Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMFA08020242
Common Nameα-N-(3-hydroxyhexadecanoyl) L-ornithine
Systematic Name(2S)-5-amino-2-(3-hydroxyhexadecanoyl) pentanoic acid
Synonymslyso-ornithine lipid; LOL
Exact Mass
386.3145 (neutral)    Calculate m/z:
FormulaC21H42N2O4
CategoryFatty Acyls [FA]
Main ClassFatty amides [FA08]
Sub ClassN-acyl amines [FA0802]
PubChem CID-
InChIKeyUUMBWNXCQGDFKZ-GGYWPGCISA-N  Show lipids differing only in stereochemistry/bond geometry
InChIInChI=1S/C21H42N2O4/c1-2-3-4-5-6-7-8-9-10-11-12-14-18(24)17-20(25)23-19(21(26)27
)15-13-16-22/h18-19,24H,2-17,22H2,1H3,(H,23,25)(H,26,27)/t18?,19-/m0/s1
SMILESOC(=O)[C@@H](NC(=O)CC(O)CCCCCCCCCCCCC)CCCN
StatusActive
ReferencesOrnithine lipids and their structural modifications: from A to E and beyond. Miguel A. Vences-Guzman, Otto Geiger and Christian Sohlenkamp. Federation of European Microbiological Society (FEMS) Microbiol Letters. Volume 335, 2012, pp. 1–10. DOI: 10.1111/j.1574-6968.2012.02623.x

https://onlinelibrary.wiley.com/doi/pdf/10.1111/j.1574-6968.2012.02623.x
Calculated physicochemical properties (?):
 Heavy Atoms27Rings0Aromatic Rings0Rotatable Bonds19
 van der Waals
Molecular Volume
423.74Topological Polar
Surface Area
112.65Hydrogen
Bond Donors
4Hydrogen
Bond Acceptors
6
 logP4.60Molar
Refractivity
111.07