heptosyl-Kdo2-lipid A (PAMDB120294)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120294
Identification
Name: heptosyl-Kdo2-lipid A
Description:A lipid A oxoanion obtained via deprotonation of the carboxy and phosphate OH groups of 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-(Kdo)2-lipid A
  • heptosyl-(KDO)2-lipid A hexaanion
  • L-α-D-Hep-(1→5)-[α-Kdo-(2→4)]-α-Kdo-(2→6)-lipid A hexaanion
  • L-α-D-Hep-(1→5)-[α-Kdo-(2→4)]-α-Kdo-(2→6)-lipid A(6−)
Chemical Formula: C117H208N2O45P2
Average Molecular Weight: 2424.864
Monoisotopic Molecular Weight: 2429.3994
InChI Key: HPDZKCJEWNZSML-YPJVYCBMSA-H
InChI:InChI=1S/C117H214N2O45P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-94(132)153-83(66-60-54-48-42-35-29-23-17-11-5)72-96(134)157-110-98(119-92(130)71-82(65-59-53-47-41-34-28-22-16-10-4)152-93(131)67-61-55-49-43-36-30-24-18-12-6)111(150-78-89-100(136)109(156-95(133)70-81(124)64-58-52-46-40-33-27-21-15-9-3)97(112(154-89)164-166(147,148)149)118-91(129)69-80(123)63-57-51-45-39-32-26-20-14-8-2)155-90(108(110)163-165(144,145)146)79-151-116(114(140)141)74-88(160-117(115(142)143)73-84(125)99(135)105(161-117)86(127)76-121)107(106(162-116)87(128)77-122)159-113-103(139)101(137)102(138)104(158-113)85(126)75-120/h80-90,97-113,120-128,135-139H,7-79H2,1-6H3,(H,118,129)(H,119,130)(H,140,141)(H,142,143)(H2,144,145,146)(H2,147,148,149)/p-6/t80-,81-,82-,83-,84-,85+,86?,87-,88-,89-,90-,97-,98-,99-,100-,101+,102+,103+,104?,105-,106-,107-,108-,109-,110-,111-,112-,113?,116-,117-/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)COC5(C([O-])=O)(OC(C(O)CO)C(OC3(OC(C(CO)O)C(C(O)C3O)O))C(OC4(C(=O)[O-])(OC(C(O)CO)C(O)C(O)C4))C5))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 Weight2427.892 g/molPubChem
XLogP3-AA19.5 PubChem
Hydrogen Bond Donor Count18 PubChem
Hydrogen Bond Acceptor Count45 PubChem
Rotatable Bond Count99 PubChem
Exact Mass2427.379 g/molPubChem
Monoisotopic Mass2426.376 g/molPubChem
Topological Polar Surface Area755 A^2PubChem
Heavy Atom Count166 PubChem
Formal Charge-5 PubChem
Complexity4090 PubChem
Isotope Atom Count0 PubChem
Defined Atom Stereocenter Count23 PubChem
Undefined Atom Stereocenter Count7 PubChem
Defined Bond Stereocenter Count0 PubChem
Undefined Bond Stereocenter Count0 PubChem
Covalently-Bonded Unit Count1 PubChem
Biological Properties
Cellular Locations: Not Available
Reactions:
α-D-Kdo-(2→4)-α-D-Kdo-(2→6)-lipid A + ADP-L-glycero-beta-D-manno-heptose → heptosyl-Kdo2-lipid A + ADP + Hydrogen ion
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
CHEBI61502
BIGG2374859
PUBCHEM25246017