(2-{8,9-dioxo-2,6-diazabicyclo[5.2.0]nonan-2-yl}ethyl)phosphonic acid

• ChemBase ID: 153287
• Molecular Formular: C9H15N2O5P
• Molecular Mass: 262.199561
• Monoisotopic Mass: 262.07185822
• SMILES: C1CNC2C(C(=O)C2=O)N(C1)CCP(=O)(O)O
• Canonical SMILES: O=C1C(=O)C2C1NCCCN2CCP(=O)(O)O
• InChI: InChI=1S/C9H15N2O5P/c12-8-6-7(9(8)13)11(3-1-2-10-6)4-5-17(14,15)16/h6-7,10H,1-5H2,(H2,14,15,16)
• InChIKey: QGGOFUZYYGMLDO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-{8,9-dioxo-2,6-diazabicyclo[5.2.0]nonan-2-yl}ethyl)phosphonic acid
• IUPAC Traditional name: 2-{8,9-dioxo-2,6-diazabicyclo[5.2.0]nonan-2-yl}ethylphosphonic acid
• Synonyms: P-[2-(8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)ethyl]-phosphonic acid; WAY-126090; EAA-090

Database IDs

• CAS Number: 144912-63-0
• MDL Number: MFCD00912427
• PubChem SID: 162247426
• PubChem CID: 68739521

CALCULATED PROPERTIES

• Acid pKa: 1.2461336
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -2.856061
• LogD (pH = 7.4): -3.408593
• Log P: -2.8688633
• Molar Refractivity: 58.8549 cm^3
• Polarizability: 23.44775 Å^3
• Polar Surface Area: 106.94 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: ≥2 mg/mL
• Apperance: light yellow to yellow powder

Safety Information

• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C9H13N2O5P

DETAILS

Sigma Aldrich - SML0206

Biochem/physiol Actions
EAA-090 is a potent NMDA receptor antagonist with neuroprotective properties. In isoflurane-anesthetized dogs, EAA-090 reduces the minimum alveolar concentration (MAC) of isoflurane and increases systolic, mean, and diastolic arterial blood pressure.