glucosyl-(heptosyl)2-Kdo2-lipid A (PAMDB120523)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120523
Identification
Name: glucosyl-(heptosyl)2-Kdo2-lipid A
Description:A lipid A oxoanion obtained via deprotonation of the carboxy and phosphate OH groups of glucosyl-(heptosyl)2-(KDO)2-lipid A; major species at pH 7.3.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • α-D-Glc-(1→3)-L-α-D-Hep-(1→3)-L-α-D-Hep-(1→5)-[α-Kdo-(2→4)]-α-Kdo-(2→6)-lipid A hexaanion
  • α-D-Glc-(1→3)-L-α-D-Hep-(1→3)-L-α-D-Hep-(1→5)-[α-Kdo-(2→4)]-α-Kdo-(2→6)-lipid A(6−)
  • glucosyl-(heptosyl)2-(KDO)2-lipid A
  • glucosyl-(heptosyl)2-(Kdo)2-lipid A
  • glucosyl-(heptosyl)2-(KDO)2-lipid A hexaanion
Chemical Formula: C130H230N2O56P2
Average Molecular Weight: 2779.174
Monoisotopic Molecular Weight: 2783.5156
InChI Key: UMRPQNDYTAXFNB-PSSXMBRZSA-H
InChI:InChI=1S/C130H236N2O56P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-98(148)173-85(66-60-54-48-42-35-29-23-17-11-5)72-100(150)178-119-102(132-96(146)71-84(65-59-53-47-41-34-28-22-16-10-4)172-97(147)67-61-55-49-43-36-30-24-18-12-6)122(170-80-93-105(153)118(177-99(149)70-83(139)64-58-52-46-40-33-27-21-15-9-3)101(123(175-93)188-190(167,168)169)131-95(145)69-82(138)63-57-51-45-39-32-26-20-14-8-2)176-94(117(119)187-189(164,165)166)81-171-129(127(160)161)74-91(184-130(128(162)163)73-86(140)103(151)114(185-130)89(143)77-135)116(115(186-129)90(144)78-136)181-125-110(158)121(109(157)112(179-125)87(141)75-133)183-126-111(159)120(108(156)113(180-126)88(142)76-134)182-124-107(155)106(154)104(152)92(79-137)174-124/h82-94,101-126,133-144,151-159H,7-81H2,1-6H3,(H,131,145)(H,132,146)(H,160,161)(H,162,163)(H2,164,165,166)(H2,167,168,169)/p-6/t82-,83-,84-,85-,86-,87+,88+,89?,90-,91-,92-,93-,94-,101-,102-,103-,104-,105-,106+,107-,108-,109-,110+,111+,112?,113?,114-,115-,116-,117-,118-,119-,120+,121+,122-,123-,124+,125?,126?,129-,130-/m1/s1
CAS number: Not Available
IUPAC Name:Not Available
Traditional IUPAC Name: Not Available
SMILES:CCCCCCCCCCCCCC(=O)OC(CC(OC2(C(C(OCC1(OC(OP([O-])(=O)[O-])C(NC(=O)CC(O)CCCCCCCCCCC)C(OC(=O)CC(O)CCCCCCCCCCC)C(O)1))OC(C2OP([O-])([O-])=O)COC7(C([O-])=O)(OC(C(O)CO)C(OC5(OC(C(CO)O)C(C(OC4(OC(C(CO)O)C(C(OC3(C(C(C(C(CO)O3)O)O)O))C4O)O))C5O)O))C(OC6(C(=O)[O-])(OC(C(O)CO)C(O)C(O)C6))C7))NC(CC(CCCCCCCCCCC)OC(CCCCCCCCCCC)=O)=O))=O)CCCCCCCCCCC
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassOrganic oxygen compounds
Class Organooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct Parent Acylaminosugars
Alternative Parents
Substituents
  • Oligosaccharide phosphate
  • Oligosaccharide
  • Hexacarboxylic acid or derivatives
  • Acylaminosugar
  • Saccharolipid
  • Hexose phosphate
  • N-acyl-alpha-hexosamine
  • Fatty acyl glycoside
  • C-glucuronide
  • Alkyl glycoside
  • O-glycosyl compound
  • C-glycosyl compound
  • Glycosyl compound
  • Fatty acid ester
  • Ketal
  • Beta-hydroxy acid
  • Pyran
  • Fatty acyl
  • Phosphoric acid ester
  • Oxane
  • Hydroxy acid
  • Organic phosphoric acid derivative
  • N-acyl-amine
  • Fatty amide
  • Alkyl phosphate
  • Carboxamide group
  • Carboxylic acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Oxacycle
  • Polyol
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Primary alcohol
  • Organonitrogen compound
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-6
Melting point: Not Available
Experimental Properties: Not Available
Predicted Properties
PropertyValueSource
Molecular Weight2782.2 g/molPubChem
XLogP3-AA15.7 PubChem
Hydrogen Bond Donor Count25 PubChem
Hydrogen Bond Acceptor Count56 PubChem
Rotatable Bond Count106 PubChem
Exact Mass2781.495 g/molPubChem
Monoisotopic Mass2780.492 g/molPubChem
Topological Polar Surface Area934 A^2PubChem
Heavy Atom Count190 PubChem
Formal Charge-5 PubChem
Complexity4860 PubChem
Isotope Atom Count0 PubChem
Defined Atom Stereocenter Count27 PubChem
Undefined Atom Stereocenter Count14 PubChem
Defined Bond Stereocenter Count0 PubChem
Undefined Bond Stereocenter Count0 PubChem
Covalently-Bonded Unit Count1 PubChem
Biological Properties
Cellular Locations: Not Available
Reactions:
glucosyl-(heptosyl)2-Kdo2-lipid A + ATP → Hydrogen ion + glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate + ADP
UDP-α-D-glucose + (heptosyl)2-Kdo2-lipid A → Hydrogen ion + glucosyl-(heptosyl)2-Kdo2-lipid A + UDP
Pathways:
Spectra
Spectra: Not Available
References
References:
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI61997
PUBCHEM25245615