Structure Database (LMSD)

Common Name
Bourgeanic acid
Systematic Name
3S-hydroxy-2S,4R,6R-trimethyloctanoyloxy 3S-hydroxy-2S,4R,6R-trimethyloctanoic acid
Synonyms
LM ID
LMFA07090176
Formula
C22H42O5
Exact Mass
Calculate m/z
386.303225
Sum Composition
FAHFA 22:1;O2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty esters [FA07]
Fatty acid estolides [FA0709]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Ramalina bourgaeana (#643221)
Lecanoromycetes (#147547)
Absolute configuration of bourgeanic acid: X-ray crystal structure of a 4-bromophenacyl derivative of hemibourgeanic acid.,
Tetrahedron Letts, 1986

String Representations

InChiKey (Click to copy)
ZQEUMOKDJCSNHB-IHRHECOVSA-N
InChi (Click to copy)
InChI=1S/C22H42O5/c1-9-13(3)11-15(5)19(23)17(7)22(26)27-20(18(8)21(24)25)16(6)12-14(4)10-2/h13-20,23H,9-12H2,1-8H3,(H,24,25)/t13-,14-,15-,16-,17+,18+,19+,20+/m1/s1
SMILES (Click to copy)
C([C@@H](C)[C@@H](OC(=O)[C@@H](C)[C@@H](O)[C@H](C)C[C@H](C)CC)[C@H](C)C[C@H](C)CC)(=O)O

Other Databases

CHEBI ID
144204
PubChem CID
10905154

Calculated Physicochemical Properties

Heavy Atoms 27
Rings
Aromatic Rings
Rotatable Bonds 14
Van der Waals Molecular Volume 427.83
Topological Polar Surface Area 83.83
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 5
logP 5.33
Molar Refractivity 109.35

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Created at
1st May 2024
Updated at
1st May 2024