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74713-59-0 molecular structure
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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 and InChIs

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

Cite this record

CBID:90887 http://www.chembase.cn/molecule-90887.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
74713-59-0
MDL Number
MFCD00236496
PubChem SID
162077596
24897955
PubChem CID
5702614

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 5702614 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 13.677088  H Acceptors
H Donor LogD (pH = 5.5) 7.3088045 
LogD (pH = 7.4) 7.3088055  Log P 7.308806 
Molar Refractivity 128.9677 cm3 Polarizability 50.832943 Å3
Polar Surface Area 69.56 Å2 Rotatable Bonds 22 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Dichloromethane expand Show data source
DMSO or ethanol: soluble expand Show data source
Ethyl Acetate expand Show data source
Methanol expand Show data source
Apperance
Off White Solid expand Show data source
waxy solid expand Show data source
Melting Point
68-70°C expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Certificate of Analysis
Download expand Show data source
Shipped in
wet ice expand Show data source
Empirical Formula (Hill Notation)
C26H51NO3 expand Show data source

DETAILS

DETAILS

Apollo Scientific Apollo Scientific Sigma Aldrich Sigma Aldrich TRC TRC
Apollo Scientific Ltd - OR6270T external link
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 external link
Biochem/physiol Actions
Synthetic anaolgue of natural ceramide, activates protein kinase C, stimulates IL-2 production and induces apoptosis.
Toronto Research Chemicals - C262700 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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