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N-[(2R,3S,4E)-1,3-dihydroxyoctadec-4-en-2-yl]acetamide
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ChemBase ID:
133129
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Molecular Formular:
C20H39NO3
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Molecular Mass:
341.52856
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Monoisotopic Mass:
341.29299411
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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
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Cite this record
CBID:133129 http://www.chembase.cn/molecule-133129.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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N-[(2R,3S,4E)-1,3-dihydroxyoctadec-4-en-2-yl]acetamide
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IUPAC Traditional name
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N-[(2R,3S,4E)-1,3-dihydroxyoctadec-4-en-2-yl]acetamide
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Synonyms
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(2S,3R,4E)-2-(Acetylamino)-4-octadecene-1,3-diol
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N-Acetoyl-D-erythro-sphingosine
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Acetyl ceramide
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C2 Ceramide (d18:1/2:0)
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C2 ceramide
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N-Acetyl-D-sphingosine
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CAS Number
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MDL Number
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PubChem SID
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PubChem CID
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
Acid pKa
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13.590839
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H Acceptors
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3
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H Donor
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3
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LogD (pH = 5.5)
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4.3854265
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LogD (pH = 7.4)
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4.3854265
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Log P
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4.3854265
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Molar Refractivity
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101.3358 cm3
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Polarizability
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39.77093 Å3
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Polar Surface Area
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69.56 Å2
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Rotatable Bonds
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16
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Lipinski's Rule of Five
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true
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DETAILS
DETAILS
Sigma Aldrich
Sigma Aldrich -
A7191
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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. |
PATENTS
PATENTS
PubChem Patent
Google Patent