(2S,3S,4S)-3-(carboxymethyl)-4-(prop-1-en-2-yl)pyrrolidine-2-carboxylic acid

• ChemBase ID: 127966
• Molecular Formular: C10H15NO4
• Molecular Mass: 213.2304
• Monoisotopic Mass: 213.10010797
• SMILES: CC(=C)[C@H]1CN[C@@H]([C@H]1CC(=O)O)C(=O)O
• Canonical SMILES: OC(=O)C[C@H]1[C@H](CN[C@@H]1C(=O)O)C(=C)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S)-3-(carboxymethyl)-4-(prop-1-en-2-yl)pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: kainate; kainic acid
• Synonyms: (3S,4S)-3-(Carboxymethyl)-4-prop-1-en-2-yl-L-proline; 2-Carboxy-3-carboxymethyl-4-isopropenyl-pyrrolidine; Kainic acid; ([rel-(2α,3β,4β)]-2-Caroxy-4-(1-methylethenyl)-3-pyrrolidineacetic Acid; (2S,3S,4S)-rel-2-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic Acid; rac Kainic Acid; (2S,3S,4S)-3-(carboxymethyl)-4-prop-1-en-2-ylpyrrolidine-2-carboxylic acid

Database IDs

• CAS Number: 487-79-6; 73209-05-9
• Beilstein Number: 86660
• PubChem SID: 162222282
• PubChem CID: 10255
• CHEBI ID: 31746
• CHEMBL: 27527
• Chemspider ID: 9837
• KEGG ID: C12819
• MeSH Name: Kainic+acid
• Unique Ingredient Identifier: SIV03811UC
• Wikipedia Title: Kainic_acid

CALCULATED PROPERTIES

• Acid pKa: 1.7361971
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -3.3863163
• LogD (pH = 7.4): -5.153439
• Log P: -2.3627985
• Molar Refractivity: 52.201 cm^3
• Polarizability: 20.809425 Å^3
• Polar Surface Area: 86.63 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Off-White Solid
• Melting Point: 168-170°C; 215°C (decomposes)
• Partition Coefficient: 0.635
• pKa: 2.031
• pKb: 11.966

Safety Information

• Storage Condition: Refrigerator

Product Information

• Purity: 98%

DETAILS

Toronto Research Chemicals - K135000

A neuroexcitatory chemical that is selective for the kainic acid receptor.

REFERENCES

• Wacker, D.A., et al.: Synlett, 503 (1997)