N-[(1S)-1-{[3-({4-[(3-aminopropyl)amino]butyl}amino)propyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]butanamide; tris(trifluoromethanesulfonic acid)

• ChemBase ID: 133457
• Molecular Formular: C26H44F9N5O12S3
• Molecular Mass: 885.8344888
• Monoisotopic Mass: 885.20048885
• SMILES: CCCC(=O)N[C@@H](Cc1ccc(cc1)O)C(=O)NCCCNCCCCNCCCN.C(F)(F)(F)S(=O)(=O)O.C(F)(F)(F)S(=O)(=O)O.C(F)(F)(F)S(=O)(=O)O
• Canonical SMILES: OS(=O)(=O)C(F)(F)F.OS(=O)(=O)C(F)(F)F.OS(=O)(=O)C(F)(F)F.CCCC(=O)N[C@H](C(=O)NCCCNCCCCNCCCN)Cc1ccc(cc1)O
• InChI: InChI=1S/C23H41N5O3.3CHF3O3S/c1-2-7-22(30)28-21(18-19-8-10-20(29)11-9-19)23(31)27-17-6-16-26-14-4-3-13-25-15-5-12-24;3*2-1(3,4)8(5,6)7/h8-11,21,25-26,29H,2-7,12-18,24H2,1H3,(H,27,31)(H,28,30);3*(H,5,6,7)/t21-;;;/m0.../s1
• InChIKey: QTCLKBFOFGTNMC-YDULTXHLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(1S)-1-{[3-({4-[(3-aminopropyl)amino]butyl}amino)propyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]butanamide; tris(trifluoromethanesulfonic acid)
• IUPAC Traditional name: N-[(1S)-1-{[3-({4-[(3-aminopropyl)amino]butyl}amino)propyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]butanamide; tris(trifluoromethanesulfonic acid)
• Synonyms: PhTX-343; S-N-[3-[[4-[(3-Aminopropyl)amino]butyl]amino]propyl]-4-hydroxy-α-[(1-oxobutyl)amino]-benzenepropanamide tris-trifluoroacetate; Philanthotoxin 343 tris(trifluoroacetate) salt

Database IDs

• CAS Number: 115976-93-7
• MDL Number: MFCD00661073
• PubChem SID: 162227734; 24898266
• PubChem CID: 16219835

CALCULATED PROPERTIES

• Acid pKa: 8.4000025
• H Acceptors: 6
• H Donor: 6
• LogD (pH = 5.5): -8.792369
• LogD (pH = 7.4): -6.345028
• Log P: -0.9947452
• Molar Refractivity: 125.1272 cm^3
• Polarizability: 49.234535 Å^3
• Polar Surface Area: 128.51 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: methanol: >8 mg/mL (solutions should be freshly prepared.)
• Apperance: light yellow-green solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: rat ... Chrm2(81645), Chrm3(24260)

DETAILS

Sigma Aldrich - P206

Caution
Hygroscopic
Legal Information
Sold under license from Columbia University.
Reconstitution
Addition of 1 mL of solvent to vial yields a 1 mM solution.
Biochem/physiol Actions
Blocks NMDA-gated ion channels; synthetic analog of the wasp polyamine amide toxin δ-philanthotoxin.