N-[(2S)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl]octadec-9-enamide

• ChemBase ID: 154164
• Molecular Formular: C27H45NO3
• Molecular Mass: 431.6511
• Monoisotopic Mass: 431.33994431
• SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)N[C@@H](Cc1ccc(cc1)O)CO
• Canonical SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)N[C@@H](Cc1ccc(cc1)O)CO
• InChI: InChI=1S/C27H45NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-27(31)28-25(23-29)22-24-18-20-26(30)21-19-24/h9-10,18-21,25,29-30H,2-8,11-17,22-23H2,1H3,(H,28,31)/t25-/m0/s1
• InChIKey: ICDMLAQPOAVWNH-VWLOTQADSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl]octadec-9-enamide
• IUPAC Traditional name: N-[(2S)-1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl]octadec-9-enamide
• Synonyms: (N-[(S)-2-Hydroxy-1-(4-hydroxybenzyl)-ethyl]-octadec-9-enoamide; OMDM-1

Database IDs

• MDL Number: MFCD05865240
• PubChem SID: 162248303
• PubChem CID: 71311808

CALCULATED PROPERTIES

• Acid pKa: 9.50429
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 7.279722
• LogD (pH = 7.4): 7.2763834
• Log P: 7.279766
• Molar Refractivity: 131.4321 cm^3
• Polarizability: 51.209774 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble ~24 mg/mL
• Apperance: off-white powder

Safety Information

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

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C27H45NO3

DETAILS

Sigma Aldrich - O2389

Biochem/physiol Actions
Potent, selective inhibitor of anadamide cellular uptake with low affinity for CB1 and CB2 receptors, no activity at VR1 receptor or fatty acid amide hydrolase (FAAH); stable to enzymatic hydrolysis by rat brain homogenates.