Dihydrokainic acid
Basic information
- CAS
52497-36-6- Standard SMILES
CC(C)[C@H]1CN[C@H](C(=O)O)[C@H]1CC(=O)O- InChIKey
JQPDCKOQOOQUSC-OOZYFLPDSA-N- Molecular formula
- C10H17NO4
- Average molar mass
- 215.25 g/mol
- Monoisotopic mass
- 215.11575802
Overview
Dihydrokainic acid is a dicarboxylic acid. It is functionally related to a kainic acid.
Names & identifiers
- Preferred name
- Dihydrokainic acid
- IUPAC
- (2S,3S,4R)-3-(carboxymethyl)-4-propan-2-ylpyrrolidine-2-carboxylic acid
- English name
- (2S,3S,4R)-2-Carboxy-4-isopropyl-3-pyrrolidineacetic acid
- Molecular formula
- C10H17NO4
- Molecular weight
- 215.25
Names & synonyms
Dihydrokainic acid52497-36-6MQ4LMC2HN5(2S,3S,4R)-2-carboxy-4-(1-methylethyl)-3-pyrrolidineacetic acid(3S,4R)-3-(carboxymethyl)-4-(propan-2-yl)-L-prolineCHEBI:43562DTXSID20200489(2S-(2alpha,3beta,4beta))-2-Carboxy-4-(1-methylethyl)-3-pyrrolidineacetic acidRefChem:133855DTXCID70122980(2S-(2 alpha,3 beta,4 beta))-2-carboxy-4-(1-methylethyl)-3-pyrrolidineacetic acid637-065-5
Show more names
DHKDihydrokainic acid, EAAT2 (GLT-1) inhibitor2-Carboxy-4-isopropyl-3-pyrrolidineacetic acid(2S,3S,4R)-3-(carboxymethyl)-4-isopropyl-proline(2S,3R,4R)-2-Carboxy-4-iospropyl-3-pyrrolidineacetic acid3-Pyrrolidineacetic acid, 2-carboxy-4-(1-methylethyl)-, (2S,3S,4R)-(2S,3S,4R)-3-(carboxymethyl)-4-propan-2-yl-2-pyrrolidinecarboxylic acid
(2S,3S,4R)-2-Carboxy-4-isopropyl-3-pyrrolidineacetic acidCHEMBL279561(2S,3S,4R)-3-(carboxymethyl)-4-isopropylpyrrolidine-2-carboxylic acid(2S,3S,4R)-3-(carboxymethyl)-4-(propan-2-yl)pyrrolidine-2-carboxylic acid(2S,3S,4R)-3-(carboxymethyl)-4-propan-2-ylpyrrolidine-2-carboxylic acid1ftk1xhyUNII-MQ4LMC2HN5
Database identifiers
- CAS
52497-36-6- PubChem CID
- 107883
- DTXSID
DTXSID20200489- ChEMBL
CHEMBL279561- ChEBI
CHEBI:43562- UNII
- MQ4LMC2HN5
- EC Number
- 637-065-5
- Nikkaji
- J493.199H
Properties
Computed structural properties
- XLogP
- -1.7
- 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
- 264
Physicochemical properties
- Melting point
- 285 °C · 285 °C (decomp)
- Boiling point
- 416.6 · 416.6±30.0 °C(Predicted)
- Density
- 1.187 · 1.187±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 2 O: · H2O: >10 mg/mL
- form
- solid
- pka
- 2.11 · 2.11±0.60(Predicted)
- color
- White
- Water Solubility
- 25 mM · Soluble to 25 mM in water
- InChI
- 1S/C10H17NO4/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13/h5-7,9,11H,3-4H2,1-2H3,(H,12,13)(H,14,15)/t6-,7+,9-/m0/s1
- InChIKey
- JQPDCKOQOOQUSC-OOZYFLPDSA-N
- SMILES
- CC(C)[C@H]1CN[C@@H]([C@H]1CC(O)=O)C(O)=O
- FDA UNII
- 4 LMC2HN5 · MQ4LMC2HN5
- UNSPSC Code
- 12352106 · 12352106
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- risk_code
- 20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H312-H332-H302
- Precautionary statements
- P261-P271-P304+P340-P312-P280-P302+P352-P312-P322-P363-P501-P264-P270-P301+P312-P330-P501
Chemistry & industry
Applications
DescriptionDihydrokainic acid (DHK) is an inhibitor of excitatory amino acid transporter 2 (EAAT2; Ki = 23 μM for glutamate uptake by COS cells expressing EAAT2). It is selective for EEAT2 over EAAT1 and EAAT3 (Ki = >3 mM for both). DHK microinfusion (5 nmol) into the rat infralimbic cortex reduces the time spent immobile in the forced swim test, indicating antidepressant-like behavior, an effect that is blocked by the AMPA receptor antagonist NBQX and the serotonin (5-HT) receptor subtype 5-HT1A antagonist WAY-100635 . It also increases glutamate and serotonin levels and the expression of c-Fos in the dorsal raphe nucleus. In contrast, DHK microinjection (6.25 nmol) into the rat prefrontal cortex (PFC) increases the latency to drink sucrose in a sucrose intake test, indicating anhedonia-like behavior. It also impairs memory acquisition, consolidation, and retrieval in mice in the novel object recognition test.
UsesDihydrokainic acid has been used as a glutamate transporter (GLT-1) inhibitor in the glutamate uptake assay of astrocytes and glial cells. It may be used as a GLT-1 inhibitor in Lateral habenula (LHb).
Additional notes
DefinitionChEBI: Dihydrokainic acid is a dicarboxylic acid. It is functionally related to a kainic acid.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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