Structure Database (LMSD)

Common Name
3R-hydroxy-tetradecanoic acid
Systematic Name
3R-hydroxy-tetradecanoic acid
Synonyms
  • Tetradecanoic acid, 3-hydroxy-, (R)-
  • Tetradecanoic acid, 3-hydroxy-, D-(-)-
  • (3R)-3-Hydroxytetradecanoic acid
  • (R)-(-)-3-Hydroxytetradecanoic acid
  • (R)-3-Hydroxymyristic acid
  • (R)-3-Hydroxytetradecanoic acid
  • D-(-)-beta-Hydroxymyristic acid
  • D-3-Hydroxyte
LM ID
LMFA01050322
Formula
C14H28O3
Exact Mass
Calculate m/z
244.203845
Sum Composition
FA 14:0;O
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]
Hydroxy fatty acids [FA0105]

Biological Context

Lipopolysaccharides (LPS) are components of the cell walls of Gram-negative bacteria. LPS is composed of polysaccharides and lipid A, where lipid A is a phosphoglycolipid containing acyl chains composed of 10 to 16 carbons.1,2 The lipid A component of LPS is detected by Toll-like receptor 4 of mammalian leukocytes and, thus, is a key determinant in immune response.1 (R)-3-hydroxy Myristic acid is a form of the 14:0 lipid myristic acid that is found in the lipid A component of some Gram-negative bacteria, including Escherichia, Haemophilus, Actinobacillus, and Campylobacter species.2,3 [Matreya, LLC. Catalog No. 1735]

This information has been provided by Cayman Chemical

References

1. Masoud, H., Weintraub, S.T., Wang, R., et al. Investigation of the structure of lipid A from Actinobacillus actinomycetemcomitans strain Y4 and human clinical isolate PO 1021-7. Eur. J. Biochem. 200(3), 775-781 (1991).
2. Rietschel, E.T., Kirikae, T., Schade, F.U., et al. Bacterial endotoxin: Molecular relationships of structure to activity and function. FEBS J. 8(2), 217-225 (1994).
3. Raetz, C.R., Reynolds, C.M., Trent, M.S., et al. Lipid A modification systems in Gram-negative bacteria. Annu. Rev. Biochem. 76, 295-329 (2007).

String Representations

InChiKey (Click to copy)
ATRNZOYKSNPPBF-CYBMUJFWSA-N
InChi (Click to copy)
InChI=1S/C14H28O3/c1-2-3-4-5-6-7-8-9-10-11-13(15)12-14(16)17/h13,15H,2-12H2,1H3,(H,16,17)/t13-/m1/s1
SMILES (Click to copy)
C(C[C@H](O)CCCCCCCCCCC)(=O)O

Other Databases

LIPIDAT ID
4962
HMDB ID
HMDB0010731
CHEBI ID
42539
PubChem CID
5288266
SwissLipids ID
SLM:000485323
Cayman ID
16871
PDB ID
FTT

Calculated Physicochemical Properties

Heavy Atoms 17
Rings 0
Aromatic Rings 0
Rotatable Bonds 12
Van der Waals Molecular Volume 274.49
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 4.03
Molar Refractivity 70.62

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Updated at
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