(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-phenylpropanamido]-4-methylpentanamido]-N-[(1S)-4-carbamimidamido-1-carbamoylbutyl]-4-methylpentanamide; trifluoroacetic acid

• ChemBase ID: 154906
• Molecular Formular: C32H52F3N9O8
• Molecular Mass: 747.8059896
• Monoisotopic Mass: 747.38909433
• SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CO)N.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.OC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N)CCCNC(=N)N)CC(C)C)CC(C)C)Cc1ccccc1)N
• InChI: InChI=1S/C30H51N9O6.C2HF3O2/c1-17(2)13-22(27(43)36-21(25(32)41)11-8-12-35-30(33)34)38-28(44)23(14-18(3)4)39-29(45)24(37-26(42)20(31)16-40)15-19-9-6-5-7-10-19;3-2(4,5)1(6)7/h5-7,9-10,17-18,20-24,40H,8,11-16,31H2,1-4H3,(H2,32,41)(H,36,43)(H,37,42)(H,38,44)(H,39,45)(H4,33,34,35);(H,6,7)/t20-,21-,22-,23-,24-;/m0./s1
• InChIKey: UUNMFWMQJXBTAA-VHIJBDTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-phenylpropanamido]-4-methylpentanamido]-N-[(1S)-4-carbamimidamido-1-carbamoylbutyl]-4-methylpentanamide; trifluoroacetic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-hydroxypropanamido]-3-phenylpropanamido]-4-methylpentanamido]-N-[(1S)-4-carbamimidamido-1-carbamoylbutyl]-4-methylpentanamide; trifluoroacetic acid
• Synonyms: L-Seryl-L-phenylalanyl-L-leucyl-L-leucyl-L-Arginine amide trifluoroacetate salt; Ser-Phe-Leu-Leu-Arg-amide trifluoroacetate salt; Thrombin Receptor Activator for Peptide 5 (TRAP-5) trifluoroacetate salt; SFLLR-NH2 trifluoroacetate salt

Database IDs

• MDL Number: MFCD18782167
• PubChem SID: 162249044
• PubChem CID: 71312024

CALCULATED PROPERTIES

• Acid pKa: 11.679374
• H Acceptors: 10
• H Donor: 10
• LogD (pH = 5.5): -5.7492485
• LogD (pH = 7.4): -4.116464
• Log P: -1.8233638
• Molar Refractivity: 178.4448 cm^3
• Polarizability: 65.80233 Å^3
• Polar Surface Area: 267.64 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: ≥2 mg/mL
• Apperance: white to off-white powder

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C30H51N9O6 · xC2HF3O2

DETAILS

Sigma Aldrich - S8701

Biochem/physiol Actions
SFLLR-NH2 is a PAR-1 (Protease-Activated Receptor) selective activating peptide, also known as Thrombin Receptor Activating Peptide 5 (TRAP-5). Protease-activated receptors (PARs) are present on various organs including, platelets, mast cell, gallblader, oesophagus etc, and regulate various physiological processes including human platelet aggregation, vascular contraction/relaxation, and an increase in endothelial permeability. Recent papers indicated that PAR′s are also involved in sensory processing and proliferation of astrocytes.