3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-1,2,3,4-tetrahydropyrimidin-2-one

• ChemBase ID: 127785
• Molecular Formular: C16H13N3O4
• Molecular Mass: 311.29212
• Monoisotopic Mass: 311.09060591
• SMILES: O=C1N(c2c(O)cccc2)CC=C(c2cccc([N+](=O)[O-])c2)N1
• Canonical SMILES: O=C1NC(=CCN1c1ccccc1O)c1cccc(c1)[N+](=O)[O-]
• InChI: InChI=1S/C16H13N3O4/c20-15-7-2-1-6-14(15)18-9-8-13(17-16(18)21)11-4-3-5-12(10-11)19(22)23/h1-8,10,20H,9H2,(H,17,21)
• InChIKey: RCEFMOGVOYEGJN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-1,2,3,4-tetrahydropyrimidin-2-one
• IUPAC Traditional name: icilin
• Synonyms: 1-(2-Hydroxyphenyl)-4-(3-nitrophenyl)-1,2,3,6-tetra-hydro-pyrimidin-2-one; Icilin; AG-3-5; Icilin

Database IDs

• CAS Number: 36945-98-9
• MDL Number: MFCD01689072
• PubChem SID: 24277906; 162222103
• PubChem CID: 161930
• Chemspider ID: 142218
• IUPHAR ligand ID: 2429
• Wikipedia Title: Icilin

CALCULATED PROPERTIES

• Acid pKa: 8.629373
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.1703713
• LogD (pH = 7.4): 2.1459794
• Log P: 2.1706915
• Molar Refractivity: 85.4781 cm^3
• Polarizability: 31.21678 Å^3
• Polar Surface Area: 98.39 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble15 mg/mL
• Apperance: yellow solid

Safety Information

• RTECS: UW7397500
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 26-36; R
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C16H13N3O4

DETAILS

Sigma Aldrich - I9532

Biochem/physiol Actions
Icilin is a potent agonist at the CMR1 cold- and menthol-sensitive receptor.