Structure Database (LMSD)

OH O O HO HO O P OH O OH P HO O O O O HO O O NH O O HO NH O O O O
Common Name
Rhodobacter sphaeroides Lipid A
Systematic Name
Synonyms
LM ID
LMSL01050004
Formula
C76H140N2O24P2
Exact Mass
Calculate m/z
1526.927134
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Saccharolipids [SL]
Acylaminosugars [SL01]
Pentaacylaminosugars [SL0105]

String Representations

InChiKey (Click to copy)
CCKKFUQFWHEHKD-DTSHGSGKSA-N
InChi (Click to copy)
InChI=1S/C76H140N2O24P2/c1-6-11-16-21-25-28-29-32-36-41-46-51-66(85)96-61(50-45-40-35-31-27-23-18-13-8-3)55-65(84)78-70-74(100-68(87)54-60(82)48-42-37-20-15-10-5)72(101-103(89,90)91)62(56-79)97-75(70)95-57-63-71(88)73(99-67(86)53-59(81)49-44-38-33-24-19-14-9-4)69(76(98-63)102-104(92,93)94)77-64(83)52-58(80)47-43-39-34-30-26-22-17-12-7-2/h28-29,59-63,69-76,79,81-82,88H,6-27,30-57H2,1-5H3,(H,77,83)(H,78,84)(H2,89,90,91)(H2,92,93,94)/b29-28-/t59-,60-,61-,62-,63-,69-,70-,71-,72-,73-,74-,75-,76-/m1/s1
SMILES (Click to copy)
O(P(O)(=O)O)[C@@H]1[C@H](NC(=O)CC(=O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCCCC)[C@H](O)[C@@H](CO[C@H]2[C@H](NC(=O)C[C@H](OC(CCCCC/C=C\CCCCCC)=O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCC)[C@H](OP(O)(O)=O)[C@@H](CO)O2)O1

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Cereibacter sphaeroides (#1063)
Alphaproteobacteria (#28211)
The Role of Carbohydrates in the Lipopolysaccharide (LPS)/Toll-Like Receptor 4 (TLR4) Signalling.,
Int J Mol Sci, 2017
Pubmed ID: 29099761

Other Databases

PubChem CID
171121060

Calculated Physicochemical Properties

Heavy Atoms 104
Rings 2
Aromatic Rings 0
Rotatable Bonds 69
Van der Waals Molecular Volume 1552.78
Topological Polar Surface Area 400.44
Hydrogen Bond Donors 10
Hydrogen Bond Acceptors 26
logP 18.74
Molar Refractivity 403.15

Admin

Created at
29th Jun 2020
Updated at
29th Jun 2020