(2S)-2-[(3R)-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2-oxopyrrolidin-1-yl]-3-methylbutanoic acid

• ChemBase ID: 151542
• Molecular Formular: C24H26N2O5
• Molecular Mass: 422.47364
• Monoisotopic Mass: 422.18417194
• SMILES: CC(C)[C@@H](C(=O)O)N1CC[C@H](C1=O)NC(=O)OCC1c2ccccc2c2c1cccc2
• Canonical SMILES: O=C(N[C@@H]1CCN(C1=O)[C@H](C(=O)O)C(C)C)OCC1c2ccccc2c2c1cccc2
• InChI: InChI=1S/C24H26N2O5/c1-14(2)21(23(28)29)26-12-11-20(22(26)27)25-24(30)31-13-19-17-9-5-3-7-15(17)16-8-4-6-10-18(16)19/h3-10,14,19-21H,11-13H2,1-2H3,(H,25,30)(H,28,29)/t20-,21+/m1/s1
• InChIKey: PEMHOAIHPQJNIM-RTWAWAEBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(3R)-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2-oxopyrrolidin-1-yl]-3-methylbutanoic acid
• IUPAC Traditional name: (2S)-2-[(3R)-3-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2-oxopyrrolidin-1-yl]-3-methylbutanoic acid
• Synonyms: Fmoc-Gly-Val Freidinger’s lactam; N-Fmoc-Freidinger’s lactam; Fmoc-Gly-Val Freidinger 内酰胺; N-Fmoc-Freidinger 内酰胺

Database IDs

• CAS Number: 957507-85-6
• MDL Number: MFCD03100546
• PubChem SID: 162245695; 24850721
• PubChem CID: 16211400

CALCULATED PROPERTIES

• Acid pKa: 3.685084
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.3383801
• LogD (pH = 7.4): -0.1598252
• Log P: 3.1515963
• Molar Refractivity: 113.9146 cm^3
• Polarizability: 45.52716 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (HPLC)
• Empirical Formula (Hill Notation): C24H26N2O5

DETAILS

Sigma Aldrich - 17816

Other Notes
Fmoc-protected conformationally restricted dipeptide peptidomimetic for Gly-Val-OH.1,2
Packaging
500 mg in poly bottle