Structure Database (LMSD)

Common Name
(+)-Cerulenin
Systematic Name
2R,3S-Epoxy-4-oxo-7E,10E-dodecadienamide
Synonyms
  • 2S,3R-epoxy-4-0x0-7,10- 67 trans,trans-dodecadienoic acid
LM ID
LMFA08010032
Formula
C12H17NO3
Exact Mass
Calculate m/z
223.120844
Sum Composition
NA 12:4;O2
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty amides [FA08]
Primary amides [FA0801]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Oxo fatty acids [FA0106]
Epoxy fatty acids [FA0107]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Cephalosporium caerulens (#150420)
Sordariomycetes (#147550)
Stereoselective syntheses of (+)- and (−)-tetrahydrocerulenin from D-glucose The correct absolute configuration of natural cerulenin,
Tetrahedron Letts, 1978

String Representations

InChiKey (Click to copy)
GVEZIHKRYBHEFX-NQQPLRFYSA-N
InChi (Click to copy)
InChI=1S/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/b3-2+,6-5+/t10-,11-/m1/s1
SMILES (Click to copy)
C([C@]1([H])O[C@]1([H])C(=O)CC/C=C/C/C=C/C)(=O)N

Other Databases

Wikipedia
Cerulenin
KEGG ID
C12058
CHEBI ID
171741
PubChem CID
5282054
PDB ID
1X9

Calculated Physicochemical Properties

Heavy Atoms 16
Rings 1
Aromatic Rings
Rotatable Bonds 7
Van der Waals Molecular Volume 230.61
Topological Polar Surface Area 72.69
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 4
logP 1.68
Molar Refractivity 61.69

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Created at
8th Jan 2026
Updated at
8th Jan 2026