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124753-97-5 molecular structure
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N-[(2S,3R,4E)-1,3-dihydroxyoctadec-4-en-2-yl]hexanamide

ChemBase ID: 133904
Molecular Formular: C24H47NO3
Molecular Mass: 397.63488
Monoisotopic Mass: 397.35559437
SMILES and InChIs

SMILES:
CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)NC(=O)CCCCC)O
Canonical SMILES:
CCCCCCCCCCCCC/C=C/[C@H]([C@@H](NC(=O)CCCCC)CO)O
InChI:
InChI=1S/C24H47NO3/c1-3-5-7-8-9-10-11-12-13-14-15-16-18-19-23(27)22(21-26)25-24(28)20-17-6-4-2/h18-19,22-23,26-27H,3-17,20-21H2,1-2H3,(H,25,28)/b19-18+/t22-,23+/m0/s1
InChIKey:
NPRJSFWNFTXXQC-QFWQFVLDSA-N

Cite this record

CBID:133904 http://www.chembase.cn/molecule-133904.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]hexanamide
IUPAC Traditional name
C6 ceramide
Synonyms
N-[(1S,2R,3E)-2-Hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]hexanamide
N-Hexanoy-D-sphingosine
N-Hexanoylsphingosine
C6 Ceramide
C6 ceramide
Caproyl ceramide
N-Caproyl-D-sphingosine
N-Hexanoyl-D-sphingosine
CAS Number
124753-97-5
MDL Number
MFCD00870174
PubChem SID
24895750
162228181
PubChem CID
5702613

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 5702613 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 13.63898  H Acceptors
H Donor LogD (pH = 5.5) 6.4196672 
LogD (pH = 7.4) 6.419668  Log P 6.4196687 
Molar Refractivity 119.7657 cm3 Polarizability 47.144634 Å3
Polar Surface Area 69.56 Å2 Rotatable Bonds 20 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Methanol expand Show data source
Apperance
Off White Powder expand Show data source
Melting Point
76-77°C expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
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
Purity
≥98% (TLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Biological Source
from synthetic expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - H6524 external link
Biochem/physiol Actions
Cell-permeable analog of ceramide; stimulates protein phosphatase 2A; activates MAP kinase; induces apoptosis in human leukemia HL-60 cells
Toronto Research Chemicals - C262600 external link
A biologically active, cell permeable, but nonphysiologic ceramide analog. It stimulates protein phosphatase 2A at concentrations as low as 10 nM and activiates MAP kinase. It induces apoptosis and inhibits glycoproptein traffic by the secretory pathway

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Liu, Z., et al.: J. Neurochem., 106, 2463 (2008)
  • • Heakal, Y., et al.: Mol. Cancer Res., 7, 724 (2008)
  • • Chen-Quay, S., et al.: J. Pharm. Sci., 98, 606 (2008)
  • • Mahdy, A., et al.: Mol. Ther., 17, 430 (2008)
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PATENTS

PATENTS

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INTERNET

INTERNET

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