Structure Database (LMSD)

O HO O O OH P OH HO O HO O NH O HO
Common Name
Lipid X
Systematic Name
2,3-bis-(3R-hydroxy-tetradecanoyl)-αD-glucosamine-1-phosphate
Synonyms
LM ID
LMSL01020001
Formula
C34H66NO12P
Exact Mass
Calculate m/z
711.432267
Status
Active
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Main

Classification

Category
Main Class
Sub Class
Saccharolipids [SL]
Acylaminosugars [SL01]
Diacylaminosugars [SL0102]

String Representations

InChiKey (Click to copy)
HEHQDWUWJVPREQ-XQJZMFRCSA-N
InChi (Click to copy)
InChI=1S/C34H66NO12P/c1-3-5-7-9-11-13-15-17-19-21-26(37)23-29(39)35-31-33(32(41)28(25-36)45-34(31)47-48(42,43)44)46-30(40)24-27(38)22-20-18-16-14-12-10-8-6-4-2/h26-28,31-34,36-38,41H,3-25H2,1-2H3,(H,35,39)(H2,42,43,44)/t26-,27-,28-,31-,32-,33-,34-/m1/s1
SMILES (Click to copy)
O(P(=O)(O)O)[C@@H]1[C@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@H](O)[C@@H](CO)O1

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Escherichia coli (#562)
Gammaproteobacteria (#1236)
Fatty acyl derivatives of glucosamine 1-phosphate in Escherichia coli and their relation to lipid A. Complete structure of A diacyl GlcN-1-P found in a phosphatidylglycerol-deficient mutant.,
J Biol Chem, 1983
Pubmed ID: 6345522

Other Databases

CHEBI ID
16942
PubChem CID
123907
PDB ID
LP5

Calculated Physicochemical Properties

Heavy Atoms 48
Rings 1
Aromatic Rings 0
Rotatable Bonds 30
Van der Waals Molecular Volume 715.43
Topological Polar Surface Area 214.38
Hydrogen Bond Donors 7
Hydrogen Bond Acceptors 13
logP 7.54
Molar Refractivity 185.43

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Created at
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Updated at
20th Oct 2021