(2S)-5-carbamimidamido-N-[(1S)-1-carbamoyl-2-phenylethyl]-2-[(3R,5S,7s)-adamantan-1-ylformamido]pentanamide; trifluoroacetic acid

• ChemBase ID: 154322
• Molecular Formular: C28H39F3N6O5
• Molecular Mass: 596.6416696
• Monoisotopic Mass: 596.29340304
• SMILES: c1ccc(cc1)C[C@H](NC(=O)[C@@H](NC(=O)[C@@]12C[C@H]3C[C@@H](C1)C[C@H](C2)C3)CCCNC(=N)N)C(=O)N.C(=O)(O)C(F)(F)F
• Canonical SMILES: OC(=O)C(F)(F)F.NC(=N)NCCC[C@@H](C(=O)N[C@H](C(=O)N)Cc1ccccc1)NC(=O)[C@]12C[C@@H]3C[C@@H](C2)C[C@@H](C1)C3
• InChI: InChI=1S/C26H38N6O3.C2HF3O2/c27-22(33)21(12-16-5-2-1-3-6-16)31-23(34)20(7-4-8-30-25(28)29)32-24(35)26-13-17-9-18(14-26)11-19(10-17)15-26;3-2(4,5)1(6)7/h1-3,5-6,17-21H,4,7-15H2,(H2,27,33)(H,31,34)(H,32,35)(H4,28,29,30);(H,6,7)/t17-,18+,19-,20-,21-,26-;/m0./s1
• InChIKey: GPVFYPYIOXHDCU-CFIUKZCSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-5-carbamimidamido-N-[(1S)-1-carbamoyl-2-phenylethyl]-2-[(3R,5S,7s)-adamantan-1-ylformamido]pentanamide; trifluoroacetic acid
• IUPAC Traditional name: (2S)-5-carbamimidamido-N-[(1S)-1-carbamoyl-2-phenylethyl]-2-[(3R,5S,7s)-adamantan-1-ylformamido]pentanamide; trifluoroacetic acid
• Synonyms: 1-Adamantanecarbonyl-Arg-Phe-NH2 trifluoroacetate salt; RF9 trifluoroacetate salt

Database IDs

• CAS Number: 876310-60-0(freebase)
• PubChem SID: 162248461
• PubChem CID: 71311841

CALCULATED PROPERTIES

• Acid pKa: 12.491646
• H Acceptors: 6
• H Donor: 6
• LogD (pH = 5.5): -1.1695342
• LogD (pH = 7.4): -1.1652054
• Log P: 0.9407474
• Molar Refractivity: 142.8501 cm^3
• Polarizability: 51.61889 Å^3
• Polar Surface Area: 163.19 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble20 mg/mL

Safety Information

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

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C26H38N6O3 · xC2HF3O2

DETAILS

Sigma Aldrich - R4282

Biochem/physiol Actions
RF9 is a neuropeptide FF receptor antagonist. NPFF is a member of the FMRFamide (Phe-Met-Arg-PheNH2) family of neuropeptides, which are implicated in nociception and regulation of opioid analgesia. NPFF exhibits antiopioid activity (hyperalgesia). NPFF antagonists are expected to improve the therapeutic efficacy of opioids for treatment of chronic pain. The affinity of RF9 for NPFF1R and NPFF2R is 58 and 75 nM, respectively. RF9 acts as a potent competitive antagonist of NPFF at NPFF2R RF9 exhibits no agonist activity in GTPgS assays.