Basic information
- CAS
487-79-6- Standard SMILES
C=C(C)[C@H]1CN[C@H](C(=O)O)[C@H]1CC(=O)O- InChIKey
VLSMHEGGTFMBBZ-OOZYFLPDSA-N- Molecular formula
- C10H15NO4
- Average molar mass
- 213.23 g/mol
- Monoisotopic mass
- 213.10010796
Overview
Kainic acid is a dicarboxylic acid, a pyrrolidinecarboxylic acid, a non-proteinogenic L-alpha-amino acid and a L-proline derivative. It has a role as an antinematodal drug and an excitatory amino acid agonist. It is a conjugate acid of a kainate(1-).
Names & identifiers
- Preferred name
- alpha-Kainic acid
- IUPAC
- (2S,3S,4S)-3-(carboxymethyl)-4-prop-1-en-2-ylpyrrolidine-2-carboxylic acid
- English name
- KAINIC ACID
- Molecular formula
- C10H15NO4
- Molecular weight
- 213.23
Names & synonyms
kainic acid487-79-6DigeninDigenic acidHelminalL-alpha-Kainic acidalpha-Kainic acidAcide kainiqueAcido kainicoAcidum kainicumDTXSID7040526NSC136038
Show more names
KAINATE(-)-α-Kainic AcidKainicC12819(3aαKainicaci,4-beta))-
SIV03811UC2-Carboxy-4-isopropenyl-3-pyrrolidineacetic acidNSC-759587(2S,3S,4S)-3-(carboxymethyl)-4-prop-1-en-2-ylpyrrolidine-2-carboxylic acid(3S,4R)-3-(carboxymethyl)-4-(prop-1-en-2-yl)-L-prolineDTXCID5020526CHEBI:31746(2S-(2alpha,3beta,4beta))-2-carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic acid
Database identifiers
- CAS
487-79-6、59905-23-6、73209-05-9- PubChem CID
- 10255
- DTXSID
DTXSID7040526- ChEMBL
CHEMBL275040- ChEBI
CHEBI:31746- UNII
- SIV03811UC、WRW5P6M3EM
- Nikkaji
- J9.244D
Properties
Computed structural properties
- XLogP
- -1.8
- Topological polar surface area
- 86.6 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 300
Experimental & physicochemical properties
Collision Cross Section144.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 253 · 253-254 C
- alpha
- 24 · D24 -14.8° (c = 1.01)
- Boiling point
- 353.22 °C · 353.22°C (rough estimate)
- Density
- 1.2177 · 1.2177 (rough estimate)
- refractive index
- 1.4368 · 1.4368 (estimate)
- storage temp.
- 2 · Keep in dark place,Sealed in dry,2-8°C
- solubility
- 2 O: · H2O: soluble
- form
- White to off-white solid.
- pka
- 2.03 · 2.03±0.60(Predicted)
- color
- White
- optical activity
- -14.824 · -14.824 (H2O)
- Water Solubility
- 25 mM · Soluble to 25 mM in water
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in distilled water may be stored at -20° for up to 3 months.
- InChI
- InChI=1S/C10H15NO4/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13/h6-7,9,11H,1,3-4H2,2H3,(H,12,13)(H,14,15)/t6-,7+,9-/m0/s1
- InChIKey
- VLSMHEGGTFMBBZ-OOZYFLPDSA-N
- SMILES
- N1C[C@H](C(C)=C)[C@H](CC(O)=O)[C@H]1C(O)=O
- FDA UNII
- 3811 UC · SIV03811UC
- EPA Substance Registry System
- 3 · 3-Pyrrolidineacetic acid, 2-carboxy-4-(1-methylethenyl)-, (2S,3S,4S)- (487-79-6)
- UNSPSC Code
- 12352106 · 12352106
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H312-H332
- Precautionary statements
- 261 · P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501
- Hazard Codes
- Xn
- Risk Statements
- 20 · 20/21/22
- Safety Statements
- 22 · 22-24/25-36
- WGK Germany
- 3 · 3
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety data
- wgk
- 3
- risk_code
- 20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 22-24/25-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H312-H332
- Precautionary statements
- P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice.
Drugs that bind to and activate excitatory amino acid receptors.
Applications
DescriptionKainic acid (487-79-6) is a conformationally restricted glutamate analog which acts as a selective agonist at kainate receptors. CNS stimulant and neurotoxin. Kainic acid is a classic neuroexcitatory agent for induction of seizures in laboratory animals (typical dose 10-30 mg/kg).
Usesexcitory amino acid, neurotoxin, neurobiology tool
UsesNeurobiological tool.
Usesglutamate receptor agonist, anthelmintic
Uses(-)-α-Kainic Acid is a naturally occurring neuroexcitatory chemical that is an selective agonist for a subtype of ionotropic glutamate receptor. Administration of (-)-α-Kainic Acid has been shown to increase production of reactive oxygen species, mitochondrial dysfunction, and apoptosis in neurons in many regions of the brain, particularly in the hippocampal subregions and in the hilus of dentate gyrus.
Upstream & downstream products
Upstream raw materials
Suppliers4 total
凯试（上海）科技有限公司021-50135380 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 · [email protected]
北京百灵威科技有限公司18210857532 18210857532 · [email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]
Additional notes
DefinitionChEBI: Kainic acid is a dicarboxylic acid, a pyrrolidinecarboxylic acid, a L-proline derivative and a non-proteinogenic L-alpha-amino acid. It has a role as an antinematodal drug and an excitatory amino acid agonist. It is a conjugate acid of a kainate(1-).
Related reactions
1 records
Compound notes
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