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1H-Indole-3-acetic acid (FDB000933)

Record Information
Version1.0
Creation date2010-04-08 22:04:46 UTC
Update date2020-04-21 18:03:36 UTC
Primary IDFDB000933
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name1H-Indole-3-acetic acid
DescriptionWidely distributed in higher plants Indole-3-acetic acid, also known as IAA, is a heterocyclic compound that is a phytohormone called auxin. This colourless solid is probably the most important plant auxin. The molecule is derived from indole, containing a carboxymethyl group (acetic acid). 1H-Indole-3-acetic acid is found in many foods, some of which are lettuce, cherry tomato, chinese bayberry, and okra.
CAS Number87-51-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.38 g/LALOGPS
logP1.87ALOGPS
logP1.71ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)4.66ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity48.45 m³·mol⁻¹ChemAxon
Polarizability17.74 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H9NO2
IUPAC name2-(1H-indol-3-yl)acetic acid
InChI IdentifierInChI=1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)
InChI KeySEOVTRFCIGRIMH-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CC1=CNC2=C1C=CC=C2
Average Molecular Weight175.184
Monoisotopic Molecular Weight175.063328537
Classification
Description Belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolyl carboxylic acids and derivatives
Direct ParentIndole-3-acetic acid derivatives
Alternative Parents
Substituents
  • Indole-3-acetic acid derivative
  • 3-alkylindole
  • Indole
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Foods
  • Dairy products
  • Eggs
  • Meats

    • Grains:

    Nuts and legumes:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 68.56%; H 5.18%; N 8.00%; O 18.27%DFC
    Melting PointMp 164-165°DFC
    Boiling PointNot Available
    Experimental Water Solubility1.5 mg/mL at 20 oCSHIU,WY et al. (1990)
    Experimental logP1.41HANSCH,C ET AL. (1995)
    Experimental pKapKa2 16.9 (NH)DFC
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV Data289 (e 8700) (MeOH) (Berdy)DFC
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    EI-MSMass Spectrum (Electron Ionization)splash10-001i-1900000000-3ffc47eb6c977956ad932014-09-20View Spectrum
    GC-MS1H-Indole-3-acetic acid, 2 TMS, GC-MS Spectrumsplash10-0udi-0391000000-7581f14fe5be5b2b2954Spectrum
    GC-MS1H-Indole-3-acetic acid, 2 TMS, GC-MS Spectrumsplash10-0udi-0691000000-de9ac4f748d50db109eaSpectrum
    GC-MS1H-Indole-3-acetic acid, 2 TMS, GC-MS Spectrumsplash10-0udi-0591000000-9687f83d1372abe23c3cSpectrum
    GC-MS1H-Indole-3-acetic acid, 2 TMS, GC-MS Spectrumsplash10-0udi-1793100000-7c78003038436ec5a902Spectrum
    GC-MS1H-Indole-3-acetic acid, 1 TMS, GC-MS Spectrumsplash10-00ai-7910000000-4aa7b8244f32048c76bcSpectrum
    GC-MS1H-Indole-3-acetic acid, 2 TMS, GC-MS Spectrumsplash10-0fk9-9250000000-a5f931fc3292056dba65Spectrum
    GC-MS1H-Indole-3-acetic acid, 1 TMS, GC-MS Spectrumsplash10-001i-1920000000-f0ecee61454a589493afSpectrum
    GC-MS1H-Indole-3-acetic acid, 2 TMS, GC-MS Spectrumsplash10-0udi-1692000000-ce863a1ca2a657cb41d5Spectrum
    GC-MS1H-Indole-3-acetic acid, non-derivatized, GC-MS Spectrumsplash10-003r-0900000000-1edcb4977a52155bc130Spectrum
    GC-MS1H-Indole-3-acetic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-0391000000-7581f14fe5be5b2b2954Spectrum
    GC-MS1H-Indole-3-acetic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-0691000000-de9ac4f748d50db109eaSpectrum
    GC-MS1H-Indole-3-acetic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-0591000000-9687f83d1372abe23c3cSpectrum
    GC-MS1H-Indole-3-acetic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-1793100000-7c78003038436ec5a902Spectrum
    GC-MS1H-Indole-3-acetic acid, non-derivatized, GC-MS Spectrumsplash10-00ai-7910000000-4aa7b8244f32048c76bcSpectrum
    GC-MS1H-Indole-3-acetic acid, non-derivatized, GC-MS Spectrumsplash10-0fk9-9250000000-a5f931fc3292056dba65Spectrum
    GC-MS1H-Indole-3-acetic acid, non-derivatized, GC-MS Spectrumsplash10-001i-1920000000-f0ecee61454a589493afSpectrum
    GC-MS1H-Indole-3-acetic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-1692000000-ce863a1ca2a657cb41d5Spectrum
    GC-MS1H-Indole-3-acetic acid, non-derivatized, GC-MS Spectrumsplash10-0udi-0691000000-f6073f8f35a6930b5aacSpectrum
    Predicted GC-MS1H-Indole-3-acetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0059-1900000000-ab74ec83b16ac0b97d12Spectrum
    Predicted GC-MS1H-Indole-3-acetic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-7920000000-8dab2ad22251c9fbd21cSpectrum
    Predicted GC-MS1H-Indole-3-acetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS1H-Indole-3-acetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS1H-Indole-3-acetic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS1H-Indole-3-acetic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS1H-Indole-3-acetic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-0900000000-f6dbb01a35af3042d1262012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-0900000000-2ae231b7d0e2cd50aed82012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-6900000000-9eae14faa16b8f8259da2012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-003r-0900000000-1edcb4977a52155bc1302012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00e9-0900000000-187b48f2258823cbc6a22012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-001i-0900000000-30b7a73fa446d0e3c8d32012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-0900000000-bbe0fb5a48f89ea6e3832012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-0900000000-97850f400d80de2783342012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-0900000000-600545759ef108827b9e2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0kxr-5900000000-ba2eed29832f9ee489212012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-004l-5900000000-a0b30710f83e53b6f3db2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-9500000000-146ac0a20f9d53e762912012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-053r-9600000000-d9258b3c6b5c6f748f6e2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004i-9300000000-b59628beb41b424daf4a2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (UPLC Waters, Quattro Ultima Pt Micromass) , Positive (Annotated)splash10-004i-0900000000-755373c9248cfb6425fc2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-004i-0900000000-2b3df7a1dd85faea67052012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-003r-0900000000-9522ab089ab89b64f96a2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-001i-0900000000-b735e95cb23091491c2e2012-08-31View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-2a3dd24f136523e6ce1e2015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053r-0900000000-77436493836245345cb82015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lr-1900000000-4e0b6f24d03c0b25800f2015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00e9-0900000000-1d045a56f3669a1c93912015-04-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05ai-0900000000-518778c36bacbf77b9012015-04-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5c-3900000000-323fc64084836756be302015-04-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-2a3dd24f136523e6ce1e2015-05-27View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, 15.09 MHz, DMSO-d6, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
    2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
    ChemSpider ID780
    ChEMBL IDCHEMBL82411
    KEGG Compound IDC00954
    Pubchem Compound ID802
    Pubchem Substance IDNot Available
    ChEBI ID16411
    Phenol-Explorer IDNot Available
    DrugBank IDDB07950
    HMDB IDHMDB00197
    CRC / DFC (Dictionary of Food Compounds) IDBNC14-M:BNC14-M
    EAFUS IDNot Available
    Dr. Duke IDINDOLE-ACETIC-ACID|BETA-INDOLACETIC-ACID|INDOLE-3-ACETIC-ACID
    BIGG ID1485312
    KNApSAcK IDC00000100
    HET IDIAC
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDrw1251501
    SuperScent IDNot Available
    Wikipedia IDIndole-3-acetic_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
    allelochemicDUKE
    cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    herbicide24527 A substance used to destroy plant pests.DUKE
    hormone24621 Originally referring to an endogenous compound that is formed in specialized organ or group of cells and carried to another organ or group of cells, in the same organism, upon which it has a specific regulatory function, the term is now commonly used to include non-endogenous, semi-synthetic and fully synthetic analogues of such compounds.DUKE
    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
    pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
    EnzymesNot Available
    Pathways
    NameSMPDB LinkKEGG Link
    Tryptophan MetabolismSMP00063 map00380
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    Flavours
    FlavorCitations
    odorless
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    mild
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    sour
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    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).