2-[3-(4-pentylphenyl)prop-2-enamido]benzoic acid

• ChemBase ID: 105192
• Molecular Formular: C21H23NO3
• Molecular Mass: 337.41222
• Monoisotopic Mass: 337.1677936
• SMILES: CCCCCc1ccc(/C=C/C(=O)Nc2c(cccc2)C(=O)O)cc1
• Canonical SMILES: CCCCCc1ccc(cc1)/C=C/C(=O)Nc1ccccc1C(=O)O
• InChI: InChI=1S/C21H23NO3/c1-2-3-4-7-16-10-12-17(13-11-16)14-15-20(23)22-19-9-6-5-8-18(19)21(24)25/h5-6,8-15H,2-4,7H2,1H3,(H,22,23)(H,24,25)
• InChIKey: GAMRBCZMOOMBSQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[3-(4-pentylphenyl)prop-2-enamido]benzoic acid
• IUPAC Traditional name: 2-[3-(4-pentylphenyl)prop-2-enamido]benzoic acid
• Synonyms: 2-[[1-oxo-3-(4-Pentylphenyl)-2-propen-1-yl]amino]-benzoic acid; N-(4-Pentylcinnamoyl)anthranilic acid; N-(p-Amylcinnamoyl)anthranilic acid; ACA; N-(p-AMYLCINNAMOYL) ANTHRANILIC ACID

Database IDs

• CAS Number: 110683-10-8; 99196-74-4
• MDL Number: MFCD00211365
• PubChem SID: 162093646
• PubChem CID: 5353376

CALCULATED PROPERTIES

• Acid pKa: 3.5528402
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.228843
• LogD (pH = 7.4): 2.8107445
• Log P: 6.1696672
• Molar Refractivity: 102.0386 cm^3
• Polarizability: 37.929955 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL
• Apperance: white to off-white powder

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• European Hazard Symbols: Nature polluting (N)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 50/53
• Safety Statements: 60-61
• GHS Pictograms: GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H410
• GHS Precautionary statements: P273-P501
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC); 99%
• Empirical Formula (Hill Notation): C21H23NO3

DETAILS

MP Biomedicals - 02159020

Purity: 99%
A close structural analog to ono-rs-082 which is a less potent PLA₂ inhibitor. Also demonstrates some leukotriene antagonistic activity.

Sigma Aldrich - A8486

Biochem/physiol Actions
Broad spectrum phospholipase A2 (PLA2) inhibitor and TRP channel blocker.
Application
N-(p-Amylcinnamoyl)anthranilic acid is a broad spectrum PLA2 inhibitor and TRP channel blocker. N-(p-Amylcinnamoyl)anthranilic acid has been used to study the functional expression of TRPM2 channels in dopaminergic SNc neurons.

REFERENCES

• Banga, H.S., et al., Proc. Natl. Acad. Sci. USA, 83 : 9197 (1986).
• Nakai, H., et al., J. Med. Chem., 21 : 78, (1986).