CHEBI:16942 - lipid X

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ChEBI Name lipid X
ChEBI ID CHEBI:16942
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:870, CHEBI:19303, CHEBI:11413
Supplier Information
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Formula C34H66NO12P
Net Charge 0
Average Mass 711.86114
Monoisotopic Mass 711.432
InChI 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
InChIKey HEHQDWUWJVPREQ-XQJZMFRCSA-N
SMILES CCCCCCCCCCC[C@@H](O)CC(=O)N[C@H]1[C@H](O[C@H](CO)[C@@H](O)[C@@H]1OC(=O)C[C@H](O)CCCCCCCCCCC)OP(O)(O)=O
Metabolite of Species Details
Escherichia coli (NCBI:txid562) See: PubMed
Roles Classification
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
2,3-Bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate KEGG COMPOUND
2,3-Bis[(3R)-3-hydroxymyristoyl]-alpha-D-glucosaminyl 1-phosphate KEGG COMPOUND
Lipid X KEGG COMPOUND
Manual Xrefs Databases
C04824 KEGG COMPOUND
LMSL01020001 LIPID MAPS
LP5 PDBeChem
View more database links
Registry Numbers Types Sources
4629355 Beilstein Registry Number Beilstein
86559-73-1 CAS Registry Number ChemIDplus
Last Modified
25 January 2016