N-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-3-[4-(2-{[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]carbamoyl}eth-1-en-1-yl)phenyl]prop-2-enamide hydrate dihydrochloride

• ChemBase ID: 154252
• Molecular Formular: C30H32Cl2N6O3
• Molecular Mass: 595.51948
• Monoisotopic Mass: 594.19129427
• SMILES: c1c(ccc(c1)/C=C/C(=O)Nc1ccc(cc1)C1=NCCN1)/C=C/C(=O)Nc1ccc(cc1)C1=NCCN1.O.Cl.Cl
• Canonical SMILES: O=C(Nc1ccc(cc1)C1=NCCN1)/C=C/c1ccc(cc1)/C=C/C(=O)Nc1ccc(cc1)C1=NCCN1.O.Cl.Cl
• InChI: InChI=1S/C30H28N6O2.2ClH.H2O/c37-27(35-25-11-7-23(8-12-25)29-31-17-18-32-29)15-5-21-1-2-22(4-3-21)6-16-28(38)36-26-13-9-24(10-14-26)30-33-19-20-34-30;;;/h1-16H,17-20H2,(H,31,32)(H,33,34)(H,35,37)(H,36,38);2*1H;1H2
• InChIKey: DKFSVQGRETYFBG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-3-[4-(2-{[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]carbamoyl}eth-1-en-1-yl)phenyl]prop-2-enamide hydrate dihydrochloride
• IUPAC Traditional name: N-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-3-[4-(2-{[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]carbamoyl}eth-1-en-1-yl)phenyl]prop-2-enamide hydrate dihydrochloride
• Synonyms: N,N′-Bis[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl]-3,3′-p-phenylene-bis-acrylamide dihydrochloride; GW4869

Database IDs

• CAS Number: 6823-69-4
• PubChem SID: 24724460; 162248391
• PubChem CID: 71311822

CALCULATED PROPERTIES

• Acid pKa: 13.989559
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.1430306
• LogD (pH = 7.4): -0.2599959
• Log P: 3.6679885
• Molar Refractivity: 154.5362 cm^3
• Polarizability: 55.91341 Å^3
• Polar Surface Area: 106.98 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble0.2 mg/mL
• Apperance: light yellow to yellow powder
• Melting Point: >300 °C

Safety Information

• Storage Condition: desiccated; protect from light; under inert gas
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (NMR)
• Empirical Formula (Hill Notation): C30H28N6O2 · 2HCl

DETAILS

Sigma Aldrich - D1692

Biochem/physiol Actions
A cell-permeable, potent, specific, non-competitive inhibitor of N-SMase (neutral sphingomyelinase)