Structure Database (LMSD)

HO HO OH OH OH OH O O OH OH HO
Common Name
Bastimolide A
Systematic Name
9S,11R,15S,19R,21R,23R,27S,31R,35R-nonahydroxy-3,40,40-trimethyl-2Z-hentetraconten-39S-olide
Synonyms
LM ID
LMFA07040112
Formula
C44H84O11
Exact Mass
Calculate m/z
788.601365
Sum Composition
FA 44:2;O9
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty esters [FA07]
Lactones [FA0704]

String Representations

InChiKey (Click to copy)
GMYBARKHHWBGAC-UEJQJJBFSA-N
InChi (Click to copy)
InChI=1S/C44H84O11/c1-32-14-6-5-7-15-37(49)29-38(50)24-10-20-35(47)22-12-26-40(52)31-41(53)30-39(51)25-11-21-34(46)18-8-16-33(45)17-9-19-36(48)23-13-27-42(44(2,3)4)55-43(54)28-32/h28,33-42,45-53H,5-27,29-31H2,1-4H3/b32-28-/t33-,34+,35+,36-,37+,38-,39-,40-,41-,42+/m1/s1
SMILES (Click to copy)
C1(C)=CC(=O)O[C@H](C(C)(C)C)CCC[C@H](O)CCC[C@H](O)CCC[C@H](O)CCC[C@@H](O)C[C@@H](O)C[C@H](O)CCC[C@@H](O)CCC[C@@H](O)C[C@@H](O)CCCCC1

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Okeania hirsuta (#1458930)
Bastimolide A, a Potent Antimalarial Polyhydroxy Macrolide from the Marine Cyanobacterium Okeania hirsuta.,
J Org Chem, 2015
Pubmed ID: 26222145

Other Databases

PubChem CID
145952701

Calculated Physicochemical Properties

Heavy Atoms 55
Rings 1
Aromatic Rings 0
Rotatable Bonds 1
Van der Waals Molecular Volume 848.81
Topological Polar Surface Area 210.44
Hydrogen Bond Donors 9
Hydrogen Bond Acceptors 11
logP 9.16
Molar Refractivity 222.32

Admin

Created at
27th May 2020
Updated at
27th May 2020