Structure Database (LMSD)

Common Name
7S,10S-diHOME
Systematic Name
7S,10S-dihydroxy-8E-octadecenoic acid
Synonyms
LM ID
LMFA02000060
Formula
C18H34O4
Exact Mass
Calculate m/z
314.24571
Sum Composition
FA 18:1;O2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Octadecanoids [FA02]
Other Octadecanoids [FA0200]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Hydroxy fatty acids [FA0105]

Biological Context

7(S),10(S)-DiHOME is a hydroxy fatty acid and metabolite of oleic acid that is produced by P. aeruginosa from vegetable oils.1 It is active against the food-borne pathogenic bacteria S. aureus, S. typhimurium, L. monocytogenes, B. subtilis, and E. coli (MIC50s = 31.3, 125, 125, 62.5, and 250 µg/ml, respectively), as well as the plant pathogenic bacteria Erwinia, R. solanacearum, C. glutamicum, and P. syringae (MIC90s = 125, 125, 250, and 500 µg/ml, respectively).2,1

This information has been provided by Cayman Chemical

References

1. Sohn, H.-R., Bae, J.-H., Hou, C.T., et al. Antibacterial activity of a 7,10-dihydroxy-8(E)-octadecenoic acid against plant pathogenic bacteria. Enzyme Microb. Technol. 53(3), 152-153 (2013).
2. Chen, K.Y., Kim, I.H., Hou, C.T., et al. Monoacylglycerol of 7,10-dihydroxy-8(E)-octadecenoic acid enhances antibacterial activities against food-borne bacteria. J. Agric. Food Chem. 67(29), 8191-8196 (2019).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Stereoselective oxidation of regioisomeric octadecenoic acids by fatty acid dioxygenases.,
J Lipid Res, 2011
Pubmed ID: 21852690
Pseudomonas aeruginosa (#287)
Gammaproteobacteria (#1236)
Biochemical characterization of the oxygenation of unsaturated fatty acids by the dioxygenase and hydroperoxide isomerase of Pseudomonas aeruginosa 42A2.,
J Biol Chem, 2010
Pubmed ID: 20075076

String Representations

InChiKey (Click to copy)
IPRLELFMTNDNMN-WLFRDLTRSA-N
InChi (Click to copy)
InChI=1S/C18H34O4/c1-2-3-4-5-6-8-11-16(19)14-15-17(20)12-9-7-10-13-18(21)22/h14-17,19-20H,2-13H2,1H3,(H,21,22)/b15-14+/t16-,17-/m0/s1
SMILES (Click to copy)
C(CCCCC[C@H](O)/C=C/[C@@H](O)CCCCCCCC)(=O)O

Other Databases

CHEBI ID
165759
PubChem CID
14951704
Cayman ID
33447

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 0
Aromatic Rings 0
Rotatable Bonds 15
Van der Waals Molecular Volume 349.84
Topological Polar Surface Area 77.76
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 4
logP 4.62
Molar Refractivity 90.89

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Created at
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Updated at
19th Jul 2021