Record Information
Version1.0
Creation date2010-04-08 22:04:46 UTC
Update date2024-11-29 22:27:21 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
Synonyms
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
    Physico-Chemical Properties - Experimental
    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
    Processing...
    Biological Effects and Interactions
    Health Effects / Bioactivities
    EnzymesNot Available
    Pathways
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    Flavours
    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).