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CHEBI:87242 - palmitoyllipid A

ChEBI IDCHEBI:87242
ChEBI Namepalmitoyllipid A
Stars
DefinitionA member of the class of lipid As that is lipid A in which the free OH group on the N-hydroxytetradecanoyl group is carrying a palimitoyl group.
Last Modified20 January 2017
SubmitterSteve
DownloadsMolfile
FormulaC110H208N2O26P2
Net Charge0
Average Mass2036.810
Monoisotopic Mass2035.44906
SMILESCCCCCCCCCCCCCCCC(=O)O[C@H](CCCCCCCCCCC)CC(=O)N[C@H]1[C@@H](OP(=O)(O)O)O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](OP(=O)(O)O)[C@H](OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@H]2NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@@H](O)[C@@H]1OC(=O)C[C@H](O)CCCCCCCCCCC
InChIInChI=1S/C110H208N2O26P2/c1-8-15-22-29-36-43-45-46-48-55-62-68-75-82-98(117)130-91(78-71-64-57-50-39-32-25-18-11-4)85-96(115)111-103-107(135-101(120)84-90(114)77-70-63-56-49-38-31-24-17-10-3)105(122)95(134-110(103)138-140(126,127)128)89-129-109-104(112-97(116)86-92(79-72-65-58-51-40-33-26-19-12-5)131-99(118)81-74-67-60-53-42-35-28-21-14-7)108(106(94(88-113)133-109)137-139(123,124)125)136-102(121)87-93(80-73-66-59-52-41-34-27-20-13-6)132-100(119)83-76-69-61-54-47-44-37-30-23-16-9-2/h90-95,103-110,113-114,122H,8-89H2,1-7H3,(H,111,115)(H,112,116)(H2,123,124,125)(H2,126,127,128)/t90-,91-,92-,93-,94-,95-,103-,104-,105-,106-,107-,108-,109-,110-/m1/s1
InChIKeyVOXDTCSXQHOYKC-XGEOUJBZSA-N
Species of MetaboliteComponentSourceComments
Salmonella enterica (ncbitaxon:28901) - PubMed (12537693)
Salmonella typhimurium (ncbitaxon:90371) - PubMed (11013210)
Roles Classification
Biological Role:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
ChEBI Ontology
Outgoing Relation(s)
palmitoyllipid A (CHEBI:87242) has role bacterial metabolite (CHEBI:76969)
palmitoyllipid A (CHEBI:87242) is a dodecanoate ester (CHEBI:87659)
palmitoyllipid A (CHEBI:87242) is a hexadecanoate ester (CHEBI:25835)
palmitoyllipid A (CHEBI:87242) is a lipid As (CHEBI:25051)
palmitoyllipid A (CHEBI:87242) is a tetradecanoate ester (CHEBI:87691)
palmitoyllipid A (CHEBI:87242) is conjugate acid of palmitoyllipid A(4−) (CHEBI:87048)
Incoming Relation(s)
palmitoyllipid A(4−) (CHEBI:87048) is conjugate base of palmitoyllipid A (CHEBI:87242)
IUPAC Name 
2-deoxy-6-O-(2-deoxy-2-{[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino}-4-O-phosphono-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosyl)-2-{[(3R)-3-(hexadecanoyloxy)tetradecanoyl]amino}-3-O-[(3R)-3-hydroxytetradecanoyl]-1-O-phosphono-α-D-glucopyranose
Synonyms  Source
hexadecanoyllipid AChEBI
heptaacyl lipid AChEBI
hepta-acyl lipid AChEBI
Manual XrefsDatabases
HEPTA-ACYLATED-LIPID-AMetaCyc
Registry NumbersSources
Reaxys:9382574Reaxys
Citations