Record Information
Version1.0
Creation date2010-04-08 22:04:46 UTC
Update date2018-01-23 18:46:59 UTC
Primary IDFDB000935
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIndole-beta-carboxylic acid
DescriptionPresent in plants, e.g. apple (Pyrus malus), garden pea (Pisum sativum) and brassicas Indole-3-carboxylic acid is a normal urinary indolic tryptophan metabolite (PMID 4844607) and has been found elevated in patients with liver diseases (PMID 13905029). Indole-beta-carboxylic acid is found in many foods, some of which are brussel sprouts, pomes, pulses, and cucumber.
CAS Number771-50-6
Structure
Thumb
Synonyms
SynonymSource
Indole-3-carboxylateGenerator
3-CarboxyindoleHMDB
1H-Indole-3-carboxylateHMDB
1H-Indole-3-carboxylic acidHMDB
3-Indole carboxylic acidHMDB
3-IndolecarboxylateHMDB
3-Indolecarboxylic acidHMDB
3-IndoleformateHMDB
3-Indoleformic acidHMDB
3-IndolylcarboxylateHMDB
3-Indolylcarboxylic acidHMDB
Indole - 3 carboxylateHMDB
Indole - 3 carboxylic acidHMDB
Indole-3-carboxylicacidHMDB
Indole-3-carboxylic acidKEGG
3-Indole Carboxylic acidbiospider
ICObiospider
Indole - 3 Carboxylatebiospider
Indole - 3 Carboxylic acidbiospider
Indole-b-carboxylic aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility2.42 g/LALOGPS
logP1.79ALOGPS
logP1.73ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.52ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.4 m³·mol⁻¹ChemAxon
Polarizability15.96 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC9H7NO2
IUPAC name1H-indole-3-carboxylic acid
InChI IdentifierInChI=1S/C9H7NO2/c11-9(12)7-5-10-8-4-2-1-3-6(7)8/h1-5,10H,(H,11,12)
InChI KeyKMAKOBLIOCQGJP-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C1=CNC2=CC=CC=C12
Average Molecular Weight161.1574
Monoisotopic Molecular Weight161.047678473
Classification
Description belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolecarboxylic acids and derivatives
Direct ParentIndolecarboxylic acids and derivatives
Alternative Parents
Substituents
  • Indolecarboxylic acid derivative
  • Indole
  • Pyrrole-3-carboxylic acid
  • Pyrrole-3-carboxylic acid or derivatives
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Vinylogous amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 67.08%; H 4.38%; N 8.69%; O 19.86%DFC
Melting PointMp 210-218° (198-200°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP1.99HANSCH,C ET AL. (1995)
Experimental pKapKa2 15.59 (25°,NH)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03xu-0900000000-cc599488e0b8dc7f1a65View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00xu-9640000000-dff74635f047e367f224View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0900000000-104208fcdd8732ebadf0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014l-4900000000-6b0c749e944b64d5385cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014u-9300000000-0af5d90221e77a572181View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-0900000000-8c45f845ef01c19b445cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-014l-1900000000-1c77378b797771275320View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qToF , Positivesplash10-0udi-0900000000-946741c676c658f5309fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-8c45f845ef01c19b445cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-02t9-0900000000-6053c6788a142676471bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014l-1900000000-1995f9dbe32f987d490aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014l-9800000000-670cc23cba665a2c274cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00ko-9100000000-933c5733f214b898f898View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03xu-0900000000-3f9d7c7294f2ea5a6c2cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014l-0900000000-a2251627ca78c6acb131View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014l-0900000000-391c26d59d3501f7004cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-9af372afcef18a3b9f32View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-265f90afc22f3879b03eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-3e251a670db5df960fd6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0900000000-ff43090393a4f119b73aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014l-1900000000-1c77378b797771275320View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0900000000-bac7fe6d41164b57962aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-75aeec0d90802e4f4ce6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0900000000-4057c3f38ac935f3f96bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02t9-0900000000-92711ed9a44b0be75d6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-4f69556e7cb4da6b44d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0900000000-c48621befefcf6da4d50View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID63063
ChEMBL IDCHEMBL387527
KEGG Compound IDC19837
Pubchem Compound ID69867
Pubchem Substance IDNot Available
ChEBI ID24809
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03320
CRC / DFC (Dictionary of Food Compounds) IDBNC72-C:BNC72-C
EAFUS IDNot Available
Dr. Duke IDINDOLE-3-CARBOXYLIC-ACID
BIGG IDNot Available
KNApSAcK IDC00000113
HET IDICO
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
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).