2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate (PAMDB000905)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000905
Identification
Name: 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate
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.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
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]
Chemical Formula: C68H129N2O20P
Average Molecular Weight: 1325.727
Monoisotopic Molecular Weight: 1324.88763109
InChI Key: HLDJGHAAKRKPAV-XFXUPMIZSA-N
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
CAS number: Not Available
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
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
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
Chemical Taxonomy
Taxonomy DescriptionThis 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.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Saccharolipids
Sub ClassNot Available
Direct Parent Saccharolipids
Alternative Parents
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
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00334 mg/mLALOGPS
logP5.9ALOGPS
logP14.56ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)1.03ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area359.5 Å2ChemAxon
Rotatable Bond Count60ChemAxon
Refractivity368.87 m3·mol-1ChemAxon
Polarizability154.92 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
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'-diphosphate
Adenosine 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'-bisphosphate
UDP-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-phosphate
Adenosine 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'-bisphosphate
2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate + Adenosine triphosphate <> Hydrogen ion + lipid IV<sub>A</sub> + ADP
Pathways:
Spectra
Spectra:
References
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
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID18380
HMDB IDNot Available
Pubchem Compound ID440543
Kegg IDC04932
ChemSpider ID389445
Wikipedia IDNot Available
BioCyc IDBISOHMYR-GLC
EcoCyc IDBISOHMYR-GLC