Compound: Icilin
SMILES: O=[N+]([O-])c1cc(C=2NC(=O)N(c3c(O)cccc3)CC2)ccc1
InChIKey: RCEFMOGVOYEGJN-UHFFFAOYSA-N
Synonyms: Icilin, 36945-98-9, AG 3-5, 3,6-Dihydro-1-(2-hydroxyphenyl)-4-(3-nitrophenyl)-2(1H)-pyrimidinone, 2(1H)-Pyrimidinone, 3,6-dihydro-1-(2-hydroxyphenyl)-4-(3-nitrophenyl)-, CS70PZQ4QJ, DTXSID70190442, 1-(2-hydroxyphenyl)-4-(3-nitrophenyl)-3,6-dihydropyrimidin-2-one, AG-3-5 compound, RefChem:789652, DTXCID80112933, 636-832-1, 3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one, MFCD01689072, AG-3-5, ICILLIN, 3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-1,4-dihydropyrimidin-2-one, CHEMBL258405, SMR000299977, Icilin(AG 3-5), SR-01000075377, UNII-CS70PZQ4QJ, AG 3-5 cpd, BRN 0700310, 3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-3,4-dihydro-2(1H)-pyrimidinone, 3,6-Dihydro-1-(2-hydroxyphenyl)-4-(3-nitrophenyl)-2(1H)-pyrimidinone; 1-(2-Hydroxyphenyl)-4-(3-nitrophenyl)-1,2,3,6-tetrahydropyrimidin-2-one; AG 3-5, Icilin,AG-3-5, ICILIN?, Tocris-1531, ICILIN [MI], Lopac-I-9532, 1-(2-Hydroxyphenyl)-4-(3-nitrophenyl)-1,2,3,6-tetrahydropyrimidine-2-one, 3,4-Dihydro-3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-(1H)-pyrimidin-2-one, Icilin - Bio-X trade mark, Lopac0_000426, 5-24-03-00255 (Beilstein Handbook Reference), MLS000693445, MLS002153471, SCHEMBL663503, GTPL2429, orb1307393, SCHEMBL29450389, SCHEMBL29528215, CHEBI:92845, EX-A279, RCEFMOGVOYEGJN-UHFFFAOYSA-N, HMS2769B07, HMS3261E14, HMS3268C05, HMS3412H21, HMS3648E15, HMS3676H21, Icilin, >=97% (HPLC), solid, Tox21_500426, BDBM50241426, HB1153, STK134504, 3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-1,2,3,4-tetrahydropyrimidin-2-one, AKOS000370368, CCG-204518, CCG-221730, CS-1922, FI66396, LP00426, SDCCGSBI-0050411.P002, SMP2_000128, NCGC00015571-01, NCGC00015571-02, NCGC00015571-03, NCGC00015571-04, NCGC00015571-05, NCGC00015571-07, NCGC00015571-15, NCGC00025205-01, NCGC00025205-02, NCGC00025205-03, NCGC00261111-01, AC-35209, AS-35111, BI164563, DA-33568, HY-11062, SY240208, EU-0100426, C20171, I 9532, Q5986473, SR-01000075377-1, SR-01000075377-2, SR-01000075377-4, SR-01000075377-9, BRD-K48869804-001-04-7, BRD-K48869804-001-09-6, 1-(2'-HYDROXYPHENYL)-4-(3''-NITROPHENYL)-1,2,3,6-TETRAHYDROPYRIMIDINE-2-ONE, AG-3-5; 1-(2-Hydroxyphenyl)-4-(3-nitrophenyl)-1,2,3,6-tetrahydropyrimidin-2-one
Theoretical properties:
molecular_formula: C16H13N3O4
molecular_weight: 311.29 g/mol
exact_mass: 311.09060590 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 2
heavy_atom_count: 23
topological_polar_surface_area: 98.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: 45.2 [ug/mL] (The mean of the results at pH 7.4)
Descriptions:
pubchem: 3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-1,4-dihydropyrimidin-2-one is a C-nitro compound.
chembl: ICILLIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Icilin (AG-3-5) is a synthetic super-agonist of the transient receptor potential M8 (TRPM8) ion channel. Although structurally not related to menthol, it produces an extreme sensation of cold, both in humans and animals. It is almost 200 times more potent than menthol, and 2.5 times more efficacious. Despite their similar effects, icilin activates the TRPM8 receptor in a different way than menthol does. Icilin has been shown to be effective in the treatment of pruritus in an experimental model of itch. It is now used as a research tool for the study of TRP channels, although despite its high potency it is less selective for TRPM8 over other related ion channels than are other compounds such as WS-12.