Identification

PhytoHub ID
PHUB001475
Name
5-Hydroxyindole acetic acid
Systematic Name
Not Available
Synonyms
  • 5-HIAA
  • 5-Hydroxyindole-3-acetic acid
  • 5-hydroxyindoleacetic acid
CAS Number
Not Available
Average Mass
191.186
Monoisotopic Mass
191.058243154
Chemical Formula
C10H9NO3
IUPAC Name
hydroxyindoleacetic acid
InChI Key
DUUGKQCEGZLZNO-UHFFFAOYSA-N
InChI Identifier
InChI=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)
SMILES
OC(=O)CC1=CNC2=C1C=C(O)C=C2
Structure

Calculated Properties

Solubility (ALOGPS)
1.80e+00 g/l
LogS (ALOGPS)
-2.03
LogP (ALOGPS)
1.28
Hydrogen Acceptors
3
Hydrogen Donors
3
Rotatable Bond Count
2
Polar Surface Area
73.32
Refractivity
50.43300000000001
Polarizability
18.705822330549697
Formal Charge
0
Physiological Charge
-1
pKa (strongest basic)
-5.508018305769369
pKa (strongest acidic)
4.215990424188327
Number of Rings
2
Rule of Five
Yes
Bioavailability
Yes
Ghose Filter
Yes
Veber's Rule
No
MDDR-like Rule
No

Precursor Taxonomy

PrecursorFamilyClassSub-class
SerotoninN-containing compoundsAminesNot AvailableShow Precursor

Classyfire Taxonomy

Kingdom Name
Organic compounds
Class
Indoles and derivatives
Super-class
Organoheterocyclic compounds
Sub-class
Indolyl carboxylic acids and derivatives
Direct Parent Name
Indole-3-acetic acid derivatives
Alternative Parent Names
["1-hydroxy-2-unsubstituted benzenoids", "3-alkylindoles", "Azacyclic compounds", "Carbonyl compounds", "Carboxylic acids", "Heteroaromatic compounds", "Hydrocarbon derivatives", "Hydroxyindoles", "Monocarboxylic acids and derivatives", "Organic oxides", "Organonitrogen compounds", "Organopnictogen compounds", "Substituted pyrroles"]
External Descriptor Annotations
["indole-3-acetic acids"]
Substituent Names
["1-hydroxy-2-unsubstituted benzenoid", "3-alkylindole", "Aromatic heteropolycyclic compound", "Azacycle", "Benzenoid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Heteroaromatic compound", "Hydrocarbon derivative", "Hydroxyindole", "Indole", "Indole-3-acetic acid derivative", "Monocarboxylic acid or derivatives", "Organic nitrogen compound", "Organic oxide", "Organic oxygen compound", "Organonitrogen compound", "Organooxygen compound", "Organopnictogen compound", "Pyrrole", "Substituted pyrrole"]

Spectra

No spectra information available

Food Sources

PrecursorFood SourceFood Source Group
SerotoninBananaFruit, Tropical fruits PublicationsShow
SerotoninCherry tomatoVegetables, Fruit vegetables PublicationsShow
SerotoninChinese cabbageVegetables, Cabbages PublicationsShow
SerotoninEggplantVegetables, Fruit vegetables PublicationsShow
SerotoninGrapeFruit, Berries PublicationsShow
SerotoninHot chili (Capsicum annuum, C. frutescens)Vegetables, Fruit vegetables PublicationsShow
SerotoninKiwiFruit, Tropical fruits PublicationsShow
SerotoninPeachFruit, Drupes PublicationsShow
SerotoninPineappleFruit, Tropical fruits PublicationsShow
SerotoninSpinachVegetables, Leaf vegetables PublicationsShow
SerotoninTomatoVegetables, Fruit vegetables PublicationsShow

Metabolism

PrecursorMetaboliteSpeciesBiofluidsOriginFormulaMonoisotopic mass
Serotonin 5-Hydroxyindole acetic acidhumanblood, urinehost metabolismC10H9NO3191.058243154 Publications
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