Structure Database (LMSD)
Common Name
2-hexadecenal
Systematic Name
2-hexadecenal
Synonyms
3D model of 2-hexadecenal
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Sphingosine-1-phosphate (S1P), a bioactive lipid involved in many signaling processes, is irreversibly degraded by the membrane-bound S1P lyase. (E)-2-Hexadecenal is a sphingolipid degradation product resulting from the action of S1P lyase. It can be further oxidized to (2E)-hexadecenoic acid by long-chain fatty aldehyde dehydrogenase prior to activation via coupling to coenzyme A. (E)-2-Hexadecenal has been shown to induce cytoskeletal reorganization that results in cell rounding, detachment, activation of downstream JNK targets, and eventual apoptosis in various cell types.1 It reacts readily with deoxyguanosine and DNA to form aldehyde-derived DNA adducts.2
This information has been provided by Cayman Chemical
References
2. Kumar, A., Byun, H.S., Bittman, R., et al. The sphingolipid degradation product trans-2-hexadecenal induces cytoskeletal reorganization and apoptosis in a JNK-dependent manner. Cell. Signal. 23(7), 1144-1152 (2011).
String Representations
InChiKey (Click to copy)
KLJFYXOVGVXZKT-CCEZHUSRSA-N
InChi (Click to copy)
InChI=1S/C16H30O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h14-16H,2-13H2,1H3/b15-14+
SMILES (Click to copy)
C(CCCCCC)CCCCCC/C=C/C([H])=O
Other Databases
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
Calculated Physicochemical Properties
Heavy Atoms
17
Rings
0
Aromatic Rings
0
Rotatable Bonds
13
Van der Waals Molecular Volume
288.87
Topological Polar Surface Area
17.07
Hydrogen Bond Donors
0
Hydrogen Bond Acceptors
1
logP
5.44
Molar Refractivity
76.28
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Updated at
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