10-(3-aminopropyl)-3,4-dimethyl-9,10-dihydroacridin-9-one; oxalic acid

• ChemBase ID: 154431
• Molecular Formular: C20H22N2O5
• Molecular Mass: 370.39908
• Monoisotopic Mass: 370.15287181
• SMILES: Cc1ccc2c(c1C)n(c1ccccc1c2=O)CCCN.C(=O)(C(=O)O)O
• Canonical SMILES: OC(=O)C(=O)O.NCCCn1c2ccccc2c(=O)c2c1c(C)c(C)cc2
• InChI: InChI=1S/C18H20N2O.C2H2O4/c1-12-8-9-15-17(13(12)2)20(11-5-10-19)16-7-4-3-6-14(16)18(15)21;3-1(4)2(5)6/h3-4,6-9H,5,10-11,19H2,1-2H3;(H,3,4)(H,5,6)
• InChIKey: IIELZHYJYZBSGG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 10-(3-aminopropyl)-3,4-dimethyl-9,10-dihydroacridin-9-one; oxalic acid
• IUPAC Traditional name: 10-(3-aminopropyl)-3,4-dimethylacridin-9-one; oxalic acid
• Synonyms: 10-(3-Aminopropyl)-3,4-dimethyl-9-acridone oxalate; ER-27319

Database IDs

• MDL Number: MFCD07784502
• PubChem SID: 162248570; 24724472
• PubChem CID: 9799508

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.40160373
• LogD (pH = 7.4): 1.0883728
• Log P: 3.4127736
• Molar Refractivity: 86.856 cm^3
• Polarizability: 32.992313 Å^3
• Polar Surface Area: 46.33 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble28 mg/mL
• Apperance: solid

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 21/22
• Safety Statements: 24/25
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302 + H312
• GHS Precautionary statements: P280
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H22N2O5

DETAILS

Sigma Aldrich - E0656

Biochem/physiol Actions
Selective Syk inhibitor. Induces tyrosine phosphorylation of Syk that has been demonstrated as critical for degranulation.
ER-27319 inhibits Syk activation with an IC50 = 10 μM. ER-27319 inhibits Syk by preventing the phosphorylated ITAM domain of FcεRI γ from activating Syk. ER-27319 does NOT inhibit previously activated Syk.1