CHEBI:27422 - (KDO)2-(lauroyl)-lipid IVA

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name (KDO)2-(lauroyl)-lipid IVA
ChEBI ID CHEBI:27422
ChEBI ASCII Name (KDO)2-(lauroyl)-lipid IVA
Definition A lipid A comprising lipid IVA glycosylated with two 3-deoxy-D-manno-octulosonic acid (KDO) residues and carrying an additional dodecanoyl group.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:6393, CHEBI:25015, CHEBI:61554
Supplier Information
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Formula C96H176N2O38P2
Net Charge 0
Average Mass 2028.36280
Monoisotopic Mass 2027.138
InChI InChI=1S/C96H176N2O38P2/c1-6-11-16-21-26-31-36-41-46-51-66(101)56-76(107)97-81-89(130-79(110)57-67(102)52-47-42-37-32-27-22-17-12-7-2)85(114)74(128-92(81)136-138(122,123)124)64-125-91-82(98-77(108)59-69(54-49-44-39-34-29-24-19-14-9-4)127-78(109)55-50-45-40-35-30-25-20-15-10-5)90(131-80(111)58-68(103)53-48-43-38-33-28-23-18-13-8-3)88(135-137(119,120)121)75(129-91)65-126-95(93(115)116)61-73(84(113)87(133-95)72(106)63-100)132-96(94(117)118)60-70(104)83(112)86(134-96)71(105)62-99/h66-75,81-92,99-106,112-114H,6-65H2,1-5H3,(H,97,107)(H,98,108)(H,115,116)(H,117,118)(H2,119,120,121)(H2,122,123,124)/t66-,67-,68-,69-,70-,71-,72-,73-,74-,75-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,95-,96-/m1/s1
InChIKey JVUUYJGQIVCMIU-ZODGSCPMSA-N
SMILES [H][C@@]1(O[C@@](C[C@@H](O)[C@H]1O)(O[C@@H]1C[C@@](OC[C@H]2O[C@@H](OC[C@H]3O[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]3O)[C@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H]2OP(O)(O)=O)(O[C@]([H])([C@H](O)CO)[C@@H]1O)C(O)=O)C(O)=O)[C@H](O)CO
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 (KDO)2-(lauroyl)-lipid IVA (CHEBI:27422) has role Escherichia coli metabolite (CHEBI:76971)
(KDO)2-(lauroyl)-lipid IVA (CHEBI:27422) is a lipid As (CHEBI:25051)
(KDO)2-(lauroyl)-lipid IVA (CHEBI:27422) is conjugate acid of (KDO)2-(lauroyl)-lipid IVA(6−) (CHEBI:61524)
Incoming (KDO)2-(lauroyl)-lipid IVA(6−) (CHEBI:61524) is conjugate base of (KDO)2-(lauroyl)-lipid IVA (CHEBI:27422)
IUPAC Name
3-deoxy-α-D-manno-oct-2-ulopyranonosyl-(2→4)-3-deoxy-α-D-manno-oct-2-ulopyranonosyl-(2→6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[(3R)-3-(dodecanoyloxy)tetradecanamido]-4-O-phosphono-β-D-glucopyranosyl-(1→6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[(3R)-3-hydroxytetradecanamido]-1-O-phosphono-α-D-glucopyranose
Synonym Source
Lauroyl-KDO2-lipid IV(A) KEGG COMPOUND
Manual Xrefs Databases
C06251 KEGG COMPOUND
LMSL02000002 LIPID MAPS
View more database links
Last Modified
25 January 2016