Dihydrokainic acid , CAS No.52497-36-6

CAS: 52497-36-6 Cat. No.: D275323 Molecular Weight: 215.25 EC Number: 637-065-5

Synonyms

3-Pyrrolidineacetic acid, 2-carboxy-4-(1-methylethyl)-, (2S,3S,4R)- | Dihydrokainate | (2S,3S,4R)-3-(carboxymethyl)-4-isopropylpyrrolidine-2-carboxylic acid | PDSP2_001490 | FT-0661040 | SR-01000597697 | AKOS024456387 | NCGC00261060-01 | XD160600 | Tox21_

Storage

Store at 2-8°C,Desiccated

Shipped In

Wet ice

Overview

Store at +4°C. Store under desiccating conditions. The product can be stored for up to 12 months.

Specifications

Synonyms

3-Pyrrolidineacetic acid, 2-carboxy-4-(1-methylethyl)-, (2S, 3S, 4R)- | Dihydrokainate | (2S, 3S, 4R)-3-(carboxymethyl)-4-isopropylpyrrolidine-2-carboxylic acid | PDSP2_001490 | FT-0661040 | SR-01000597697 | AKOS024456387 | NCGC00261060-01 | XD160600 | Tox21_

Biochemical and Physiological Mechanisms

Selective, non-transportable inhibitor of glutamate transporter EAAT2 (GLT-1) (K i = 23 μM). 130-fold selective over EAAT1 and EAAT3 (K i > 3 mM).

Storage

Store at 2-8°C, Desiccated

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Refer to SDS for further information. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Names and Identifiers

• Canonical Smiles: CC(C)C1CNC(C1CC(=O)O)C(=O)O
• IUPAC Name: (2S,3S,4R)-3-(carboxymethyl)-4-propan-2-ylpyrrolidine-2-carboxylic acid
• InChIKey: JQPDCKOQOOQUSC-OOZYFLPDSA-N
• 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
• Isomeric SMILES: CC(C)[C@H]1CN[C@@H]([C@H]1CC(=O)O)C(=O)O
• Molecular Weight: 215.25
• Reaxy-Rn: 175742
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=175742&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Kainoids

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives
• Direct Parent: Kainoids
• Alternative Parents: Proline and derivatives L-alpha-amino acids Pyrrolidine carboxylic acids Dicarboxylic acids and derivatives Amino acids Dialkylamines Carboxylic acids Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Kainoid skeleton - Proline or derivatives - Alpha-amino acid - Alpha-amino acid or derivatives - L-alpha-amino acid - Pyrrolidine carboxylic acid - Pyrrolidine carboxylic acid or derivatives - Dicarboxylic acid or derivatives - Pyrrolidine - Amino acid - Carboxylic acid - Secondary aliphatic amine - Azacycle - Organoheterocyclic compound - Secondary amine - Organonitrogen compound - Organic oxide - Organopnictogen compound - Organic nitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxygen compound - Amine - Carbonyl group - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as kainoids. These are non-proteigenous amino acids with a structure characterized by the presence of a pyrrolidine ring bearing two dicarboxylic acid groups.
• External Descriptors: dicarboxylic acid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

GRIK3 Tclin Glutamate receptor ionotropic kainate 3 (50 Activities)

Discover Target: GRIK3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC1A1 Tchem Excitatory amino acid transporter 3 (527 Activities)

Discover Target: SLC1A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC1A3 Tchem Excitatory amino acid transporter 1 (586 Activities)

Discover Target: SLC1A3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GRIK1 Tclin Glutamate receptor ionotropic kainate 1 (340 Activities)

Discover Target: GRIK1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Grik2 Glutamate receptor ionotropic kainate 2 (298 Activities)

Discover Target: Grik2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slc1a2 Excitatory amino acid transporter 2 (39 Activities)

Discover Target: Slc1a2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rattus norvegicus (775804 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Grin1 Glutamate NMDA receptor (6467 Activities)

Discover Target: Grin1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Gria2 Glutamate receptor ionotropic, AMPA (2103 Activities)

Discover Target: Gria2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water to 25 mM
• Molecular Weight: 215.250 g/mol
• XLogP3: -1.700
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 215.116 Da
• Monoisotopic Mass: 215.116 Da
• Topological Polar Surface Area: 86.600 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 264.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Xuemin Liu, Jiang Xu, Yaping Zhao, Huahong Shi, Ching-Hua Huang.  (2019)  Hydrophobic sorption behaviors of 17β-Estradiol on environmental microplastics.  CHEMOSPHERE,      [PMID:30959457] [10.1016/j.chemosphere.2019.03.162]