N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide

• ChemBase ID: 155732
• Molecular Formular: C26H37NO2
• Molecular Mass: 395.57748
• Monoisotopic Mass: 395.28242943
• SMILES: CCCCC/C=C/C/C=C/C/C=C/C/C=C/CCCC(=O)Nc1ccc(cc1)O
• Canonical SMILES: CCCCC/C=C/C/C=C/C/C=C/C/C=C/CCCC(=O)Nc1ccc(cc1)O
• InChI: InChI=1S/C26H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-26(29)27-24-20-22-25(28)23-21-24/h6-7,9-10,12-13,15-16,20-23,28H,2-5,8,11,14,17-19H2,1H3,(H,27,29)
• InChIKey: IJBZOOZRAXHERC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide
• IUPAC Traditional name: N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide
• Synonyms: AM404; N-(4-Hydroxyphenyl)-arachidonylamide

Database IDs

• CAS Number: 183718-77-6
• MDL Number: MFCD03095721
• PubChem SID: 24895490; 162249870
• PubChem CID: 5353402

CALCULATED PROPERTIES

• Molar Refractivity: 130.2122 cm^3
• Polarizability: 48.05595 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false
• Acid pKa: 9.461591
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 7.71786
• LogD (pH = 7.4): 7.714177
• Log P: 7.7179074

PROPERTIES

Physical Property

• Apperance: ethanol solution
• Flash Point: 14 °C; 57.2 °F

Safety Information

• European Hazard Symbols: Flammable (F)
• UN Number: 1170
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11
• Safety Statements: 16
• GHS Pictograms: GHS02
• GHS Signal Word: Danger
• GHS Hazard statements: H225
• GHS Precautionary statements: P210
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1170 3/PG 2
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... CNR1(1268), CNR2(1269)mouse ... Cnr2(12802)rat ... Cnr1(25248), Faah(29347), Trpv1(83810)

Product Information

• Purity: ≥98%
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C26H37NO2

DETAILS

Sigma Aldrich - H1911

Other Notes
To change the solvent, simply evaporate the ethanol under a gentle stream of nitrogen and immediately add the solvent of choice.
Application
Potentiates the activity of endogenous anandamide by blocking its re-uptake into presynaptic membranes. AM404 selectively inhibits the carrier-mediated transport of anandamide without affecting anandamide hydrolysis.