Structure Database (LMSD)

Common Name
Agardhilactone
Systematic Name
6S-{(1R,2R,3S,5S)-2-[8S-Hydroxy-1E,4Z,6E-decatrien-1-yl]-6-oxabicyclo[3.1.0]hex-3-yl}tetrahydro-2H-pyran-2-one
Synonyms
LM ID
LMFA07040131
Formula
C20H28O4
Exact Mass
Calculate m/z
332.19876
Sum Composition
FA 20:6;O2
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty esters [FA07]
Lactones [FA0704]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Agardhiella subulata (#31443)
Florideophyceae (#2806)
Synthesis and structural revision of marine eicosanoid agardhilactone,
Tetrahedron Letts, 2005

String Representations

InChiKey (Click to copy)
YFHYWHWBWQBXAP-OLMCNAGDSA-N
InChi (Click to copy)
InChI=1S/C20H28O4/c1-2-14(21)9-6-4-3-5-7-10-15-16(13-18-20(15)24-18)17-11-8-12-19(22)23-17/h3-4,6-7,9-10,14-18,20-21H,2,5,8,11-13H2,1H3/b4-3-,9-6+,10-7+/t14-,15+,16-,17-,18+,20-/m0/s1
SMILES (Click to copy)
C1(=O)O[C@H]([C@H]2C[C@H]3O[C@H]3[C@@H]2/C=C/C/C=C\C=C\[C@@H](O)CC)CCC1

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 3
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 342.08
Topological Polar Surface Area 61.13
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 4
logP 4.46
Molar Refractivity 94.37

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Created at
7th Sep 2020
Updated at
7th Sep 2020