4-[(2S,3R)-3-(3,5-dioxopiperazin-1-yl)butan-2-yl]piperazine-2,6-dione

• ChemBase ID: 153963
• Molecular Formular: C12H18N4O4
• Molecular Mass: 282.29572
• Monoisotopic Mass: 282.13280508
• SMILES: C[C@H]([C@H](C)N1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1
• Canonical SMILES: C[C@H]([C@@H](N1CC(=O)NC(=O)C1)C)N1CC(=O)NC(=O)C1
• InChI: InChI=1S/C12H18N4O4/c1-7(15-3-9(17)13-10(18)4-15)8(2)16-5-11(19)14-12(20)6-16/h7-8H,3-6H2,1-2H3,(H,13,17,18)(H,14,19,20)/t7-,8+
• InChIKey: OBYGAPWKTPDTAS-OCAPTIKFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(2S,3R)-3-(3,5-dioxopiperazin-1-yl)butan-2-yl]piperazine-2,6-dione
• IUPAC Traditional name: 4-[(2S,3R)-3-(3,5-dioxopiperazin-1-yl)butan-2-yl]piperazine-2,6-dione
• Synonyms: meso-4,4′-(3,2-butanediyl)-bis(2,6-piperazinedione); ICRF-193

Database IDs

• CAS Number: 21416-88-6
• MDL Number: MFCD01702964
• PubChem SID: 24896062; 162248102
• PubChem CID: 119081

CALCULATED PROPERTIES

• Acid pKa: 11.198703
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -2.246287
• LogD (pH = 7.4): -2.2362783
• Log P: -2.23608
• Molar Refractivity: 68.672 cm^3
• Polarizability: 27.119255 Å^3
• Polar Surface Area: 98.82 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble4 mg/mL

Safety Information

• RTECS: TL6380200
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-43
• Safety Statements: 36/37
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H317
• GHS Precautionary statements: P280-P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥95%
• Empirical Formula (Hill Notation): C12H18N4O4

DETAILS

Sigma Aldrich - I4659

Biochem/physiol Actions
ICRF-193 induces a G2 checkpoint that is associated with an ATR-dependent inhibition of polo-like kinase 1 (plk1) activity and a decrease in cyclin B1 phosphorylation.1 Induces apoptosis in several cell lines including K562 and Molt-4 cells.2,,,1 ICRF-193 is a topoisomerase II inhibitor, more potent against topoisomerase II-β than topoisomerase II-α3, and may in addition cause DNA strand breaks.4