00000116
Chemspider ID8298
KEGG Compound IDC11284
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIndolebutyric acid
NuGOwiki LinkHMDB02096
Metagene LinkHMDB02096
METLIN ID6485
PubChem Compound8617
PDB ID3IB
ChEBI ID33070
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. [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. [12555338 ]
  3. Meininger V, Chaineau E, Soudiere B: [Effect of naftidrofuryl (LS129) on axonal growth] Rev Neurol (Paris). 1994;150(2):115-22. [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] Nippon Sanka Fujinka Gakkai Zasshi. 1992 Jun;44(6):663-8. [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. [7130309 ]
  6. Marklova E, Albahri Z, Nozickova M: HPLC profiling of Trp-related metabolites in humans. Adv Exp Med Biol. 2003;527:739-44. [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. [6025019 ]

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. [10592235 ]