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Structure Database (LMSD)

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Common Name

20-acetoxy-clavulone III

Systematic Name

methyl 4R,12S,20-triacetoxy-9-oxo-5E,7Z,10Z,13Z-prostatetraenoate-cyclo[8,12]

Synonyms

LM ID

LMFA03120007

Formula

C₂₇H₃₆O₉

Exact Mass

Calculate m/z

504.235935

Sum Composition

FA 27:9;O7

Status

Active

Show lipids differing only in stereochemistry/bond geometry

Main

Classification

String Representations

InChiKey (Click to copy)

LHIPZWGSDUHLAW-KAJQFPCGSA-N

InChi (Click to copy)

InChI=1S/C27H36O9/c1-20(28)34-19-10-8-6-5-7-9-17-27(36-22(3)30)18-16-25(31)24(27)13-11-12-23(35-21(2)29)14-15-26(32)33-4/h7,9,11-13,16,18,23H,5-6,8,10,14-15,17,19H2,1-4H3/b9-7-,12-11+,24-13+/t23-,27-/m0/s1

SMILES (Click to copy)

[C@]1(OC(=O)C)(C/C=C\CCCCCOC(=O)C)C=CC(=O)/C/1=C\C=C\[C@H](OC(C)=O)CCC(OC)=O

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Clavularia viridis (#153213)

Anthozoa (#6101)

Novel C-20-oxygenated prostanoids, 20-acetoxyclavulones, from the stolonifer clavularia viridis quoy and gaimard,
Tetrahedron Letts, 1983

DOI: 10.1016/S0040-4039(00)85917-1

Other Databases

LIPIDBANK ID

XPR8007

PubChem CID

5283221

Calculated Physicochemical Properties

Heavy Atoms 36

Rings 1

Aromatic Rings 0

Rotatable Bonds 19

Van der Waals Molecular Volume 518.65

Topological Polar Surface Area 122.27

Hydrogen Bond Donors 0

Hydrogen Bond Acceptors 9

logP 4.72

Molar Refractivity 133.04

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Created at

Updated at

31st Jan 2024