(9E)-octadec-9-enamide

• ChemBase ID: 3433
• Molecular Formular: C18H35NO
• Molecular Mass: 281.4766
• Monoisotopic Mass: 281.27186475
• SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)N
• Canonical SMILES: CCCCCCCC/C=C/CCCCCCCC(=O)N
• InChI: InChI=1S/C18H35NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H2,19,20)/b10-9+
• InChIKey: FATBGEAMYMYZAF-MDZDMXLPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9E)-octadec-9-enamide; octadec-9-enamide
• IUPAC Traditional name: elaidoylamide; @elaidoylamide; 9-octadecenamide; octadec-9-enamide
• Synonyms: trans-9,10-Octadecenoamide; (9E)-9-Octadecenamide; Elaidic Acid Amide; Elaidic Amide; Elaidoylamide; trans-9-Octadecenamide; Elaidamide; Elaidoylamide; Oleylamide; 9-Octadecenamide; (Z)-9-Octadecenamide; 9,10-Octadecenoamide; Oleic acid amide; cis-9,10-Octadecenoamide; ODA; Sleepamide; 18:1 amide; OLEAMIDE

Database IDs

• CAS Number: 4303-70-2; 301-02-0
• EC Number: 206-103-9
• PubChem SID: 160966872; 46508720
• PubChem CID: 5283387; 5353370
• CHEBI ID: 116314
• CHEMBL: 15927
• Chemspider ID: 4446508
• IUPHAR ligand ID: 284
• Unique Ingredient Identifier: 7L25QK8BWO
• Wikipedia Title: Oleamide

CALCULATED PROPERTIES

JChem

• Acid pKa: 16.920465
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 5.9768553
• LogD (pH = 7.4): 5.9768558
• Log P: 5.9768558
• Molar Refractivity: 89.2244 cm^3
• Polarizability: 34.883404 Å^3
• Polar Surface Area: 43.09 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 7.19
• LOG S: -6.59
• Solubility (Water): 7.31e-05 g/l

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Hexane; Insoluble in water; Tetrahydrofuran
• Apperance: Creamy solid; White Solid
• Melting Point: 102-104 °C; 91-93°C
• Boiling Point: >200 °C
• Flash Point: >200 °C
• Density: 0.879 g/cm^3

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• NFPA704:
  

  0

  1

  0

Product Information

• Purity: ≥98%

DETAILS

MP Biomedicals - 02195936

Purity: >98%
A neuroactive signaling fatty acid amide present in the CSF which induces sleep. Serves as a novel modulator of 5-hydroxytryptamine (serotonin) receptors and as a substrate for neuroblastoma (mouse) anandamide amidohydrolase.

DrugBank - DB03784

Drug information: experimental

Toronto Research Chemicals - E500000

Structural analog of oleamide (cis-9,10-octadecenoamide), a sleep-inducing fatty acid amide found naturally in cerebrospinal fluid.

REFERENCES

• Cravatt, B.F., et al., Science , 268(5216) : 1506-1509 (1995).
• Cravatt, F.B., et al.: Science, 268, 1506 (1995)
• Patterson, J.E., et al.: J. Am. Chem. Soc., 118, 5938 (1995)
• Boger, D.L., et al.: Proc. Natl. Acad. Sci. USA, 95, 4810 (1998)