(2E)-N-hydroxy-3-[1-methyl-4-(2-phenylacetyl)-1H-pyrrol-2-yl]prop-2-enamide

• ChemBase ID: 5001
• Molecular Formular: C16H16N2O3
• Molecular Mass: 284.30984
• Monoisotopic Mass: 284.11609238
• SMILES: n1(cc(C(=O)Cc2ccccc2)cc1/C=C/C(=O)NO)C
• Canonical SMILES: ONC(=O)/C=C/c1cc(cn1C)C(=O)Cc1ccccc1
• InChI: InChI=1S/C16H16N2O3/c1-18-11-13(10-14(18)7-8-16(20)17-21)15(19)9-12-5-3-2-4-6-12/h2-8,10-11,21H,9H2,1H3,(H,17,20)/b8-7+
• InChIKey: UFQOXIMRSMFQRI-BQYQJAHWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-N-hydroxy-3-[1-methyl-4-(2-phenylacetyl)-1H-pyrrol-2-yl]prop-2-enamide; N-hydroxy-3-[1-methyl-4-(2-phenylacetyl)-1H-pyrrol-2-yl]prop-2-enamide
• IUPAC Traditional name: (2E)-N-hydroxy-3-[1-methyl-4-(2-phenylacetyl)pyrrol-2-yl]prop-2-enamide; N-hydroxy-3-[1-methyl-4-(2-phenylacetyl)pyrrol-2-yl]prop-2-enamide
• Synonyms: (2E)-N-hydroxy-3-[1-methyl-4-(phenylacetyl)-1H-pyrrol-2-yl]prop-2-enamide; 3-(1-Methyl-4-phenylacetyl-1H-2-pyrrolyl)-N-hydroxy-2-propenamide; APHA Compound 8

Database IDs

• CAS Number: 676599-90-9
• PubChem SID: 99443821; 160968433
• PubChem CID: 10379137

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.522459
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.9414696
• LogD (pH = 7.4): 1.9382654
• Log P: 1.9415106
• Molar Refractivity: 81.3044 cm^3
• Polarizability: 30.314362 Å^3
• Polar Surface Area: 71.33 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.89
• LOG S: -3.72
• Solubility (Water): 5.39e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: insoluble
• Apperance: solid

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 22-41-43
• Safety Statements: 26-36/37/39
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H317-H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C16H16N2O3

DETAILS

DrugBank - DB07350

Drug information: experimental

Sigma Aldrich - A2478

Biochem/physiol Actions
One of a class of aroyl pyrrole hydroxy amide (APHA) compounds showing histone deacetylase (HDAC) inhibition, Compound 8 is the most potent and HDAC class I-selective.1