Structure Database (LMSD)

Common Name
Anteisoheptadecanoic acid
Systematic Name
14-methyl-hexadecanoic acid
Synonyms
  • (+)-14-methyl palmitic acid
  • Anteisomargaric acid
LM ID
LMFA01020011
Formula
C17H34O2
Exact Mass
Calculate m/z
270.255881
Sum Composition
FA 17:0
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]
Branched fatty acids [FA0102]

Biological Context

14-methyl Palmitic acid is a methylated fatty acid that has been found in bacteria, bovine milk fat, Aegean jellyfish (A. aurita), and one-humped camel (C. dromedarius) meat and fat.1,2,3,4 It is also found in human breast milk and levels are decreased in mature breast milk compared to colostrum.5 14-methyl Palmitic acid is produced in Florida manatee (T. manatus latirostris) liver in response to brevetoxin exposure.6 [Matreya, LLC. Catalog No. 1616]

This information has been provided by Cayman Chemical

References

1. Kariotoglou, D.M., and Mastronicolis, S.K. Sphingophosphonolipids, phospholipids, and fatty acids from Aegean jellyfish Aurelia aurita. Lipids 36(11), 1255-1264 (2001).
2. Nickels, J.D., Chatterjee, S., Mostofian, B., et al. Bacillus subtilis lipid extract, a branched-chain fatty acid model membrane. J. Phys. Chem. Lett. 8(17), 4214-4217 (2017).
5. Jie, L., Qui, C., Sun, J., et al. The impact of lactation and gestational age on the composition of branched-chain fatty acids in human breast milk. Food Funct. 9(3), 1747-1754 (2018).
3. Henke, A., Westreicher-Kristen, E., Molkentin, J., et al. Effect of dietary quebracho tannin extract on milk fatty acid composition in cows. J. Dairy Sci. 100(8), 6229-6238 (2017).
4. Rawdah, T.N., El-Faer, M.Z., and Koreish, S.A. Fatty acid composition of the meat and fat of the one-humped camel Camelus dromedarius. Meat Sci. 37(1), 149-155 (1994).
6. Wetzel, D.L., Reynolds, J.E., III, Sprinkle, J.M., et al. Fatty acid profiles as a potential lipidomic biomarker of exposure to brevetoxin for endangered Florida manatees (Trichechus manatus latirostris). Sci. Total. Environ. 408(24), 6124-6133 (2010).

String Representations

InChiKey (Click to copy)
FXUKWLSZZHVEJD-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C17H34O2/c1-3-16(2)14-12-10-8-6-4-5-7-9-11-13-15-17(18)19/h16H,3-15H2,1-2H3,(H,18,19)
SMILES (Click to copy)
C(CCCC(C)CC)CCCCCCCCC(=O)O

Other Databases

HMDB ID
HMDB0031067
CHEBI ID
84874
LIPIDBANK ID
DFA0236
PubChem CID
22207
PlantFA ID
10213
Cayman ID
24820

Calculated Physicochemical Properties

Heavy Atoms 19
Rings 0
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 317.60
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 5.80
Molar Refractivity 82.49

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Updated at
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