Structure Database (LMSD)

Common Name
Juniperic acid
Systematic Name
16-hydroxy-hexadecanoic acid
Synonyms
  • Juniperinic acid
LM ID
LMFA01050051
Formula
C16H32O3
Exact Mass
Calculate m/z
272.235146
Sum Composition
FA 16:0;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
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View BMRB ID(NMR) spectrum
View NP-MRD ID(NMR) spectrum
View studies deposited in Metabolomics Workbench in which this molecule has been identified

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Hydroxy fatty acids [FA0105]

Biological Context

16-hydroxy Hexadecanoic acid is a metabolite of the saturated fatty acid palmitic acid (16:0) that has been hydroxylated on its terminal (ω) carbon. It is produced by ω-hydroxylation of palmitic acid by cytochrome P450 in both plants and animals.1,2,3,4 In plants, it is commonly a component of cutin.5,2

This information has been provided by Cayman Chemical

References

1. Aoyama, T., Hardwick, J.P., Imaoka, S., et al. Clofibrate-inducible rat hepatic P450s IVA1 and IVA3 catalyze the ω- and (ω-1)-hydroxylation of fatty acids and the (ω-1)-hydroxylation of prostaglandins E1 and F2α. J. Lipid Res. 31(8), 1477-1482 (1990).
2. Peshel, S., Franke, R., Schreiber, L., et al. Composition of the cuticle of developing sweet cherry fruit. Phytochemistry 68(7), 1017-1025 (2007).
3. Benveniste, I., Saito, T., Wang, Y., et al. Evolutionary relationship and substrate specificity of Arabidopsis thaliana fatty acid ω-hydroxylase. Plant Sci. 170(2), 326-328 (2006).
3. Benveniste, I., Saito, T., Wang, Y., et al. Evolutionary relationship and substrate specificity of Arabidopsis thaliana fatty acid ω-hydroxylase. Plant Sci. 170(2), 326-328 (2006).
4. Roman, L.J., Palmer, C.N.A., Clark, J.E., et al. Expression of rabbit cytochromes P4504A which catalyze the ω-hydroxylation of arachidonic acid, fatty acid, and prostaglandins. Arch. Biochem. Biophys. 307(1), 57-65 (1993).
5. Li, H., Pinot, F., Sauveplane, V., et al. Cytochrome P450 family member CYP704B2 catalyzes the ω-hydroxylation of fatty acids and is require for anther cutin biosynthesis and pollen exine formation in rice. Plant Cell 22(1), 173-190 (2010).

String Representations

InChiKey (Click to copy)
UGAGPNKCDRTDHP-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C16H32O3/c17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(18)19/h17H,1-15H2,(H,18,19)
SMILES (Click to copy)
C(CCCCCCCCCCCCCO)CC(=O)O

Other Databases

KEGG ID
C18218
HMDB ID
HMDB0006294
CHEBI ID
55328
LIPIDBANK ID
DFA0317
PubChem CID
10466
PlantFA ID
10261
SwissLipids ID
SLM:000389680
Cayman ID
9000789
PDB ID
16Y

Calculated Physicochemical Properties

Heavy Atoms 19
Rings 0
Aromatic Rings 0
Rotatable Bonds 15
Van der Waals Molecular Volume 309.09
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 4.81
Molar Refractivity 79.85

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Updated at
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