Structure Database (LMSD)

Common Name
Gaidic acid
Systematic Name
2-hexadecenoic acid
Synonyms
  • 2-palmitoleic acid
  • C16:1n-14
LM ID
LMFA01030054
Formula
C16H30O2
Exact Mass
Calculate m/z
254.22458
Sum Composition
FA 16:1
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]

Biological Context

Formation of cis monoenoic acids from unsaturated fatty acids, such as palmitoleic acid (9-cis-hexadecenoic acid) from palmitic acid occurs readily in animal tissues.1 Δ2-trans-Hexadecenoic acid is an intermediate formed in the β-oxidation of palmitic acid.2 In a model meant to simulate gastric ulceration, Δ2-trans-hexadecenoic acid at 10 mg/kg significantly inhibits gastric juice secretion in pylorus-ligated rats.3

This information has been provided by Cayman Chemical

References

1. Mimura, T., Kohda, I., Maeda, K., et al. Inhibitory effects of unsaturated fatty acids of trans-2-C10:1 to trans-2-C16:1 several C18:n and C20:n on gastric secretion and experimental ulceration in rats. J. Pharmacobiodyn. 6(8), 527-538 (1983).
2. Jones, J.A., and Blecher, M. Synthesis and characterization of 3-ketohexadecanoic acid-1-14C, DL-3-hydroxyhexadecanoic acid-1-14C, and trans-2-hexadecenoic acid-1-14C. J. Lipid Res. 7(3), 422-426 (1966).
3. Nakano, M., and Fujino, Y. Enzymatic formation of hexadecenoic acid from palmitic acid. Agr. Biol. Chem. 39(3), 707-710 (1975).

Reactions

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Reactions graph legend

String Representations

InChiKey (Click to copy)
ZVRMGCSSSYZGSM-CCEZHUSRSA-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/h14-15H,2-13H2,1H3,(H,17,18)/b15-14+
SMILES (Click to copy)
C(CCCCCC)CCCCCC/C=C/C(=O)O

Other Databases

HMDB ID
HMDB0010735
CHEBI ID
37252
LIPIDBANK ID
DFA0093
PubChem CID
5282743
PlantFA ID
10475
Cayman ID
11132

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