Structure Database (LMSD)

O OH O O
Common Name
FAHFA 20:0/11O(FA 18:3(9Z,12Z,15Z)[R])
Systematic Name
11R-(eicosanoyloxy)octadeca-9Z,12Z,15Z-trienoic acid
Synonyms
  • Mayolene-20
  • 11-eicosanoyl-11R-hydroxyoctadeca-9Z,12Z,15Z-trienoic acid
LM ID
LMFA07090153
Formula
C38H68O4
Exact Mass
Calculate m/z
588.51176
Sum Composition
FAHFA 38:3;O
Abbrev Chains
FAHFA 20:0/18:3;O
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty esters [FA07]
Fatty acid estolides [FA0709]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]

String Representations

InChiKey (Click to copy)
TWSDQPAKNQMSSC-QXDCLJFISA-N
InChi (Click to copy)
InChI=1S/C38H68O4/c1-3-5-7-9-10-11-12-13-14-15-16-17-18-19-23-27-31-35-38(41)42-36(32-28-24-8-6-4-2)33-29-25-21-20-22-26-30-34-37(39)40/h6,8,28-29,32-33,36H,3-5,7,9-27,30-31,34-35H2,1-2H3,(H,39,40)/b8-6-,32-28-,33-29-/t36-/m0/s1
SMILES (Click to copy)
C(CCCCCCC/C=C\[C@@H](OC(CCCCCCCCCCCCCCCCCCC)=O)/C=C\C/C=C\CC)(=O)O

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Pieris rapae (#64459)
Insecta (#50557)
Mayolenes: labile defensive lipids from the glandular hairs of a caterpillar (Pieris rapae).,
Proc Natl Acad Sci U S A, 2002
Pubmed ID: 11997469

Other Databases

CHEBI ID
186572
PubChem CID
73242180

Calculated Physicochemical Properties

Heavy Atoms 42
Rings 0
Aromatic Rings 0
Rotatable Bonds 33
Van der Waals Molecular Volume 687.92
Topological Polar Surface Area 63.60
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 4
logP 12.51
Molar Refractivity 181.45

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Created at
-
Updated at
14th Jun 2023