Record Information |
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Version | 2.0 |
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Creation Date | 2012-10-10 12:12:49 -0600 |
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Update Date | 2015-06-03 17:25:45 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | lipid II(A) |
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Description | Lipid II is a membrane-anchored cell-wall precursor that is essential for bacterial cell-wall biosynthesis. It is the target for at least four different classes of antibiotic, including the clinically important glycopeptide antibiotic vancomycin. Lipid II consists of one GlcNAc-MurNAc-pentapeptide subunit linked to a polyiosoprenoid anchor 11 subunits long via a pyrophosphate linker. |
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Structure | |
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Synonyms: | - (2R,5R,8S,13R,16S,19R)-19-{(2R,3R,4R,5S,6R)-3-Acetamido-5-{(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy}-6-(hydroxymethyl)-2-({({(2Z,6Z,10Z,14Z,18Z,22Z,
26Z,30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaen-1-yloxy}phosphinato)oxyphosphinato}oxy)tetrahydro-2H-pyran-4-yloxy}-8-(4R)-4-amm
onio-4-carboxylatobutyl-13-carboxylato-2,5,16-trimethyl-4,7,10,15,18-pentaoxo-3,6,9,14,17-pentaazaicosan-1-
- (2R,6S)-6-(4R)-4-(2S)-2-(2R)-2-(2R,3S,4R,5R,6R)-5-acetamido-3-(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yloxy-2-(hydroxymethyl)-6-oxido-oxido-(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-undecaenoxyphosphoryloxyphosphoryloxyoxan-4-yloxypropanoylaminopropanoylamino-4-carboxylatobutanoylamino-2-azaniumyl-7-(2R)-1-(1R)-1-carboxylatoethylamino-1-oxopropan-2-ylamino-7-oxoheptanoate
- (2R,6S)-6-(4R)-4-(2S)-2-(2R)-2-(2R,3S,4R,5R,6R)-5-acetamido-3-(2R,3R,4R,5S,6R)-3-acetamido-4,5-Dihydroxy-6-(hydroxymethyl)oxan-2-yloxy-2-(hydroxymethyl)-6-oxido-oxido-(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-undecaenoxyphosphoryloxyphosphoryloxyoxan-4-yloxypropanoylaminopropanoylamino-4-carboxylatobutanoylamino-2-azaniumyl-7-(2R)-1-(1R)-1-carboxylatoethylamino-1-oxopropan-2-ylamino-7-oxoheptanoic acid
- N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimelyl-D-alanyl-D-alanine-diphosphoundecaprenyl-N-acetylglucosamine
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Chemical Formula: | C95H152N8O28P2 |
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Weight: | Average: 1916.2077 Monoisotopic: 1915.019129344 |
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InChI Key: | OXJNZXDFVLDLEI-DYDCPVFNSA-J |
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InChI: | InChI=1S/C95H156N8O28P2/c1-58(2)30-19-31-59(3)32-20-33-60(4)34-21-35-61(5)36-22-37-62(6)38-23-39-63(7)40-24-41-64(8)42-25-43-65(9)44-26-45-66(10)46-27-47-67(11)48-28-49-68(12)54-55-125-132(121,122)131-133(123,124)130-95-82(101-74(18)107)86(85(79(57-105)128-95)129-94-81(100-73(17)106)84(110)83(109)78(56-104)127-94)126-72(16)89(113)97-70(14)88(112)103-77(93(119)120)52-53-80(108)102-76(51-29-50-75(96)92(117)118)90(114)98-69(13)87(111)99-71(15)91(115)116/h30,32,34,36,38,40,42,44,46,48,54,69-72,75-79,81-86,94-95,104-105,109-110H,19-29,31,33,35,37,39,41,43,45,47,49-53,55-57,96H2,1-18H3,(H,97,113)(H,98,114)(H,99,111)(H,100,106)(H,101,107)(H,102,108)(H,103,112)(H,115,116)(H,117,118)(H,119,120)(H,121,122)(H,123,124)/p-4/b59-32+,60-34+,61-36-,62-38-,63-40-,64-42-,65-44-,66-46-,67-48-,68-54-/t69-,70+,71-,72-,75-,76+,77-,78-,79-,81-,82-,83-,84-,85-,86-,94-,95-/m1/s1 |
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CAS number: | Not Available |
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IUPAC Name: | (4R)-N-[(1S,5R)-5-amino-5-carboxy-1-{[(1R)-1-{[(1R)-1-carboxyethyl]carboximidato}ethyl]-C-hydroxycarbonimidoyl}pentyl]-4-carboxy-4-{[(2S)-2-{[(2R)-2-{[(2R,3S,4R,5R,6R)-3-{[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-2-yl]oxy}-6-{[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}-2-(hydroxymethyl)-5-[(1-oxidoethylidene)amino]oxan-4-yl]oxy}-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}butanecarboximidate |
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Traditional IUPAC Name: | (4R)-N-[(1S,5R)-5-amino-5-carboxy-1-{[(1R)-1-{[(1R)-1-carboxyethyl]carboximidato}ethyl]-C-hydroxycarbonimidoyl}pentyl]-4-carboxy-4-{[(2S)-2-{[(2R)-2-{[(2R,3S,4R,5R,6R)-3-{[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-2-yl]oxy}-6-{[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]oxyphosphoryl}oxy)phosphoryl]oxy}-2-(hydroxymethyl)-5-[(1-oxidoethylidene)amino]oxan-4-yl]oxy}-1-hydroxypropylidene]amino}-1-hydroxypropylidene]amino}butanecarboximidate |
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SMILES: | OC[C@@]1([H])O[C@]([H])(O[C@]2([H])[C@@]([H])(CO)O[C@]([H])(OP(O)(=O)OP(O)(=O)OC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(\C)CC\C([H])=C(/C)CC\C([H])=C(/C)CCC=C(C)C)[C@]([H])(N=C(C)[O-])[C@@]2([H])O[C@@](C)([H])C(O)=N[C@](C)([H])C(O)=N[C@]([H])(CCC([O-])=N[C@@]([H])(CCC[C@](N)([H])C(=O)O)C(O)=N[C@@](C)([H])C([O-])=N[C@@](C)([H])C(=O)O)C(=O)O)[C@]([H])(N=C(C)[O-])[C@](O)([H])[C@@]1(O)[H] |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as polyprenyl phospho carbohydrates. These are polyprenyl phosphates with a carbohydrate moiety attached to it. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Polyprenols |
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Direct Parent | Polyprenyl phospho carbohydrates |
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Alternative Parents | |
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Substituents | - Polyterpenoid
- Bactoprenol diphosphate
- Polyprenyl phospho carbohydrate
- Polyprenyl monophosphate
- Polyprenyl phosphate skeleton
- Alpha peptide
- N-acyl-alpha-hexosamine
- Disaccharide phosphate
- N-acyl-alpha amino acid or derivatives
- N-acyl-alpha-amino acid
- Alanine or derivatives
- O-glycosyl compound
- Glycosyl compound
- Disaccharide
- D-alpha-amino acid
- Organic pyrophosphate
- Isoprenoid phosphate
- Alpha-amino acid or derivatives
- Alpha-amino acid
- Tricarboxylic acid or derivatives
- Monoalkyl phosphate
- Alkyl phosphate
- Phosphoric acid ester
- Oxane
- Organic phosphoric acid derivative
- Amino acid
- Secondary alcohol
- Amino acid or derivatives
- Oxacycle
- Organoheterocyclic compound
- Ether
- Dialkyl ether
- Carboxylic acid
- Carboxylic acid derivative
- Carboximidic acid derivative
- Carboximidic acid
- Acetal
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Primary amine
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Carbonyl group
- Amine
- Alcohol
- Organic anion
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State: | Not Available |
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Charge: | -3 |
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Melting point: | Not Available |
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Experimental Properties: | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Membrane |
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Reactions: | |
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SMPDB Pathways: | |
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KEGG Pathways: | Not Available |
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EcoCyc Pathways: | Not Available |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | |
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References |
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References: | Not Available |
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Synthesis Reference: | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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Links |
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External Links: | Resource | Link |
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CHEBI ID | Not Available | HMDB ID | Not Available | Pubchem Compound ID | 52940208 | Kegg ID | Not Available | ChemSpider ID | Not Available | Wikipedia ID | Not Available | BioCyc ID | Not Available |
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