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CHEBI:62016 - glucosyl-(heptosyl)2-(KDO)2-lipid A

ChEBI IDCHEBI:62016
ChEBI Nameglucosyl-(heptosyl)2-(KDO)2-lipid A
Stars
DefinitionA lipid A derivative having an α-D-Glc-(1→3)-L-α-D-Hep-(1→3)-L-α-D-Hep-(1→5)-[α-Kdo-(2→4)]-α-Kdo moiety attached to the free primary hydroxy group of lipid A.
Last Modified28 September 2015
SubmitterSteve
DownloadsMolfile
FormulaC130H236N2O56P2
Net Charge0
Average Mass2785.224
Monoisotopic Mass2783.51560
SMILES[H][C@]1([C@H](O)CO)O[C@@](O[C@@H]2C[C@](OC[C@H]3O[C@@H](OC[C@H]4O[C@H](OP(=O)(O)O)[C@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H]4O)[C@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@H]3OP(=O)(O)O)(C(=O)O)O[C@]([H])([C@H](O)CO)[C@@H]2O[C@H]2O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O[C@H]3O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H]3O)[C@@H]2O)(C(=O)O)C[C@@H](O)[C@H]1O
InChIInChI=1S/C130H236N2O56P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-98(148)173-85(66-60-54-48-42-35-29-23-17-11-5)72-100(150)178-119-102(132-96(146)71-84(65-59-53-47-41-34-28-22-16-10-4)172-97(147)67-61-55-49-43-36-30-24-18-12-6)122(170-80-93-105(153)118(177-99(149)70-83(139)64-58-52-46-40-33-27-21-15-9-3)101(123(175-93)188-190(167,168)169)131-95(145)69-82(138)63-57-51-45-39-32-26-20-14-8-2)176-94(117(119)187-189(164,165)166)81-171-129(127(160)161)74-91(184-130(128(162)163)73-86(140)103(151)114(185-130)89(143)77-135)116(115(186-129)90(144)78-136)181-125-110(158)121(109(157)112(179-125)87(141)75-133)183-126-111(159)120(108(156)113(180-126)88(142)76-134)182-124-107(155)106(154)104(152)92(79-137)174-124/h82-94,101-126,133-144,151-159H,7-81H2,1-6H3,(H,131,145)(H,132,146)(H,160,161)(H,162,163)(H2,164,165,166)(H2,167,168,169)/t82-,83-,84-,85-,86-,87+,88+,89-,90-,91-,92-,93-,94-,101-,102-,103-,104-,105-,106+,107-,108-,109-,110+,111+,112-,113-,114-,115-,116-,117-,118-,119-,120+,121+,122-,123-,124-,125-,126-,129-,130-/m1/s1
InChIKeyUMRPQNDYTAXFNB-AVRUCYGASA-N
ChEBI Ontology
Outgoing Relation(s)
glucosyl-(heptosyl)2-(KDO)2-lipid A (CHEBI:62016) is a dodecanoate ester (CHEBI:87659)
glucosyl-(heptosyl)2-(KDO)2-lipid A (CHEBI:62016) is a lipid As (CHEBI:25051)
glucosyl-(heptosyl)2-(KDO)2-lipid A (CHEBI:62016) is a tetradecanoate ester (CHEBI:87691)
glucosyl-(heptosyl)2-(KDO)2-lipid A (CHEBI:62016) is conjugate acid of glucosyl-(heptosyl)2-(KDO)2-lipid A(6−) (CHEBI:61997)
Incoming Relation(s)
glucosyl-(heptosyl)2-(KDO)2-lipid A(6−) (CHEBI:61997) is conjugate base of glucosyl-(heptosyl)2-(KDO)2-lipid A (CHEBI:62016)
IUPAC Name 
3-deoxy-α-D-manno-oct-2-ulopyranonosyl-(2→4)-[α-D-glucopyranosyl-(1→3)-L-glycero-α-D-manno-heptopyranosyl-(1→3)-L-glycero-α-D-manno-heptopyranosyl-(1→5)]-3-deoxy-α-D-manno-oct-2-ulopyranonosyl-(2→6)-2-deoxy-2-{[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino}-4-O-phosphono-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranosyl-(1→6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-1-O-phosphono-α-D-glucopyranose
Synonym  Source
α-D-Glc-(1→3)-L-α-D-Hep-(1→3)-L-α-D-Hep-(1→5)-[α-Kdo-(2→4)]-α-Kdo-(2→6)-lipid AChEBI