2-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-7-yl)-N-[4-(propan-2-yl)phenyl]acetamide

• ChemBase ID: 154399
• Molecular Formular: C18H21N5O3
• Molecular Mass: 355.39104
• Monoisotopic Mass: 355.16443956
• SMILES: CC(C)c1ccc(cc1)NC(=O)Cn1cnc2c1c(=O)n(c(=O)n2C)C
• Canonical SMILES: O=C(Cn1cnc2c1c(=O)n(C)c(=O)n2C)Nc1ccc(cc1)C(C)C
• InChI: InChI=1S/C18H21N5O3/c1-11(2)12-5-7-13(8-6-12)20-14(24)9-23-10-19-16-15(23)17(25)22(4)18(26)21(16)3/h5-8,10-11H,9H2,1-4H3,(H,20,24)
• InChIKey: HEQDZPHDVAOBLN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-7-yl)-N-[4-(propan-2-yl)phenyl]acetamide
• IUPAC Traditional name: 2-(1,3-dimethyl-2,6-dioxopurin-7-yl)-N-(4-isopropylphenyl)acetamide
• Synonyms: 1,2,3,6-Tetrahydro-1,3-dimethyl-N-[4-(1-methylethyl)phenyl]-2,6-dioxo-7H-purine-7-acetamide; 2-(1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)-N-(4-isopropylphenyl)acetamide; HC-030031; HC-030031; HC 030031

Database IDs

• CAS Number: 349085-38-7
• MDL Number: MFCD02007349
• PubChem SID: 162248538
• PubChem CID: 1150897

CALCULATED PROPERTIES

• Polar Surface Area: 87.54 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• Acid pKa: 13.577334
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.6116487
• LogD (pH = 7.4): 1.6116484
• Log P: 1.6116488
• Molar Refractivity: 98.3839 cm^3
• Polarizability: 35.951405 Å^3

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO: soluble30 mg/mL; Methanol
• Apperance: off-white powder; White Solid
• Melting Point: 221-223°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: room temp

Pharmacology Properties

• Target: Others

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C18H21N5O3

DETAILS

Sigma Aldrich - H4415

Biochem/physiol Actions
HC-030031 is a selective TRPA1 channel blocker, antagonizing formalin-evoked calcium influx and formalin-induced pain. IC50 is 5 μM. TRPA1 antagonism is a promising therapeutic target for chronic inflammatory or neurogenic pain.1
HC-030031 is a selective TRPA1 channel blocker. HC-030031 antagonizes formalin-evoked calcium influx. IC50 is 5 μM.

Toronto Research Chemicals - H115000

A TRPA1 (transient receptor potential) selective antagonist, attenuates inflammatory- and neuropathy-induced mechanical hypersensitivity.

REFERENCES

• Jordt, S., et al.: Nature, 427, 260 (2004)
• Macpherson, L., et al.: Curr. Biol., 15, 929 (2004)
• Dai, Y., et al.: J. Clin. Invest., 117, 1979 (2004)
• Doerner, J., et al.: J. Biol. Chem., 282, 13180 (2004)