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-HIAA or 5-hydroxy-1H-indole-3-acetate, 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 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 black mulberries (Morus nigra), anises (Pimpinella anisum), orange bell peppers (Capsicum annuum), mulberries (Morus), and bilberries (Vaccinium myrtillus). 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 hereditary spastic paraplegia, crohn's disease, metabolic syndrome, and perillyl alcohol administration for cancer treatment; 5-hydroxyindoleacetic acid has also been linked to the inborn metabolic disorder carbamoyl phosphate synthetase deficiency. Based on a literature review a significant number of articles have been published on 5-Hydroxyindoleacetic acid.
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
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-Hydroxyindolamine acetic acidMeSH, HMDB
Hydroxyindoleacetic acidMeSH, HMDB
5 Hydroxy 3 indoleacetic acidMeSH, HMDB
5 Hydroxyindolamine acetic acidMeSH, HMDB
5-Hydroxy-3-indoleacetic acidMeSH, HMDB
Acetic acid, 5-hydroxyindolamineMeSH, HMDB
Acid, hydroxyindoleaceticMeSH, HMDB
Acid, 5-hydroxy-3-indoleaceticMeSH, HMDB
Acid, 5-hydroxyindolamine aceticMeSH, HMDB
(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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    GC-MS5-Hydroxyindole-3-acetic acid, non-derivatized, GC-MS Spectrumsplash10-0006-0390100000-f473f1a32542afd5d101Spectrum
    GC-MS5-Hydroxyindole-3-acetic acid, 3 TMS, GC-MS Spectrumsplash10-0006-1490100000-a72832b1524478059ef7Spectrum
    GC-MS5-Hydroxyindole-3-acetic acid, 2 TMS, GC-MS Spectrumsplash10-014i-0191000000-660345027702653fc000Spectrum
    GC-MS5-Hydroxyindole-3-acetic acid, non-derivatized, GC-MS Spectrumsplash10-014i-0293000000-66850e233e11ec787808Spectrum
    GC-MS5-Hydroxyindole-3-acetic acid, non-derivatized, GC-MS Spectrumsplash10-0006-0191200000-99e904e0c2698a9ec34dSpectrum
    GC-MS5-Hydroxyindole-3-acetic acid, non-derivatized, GC-MS Spectrumsplash10-0006-0390100000-f473f1a32542afd5d101Spectrum
    GC-MS5-Hydroxyindole-3-acetic acid, non-derivatized, GC-MS Spectrumsplash10-0006-1490100000-a72832b1524478059ef7Spectrum
    GC-MS5-Hydroxyindole-3-acetic acid, non-derivatized, GC-MS Spectrumsplash10-014i-0191000000-660345027702653fc000Spectrum
    GC-MS5-Hydroxyindole-3-acetic acid, non-derivatized, GC-MS Spectrumsplash10-0006-0390100000-77c9d80e625d0da33fcfSpectrum
    GC-MS5-Hydroxyindole-3-acetic acid, non-derivatized, GC-MS Spectrumsplash10-014i-0691000000-ad9e4829206c93db526aSpectrum
    Predicted GC-MS5-Hydroxyindole-3-acetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0005-0900000000-4aceed1a9f20cfdd5d35Spectrum
    Predicted GC-MS5-Hydroxyindole-3-acetic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0229-5093000000-805b9af9a37ffd246f4cSpectrum
    Predicted GC-MS5-Hydroxyindole-3-acetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS5-Hydroxyindole-3-acetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS5-Hydroxyindole-3-acetic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS5-Hydroxyindole-3-acetic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS5-Hydroxyindole-3-acetic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS5-Hydroxyindole-3-acetic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS5-Hydroxyindole-3-acetic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS5-Hydroxyindole-3-acetic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS5-Hydroxyindole-3-acetic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS5-Hydroxyindole-3-acetic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS5-Hydroxyindole-3-acetic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS5-Hydroxyindole-3-acetic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MS5-Hydroxyindole-3-acetic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0900000000-931e6e7603f58232f0e0Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0002-0900000000-ec9ed3a4a7ed491064e7Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014l-8900000000-b4144894cf8f60daf9faSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-e3daf51d70668c08950dSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-052b-0900000000-88af3a616d054b8917e4Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-0900000000-cefb365d8f0aad3d766dSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-0900000000-12e9d882014f1a7bfd4dSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-0900000000-7890fc93271437e3d2d7Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-004i-1900000000-6c0974626895f2a0c437Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-003r-1900000000-9aa2c699af3e125036f7Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-3900000000-42fd55964480ac872c0eSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-000x-6900000000-61fc171a48c42517d25fSpectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9400000000-0fd99ccea1ed33b42bfaSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-5f8ae429e297482d98b9Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-0900000000-759a3410e0268ce0d589Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l2-0900000000-0f6f5a0c9905b0c5883dSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0900000000-4bf1424d8b0a831cae16Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006w-0900000000-3e62c4d79b28ba65eab6Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007p-2900000000-d626b2b22dd1b2bc9517Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-5f8ae429e297482d98b9Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006t-0900000000-759a3410e0268ce0d589Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l2-0900000000-0f6f5a0c9905b0c5883dSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0900000000-4bf1424d8b0a831cae16Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006w-0900000000-3e62c4d79b28ba65eab6Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-007p-2900000000-d626b2b22dd1b2bc9517Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR SpectrumSpectrum
    2D NMR[1H,13C] 2D NMR SpectrumSpectrum
    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.