CHEBI:27692 - lipid II

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name lipid II
ChEBI ID CHEBI:27692
Definition An undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl peptide in which the peptide element is L-alanyl-D-γ-glutamyl-L-lysyl-D-alanyl-D-alanine.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Steve Jupe
Secondary ChEBI IDs CHEBI:13343, CHEBI:63162, CHEBI:27203, CHEBI:9873
Supplier Information
Download Molfile XML SDF
Formula C94H156N8O26P2
Net Charge 0
Average Mass 1876.23000
Monoisotopic Mass 1875.06060
InChI InChI=1S/C94H156N8O26P2/c1-59(2)31-21-32-60(3)33-22-34-61(4)35-23-36-62(5)37-24-38-63(6)39-25-40-64(7)41-26-42-65(8)43-27-44-66(9)45-28-46-67(10)47-29-48-68(11)49-30-50-69(12)54-56-122-129(118,119)128-130(120,121)127-94-82(100-75(18)106)86(85(79(58-104)125-94)126-93-81(99-74(17)105)84(109)83(108)78(57-103)124-93)123-73(16)89(112)96-71(14)88(111)102-77(92(116)117)52-53-80(107)101-76(51-19-20-55-95)90(113)97-70(13)87(110)98-72(15)91(114)115/h31,33,35,37,39,41,43,45,47,49,54,70-73,76-79,81-86,93-94,103-104,108-109H,19-30,32,34,36,38,40,42,44,46,48,50-53,55-58,95H2,1-18H3,(H,96,112)(H,97,113)(H,98,110)(H,99,105)(H,100,106)(H,101,107)(H,102,111)(H,114,115)(H,116,117)(H,118,119)(H,120,121)/b60-33+,61-35+,62-37-,63-39-,64-41-,65-43-,66-45-,67-47-,68-49-,69-54-/t70-,71+,72-,73-,76+,77-,78-,79-,81-,82-,83-,84-,85-,86-,93+,94-/m1/s1
InChIKey ULXTYUPMJXVUHQ-OVTFQNCVSA-N
SMILES C[C@@H](NC(=O)[C@@H](C)NC(=O)[C@H](CCCCN)NC(=O)CC[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](C)O[C@@H]1[C@@H](NC(C)=O)[C@H](O[C@H](CO)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1NC(C)=O)OP(O)(=O)OP(O)(=O)OC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=O)C(O)=O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing lipid II (CHEBI:27692) has role mouse metabolite (CHEBI:75771)
lipid II (CHEBI:27692) is a undecaprenyldiphospho-N-acetylmuramoyl peptide (CHEBI:27194)
lipid II (CHEBI:27692) is conjugate acid of lipid II(3−) (CHEBI:60033)
Incoming lipid II(3−) (CHEBI:60033) is conjugate base of lipid II (CHEBI:27692)
IUPAC Name
N-[(2R)-2-{[(2R,3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}-2-({hydroxy[(hydroxy{[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxy}phosphoryl)oxy]phosphoryl}oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl]oxy}propanoyl]-L-alanyl-D-γ-glutamyl-L-lysyl-D-alanyl-D-alanine
Synonyms Sources
GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol KEGG COMPOUND
Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-gamma-D-glutamyl-L-lysyl-D-alanyl-D-alanine KEGG COMPOUND
undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-D-γ-glutamyl-L-lysyl-D-alanyl-D-alanine ChEBI
Manual Xrefs Databases
C05893 KEGG COMPOUND
G10553 KEGG GLYCAN
View more database links
Registry Number Type Source
9039417 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
11716719 PubMed citation SUBMITTER
16531990 PubMed citation SUBMITTER
Last Modified
09 October 2018
General Comment
2011-12-08 Undecaprenylpyrophosphate-MurNAc[pentapeptide]-GlcNAc or lipid II is a bacteria-specific membrane component that is essential in bacterial cell-wall synthesis. It is the target of many antibiotics, the first discovered example being Vancomycin, more recently it has been demonstrated that Lipid II is the target of several other classes of natural products, including the lantibiotics, the mannopeptimycins and ramoplanin.