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CHEBI:16942 - lipid X

ChEBI IDCHEBI:16942
ChEBI Namelipid X
Stars
DefinitionAn N-acyl-D-glucosamine 1-phosphate where the N-acyl group is (R)-3-hydroxytetradecanoyl and carrying an additional (R)-3-hydroxytetradecanoyl group at the 3-position.
Secondary ChEBI IDsCHEBI:870, CHEBI:11413, CHEBI:19303
Last Modified25 January 2016
DownloadsMolfile
FormulaC34H66NO12P
Net Charge0
Average Mass711.871
Monoisotopic Mass711.43226
SMILESCCCCCCCCCCC[C@@H](O)CC(=O)N[C@H]1[C@@H](OP(=O)(O)O)O[C@H](CO)[C@@H](O)[C@@H]1OC(=O)C[C@H](O)CCCCCCCCCCC
InChIInChI=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
InChIKeyHEHQDWUWJVPREQ-XQJZMFRCSA-N
Species of MetaboliteComponentSourceComments
Escherichia coli (ncbitaxon:562) - PubMed (21988831)
Roles Classification
Biological Role:
Escherichia coli metabolite  Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
ChEBI Ontology
Outgoing Relation(s)
lipid X (CHEBI:16942) has role Escherichia coli metabolite (CHEBI:76971)
lipid X (CHEBI:16942) is a N-acyl-D-glucosamine 1-phosphate (CHEBI:21635)
lipid X (CHEBI:16942) is conjugate acid of lipid X(2−) (CHEBI:57957)
Incoming Relation(s)
lipid X(2−) (CHEBI:57957) is conjugate base of lipid X (CHEBI:16942)
IUPAC Name 
2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-1-O-phosphono-α-D-glucopyranose
Synonyms  Source
Lipid XKEGG COMPOUND
2,3-Bis[(3R)-3-hydroxymyristoyl]-alpha-D-glucosaminyl 1-phosphateKEGG COMPOUND
2,3-Bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphateKEGG COMPOUND
Manual XrefsDatabases
C04824KEGG COMPOUND
LMSL01020001LIPID MAPS
LP5PDBeChem
Registry NumbersSources
Beilstein:4629355Beilstein
CAS:86559-73-1ChemIDplus