Record Information |
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Version | 2.0 |
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Creation Date | 2015-09-08 17:50:17 -0600 |
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Update Date | 2015-09-14 16:46:39 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | galactosyl-(glucosyl)3-(heptosyl)3-Kdo2-lipid A-bisphosphate |
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Description | Galactosyl-(glucosyl)3-(heptosyl)3-Kdo2-lipid A-bisphosphate is an intermediate in lipid A-core biosynthesis pathway in E.coli. It is a substrate for the enzyme heptosyl transferase IV which catalyzes the reaction galactosyl-(glucosyl)3-(heptosyl)3-Kdo2-lipid A-bisphosphate + ADP-L-glycero-beta-D-manno-heptose -> lipid A-core + ADP + H+. It is also a product for enzyme UDP-glucose:(glucosyl)LPS alpha-1,2-glucosyltransferase which catalyzes reaction UDP-alpha-D-glucose + galactosyl-(glucosyl)2-(heptosyl)3-Kdo2-lipid A-bisphosphate -> galactosyl-(glucosyl)3-(heptosyl)3-Kdo2-lipid A-bisphosphate + UDP + H+ (BioCyc compound: CPD0-938). |
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Structure | |
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Synonyms: | - Galactosyl-(glucosyl)3-(heptosyl)3-kdo2-lipid a-bisphosphoric acid
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Chemical Formula: | C155H270N2O83P4 |
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Weight: | Average: 3613.697 Monoisotopic: 3611.597353953 |
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InChI Key: | DNFPUONWCBGXPM-AZUGHDOASA-D |
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InChI: | InChI=1S/C155H280N2O83P4/c1-7-13-19-25-31-37-38-44-50-56-62-68-106(176)217-89(66-60-54-48-42-35-29-23-17-11-5)72-108(178)225-136-110(157-104(174)71-88(65-59-53-47-41-34-28-22-16-10-4)216-105(175)67-61-55-49-43-36-30-24-18-12-6)143(213-83-100-115(183)135(224-107(177)70-87(166)64-58-52-46-40-33-27-21-15-9-3)109(144(221-100)240-244(209,210)211)156-103(173)69-86(165)63-57-51-45-39-32-26-20-14-8-2)223-102(134(136)237-241(200,201)202)85-215-154(152(196)197)74-96(234-155(153(198)199)73-90(167)111(179)129(235-155)92(169)76-159)133(132(236-154)94(171)78-161)229-149-126(194)138(141(238-242(203,204)205)130(227-149)93(170)77-160)232-150-127(195)139(142(239-243(206,207)208)131(228-150)95(172)82-212-146-123(191)119(187)121(189)128(226-146)91(168)75-158)231-148-125(193)137(116(184)101(222-148)84-214-145-122(190)117(185)112(180)97(79-162)218-145)230-151-140(120(188)114(182)99(81-164)220-151)233-147-124(192)118(186)113(181)98(80-163)219-147/h86-102,109-151,158-172,179-195H,7-85H2,1-6H3,(H,156,173)(H,157,174)(H,196,197)(H,198,199)(H2,200,201,202)(H2,203,204,205)(H2,206,207,208)(H2,209,210,211)/p-10/t86-,87-,88-,89-,90-,91+,92-,93+,94-,95+,96-,97-,98-,99-,100-,101-,102-,109-,110-,111-,112+,113-,114-,115-,116-,117+,118+,119+,120+,121+,122-,123+,124-,125-,126+,127+,128-,129-,130-,131-,132-,133-,134-,135-,136-,137+,138-,139-,140-,141-,142-,143-,144-,145?,146?,147?,148?,149-,150-,151?,154-,155-/m1/s1 |
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CAS number: | Not Available |
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IUPAC Name: | (2R,4R,5R,6R)-2-{[(2R,4R,5R,6R)-2-carboxylato-5-{[(2S,3S,4R,5R,6R)-4-{[(2R,3S,4R,5R,6R)-4-{[(3R,4S,5R,6R)-4-{[(3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-({[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-6-[(1S)-2-{[(3S,4S,5S,6R)-6-[(1S)-1,2-dihydroxyethyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-1-hydroxyethyl]-3-hydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}-6-[(1S)-1,2-dihydroxyethyl]-3-hydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-2-{[(2R,3S,4R,5R,6R)-5-[(3R)-3-(dodecanoyloxy)tetradecanamido]-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonatooxy)oxan-2-yl]methoxy}-3-(phosphonatooxy)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}oxan-4-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxane-2-carboxylate |
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Traditional IUPAC Name: | (2R,4R,5R,6R)-2-{[(2R,4R,5R,6R)-2-carboxylato-5-{[(2S,3S,4R,5R,6R)-4-{[(2R,3S,4R,5R,6R)-4-{[(3R,4S,5R,6R)-4-{[(3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3,5-dihydroxy-6-({[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-6-[(1S)-2-{[(3S,4S,5S,6R)-6-[(1S)-1,2-dihydroxyethyl]-3,4,5-trihydroxyoxan-2-yl]oxy}-1-hydroxyethyl]-3-hydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}-6-[(1S)-1,2-dihydroxyethyl]-3-hydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-2-{[(2R,3S,4R,5R,6R)-5-[(3R)-3-(dodecanoyloxy)tetradecanamido]-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonatooxy)oxan-2-yl]methoxy}-3-(phosphonatooxy)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}oxan-4-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxane-2-carboxylate |
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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](CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@H]2OP([O-])([O-])=O)(O[C@]([H])([C@H](O)CO)[C@@H]1O[C@H]1O[C@H]([C@@H](O)CO)[C@@H](OP([O-])([O-])=O)[C@H](O[C@H]2O[C@H]([C@@H](O)COC3O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]3O)[C@@H](OP([O-])([O-])=O)[C@H](OC3O[C@H](COC4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](OC4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4OC4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H]3O)[C@@H]2O)[C@@H]1O)C([O-])=O)C([O-])=O)[C@H](O)CO |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Acylaminosugars |
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Alternative Parents | |
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Substituents | - Polysaccharide
- Hexacarboxylic acid or derivatives
- Acylaminosugar
- Saccharolipid
- Hexose phosphate
- Fatty acyl glycoside
- N-acyl-alpha-hexosamine
- C-glucuronide
- Alkyl glycoside
- C-glycosyl compound
- Glycosyl compound
- O-glycosyl compound
- Ketal
- Beta-hydroxy acid
- Fatty acid ester
- Fatty acyl
- Fatty amide
- Alkyl phosphate
- Hydroxy acid
- N-acyl-amine
- Pyran
- Organic phosphoric acid derivative
- Oxane
- Phosphoric acid ester
- Secondary carboxylic acid amide
- Secondary alcohol
- Carboxamide group
- Carboxylic acid ester
- Polyol
- Oxacycle
- Organoheterocyclic compound
- Acetal
- Carboxylic acid
- Carboxylic acid derivative
- Primary alcohol
- Carbonyl group
- Organic nitrogen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organonitrogen compound
- Alcohol
- Organic anion
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State: | Not Available |
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Charge: | -10 |
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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: | Lipopolysaccharide biosynthesis | PW000831 | | lipopolysaccharide biosynthesis II | PW001905 | | lipopolysaccharide biosynthesis III | PW002059 | |
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KEGG Pathways: | - Lipopolysaccharide biosynthesis ec00540
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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: | Not Available |
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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 | 62003 | HMDB ID | Not Available | Pubchem Compound ID | 51351789 | Kegg ID | Not Available | ChemSpider ID | Not Available | Wikipedia ID | Not Available | BioCyc ID | Not Available |
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