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CHEBI:87048 - palmitoyllipid A(4−)

ChEBI IDCHEBI:87048
ChEBI Namepalmitoyllipid A(4−)
Stars
ASCII Namepalmitoyllipid A(4-)
DefinitionA lipid A oxoanion arising from deprotonation of the phosphate OH groups of palmitoyllipid A; major species at pH 7.3.
Last Modified22 August 2024
SubmitterKristian Axelsen
DownloadsMolfile
FormulaC110H204N2O26P2
Net Charge-4
Average Mass2032.778
Monoisotopic Mass2031.41995
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)/p-4/t90-,91-,92-,93-,94-,95-,103-,104-,105-,106-,107-,108-,109-,110-/m1/s1
InChIKeyVOXDTCSXQHOYKC-XGEOUJBZSA-J
ChEBI Ontology
Outgoing Relation(s)
palmitoyllipid A(4−) (CHEBI:87048) is a an acyl-lipid A(4−) (CHEBI:193142)
palmitoyllipid A(4−) (CHEBI:87048) is a lipid A oxoanion (CHEBI:60086)
palmitoyllipid A(4−) (CHEBI:87048) is conjugate base of palmitoyllipid A (CHEBI:87242)
Incoming Relation(s)
palmitoyllipid A (CHEBI:87242) is conjugate acid of palmitoyllipid A(4−) (CHEBI:87048)
IUPAC Name 
2-deoxy-6-O-(2-deoxy-2-{[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino}-4-O-phosphonato-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosyl)-2-{[(3R)-3-(hexadecanoyloxy)tetradecanoyl]amino}-3-O-[(3R)-3-hydroxytetradecanoyl]-1-O-phosphonato-α-D-glucopyranose
Synonym  Source
hexadecanoyllipid A(4−)ChEBI
UniProt Name  Source
hepta-acyl lipid A (E. coli)UniProt
Manual XrefsDatabases
HEPTA-ACYLATED-LIPID-AMetaCyc
Citations