(heptosyl)2-Kdo2-lipid A (PAMDB120518)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120518
Identification
Name: (heptosyl)2-Kdo2-lipid A
Description:A lipid A oxoanion obtained via deprotonation of the carboxy and phosphate OH groups of L-α-D-Hep-(1→3)-L-α-D-Hep-(1→5)-[α-Kdo-(2→4)]-α-Kdo-(2→6)-lipid A; major species at pH 7.3.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (heptosyl)2-(Kdo)2-lipid A
  • (heptosyl)2-(KDO)2-lipid A hexaanion
  • heptosyl-heptosyl-kdo2-lipidA
  • L-α-D-Hep-(1→3)-L-α-D-Hep-(1→5)-[α-Kdo-(2→4)]-α-Kdo-(2→6)-lipid A hexaanion
  • L-α-D-Hep-(1→3)-L-α-D-Hep-(1→5)-[α-Kdo-(2→4)]-α-Kdo-(2→6)-lipid A(6−)
Chemical Formula: C124H220N2O51P2
Average Molecular Weight: 2617.032
Monoisotopic Molecular Weight: 2621.463
InChI Key: HHPCMWTVGVTYIC-JOVNRQDYSA-H
InChI:InChI=1S/C124H226N2O51P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-96(141)164-84(66-60-54-48-42-35-29-23-17-11-5)72-98(143)168-115-100(126-94(139)71-83(65-59-53-47-41-34-28-22-16-10-4)163-95(140)67-61-55-49-43-36-30-24-18-12-6)117(161-79-91-102(145)114(167-97(142)70-82(132)64-58-52-46-40-33-27-21-15-9-3)99(118(165-91)177-179(158,159)160)125-93(138)69-81(131)63-57-51-45-39-32-26-20-14-8-2)166-92(113(115)176-178(155,156)157)80-162-123(121(151)152)74-90(173-124(122(153)154)73-85(133)101(144)110(174-124)88(136)77-129)112(111(175-123)89(137)78-130)171-120-107(150)116(106(149)109(170-120)87(135)76-128)172-119-105(148)103(146)104(147)108(169-119)86(134)75-127/h81-92,99-120,127-137,144-150H,7-80H2,1-6H3,(H,125,138)(H,126,139)(H,151,152)(H,153,154)(H2,155,156,157)(H2,158,159,160)/p-6/t81-,82-,83-,84-,85-,86+,87+,88?,89-,90-,91-,92-,99-,100-,101-,102-,103+,104+,105+,106-,107+,108?,109?,110-,111-,112-,113-,114-,115-,116+,117-,118-,119?,120?,123-,124-/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)COC6(C([O-])=O)(OC(C(O)CO)C(OC4(OC(C(CO)O)C(C(OC3(OC(C(CO)O)C(C(O)C3O)O))C4O)O))C(OC5(C(=O)[O-])(OC(C(O)CO)C(O)C(O)C5))C6))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 Weight2620.059 g/molPubChem
XLogP3-AA17.2 PubChem
Hydrogen Bond Donor Count22 PubChem
Hydrogen Bond Acceptor Count51 PubChem
Rotatable Bond Count103 PubChem
Exact Mass2619.443 g/molPubChem
Monoisotopic Mass2618.439 g/molPubChem
Topological Polar Surface Area855 A^2PubChem
Heavy Atom Count179 PubChem
Formal Charge-5 PubChem
Complexity4500 PubChem
Isotope Atom Count0 PubChem
Defined Atom Stereocenter Count27 PubChem
Undefined Atom Stereocenter Count9 PubChem
Defined Bond Stereocenter Count0 PubChem
Undefined Bond Stereocenter Count0 PubChem
Covalently-Bonded Unit Count1 PubChem
Biological Properties
Cellular Locations: Not Available
Reactions:
UDP-α-D-glucose + (heptosyl)2-Kdo2-lipid A → Hydrogen ion + glucosyl-(heptosyl)2-Kdo2-lipid A + UDP
heptosyl-Kdo2-lipid A + ADP-L-glycero-beta-D-manno-heptose → Hydrogen ion + (heptosyl)2-Kdo2-lipid A + ADP
Pathways:
Spectra
Spectra: Not Available
References
References:
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI61507
BIGG2374861
PUBCHEM25245625