(2S,3R)-2-{[(2S)-1-[(2S)-1-[(2S,3R)-2-amino-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}-3-hydroxybutanamide; trifluoroacetic acid

• ChemBase ID: 153289
• Molecular Formular: C20H32F3N5O8
• Molecular Mass: 527.4919896
• Monoisotopic Mass: 527.22029767
• SMILES: C[C@H]([C@@H](C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)N[C@@H]([C@@H](C)O)C(=O)N)N)O.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.C[C@H]([C@@H](C(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)[C@H]([C@H](O)C)N)O
• InChI: InChI=1S/C18H31N5O6.C2HF3O2/c1-9(24)13(19)18(29)23-8-4-6-12(23)17(28)22-7-3-5-11(22)16(27)21-14(10(2)25)15(20)26;3-2(4,5)1(6)7/h9-14,24-25H,3-8,19H2,1-2H3,(H2,20,26)(H,21,27);(H,6,7)/t9-,10-,11+,12+,13+,14+;/m1./s1
• InChIKey: BCWVNVCGYWOAAK-GDLIIDCZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-{[(2S)-1-[(2S)-1-[(2S,3R)-2-amino-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}-3-hydroxybutanamide; trifluoroacetic acid
• IUPAC Traditional name: (2S,3R)-2-{[(2S)-1-[(2S)-1-[(2S,3R)-2-amino-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]pyrrolidin-2-yl]formamido}-3-hydroxybutanamide; trifluoroacetic acid
• Synonyms: L-Threonyl-L-prolyl-L-prolyl-L-threoninamide trifluoroacetate; Thr-Pro-Pro-Thr-NH2 trifluoroacetate; TPPT-amide trifluoroacetate; GLYX-13 trifluoroacetate

Database IDs

• CAS Number: 117928-94-6(freeacid)
• MDL Number: MFCD20527320
• PubChem SID: 162247428
• PubChem CID: 71311638

CALCULATED PROPERTIES

• Acid pKa: 11.916108
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -5.7785063
• LogD (pH = 7.4): -4.131007
• Log P: -3.7105496
• Molar Refractivity: 101.5149 cm^3
• Polarizability: 40.21103 Å^3
• Polar Surface Area: 179.29 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: white to tan powder

Safety Information

• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C18H31N5O6 · xC2HF3O2

DETAILS

Sigma Aldrich - SML0109

Biochem/physiol Actions
GLYX-13 is a glycine-site functional partial agonist (GFPA) selective modulator of the NMDA receptor (NMDAR). It is a brain penetrable tetrapeptide which acts as a positive allosteric modulator of the NMDA receptor, acting via the glycine site. GLYX-13 has been found to be a cognitive enhancer in learning models and is currently in clinical trials as an antidepressant.