Structure Database (LMSD)

Common Name
cis-9-palmitoleic acid
Systematic Name
9Z-hexadecenoic acid
Synonyms
  • cis-9-hexadecenoic acid
  • 9Z-palmitoleic acid
  • C16:1n-7
  • Physetoleic acid
  • Zoomaric acid
  • Palmitoleic acid
  • cis-Palmitoleic acid
  • Oleopalmitic acid
  • Zoomeric acid
LM ID
LMFA01030056
Formula
Exact Mass
Calculate m/z
254.22458
Sum Composition
Status
Curated





Classification

Biological Context

Palmitoleic acid is an ω-7 monounsaturated fatty acid that has been found in macadamia and sea buckthorn oils.1,2 It increases basal and insulin-stimulated glucose uptake and glucose transporter 4 (Glut4) protein levels in 3T3-L1 adipocytes when used at a concentration of 200 µM.3 Ex vivo, palmitoleic acid (300 mg/kg per day) increases glucose uptake and aerobic and anaerobic glycolysis and reduces de novo fatty acid synthesis and activity of the lipogenic enzymes ATP citrate lyase (ACL) and glucose-6-phosphate dehydrogenase (G6PDH) in isolated murine adipocytes. Dietary administration of palmitoleic acid (300 mg/kg) reduces high-fat diet-induced insulin resistance and liver inflammation in mice.4

This information has been provided by Cayman Chemical

References

1. Yang, B., and Kallio, H.P. Fatty acid composition of lipids in sea buckthorn (Hippophaë rhamnoids L.) berries of different origins. J. Agric. Food Chem. 49(4), 1939-1947 (2001).
2. Fard, A.M., Turner, A.G., and Willett, G.D. High-resolution electrospray-ionization fourier-transform ion cyclotron resonance and gas chromatography-mass spectrometry of macadamia nut oil. Aus. J. Chem. 56(5), 499-508 (2003).
3. Bolsoni-Lopes, A., Festuccia, W.T., Chimin, P., et al. Palmitoleic acid (n-7) increases white adipocytes GLUT4 content and glucose uptake in association with AMPK activation. Lipids Health Dis. 13(199), 1-10 (2014).
4. Souza, C.O., Teixeira, A.A.S., Lima, E.A., et al. Palmitoleic acid (N-7) attenuates the immunometabolic disturbances caused by a high-fat diet independently of PPARɑ. Mediators Inflamm. 582197 (2014).

Reactions

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Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010
Pubmed ID: 20671299

String Representations

InChiKey (Click to copy)
SECPZKHBENQXJG-FPLPWBNLSA-N
InChi (Click to copy)
InChI=1S/C16H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h7-8H,2-6,9-15H2,1H3,(H,17,18)/b8-7-
SMILES (Click to copy)
C(CCCCCCC(=O)O)/C=C\CCCCCC

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
DFA0095
PubChem CID
PlantFA ID
SwissLipids ID
Cayman ID
PDB ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 18
Rings 0
Aromatic Rings 0
Rotatable Bonds 13
Van der Waals Molecular Volume 297.66
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 5.33
Molar Refractivity 77.85

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Created at
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Updated at
25th Apr 2022