Home > Compound List > Compound details
3102-57-6 molecular structure
click picture or here to close

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

ChemBase ID: 133129
Molecular Formular: C20H39NO3
Molecular Mass: 341.52856
Monoisotopic Mass: 341.29299411
SMILES and InChIs

SMILES:
CCCCCCCCCCCCC/C=C/[C@@H]([C@@H](CO)NC(=O)C)O
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+/m1/s1
InChIKey:
BLTCBVOJNNKFKC-HEQKZDDYSA-N

Cite this record

CBID:133129 http://www.chembase.cn/molecule-133129.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-[(2R,3S,4E)-1,3-dihydroxyoctadec-4-en-2-yl]acetamide
IUPAC Traditional name
N-[(2R,3S,4E)-1,3-dihydroxyoctadec-4-en-2-yl]acetamide
Synonyms
(2S,3R,4E)-2-(Acetylamino)-4-octadecene-1,3-diol
N-Acetoyl-D-erythro-sphingosine
Acetyl ceramide
C2 Ceramide (d18:1/2:0)
C2 ceramide
N-Acetyl-D-sphingosine
CAS Number
3102-57-6
MDL Number
MFCD00153903
PubChem SID
24891187
162227406
PubChem CID
10427441

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Sigma Aldrich
A7191 external link Add to cart Please log in.
Data Source Data ID
PubChem 10427441 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
DMSO: soluble expand Show data source
ethanol: soluble expand Show data source
Apperance
white powder 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
Purity
~98% (TLC) expand Show data source
Biological Source
semisynthetic expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - A7191 external link
Biochem/physiol Actions
Cell-permeable, biologically active ceramide. It induces differentiation and apoptosis in cells and has been shown to activate protein phosphatases.
Preparation Note
Prepared from D-sphingosine from bovine brain cerebrosides.
Application
N-Acetyl-D-sphingosine is a cell-permeable and biologically active ceramide. N-Acetyl-D-sphingosine induces differentiation and apoptosis in cells. N-Acetyl-D-sphingosine produces concentration-dependent impairment of vasorelaxation in response to the endothelium-dependent agonist acetylcholine in nontransgenic mice.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
    No data available
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle