Structure Database (LMSD)

Common Name
(+)-3-hydroxy behenic
Systematic Name
3-hydroxy-docosanoic acid
Synonyms
LM ID
LMFA01050078
Formula
C22H44O3
Exact Mass
Calculate m/z
356.329045
Sum Composition
FA 22:0;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]
Docosanoids [FA04]

Biological Context

3-hydroxy Docosanoic acid is a hydroxylated form of the 22-carbon saturated docosanoic acid . It is found in lipopolysaccharides from C. trachomatis and C. psittaci and in S. synnaedendra.1,2 3-hydroxy Docosanoic acid, in the form of an acyl-CoA metabolite, is an intermediate in fatty acid chain elongation from arachidic acid (C20:0) to docosanoic acid (C22:0).3

This information has been provided by Cayman Chemical

References

1. Sebolai, O.M., Kock, J.L., Pohl, C.H., et al. Report on the discovery of a novel 3-hydroxy oxylipin cascade in the yeast Saccharomycopsis synnaedendra. Prostaglandins Other Lipid Mediat. 74(1-4), 139-146 (2004).
2. Heine, H., Müller-Loennies, S., Brade, L., et al. Endotoxic activity and chemical structure of lipopolysaccharides from Chlamydia trachomatis serotypes E and L2 and Chlamydophila psittaci 6BC. Eur. J. Biochem. 270(3), 440-450 (2003).
3. Guillou, H., Zadravec, D., Martin, P.G., et al. The key roles of elongases and desaturases in mammalian fatty acid metabolism: Insights from transgenic mice. Prog. Lipid Res. 49(2), 186-199 (2010).

String Representations

InChiKey (Click to copy)
PNPWTPYWWUOMDS-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C22H44O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-21(23)20-22(24)25/h21,23H,2-20H2,1H3,(H,24,25)
SMILES (Click to copy)
C(CCCCCCCCCCC(O)CC(=O)O)CCCCCCCC

Other Databases

CHEBI ID
52348
LIPIDBANK ID
DFA0344
PubChem CID
5282921
Cayman ID
22666

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 0
Aromatic Rings 0
Rotatable Bonds 20
Van der Waals Molecular Volume 412.89
Topological Polar Surface Area 57.53
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 3
logP 7.15
Molar Refractivity 107.55

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Updated at
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