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3102-57-6 molecular structure
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N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]acetamide

ChemBase ID: 90871
Molecular Formular: C20H39NO3
Molecular Mass: 341.52856
Monoisotopic Mass: 341.29299411
SMILES and InChIs

SMILES:
O=C(N[C@H]([C@H](O)/C=C/CCCCCCCCCCCCC)CO)C
Canonical SMILES:
CCCCCCCCCCCCC/C=C/[C@H]([C@@H](NC(=O)C)CO)O
InChI:
InChI=1S/C20H39NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20(24)19(17-22)21-18(2)23/h15-16,19-20,22,24H,3-14,17H2,1-2H3,(H,21,23)/b16-15+/t19-,20+/m0/s1
InChIKey:
BLTCBVOJNNKFKC-QUDYQQOWSA-N

Cite this record

CBID:90871 http://www.chembase.cn/molecule-90871.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]acetamide
IUPAC Traditional name
C2-ceramide
Synonyms
C2 Ceeramide
N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]acetamide
N-Acetyl-D-sphingosine
Acetyl Ceramide
N-Acetylsphingosine
C2 Ceramide
CAS Number
3102-57-6
MDL Number
MFCD00153903
PubChem SID
162077580
PubChem CID
5497136

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 5497136 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 13.590839  H Acceptors
H Donor LogD (pH = 5.5) 4.3854265 
LogD (pH = 7.4) 4.3854265  Log P 4.3854265 
Molar Refractivity 101.3358 cm3 Polarizability 39.77093 Å3
Polar Surface Area 69.56 Å2 Rotatable Bonds 16 
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Dichloromethane expand Show data source
Apperance
White Solid expand Show data source
Melting Point
87-89°C expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

Apollo Scientific Apollo Scientific TRC TRC
Apollo Scientific Ltd - OR6251T external link
A biologically active, cell permeable, non-physiological ceramide analog. It inhibits cell proliferation, induces monocytic differentiation of HL-60 cells & inducesapoptosis.
Toronto Research Chemicals - C262500 external link
A biologically active, cell permeable, but nonphysiologic ceramide analog. It inhibits cell proliferation and induces monocytic differentiation of HL-60 cells and induces apoptosis. It stimulates protein phosphatase 2A and activates MAP Kinase2.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Inoue, T., et al.: J. Biol. Chem., 284, 9566 (2009)
  • • Kang, J., et al.: Bioorg. Med. Chem., 17, 1498 (2009)
  • • Rath, G., et al.: Int. J. Biochem. Cell Biol., 41, 1165 (2009)
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PATENTS

PATENTS

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INTERNET

INTERNET

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