Structure Database (LMSD)

Common Name
Macrolactin O
Systematic Name
7R-β-D-glucopyranosyl-15-oxo-13R-hydroxy-2Z,4E,8E,10Z,16E,18E,23S-tetracosahexenyl-23-olide
Synonyms
LM ID
LMFA07040104
Formula
C30H42O10
Exact Mass
Calculate m/z
562.2778
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)
DNHDESCWXZDXMN-GXNIMRGBSA-N
InChi (Click to copy)
InChI=1S/C30H42O10/c1-21-13-7-3-2-4-8-14-22(32)19-23(33)15-9-5-10-16-24(17-11-6-12-18-26(34)38-21)39-30-29(37)28(36)27(35)25(20-31)40-30/h2,4-6,8-12,14,16,18,21,23-25,27-31,33,35-37H,3,7,13,15,17,19-20H2,1H3/b4-2+,9-5-,11-6+,14-8+,16-10+,18-12-/t21-,23+,24-,25-,27-,28+,29-,30-/m1/s1
SMILES (Click to copy)
C[C@@H]1CCC/C=C/C=C/C(=O)C[C@H](C/C=C\C=C\[C@H](C/C=C/C=C\C(=O)O1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Bacillus (#1386)
Bacilli (#91061)
Macrolactins O-R, glycosylated 24-membered lactones from Bacillus sp. AH159-1.,
J Nat Prod, 2007
Pubmed ID: 17887720

Other Databases

PubChem CID
171120481

Calculated Physicochemical Properties

Heavy Atoms 40
Rings 2
Aromatic Rings 0
Rotatable Bonds 3
Van der Waals Molecular Volume 569.62
Topological Polar Surface Area 167.12
Hydrogen Bond Donors 5
Hydrogen Bond Acceptors 10
logP 4.30
Molar Refractivity 152.34

Admin

Created at
11th May 2020
Updated at
2nd Feb 2021