Basic information
- Standard SMILES
O=C(O)Cc1c[nH]c2ccc(O)cc12- InChIKey
DUUGKQCEGZLZNO-UHFFFAOYSA-N- Molecular formula
- C10H9NO3
- Average molar mass
- 191.18 g/mol
Overview
(5-hydroxyindol-3-yl)acetic acid is a member of the class of indole-3-acetic acids that is indole-3-acetic acid substituted by a hydroxy group at C-5. It has a role as a drug metabolite, a mouse metabolite and a human metabolite. It is a conjugate acid of a (5-hydroxyindol-3-yl)acetate.
Names & identifiers
- Preferred name
- 5-Hydroxyindoleacetic Acid
- IUPAC
- 2-(5-hydroxy-1H-indol-3-yl)acetic acid
- English name
- 5-Hydroxyindole-3-acetic acid
- Molecular formula
- C10H9NO3
- Molecular weight
- 191.18
Names & synonyms
Show more names
Database identifiers
- CAS
1321-73-9- ChEMBL
CHEMBL395915- ChEBI
CHEBI:27823- UNII
- YHC763JY1P
- EC Number
- 200-195-4
- Nikkaji
- J11.030B
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 73.3 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 231
Experimental & physicochemical properties
Solubility
24 mg/mL
>28.7 [ug/mL] (The mean of the results at pH 7.4)
Physical Description
Light red crystalline solid; [Sigma-Aldrich MSDS]
Solid
Collision Cross Section
148.4 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
140.9 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
148.6 Ų [M+Na]+
Physicochemical properties
- Melting point
- 161 · 161-164 °C (dec.)(lit.)
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- crystalline
- color
- off-white to purple
- Stability
- Air Sensitive, Light Sensitive
- CAS DataBase Reference
- 1321 · 1321-73-9(CAS DataBase Reference)
- NCI Dictionary of Cancer Terms
- 5 · 5-HIAA
- FDA UNII
- 763 JY1P · YHC763JY1P
- Safety Statements
- 22 · 22-24/25
- WGK Germany
- 3 · 3
- RTECS
- 3650000 · NL3650000
- F
- 8 · 8-10-23
- HazardClass
- IRRITANT
- Toxicity
- 50 · mouse,LD50,intraperitoneal,1125mg/kg (1125mg/kg),BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY),Journal of Toxicology and Environmental Health. Vol. 1, Pg. 515, 1976.
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: 1H-Indole-3-acetic acid, 5-hydroxy-
5-Hydroxyindol-3-ylacetic acid: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- F
- 8-10-23
- wgk
- 3
- rtecs
- NL3650000
- Toxicity
- mouse,LD50,intraperitoneal,1125mg/kg (1125mg/kg),BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY),Journal of Toxicology and Environmental Health. Vol. 1, Pg. 515, 1976.
- safety_code
- 22-24/25
- hazard_class
- IRRITANT
Chemistry & industry
Pharmacology
Uses & manufacturing
Applications
Uses(5-Hydroxy-1H-indol-3-yl)acetic acid is an intermediate in the preparation of magnolol derivatives with antidepressive potentials. A biochemical marker of neuroendocrine tumor.
Uses5-Hydroxyindole-3-acetic acid is an impurity of chlorpheniramine (C424300), an antihistaminic agent.
Suppliers12 total
Additional notes
DefinitionChEBI: (5-hydroxyindol-3-yl)acetic acid is a member of the class of indole-3-acetic acids that is indole-3-acetic acid substituted by a hydroxy group at C-5. It has a role as a drug metabolite, a human metabolite and a mouse metabolite. It is a conjugate acid of a (5-hydroxyindol-3-yl)acetate.
Related reactions
No reaction records under the current filter.
Linked notes
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