Structure Database (LMSD)

HO O HO O O O O O O O OH HO O P OH O OH P O HO O O NH O O HO O NH O
Common Name
Neisseria meningitidis lipid A
Systematic Name
Synonyms
LM ID
LMSL01060002
Formula
C88H166N2O25P2
Exact Mass
Calculate m/z
1713.125499
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Saccharolipids [SL]
Acylaminosugars [SL01]
Hexaacylaminosugars [SL0106]

String Representations

InChiKey (Click to copy)
SWRJHGCTVNUMIJ-JBCGXEBKSA-N
InChi (Click to copy)
InChI=1S/C88H166N2O25P2/c1-7-13-19-25-31-35-41-47-53-59-71(108-77(96)61-55-49-43-37-33-27-21-15-9-3)65-75(94)89-81-85(112-79(98)63-69(92)57-51-45-39-29-23-17-11-5)83(100)74(111-88(81)115-117(104,105)106)68-107-87-82(86(84(73(67-91)110-87)114-116(101,102)103)113-80(99)64-70(93)58-52-46-40-30-24-18-12-6)90-76(95)66-72(60-54-48-42-36-32-26-20-14-8-2)109-78(97)62-56-50-44-38-34-28-22-16-10-4/h69-74,81-88,91-93,100H,7-68H2,1-6H3,(H,89,94)(H,90,95)(H2,101,102,103)(H2,104,105,106)/t69-,70-,71-,72-,73-,74-,81-,82-,83-,84-,85-,86-,87-,88-/m1/s1
SMILES (Click to copy)
O(P(O)(=O)O)[C@@H]1[C@H](NC(=O)C[C@H](OC(=O)CCCCCCCCCCC)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(=O)CCCCCCCCCCC)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCCCC)[C@H](OP(O)(O)=O)[C@@H](CO)O2)O1

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Neisseria meningitidis (#487)
Betaproteobacteria (#28216)
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
24774162

Calculated Physicochemical Properties

Heavy Atoms 117
Rings 2
Aromatic Rings 0
Rotatable Bonds 82
Van der Waals Molecular Volume 1771.81
Topological Polar Surface Area 409.67
Hydrogen Bond Donors 10
Hydrogen Bond Acceptors 27
logP 23.52
Molar Refractivity 460.47

Admin

Created at
8th Jun 2020
Updated at
8th Jun 2020