Structure Database (LMSD)

Common Name
2-hexadecenal
Systematic Name
2-hexadecenal
Synonyms
LM ID
LMFA06000089
Formula
Exact Mass
Calculate m/z
238.229665
Sum Composition
Status
Curated

Classification

Category
Main Class
Sub Class

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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