N-[(4-hydroxy-3-methoxyphenyl)methyl]icosa-5,8,11,14-tetraenamide

• ChemBase ID: 153586
• Molecular Formular: C28H41NO3
• Molecular Mass: 439.63004
• Monoisotopic Mass: 439.30864418
• SMILES: CCCCC/C=C/C/C=C/C/C=C/C/C=C/CCCC(=O)NCc1ccc(c(c1)OC)O
• Canonical SMILES: CCCCC/C=C/C/C=C/C/C=C/C/C=C/CCCC(=O)NCc1ccc(c(c1)OC)O
• InChI: InChI=1S/C28H41NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-28(31)29-24-25-21-22-26(30)27(23-25)32-2/h7-8,10-11,13-14,16-17,21-23,30H,3-6,9,12,15,18-20,24H2,1-2H3,(H,29,31)
• InChIKey: QVLMCRFQGHWOPM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(4-hydroxy-3-methoxyphenyl)methyl]icosa-5,8,11,14-tetraenamide
• IUPAC Traditional name: N-[(4-hydroxy-3-methoxyphenyl)methyl]icosa-5,8,11,14-tetraenamide
• Synonyms: (5Z,8Z,11Z,14Z)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-5,8,11,14-Eicosatetraenamide; Arvanil; N-Vanillylarachidonamide; Arvanil

Database IDs

• CAS Number: 128007-31-8
• MDL Number: MFCD01752675
• PubChem SID: 162247725
• PubChem CID: 6510252

CALCULATED PROPERTIES

• Acid pKa: 9.928691
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 7.267124
• LogD (pH = 7.4): 7.265866
• Log P: 7.267141
• Molar Refractivity: 139.7296 cm^3
• Polarizability: 52.401306 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: liquid

Safety Information

• RTECS: JX3845000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥90%
• Empirical Formula (Hill Notation): C28H41NO3

DETAILS

Sigma Aldrich - A2098

Biochem/physiol Actions
Arvanil is an activator of cannabinoid and vanilloid receptors, and a potent inhibitor of anandamide accumulation. Arvanil inhibits growth of astrocytoma xenograft tumors in mice, mimicing the effect of neural precursor cells, that have been shown to kill TRPV1-expressing tumor cells by secreting endovanilloids.