Structure Database (LMSD)

Common Name
5S,18-diHODE
Systematic Name
5S,18-Dihydroxyoctadeca-6E,8Z-dienoic acid
Synonyms
LM ID
LMFA02000397
Formula
C18H32O4
Exact Mass
Calculate m/z
312.23006
Sum Composition
FA 18:2;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]
Hydroxy fatty acids [FA0105]
Unsaturated fatty acids [FA0103]

Reactions

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ⓘ Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
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Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Human neutrophils convert the sebum-derived polyunsaturated fatty acid Sebaleic acid to a potent granulocyte chemoattractant.,
J Biol Chem, 2008
Pubmed ID: 18287092

String Representations

InChiKey (Click to copy)
RPFAXJQGBOULPA-CQLUAUNVSA-N
InChi (Click to copy)
InChI=1S/C18H32O4/c19-16-11-9-7-5-3-1-2-4-6-8-10-13-17(20)14-12-15-18(21)22/h6,8,10,13,17,19-20H,1-5,7,9,11-12,14-16H2,(H,21,22)/b8-6-,13-10+/t17-/m1/s1
SMILES (Click to copy)
C(CCC[C@H](O)/C=C/C=C\CCCCCCCCCO)(=O)O

Other Databases

PubChem CID
71316263

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 0
Aromatic Rings 0
Rotatable Bonds 15
Van der Waals Molecular Volume 347.20
Topological Polar Surface Area 77.76
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 4
logP 4.40
Molar Refractivity 90.80

Admin

Created at
11th Jan 2023
Updated at
27th Apr 2023