Structure Database (LMSD)

Common Name
Zaragozic acid A
Systematic Name
1S-((4S-acetoxy-5R-methyl-3-methylene-6-phenylhexyl)-6-(E)-4S,6S-dimethyloct-2-enoyloxy)-4,7S-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3S,4S,5R-tricarboxylic acid
Synonyms
  • Squalestatin 1
LM ID
LMPK00000001
Formula
C35H46O14
Exact Mass
Calculate m/z
690.28876
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Polyketides [PK]
Other Polyketides [PK00]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Phoma sp. C2932 (#86977)
Dothideomycetes (#147541)
The squalestatins, novel inhibitors of squalene synthase produced by a species of Phoma. II. Structure elucidation.,
J Antibiot (Tokyo), 1992
Pubmed ID: 1624367

String Representations

InChiKey (Click to copy)
DFKDOZMCHOGOBR-NCSQYGPNSA-N
InChi (Click to copy)
InChI=1S/C35H46O14/c1-7-19(2)17-20(3)13-14-25(37)47-28-27(38)33(48-29(30(39)40)34(45,31(41)42)35(28,49-33)32(43)44)16-15-21(4)26(46-23(6)36)22(5)18-24-11-9-8-10-12-24/h8-14,19-20,22,26-29,38,45H,4,7,15-18H2,1-3,5-6H3,(H,39,40)(H,41,42)(H,43,44)/b14-13+/t19-,20+,22+,26+,27+,28+,29+,33-,34+,35-/m0/s1
SMILES (Click to copy)
O1[C@@]2(CCC(=C)[C@H]([C@H](C)CC3C=CC=CC=3)OC(C)=O)[C@@H]([C@H]([C@]1(C(=O)O)[C@](C(=O)O)([C@@H](C(=O)O)O2)O)OC(/C=C/[C@@H](C)C[C@@H](C)CC)=O)O

Other Databases

CHEBI ID
75170
PubChem CID
6438355
Cayman ID
17452
PDB ID
ZGA
GuidePharm ID
3057

Calculated Physicochemical Properties

Heavy Atoms 49
Rings 3
Aromatic Rings 1
Rotatable Bonds 19
Van der Waals Molecular Volume 662.74
Topological Polar Surface Area 227.56
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 14
logP 4.89
Molar Refractivity 174.36

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Updated at
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