| Record Information |
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| Version | 2.0 |
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| Creation Date | 2012-10-10 12:23:30 -0600 |
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| Update Date | 2015-06-03 17:26:15 -0600 |
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| Secondary Accession Numbers | |
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| Identification |
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| Name: | 2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate |
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| Description | 2,3-bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphate is an intermediate in Lipid IVA synthesis which is essesntial for the production of LPS. Lipopolysaccharide (LPS), a major outer membrane component, is composed of three domains: Lipid A, the core, which is an oligosaccharide consisting of an inner and outer region; and a distal repeating unit known as the O-antigen. Lipid A is linked to a beta-1,6-linked glucosamine disaccharide. Attached to this is the inner core containing at least two 3-deoxy-D-manno-octulosonate (KDO) units followed by two units of heptose. The outer core region and the O-antigen are attached to one of the heptose units. For some time it was thought that the minimum structure for cell viability in E. coli had the di-Kdo moiety, but viable mutants lacking Kdo and with the basic tetra-acyl form of lipid A, i.e. lacking the two secondary acyl groups (and termed 'lipid IVA'), have recently been produced. Indeed, lipid IVA may be the minimum structure required for the viability of E. coli. |
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| Structure | |
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| Synonyms: | - (2R,3S,4R,5R,6R)-3-hydroxy-2-(hydroxymethyl)-5-(3R)-3-hydroxytetradecanoylamino-6-phosphonooxyoxan-4-yl (3R)-3-hydroxytetradecanoate
- (2R,3S,4R,5R,6R)-3-Hydroxy-2-(hydroxymethyl)-5-(3R)-3-hydroxytetradecanoylamino-6-phosphonooxyoxan-4-yl (3R)-3-hydroxytetradecanoic acid
- 2,3-Bis((3R)-3-hydroxymyristoyl)-b-D-glucosaminyl 1-phosphate
- 2,3-Bis((3R)-3-hydroxymyristoyl)-b-D-glucosaminyl 1-phosphoric acid
- 2,3-Bis((3R)-3-hydroxymyristoyl)-beta-D-glucosaminyl 1-phosphoric acid
- 2,3-Bis((3R)-3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphate
- 2,3-Bis((3R)-3-hydroxymyristoyl)-β-D-glucosaminyl 1-phosphoric acid
- 2,3-Bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl 1-phosphate
- 2,3-Bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl 1-phosphoric acid
- 2,3-Bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
- 2,3-Bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphoric acid
- 2,3-Bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl 1-phosphate
- 2,3-Bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl 1-phosphoric acid
- 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate
- 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphoric acid
- 2,3-Bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphate
- 2,3-Bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphoric acid
- 2,3-Bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl 1-phosphate
- 2,3-Bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl 1-phosphoric acid
- 2,3-Bis(3R)-3-hydroxymyristoyl-a-D-glucosaminyl 1-phosphate
- 2,3-Bis(3R)-3-hydroxymyristoyl-a-D-glucosaminyl 1-phosphoric acid
- 2,3-Bis(3R)-3-hydroxymyristoyl-alpha-D-glucosaminyl 1-phosphate
- 2,3-Bis(3R)-3-hydroxymyristoyl-alpha-D-glucosaminyl 1-phosphoric acid
- 2,3-Bis(3R)-3-hydroxymyristoyl-α-D-glucosaminyl 1-phosphate
- 2,3-Bis(3R)-3-hydroxymyristoyl-α-D-glucosaminyl 1-phosphoric acid
- 2,3-Bis(b-hydoroxymyristoyl)-b-D-glucosaminyl 1-phosphate
- 2,3-Bis(b-hydoroxymyristoyl)-b-D-glucosaminyl 1-phosphoric acid
- 2,3-Bis(beta-hydoroxymyristoyl)-beta-D-glucosaminyl 1-phosphate
- 2,3-Bis(beta-hydoroxymyristoyl)-beta-D-glucosaminyl 1-phosphoric acid
- 2,3-Bis(β-hydoroxymyristoyl)-β-D-glucosaminyl 1-phosphate
- 2,3-Bis(β-hydoroxymyristoyl)-β-D-glucosaminyl 1-phosphoric acid
- 2,3-Diacylglucosamine 1-phosphate
- 2,3-Diacylglucosamine 1-phosphoric acid
- 2-Deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-1-O-phosphono-a-D-glucopyranose
- 2-Deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-1-O-phosphono-alpha-D-glucopyranose
- 2-Deoxy-3-O-(3R)-3-hydroxytetradecanoyl-2-{(3R)-3-hydroxytetradecanoylamino}-1-O-phosphono-α-D-glucopyranose
- Lipid X
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| Chemical Formula: | C34H66NO12P |
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| Weight: | Average: 711.8611
Monoisotopic: 711.432263093 |
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| InChI Key: | HEHQDWUWJVPREQ-XQJZMFRCSA-N |
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| InChI: | InChI=1S/C34H66NO12P/c1-3-5-7-9-11-13-15-17-19-21-26(37)23-29(39)35-31-33(32(41)28(25-36)45-34(31)47-48(42,43)44)46-30(40)24-27(38)22-20-18-16-14-12-10-8-6-4-2/h26-28,31-34,36-38,41H,3-25H2,1-2H3,(H,35,39)(H2,42,43,44)/t26-,27-,28-,31-,32-,33-,34-/m1/s1 |
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| CAS number: | Not Available |
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| IUPAC Name: | {[(2R,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-3-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}phosphonic acid |
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| Traditional IUPAC Name: | lipid X |
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| SMILES: | CCCCCCCCCCC[C@@H](O)CC(=O)N[C@H]1[C@@H](OP(O)(O)=O)O[C@H](CO)[C@@H](O)[C@@H]1OC(=O)C[C@H](O)CCCCCCCCCCC |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Saccharolipids |
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| Sub Class | Not Available |
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| Direct Parent | Saccharolipids |
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| Alternative Parents | |
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| Substituents | - Saccharolipid
- N-acyl-alpha-hexosamine
- Hexose monosaccharide
- Monosaccharide phosphate
- Beta-hydroxy acid
- Fatty acid ester
- Monoalkyl phosphate
- Hydroxy acid
- Fatty acyl
- Monosaccharide
- Organic phosphoric acid derivative
- Alkyl phosphate
- Oxane
- Phosphoric acid ester
- Carboxylic acid ester
- Secondary alcohol
- Carboximidic acid
- Carboximidic acid derivative
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Oxacycle
- Organoheterocyclic compound
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Carbonyl group
- Alcohol
- Organic nitrogen compound
- Organic oxygen compound
- Organonitrogen compound
- Organooxygen compound
- Primary alcohol
- 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: | -2 |
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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: | Not Available |
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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 | 16942 | | HMDB ID | Not Available | | Pubchem Compound ID | 123907 | | Kegg ID | C04824 | | ChemSpider ID | Not Available | | Wikipedia ID | Not Available | | BioCyc ID | Not Available | | Ligand Expo | LP5 |
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