Record Information
Version1.0
Creation date2010-04-08 22:04:57 UTC
Update date2019-11-26 02:56:26 UTC
Primary IDFDB001403
Secondary Accession Numbers
  • FDB030574
Chemical Information
FooDB Name5-Hydroxyindole-3-acetic acid
Description5-Hydroxyindoleacetic acid, also known as 5-hydroxyindole-3-acetate or 5-HIAA, 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. 5-Hydroxyindoleacetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Hydroxyindoleacetic acid exists in all living organisms, ranging from bacteria to humans. 5-Hydroxyindoleacetic acid has been detected, but not quantified in, several different foods, such as tea leaf willows, white cabbages, gooseberries, canola, and pepper (c. frutescens). This could make 5-hydroxyindoleacetic acid a potential biomarker for the consumption of these foods. 5-Hydroxyindoleacetic acid, with regard to humans, has been found to be associated with several diseases such as perillyl alcohol administration for cancer treatment, schizophrenia, friedreich's ataxia, and major depressive disorder; 5-hydroxyindoleacetic acid has also been linked to the inborn metabolic disorder carbamoyl phosphate synthetase deficiency.
CAS Number54-16-0
Structure
Thumb
Synonyms
SynonymSource
5-HIAAChEBI
5-Hydroxy-1H-indole-3-acetic acidChEBI
5-Hydroxyindol-3-ylacetic acidChEBI
5-Hydroxyindole-3-acetic acidChEBI
5-Hydroxy-1H-indole-3-acetateGenerator
5-Hydroxyindol-3-ylacetateGenerator
5-Hydroxyindole-3-acetateGenerator
5-HydroxyindoleacetateGenerator
Acid, 5-hydroxyindolamine aceticHMDB
Acid, hydroxyindoleaceticHMDB
5 Hydroxy 3 indoleacetic acidHMDB
5-Hydroxy-3-indoleacetic acidHMDB
Acetic acid, 5-hydroxyindolamineHMDB
5 Hydroxyindolamine acetic acidHMDB
5-Hydroxyindolamine acetic acidHMDB
Acid, 5-hydroxy-3-indoleaceticHMDB
Hydroxyindoleacetic acidHMDB
5-Hydroxy-3-indolylacetateHMDB
5-Hydroxy-iaaHMDB
5-Hydroxy-indole-3-acetateHMDB
5-Hydroxy-indole-3-acetic acidHMDB
5-HydroxyheteroauxinHMDB
5-Hydroxyindole acetateHMDB
5-OxyindoleacetateHMDB
5-Oxyindoleacetic acidHMDB
5HIAAHMDB
HydroxyindoleacetateHMDB
(5-hydroxy-1H-indol-3-yl)acetic acidbiospider
(5-hydroxyindol-3-yl)acetic acidbiospider
5-Hydroxy-IAAbiospider
5-Hydroxyindolacetic acidbiospider
5-Hydroxyindoleacetic acidbiospider
5-Hydroxyindolylacetic acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility1.8 g/LALOGPS
logP1.28ALOGPS
logP1.41ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity50.43 m³·mol⁻¹ChemAxon
Polarizability18.71 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H9NO3
IUPAC name2-(5-hydroxy-1H-indol-3-yl)acetic acid
InChI IdentifierInChI=1S/C10H9NO3/c12-7-1-2-9-8(4-7)6(5-11-9)3-10(13)14/h1-2,4-5,11-12H,3H2,(H,13,14)
InChI KeyDUUGKQCEGZLZNO-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CC1=CNC2=CC=C(O)C=C12
Average Molecular Weight191.1834
Monoisotopic Molecular Weight191.058243159
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
  • Hydroxyindole
  • Indole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Foods
  • Dairy products
  • Eggs
  • Meats
  • Grains:

    Nuts and legumes:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionNot Available
    Melting Point161-163 oC
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    Spectrum TypeDescriptionSplash KeyView
    GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0006-0390100000-f473f1a32542afd5d101JSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0006-1490100000-a72832b1524478059ef7JSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-0191000000-660345027702653fc000JSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0293000000-66850e233e11ec787808JSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-0191200000-99e904e0c2698a9ec34dJSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0390100000-f473f1a32542afd5d101JSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-1490100000-a72832b1524478059ef7JSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-0191000000-660345027702653fc000JSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-0390100000-77c9d80e625d0da33fcfJSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0691000000-ad9e4829206c93db526aJSpectraViewer | MoNA
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-0900000000-4aceed1a9f20cfdd5d35JSpectraViewer
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0229-5093000000-805b9af9a37ffd246f4cJSpectraViewer
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0900000000-931e6e7603f58232f0e0JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0002-0900000000-ec9ed3a4a7ed491064e7JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-8900000000-b4144894cf8f60daf9faJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-e3daf51d70668c08950dJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-052b-0900000000-88af3a616d054b8917e4JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-0900000000-cefb365d8f0aad3d766dJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-0900000000-12e9d882014f1a7bfd4dJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-0900000000-7890fc93271437e3d2d7JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-004i-1900000000-6c0974626895f2a0c437JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-003r-1900000000-9aa2c699af3e125036f7JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-3900000000-42fd55964480ac872c0eJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-000x-6900000000-61fc171a48c42517d25fJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9400000000-0fd99ccea1ed33b42bfaJSpectraViewer | MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-5f8ae429e297482d98b9JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-0900000000-759a3410e0268ce0d589JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l2-0900000000-0f6f5a0c9905b0c5883dJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0900000000-4bf1424d8b0a831cae16JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006w-0900000000-3e62c4d79b28ba65eab6JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007p-2900000000-d626b2b22dd1b2bc9517JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-5f8ae429e297482d98b9JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-0900000000-759a3410e0268ce0d589JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l2-0900000000-0f6f5a0c9905b0c5883dJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0900000000-4bf1424d8b0a831cae16JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006w-0900000000-3e62c4d79b28ba65eab6JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007p-2900000000-d626b2b22dd1b2bc9517JSpectraViewer
    1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
    2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
    ChemSpider ID1760
    ChEMBL IDNot Available
    KEGG Compound IDC05635
    Pubchem Compound ID1826
    Pubchem Substance IDNot Available
    ChEBI ID27823
    Phenol-Explorer IDNot Available
    DrugBank IDNot Available
    HMDB IDHMDB00763
    CRC / DFC (Dictionary of Food Compounds) IDNot Available
    EAFUS IDNot Available
    Dr. Duke IDNot Available
    BIGG ID46167
    KNApSAcK IDC00000104
    HET IDHID
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia ID5-Hydroxyindoleacetic 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 / BioactivitiesNot Available
    EnzymesNot Available
    Pathways
    NameSMPDB LinkKEGG Link
    Tryptophan MetabolismSMP00063 map00380
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSNot Available
    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.