N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]octanamide

• ChemBase ID: 90887
• Molecular Formular: C26H51NO3
• Molecular Mass: 425.68804
• Monoisotopic Mass: 425.3868945
• SMILES: O=C(N[C@H]([C@H](O)/C=C/CCCCCCCCCCCCC)CO)CCCCCCC
• Canonical SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@@H](NC(=O)CCCCCCC)CO)O
• InChI: InChI=1S/C26H51NO3/c1-3-5-7-9-10-11-12-13-14-15-16-18-19-21-25(29)24(23-28)27-26(30)22-20-17-8-6-4-2/h19,21,24-25,28-29H,3-18,20,22-23H2,1-2H3,(H,27,30)/b21-19+/t24-,25+/m0/s1
• InChIKey: APDLCSPGWPLYEQ-WRBRXSDHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]octanamide; N-[(2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]octanamide
• IUPAC Traditional name: N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]octanamide; N-[(2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]octanamide
• Synonyms: C8 Ceramide; C8 ceramide; N-Octanoyl-D-sphingosine; N-Octanoylsphingosine; N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]octanamide; [R-[R*,S*-(E)]]-N-[2-Hydroxy-1-(hydroxymethyl)-3-heptadecenyl]octanamide; D-erythro-N-Octanoylsphingosine; N-Octanoyl-C18-sphingosine; N-Octanoyl-D-erythro-sphingosine

Database IDs

• CAS Number: 74713-59-0
• MDL Number: MFCD00236496
• PubChem SID: 24897955; 162077596
• PubChem CID: 5702614

CALCULATED PROPERTIES

• Acid pKa: 13.677088
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 7.3088045
• LogD (pH = 7.4): 7.3088055
• Log P: 7.308806
• Molar Refractivity: 128.9677 cm^3
• Polarizability: 50.832943 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMSO or ethanol: soluble; Ethyl Acetate; Methanol
• Apperance: Off White Solid; waxy solid
• Melting Point: 68-70°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Shipped in: wet ice
• Empirical Formula (Hill Notation): C26H51NO3

DETAILS

Apollo Scientific Ltd - OR6270T

A biologically active, cell permeable, nonphysiologic ceramide analog. It induces phosphorylation on Thr-669 in A-431 cells by stimulation of ceramide-activated protein kinase.

Sigma Aldrich - O1882

Biochem/physiol Actions
Synthetic anaolgue of natural ceramide, activates protein kinase C, stimulates IL-2 production and induces apoptosis.

Toronto Research Chemicals - C262700

A biologically active, cell permeable, but nonphysiologic ceramide analog. It induces phosphorylation on Thr-669 in A-431 cells by stimulation of ceramide-activated protein kinase. It stimulates IL-2 secretion and induces apoptosis.

REFERENCES

• Mathias, S., et al.: Proc. Natl. Sci. USA, 88, 10009 (1991)
• Mathias, S., et al.: Science, 259, 519 (1991)
• Jarvis, W.D., et al.: Proc. Natl. Acad. Sci. USA, 91, 73 (1994)