| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation Date | 2016-09-30 22:36:12 UTC |
|---|
| Update Date | 2020-05-21 16:28:51 UTC |
|---|
| BMDB ID | BMDB0000763 |
|---|
| Secondary Accession Numbers | |
|---|
| Metabolite Identification |
|---|
| Common Name | 5-Hydroxyindoleacetic acid |
|---|
| Description | 5-5-5-hydroxyindoleacetic acid, also known as 5-5-hydroxyindoleacetic acid 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. 5-5-5-hydroxyindoleacetic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. 5-5-5-hydroxyindoleacetic acid exists in all living organisms, ranging from bacteria to humans. 5-5-5-hydroxyindoleacetic acid participates in a number of enzymatic reactions, within cattle. In particular, 5-5-5-hydroxyindoleacetic acid can be biosynthesized from 5-hydroxyindoleacetaldehyde through the action of the enzyme aldehyde dehydrogenase, mitochondrial. In addition, 5-5-5-hydroxyindoleacetic acid and S-adenosylmethionine can be converted into 5-methoxyindoleacetate and S-adenosylhomocysteine through its interaction with the enzyme acetylserotonin O-methyltransferase. In cattle, 5-5-hydroxyindoleacetic acid is involved in the metabolic pathway called the tryptophan metabolism pathway. |
|---|
| Structure | |
|---|
| Synonyms | | Value | Source |
|---|
| 5-HIAA | ChEBI | | 5-Hydroxy-1H-indole-3-acetic acid | ChEBI | | 5-Hydroxyindol-3-ylacetic acid | ChEBI | | 5-Hydroxyindole-3-acetic acid | ChEBI | | 5-Hydroxy-1H-indole-3-acetate | Generator | | 5-Hydroxyindol-3-ylacetate | Generator | | 5-Hydroxyindole-3-acetate | Generator | | 5-Hydroxyindoleacetate | Generator | | 5-Hydroxy-3-indolylacetate | HMDB | | 5-Hydroxy-iaa | HMDB | | 5-Hydroxy-indole-3-acetate | HMDB | | 5-Hydroxy-indole-3-acetic acid | HMDB | | 5-Hydroxyheteroauxin | HMDB | | 5-Hydroxyindole acetate | HMDB | | 5-Oxyindoleacetate | HMDB | | 5-Oxyindoleacetic acid | HMDB | | 5HIAA | HMDB | | Hydroxyindoleacetate | HMDB | | 5-Hydroxyindolamine acetic acid | MeSH, HMDB | | Hydroxyindoleacetic acid | MeSH, HMDB | | 5 Hydroxy 3 indoleacetic acid | MeSH, HMDB | | 5 Hydroxyindolamine acetic acid | MeSH, HMDB | | 5-Hydroxy-3-indoleacetic acid | MeSH, HMDB | | Acetic acid, 5-hydroxyindolamine | MeSH, HMDB | | Acid, hydroxyindoleacetic | MeSH, HMDB | | Acid, 5-hydroxy-3-indoleacetic | MeSH, HMDB | | Acid, 5-hydroxyindolamine acetic | MeSH, HMDB |
|
|---|
| Chemical Formula | C10H9NO3 |
|---|
| Average Molecular Weight | 191.1834 |
|---|
| Monoisotopic Molecular Weight | 191.058243159 |
|---|
| IUPAC Name | 2-(5-hydroxy-1H-indol-3-yl)acetic acid |
|---|
| Traditional Name | hydroxyindoleacetic acid |
|---|
| CAS Registry Number | 54-16-0 |
|---|
| SMILES | OC(=O)CC1=CNC2=C1C=C(O)C=C2 |
|---|
| 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) |
|---|
| InChI Key | DUUGKQCEGZLZNO-UHFFFAOYSA-N |
|---|
| Chemical Taxonomy |
|---|
| 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. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Organoheterocyclic compounds |
|---|
| Class | Indoles and derivatives |
|---|
| Sub Class | Indolyl carboxylic acids and derivatives |
|---|
| Direct Parent | Indole-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 Framework | Aromatic heteropolycyclic compounds |
|---|
| External Descriptors | |
|---|
| Ontology |
|---|
| Status | Expected but not Quantified |
|---|
| Origin | |
|---|
| Biofunction | Not Available |
|---|
| Application | Not Available |
|---|
| Cellular locations | |
|---|
| Physical Properties |
|---|
| State | Solid |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | 161 - 163 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 24 mg/mL | Not Available | | LogP | Not Available | Not Available |
|
|---|
| Predicted Properties | |
|---|
| Spectra |
|---|
| Spectra | |
|---|
