(2S,3R)-2-{[(2R)-1-[(2S)-2,6-diaminohexanoyl]pyrrolidin-2-yl]formamido}-3-hydroxybutanoic acid

• ChemBase ID: 156762
• Molecular Formular: C15H28N4O5
• Molecular Mass: 344.40662
• Monoisotopic Mass: 344.20597002
• SMILES: C[C@H]([C@@H](C(=O)O)NC(=O)[C@H]1CCCN1C(=O)[C@H](CCCCN)N)O
• Canonical SMILES: NCCCC[C@@H](C(=O)N1CCC[C@@H]1C(=O)N[C@H](C(=O)O)[C@H](O)C)N
• InChI: InChI=1S/C15H28N4O5/c1-9(20)12(15(23)24)18-13(21)11-6-4-8-19(11)14(22)10(17)5-2-3-7-16/h9-12,20H,2-8,16-17H2,1H3,(H,18,21)(H,23,24)/t9-,10+,11-,12+/m1/s1
• InChIKey: LOGFVTREOLYCPF-KXNHARMFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-{[(2R)-1-[(2S)-2,6-diaminohexanoyl]pyrrolidin-2-yl]formamido}-3-hydroxybutanoic acid
• IUPAC Traditional name: (2S,3R)-2-{[(2R)-1-[(2S)-2,6-diaminohexanoyl]pyrrolidin-2-yl]formamido}-3-hydroxybutanoic acid
• Synonyms: L-Lysyl-D-prolyl-L-threonine; Interleukin 1B antagonist

Database IDs

• CAS Number: 117027-34-6
• MDL Number: MFCD00076555
• Beilstein Number: 8289021
• PubChem SID: 162250899
• PubChem CID: 159483

CALCULATED PROPERTIES

• Acid pKa: 3.3527925
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -6.891564
• LogD (pH = 7.4): -5.2045374
• Log P: -4.4803042
• Molar Refractivity: 86.0559 cm^3
• Polarizability: 34.343258 Å^3
• Polar Surface Area: 158.98 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble10 mg/mL, clear, colorless

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: ≥95% (HPLC)
• Compostion: amino acid analysis: in accordance
• Suitability: in accordance for FAB-MS
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C15H28N4O5

DETAILS

Sigma Aldrich - 57599

Amino Acid Sequence
Lys-D-Pro-Thr
Other Notes
Antagonizes hyperalgesia evoked by interleukin-1β in a dose-dependent manner1