(2S)-2-[(2S)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]-3-phenylpropanamido]-N-[(1S)-1-{[(1S)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}-3-methylbutyl]-4-methylpentanamide; trifluoroacetic acid

• ChemBase ID: 153240
• Molecular Formular: C33H54F3N9O8
• Molecular Mass: 761.8325696
• Monoisotopic Mass: 761.40474439
• SMILES: C[C@H]([C@@H](C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N)N)O.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.CC(C[C@@H](C(=O)N[C@H](C(=O)N)CCCNC(=N)N)NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H]([C@H](O)C)N)CC(C)C)C
• InChI: InChI=1S/C31H53N9O6.C2HF3O2/c1-17(2)14-22(27(43)37-21(26(33)42)12-9-13-36-31(34)35)38-28(44)23(15-18(3)4)39-29(45)24(16-20-10-7-6-8-11-20)40-30(46)25(32)19(5)41;3-2(4,5)1(6)7/h6-8,10-11,17-19,21-25,41H,9,12-16,32H2,1-5H3,(H2,33,42)(H,37,43)(H,38,44)(H,39,45)(H,40,46)(H4,34,35,36);(H,6,7)/t19-,21+,22+,23+,24+,25+;/m1./s1
• InChIKey: QVNWOGSDGQDGHP-MKVNCOEFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]-3-phenylpropanamido]-N-[(1S)-1-{[(1S)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}-3-methylbutyl]-4-methylpentanamide; trifluoroacetic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S,3R)-2-amino-3-hydroxybutanamido]-3-phenylpropanamido]-N-[(1S)-1-{[(1S)-4-carbamimidamido-1-carbamoylbutyl]carbamoyl}-3-methylbutyl]-4-methylpentanamide; trifluoroacetic acid
• Synonyms: L-Threonyl-L-phenylalanyl-L-leucyl-L-leucyl- L-argininamide trifluoroacetate salt; Thr-Phe-Leu-Leu-Arg-NH2 trifluoroacetate salt; TFLLR-NH2 trifluoroacetate salt

Database IDs

• MDL Number: MFCD05663482
• PubChem SID: 162247379
• PubChem CID: 71311619

CALCULATED PROPERTIES

• Acid pKa: 11.681516
• H Acceptors: 10
• H Donor: 10
• LogD (pH = 5.5): -5.39751
• LogD (pH = 7.4): -3.7438345
• Log P: -1.4053278
• Molar Refractivity: 182.8636 cm^3
• Polarizability: 67.63567 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 tan lyophilized powder

Safety Information

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

Product Information

• Purity: >98% (HPLC)
• Empirical Formula (Hill Notation): C31H53N9O6 · xC2HF3O2

DETAILS

Sigma Aldrich - T7830

Amino Acid Sequence
Thr-Phe-Leu-Leu-Arg-NH2
Biochem/physiol Actions
TFLLR-NH2 is a protease-activated receptor (PARs) agonist which is more selective to PAR-1 than SFLLRN-NH2. Protease-activated receptors (PARs) are present on various organs including, plateles, 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. Specificly PAR ligands enhance glutamatergic excitatory transmission in substantia gelatinosa (SG) neurons of adult rat spinal cord slices.