(2S,3S,4S)-4-[(6R)-6-carboxy-6-methylhexa-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid

• ChemBase ID: 127185
• Molecular Formular: C15H21NO6
• Molecular Mass: 311.33034
• Monoisotopic Mass: 311.1368874
• SMILES: O=C(O)[C@H]1NC[C@H](/C(=C/C=C[C@H](C(=O)O)C)/C)[C@@H]1CC(=O)O
• Canonical SMILES: OC(=O)C[C@H]1[C@H](CN[C@@H]1C(=O)O)/C(=C/C=C[C@H](C(=O)O)C)/C
• InChI: InChI=1S/C15H21NO6/c1-8(4-3-5-9(2)14(19)20)11-7-16-13(15(21)22)10(11)6-12(17)18/h3-5,9-11,13,16H,6-7H2,1-2H3,(H,17,18)(H,19,20)(H,21,22)/t9-,10+,11-,13+/m1/s1
• InChIKey: VZFRNCSOCOPNDB-XZUYRWCXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S)-4-[(6R)-6-carboxy-6-methylhexa-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S)-4-[(6R)-6-carboxy-6-methylhexa-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
• Synonyms: Domoic acid; Domoic acid

Database IDs

• CAS Number: 14277-97-5
• MDL Number: MFCD06795841
• Beilstein Number: 46376
• PubChem SID: 162221507; 24894006
• PubChem CID: 71308186; 5282253
• CHEMBL: 420720
• Chemspider ID: 4445428
• Wikipedia Title: Domoic_acid

CALCULATED PROPERTIES

• Acid pKa: 1.6822767
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -3.7643077
• LogD (pH = 7.4): -7.298631
• Log P: -1.7909644
• Molar Refractivity: 79.034 cm^3
• Polarizability: 30.324715 Å^3
• Polar Surface Area: 123.93 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble8 mg/mL; methanol: soluble0.6 mg/mL
• Apperance: white solid
• Boiling Point: 607.2 degrees Celsius at
• Flash Point: 321°C
• Density: 1.273 g/cm^3
• Vapor Pressure: 2.62×10^-16 mmHg (34.9 fPa) at 25 °C

Safety Information

• RTECS: UX9665100
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22; R20 R21 R22
• Safety Statements: 36/37; S36 S37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... GRIK1(2897)

Product Information

• Purity: ≥90%
• Empirical Formula (Hill Notation): C15H21NO6

DETAILS

Sigma Aldrich - D6152

Biochem/physiol Actions
Potent agonist at receptors for excitatory amino acids glutamate and kainate; has highest affinity for AMPA/kainate receptor of any kainate agonist; causes excessive excitation of neurons leading to depletion of energy stores.