Structure Database (LMSD)

Common Name
Bordetella pertussis lipid A
Systematic Name
Synonyms
LM ID
LMSL01050001
Formula
C78H148N2O24P2
Exact Mass
Calculate m/z
1558.989734
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

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

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Bordetella parapertussis (#519)
Betaproteobacteria (#28216)
Structural characterization of Bordetella parapertussis lipid A.,
J Lipid Res, 2009
Pubmed ID: 19017615

String Representations

InChiKey (Click to copy)
DHSXJMRVJPCQHY-NTBWWRQUSA-N
InChi (Click to copy)
InChI=1S/C78H148N2O24P2/c1-6-11-16-21-25-29-30-34-38-43-48-53-68(87)98-63(52-47-42-37-33-28-24-19-14-9-4)57-67(86)80-72-76(102-70(89)56-62(84)51-46-41-36-32-27-23-18-13-8-3)74(103-105(91,92)93)64(58-81)99-77(72)97-59-65-73(90)75(101-69(88)55-61(83)50-44-39-20-15-10-5)71(78(100-65)104-106(94,95)96)79-66(85)54-60(82)49-45-40-35-31-26-22-17-12-7-2/h60-65,71-78,81-84,90H,6-59H2,1-5H3,(H,79,85)(H,80,86)(H2,91,92,93)(H2,94,95,96)/t60?,61?,62?,63?,64-,65-,71-,72-,73-,74-,75-,76-,77-,78-/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)CC(O)CCCCCCC)[C@H](O)[C@@H](CO[C@H]2[C@H](NC(=O)CC(OC(=O)CCCCCCCCCCCCC)CCCCCCCCCCC)[C@@H](OC(=O)CC(O)CCCCCCCCCCC)[C@H](OP(=O)(O)O)[C@@H](CO)O2)O1

Other Databases

PubChem CID
42608337

Calculated Physicochemical Properties

Heavy Atoms 106
Rings 2
Aromatic Rings 0
Rotatable Bonds 72
Van der Waals Molecular Volume 1592.66
Topological Polar Surface Area 403.60
Hydrogen Bond Donors 11
Hydrogen Bond Acceptors 26
logP 19.83
Molar Refractivity 413.99

Admin

Created at
-
Updated at
18th Nov 2021