{[7-(morpholin-4-yl)-2,3-dioxo-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinoxalin-1-yl]methyl}phosphonic acid hydrate

• ChemBase ID: 154883
• Molecular Formular: C14H17F3N3O7P
• Molecular Mass: 427.2696506
• Monoisotopic Mass: 427.07562119
• SMILES: c1c(c(cc2c1[nH]c(=O)c(=O)n2CP(=O)(O)O)N1CCOCC1)C(F)(F)F.O
• Canonical SMILES: O=c1[nH]c2cc(c(cc2n(c1=O)CP(=O)(O)O)N1CCOCC1)C(F)(F)F.O
• InChI: InChI=1S/C14H15F3N3O6P.H2O/c15-14(16,17)8-5-9-11(6-10(8)19-1-3-26-4-2-19)20(7-27(23,24)25)13(22)12(21)18-9;/h5-6H,1-4,7H2,(H,18,21)(H2,23,24,25);1H2
• InChIKey: RYQLMFHPDNKPKY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[7-(morpholin-4-yl)-2,3-dioxo-6-(trifluoromethyl)-1,2,3,4-tetrahydroquinoxalin-1-yl]methyl}phosphonic acid hydrate
• IUPAC Traditional name: [7-(morpholin-4-yl)-2,3-dioxo-6-(trifluoromethyl)-4H-quinoxalin-1-yl]methylphosphonic acid hydrate
• Synonyms: Fanapanel; MPQX; [[3,4-Dihydro-7-(4-morpholinyl)-2,3-dioxo-6-(trifluoromethyl)-1(2H)-quinoxalinyl]methyl]-phosphonic acid hydrate; ZK 200775 hydrate

Database IDs

• MDL Number: MFCD18452859
• PubChem SID: 162249021
• PubChem CID: 71312017

CALCULATED PROPERTIES

• Acid pKa: 1.5436641
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -2.0802286
• LogD (pH = 7.4): -2.172682
• Log P: 0.21720628
• Molar Refractivity: 88.1046 cm^3
• Polarizability: 31.89936 Å^3
• Polar Surface Area: 119.41 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: off-white to light brown powder

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C14H15F3N3O6P · xH2O

DETAILS

Sigma Aldrich - Z4777

General description
ZK 200775 is a selective AMPA/kainite receptor antagonist with very low affinity for NMDA associated binding sites (Ki for CNQX binding site = 32 nM vs. 2.8 uM for DCKA binding site.) ZK 200775 displays superior PK and safety profiles in in vivo studies compared to quinoxalinedione antagonists such as NBQX, showing no effects on motor behavior or cardiac events at efficacious doses in rat. Additionally, unlike other quinoxalinediones, ZK 200775 is water soluble, making this a desirable tool compound for in vivo studies.