Record Information |
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Version |
1.0 |
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Update Date |
1/22/2018 12:54:54 PM |
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Metabolite ID | PAMDB000905 |
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Identification |
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Name: |
2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate |
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Description: | 2,3,2',3'-tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate is a member of the chemical class known as Dihexoses. These are disaccharides containing two hexose carbohydrates. |
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Structure |
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Synonyms: | - 2'-3'-diacyl-GlcN(β-1'-6)2,3-diacyl-GlcN-1-P
- 2'-3'-Diacyl-GLCN(b-1'-6)2,3-diacyl-GLCN-1-P
- 2'-3'-Diacyl-GlcN(beta-1'-6)2,3-diacyl-GlcN-1-P
- 2'-3'-Diacyl-GLCN(β-1'-6)2,3-diacyl-GLCN-1-P
- 2,3,2',3'-tetrakis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-α-D-glucosamine 1-phosphate
- 2,3,2',3'-Tetrakis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-α-D-glucosamine 1-phosphoric acid
- 2,3,2',3'-Tetrakis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-a-D-glucosamine 1-phosphate
- 2,3,2',3'-Tetrakis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-a-D-glucosamine 1-phosphoric acid
- 2,3,2',3'-Tetrakis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-alpha-D-glucosamine 1-phosphate
- 2,3,2',3'-Tetrakis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-alpha-D-glucosamine 1-phosphoric acid
- 2,3,2',3'-Tetrakis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-α-D-glucosamine 1-phosphate
- 2,3,2',3'-Tetrakis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-α-D-glucosamine 1-phosphoric acid
- 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1-phosphate
- 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1-phosphoric acid
- 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphoric acid
- 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1-phosphate
- 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1-phosphoric acid
- 2,3-bis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxymyristoyl)-α-D-glucosaminyl 1-phosphate
- 2,3-Bis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxymyristoyl)-α-D-glucosaminyl 1-phosphoric acid
- 2,3-Bis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-b-D-2,3-bis(3-hydroxymyristoyl)-a-D-glucosaminyl 1-phosphate
- 2,3-Bis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-b-D-2,3-bis(3-hydroxymyristoyl)-a-D-glucosaminyl 1-phosphoric acid
- 2,3-Bis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxymyristoyl)-alpha-D-glucosaminyl 1-phosphate
- 2,3-Bis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxymyristoyl)-alpha-D-glucosaminyl 1-phosphoric acid
- 2,3-Bis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxymyristoyl)-α-D-glucosaminyl 1-phosphate
- 2,3-Bis(3-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxymyristoyl)-α-D-glucosaminyl 1-phosphoric acid
- 2,3-bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphate
- 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphoric acid
- 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-2,3-bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl 1-phosphate
- 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-2,3-bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl 1-phosphoric acid
- 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphate
- 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-2,3-bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl 1-phosphoric acid
- 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphate
- 2,3-Bis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-2,3-bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl 1-phosphoric acid
- 2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-α-phosphate
- 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-α-phosphoric acid
- 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(b-D-1,6)-2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-a-phosphate
- 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(b-D-1,6)-2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-a-phosphoric acid
- 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(beta-D-1,6)-2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-alpha-phosphate
- 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(beta-D-1,6)-2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-alpha-phosphoric acid
- 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-α-phosphate
- 2,3-Bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-(β-D-1,6)-2,3-bis-(3-hydroxytetradecanoyl)-D-glucosaminyl-α-phosphoric acid
- Lipid a disaccharide
- Lipid A dSc
- Tetraacyldisaccharide-1-phosphate
- Tetraacyldisaccharide-1-phosphoric acid
- [2-N,3-O-bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl]-(1 -> 6)-[2-N,3-O-bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl phosphate]
- [2-n,3-O-Bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl]-(1 -> 6)-[2-n,3-O-bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl phosphate]
- [2-n,3-O-Bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl]-(1 -> 6)-[2-n,3-O-bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl phosphoric acid]
- [2-N,3-O-Bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl]-(1 -> 6)-[2-N,3-O-bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl phosphate]
- [2-N,3-O-Bis(3-hydroxytetradecanoyl)-b-D-glucosaminyl]-(1 -> 6)-[2-N,3-O-bis(3-hydroxytetradecanoyl)-a-D-glucosaminyl phosphoric acid]
- [2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl]-(1 -> 6)-[2-N,3-O-bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl phosphate]
- [2-N,3-O-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl]-(1 -> 6)-[2-N,3-O-bis(3-hydroxytetradecanoyl)-alpha-D-glucosaminyl phosphoric acid]
- [2-N,3-O-Bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl]-(1 -> 6)-[2-N,3-O-bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl phosphate]
- [2-N,3-O-Bis(3-hydroxytetradecanoyl)-β-D-glucosaminyl]-(1 -> 6)-[2-N,3-O-bis(3-hydroxytetradecanoyl)-α-D-glucosaminyl phosphoric acid]
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Chemical Formula: |
C68H129N2O20P |
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Average Molecular Weight: |
1325.727 |
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Monoisotopic Molecular
Weight: |
1324.88763109 |
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InChI Key: |
HLDJGHAAKRKPAV-XFXUPMIZSA-N |
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InChI: | InChI=1S/C68H129N2O20P/c1-5-9-13-17-21-25-29-33-37-41-51(72)45-57(76)69-61-65(88-59(78)47-53(74)43-39-35-31-27-23-19-15-11-7-3)63(80)55(49-71)86-67(61)85-50-56-64(81)66(89-60(79)48-54(75)44-40-36-32-28-24-20-16-12-8-4)62(68(87-56)90-91(82,83)84)70-58(77)46-52(73)42-38-34-30-26-22-18-14-10-6-2/h51-56,61-68,71-75,80-81H,5-50H2,1-4H3,(H,69,76)(H,70,77)(H2,82,83,84)/t51?,52?,53?,54?,55-,56-,61-,62-,63-,64-,65-,66-,67-,68+/m1/s1 |
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CAS
number: |
Not Available |
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IUPAC Name: | (3R)-3-hydroxy-N-[(2R,3R,4R,5S,6R)-5-hydroxy-2-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-{[(3R)-3-hydroxy-1-oxidotetradecylidene]amino}-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-3-yl]tetradecanecarboximidate |
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Traditional IUPAC Name: |
(3R)-3-hydroxy-N-[(2R,3R,4R,5S,6R)-5-hydroxy-2-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-{[(3R)-3-hydroxy-1-oxidotetradecylidene]amino}-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-3-yl]tetradecanecarboximidate |
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SMILES: | [H]C(O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(OC[C@@]2([H])O[C@@]([H])(OP(O)(O)=O)[C@]([H])(N=C(O)CC([H])(O)CCCCCCCCCCC)[C@@]([H])(OC(=O)CC([H])(O)CCCCCCCCCCC)[C@]2([H])O)[C@]1([H])N=C(O)CC([H])(O)CCCCCCCCCCC |
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Chemical Taxonomy |
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Taxonomy Description | This compound belongs to the class of organic compounds known as saccharolipids. These 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
- Disaccharide phosphate
- Glucosamine
- Amino sugar
- O-glycosyl compound
- Glycosyl compound
- Disaccharide
- Monoalkyl phosphate
- Amino saccharide
- Fatty acid ester
- Beta-hydroxy acid
- Fatty acyl
- Alkyl phosphate
- Phosphoric acid ester
- Oxane
- Organic phosphoric acid derivative
- Organic phosphate
- Hydroxy acid
- Dicarboxylic acid or derivatives
- Secondary alcohol
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Carboximidic acid derivative
- Carboximidic acid
- Acetal
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- 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: | -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: | 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate + UDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine <> Hydrogen ion + 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate + Uridine 5'-diphosphateAdenosine triphosphate + 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate > ADP + Hydrogen ion + 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphateUDP-2,3-Bis(3-hydroxytetradecanoyl)glucosamine + 2,3-Bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl 1-phosphate <> Uridine 5'-diphosphate + 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphateAdenosine triphosphate + 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate <> ADP + 2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate + Adenosine triphosphate <> Hydrogen ion + lipid IV<sub>A</sub> + ADP |
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Pathways: |
- Lipopolysaccharide biosynthesis pae00540
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Spectra |
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Spectra: |
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References |
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References: |
- Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
- Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
- van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
- Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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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: |
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