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C6 Urea Ceramide

CAT: 0931-T36321-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0931-T36321-01Size:1 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
486991-52-0
Target
Others, Apoptosis, Autophagy, Wnt/beta-catenin
Related Pathways
Apoptosis, Cytoskeletal Signaling, Autophagy, Others, Stem Cells
Bioactivity
C6 urea ceramide is an inhibitor of neutral ceramidase.1 It increases total ceramide levels in wild-type mouse embryonic fibroblasts (MEFs) and in HT-29 colon cancer cells but not in MEFs lacking neutral ceramidase. It inhibits proliferation of, and induces apoptosis and autophagy in HT-29, but not non-cancerous RIE-1, cells when used at concentrations of 5 and 10 μM. C6 urea ceramide decreases total β-catenin, increases phosphorylated β-catenin, and induces colocalization of β-catenin with the 20S proteasome in HT-29 and HCT116, but not RIE-1, cells. It reduces tumor growth and increases C16, C18, C20, and C24 ceramide levels in tumor tissue in an HT-29 mouse xenograft model when administered at doses of 1.25, 2.5, and 5 mg/kg for five days.
Smiles
[C@@H](NC(NCCCCCC)=O)([C@@H](/C=C/CCCCCCCCCCCCC)O)CO
Molecular Formula
C25H50N2O3
Molecular Weight
426.68
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

C6 Urea Ceramide
CAS Number486991-52-0
PubChem CID10224348
IUPAC Name1-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]-3-hexylurea
Molecular FormulaC25H50N2O3
Molecular Weight426.7
XLogP7.7
Topological Polar Surface Area81.6
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count3
Rotatable Bond Count21
Heavy Atom Count30
Formal Charge0
Complexity402
SMILES
CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)NC(=O)NCCCCCC)O
InChI
InChI=1S/C25H50N2O3/c1-3-5-7-9-10-11-12-13-14-15-16-17-18-20-24(29)23(22-28)27-25(30)26-21-19-8-6-4-2/h18,20,23-24,28-29H,3-17,19,21-22H2,1-2H3,(H2,26,27,30)/b20-18+/t23-,24+/m0/s1
InChIKey
MIADELGCYXNHNP-VYQUXUJXSA-N
Chemical Structure
2D Structure
2D structure of C6 Urea Ceramide
CAS: 486991-52-0
CID: 10224348
Formula: C25H50N2O3
MW: 426.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight426.7
XLogP37.7
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count3
Rotatable Bond Count21
Exact Mass426.38214346
Monoisotopic Mass426.38214346
Topological Polar Surface Area81.6 Ų
Heavy Atom Count30
Formal Charge0
Complexity402
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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