(2S)-N-({[(1S,2R)-1-carbamoyl-2-hydroxypropyl]carbamoyl}methyl)-2-(phenylformamido)butanediamide; trifluoroacetic acid

• ChemBase ID: 154683
• Molecular Formular: C19H24F3N5O8
• Molecular Mass: 507.4177696
• Monoisotopic Mass: 507.15769741
• SMILES: C[C@H]([C@@H](C(=O)N)NC(=O)CNC(=O)[C@H](CC(=O)N)NC(=O)c1ccccc1)O.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.NC(=O)C[C@@H](C(=O)NCC(=O)N[C@H](C(=O)N)[C@H](O)C)NC(=O)c1ccccc1
• InChI: InChI=1S/C17H23N5O6.C2HF3O2/c1-9(23)14(15(19)26)22-13(25)8-20-17(28)11(7-12(18)24)21-16(27)10-5-3-2-4-6-10;3-2(4,5)1(6)7/h2-6,9,11,14,23H,7-8H2,1H3,(H2,18,24)(H2,19,26)(H,20,28)(H,21,27)(H,22,25);(H,6,7)/t9-,11+,14+;/m1./s1
• InChIKey: FAAYXOTZFOVHSZ-YPMBYOOKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-({[(1S,2R)-1-carbamoyl-2-hydroxypropyl]carbamoyl}methyl)-2-(phenylformamido)butanediamide; trifluoroacetic acid
• IUPAC Traditional name: (2S)-N-({[(1S,2R)-1-carbamoyl-2-hydroxypropyl]carbamoyl}methyl)-2-(phenylformamido)butanediamide; trifluoroacetic acid
• Synonyms: Nα-Benzoyl-L-asparaginylglycyl-L-threoninamide trifluoroacetate salt; Bz-Asn-Gly-Thr-NH2 trifluoroacetate salt; Nα-Benzoyl-Asn-Gly-Thr amide trifluoroacetate salt

Database IDs

• CAS Number: 153919-60-9(freebase)
• MDL Number: MFCD17215954
• PubChem SID: 162248821
• PubChem CID: 71311937

CALCULATED PROPERTIES

• Acid pKa: 11.632628
• H Acceptors: 6
• H Donor: 6
• LogD (pH = 5.5): -3.4335248
• LogD (pH = 7.4): -3.433547
• Log P: -3.4335246
• Molar Refractivity: 96.3548 cm^3
• Polarizability: 37.235252 Å^3
• Polar Surface Area: 193.71 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

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

Product Information

• Purity: ≥90% (HPLC)
• Empirical Formula (Hill Notation): C17H23N5O6 · xC2HF3O2

DETAILS

Sigma Aldrich - 06857

Application
Enzyme substrate for testing N-glycosylation1. Nα-Benzoyl-Asn-Gly-Thr amides can function as acceptor peptides for oligosaccharyltransferases and have been used to study their activity. 2