Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110367
Identification
Name: α-Kdo-(2→6)-lipid IVA
Description:(KDO)-lipid IVA deprotonated at both phosphono groups and at the uronic acid carboxy group. It is the major species at pH 7.3.
Structure
Thumb
Synonyms:
  • 3-Deoxy-D-manno-octulosonyl-lipid IV(A)
  • 3-deoxy-α-D-manno-oct-2-ulopyranosyl-(2->6)-2-deoxy-2-{[(3R)-3-hydroxypentadecanoyl]amino}-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-β-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-1-O-phosphono-α-D-glucopyranose
  • (KDO)-lipid IVA
Chemical Formula: C76H137N2O30P2
Average Molecular Weight: 1620.9
Monoisotopic Molecular Weight: 1624.9122642516
InChI Key: GPNCBCJEDRRCDW-XFULRARUSA-I
InChI: InChI=1S/C76H142N2O30P2/c1-5-9-13-17-21-25-29-33-37-41-53(80)45-61(86)77-65-71(104-63(88)47-55(82)43-39-35-31-27-23-19-15-11-7-3)68(91)59(102-74(65)108-110(97,98)99)51-100-73-66(78-62(87)46-54(81)42-38-34-30-26-22-18-14-10-6-2)72(105-64(89)48-56(83)44-40-36-32-28-24-20-16-12-8-4)70(107-109(94,95)96)60(103-73)52-101-76(75(92)93)49-57(84)67(90)69(106-76)58(85)50-79/h53-60,65-74,79-85,90-91H,5-52H2,1-4H3,(H,77,86)(H,78,87)(H,92,93)(H2,94,95,96)(H2,97,98,99)/p-5/t53-,54-,55-,56-,57-,58-,59-,60-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,76+/m1/s1
CAS number: Not Available
IUPAC Name:Not Available
Traditional IUPAC Name: Not Available
SMILES:CCCCCCCCCCCC(O)CC(=O)NC1(C(OP([O-])([O-])=O)OC(C(O)C(OC(CC(O)CCCCCCCCCCC)=O)1)COC2(C(NC(CC(O)CCCCCCCCCCC)=O)C(OC(CC(O)CCCCCCCCCCC)=O)C(C(O2)COC3(C([O-])=O)(O[CH](C(CO)O)C(O)C(O)C3))OP([O-])([O-])=O))
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
  • Acylaminosugar
  • Saccharolipid
  • Hexose phosphate
  • Disaccharide phosphate
  • N-acyl-alpha-hexosamine
  • C-glucuronide
  • C-glycosyl compound
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Tricarboxylic acid or derivatives
  • Beta-hydroxy acid
  • Ketal
  • Fatty acid ester
  • Fatty acyl
  • Fatty amide
  • Alkyl phosphate
  • Hydroxy acid
  • N-acyl-amine
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Pyran
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Alcohol
  • Organic oxide
  • Organic nitrogen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
  • a small molecule (KDO-LIPID-IVA)
Physical Properties
State: Not Available
Charge:-5
Melting point: Not Available
Experimental Properties: Not Available
Predicted Properties
PropertyValueSource
Molecular Weight1620.864 g/molPubChem
XLogP3-AA12.8 PubChem
Hydrogen Bond Donor Count11 PubChem
Hydrogen Bond Acceptor Count30 PubChem
Rotatable Bond Count64 PubChem
Exact Mass1619.873 g/molPubChem
Monoisotopic Mass1619.873 g/molPubChem
Topological Polar Surface Area524 A^2PubChem
Heavy Atom Count110 PubChem
Formal Charge-5 PubChem
Complexity2550 PubChem
Isotope Atom Count0 PubChem
Defined Atom Stereocenter Count19 PubChem
Undefined Atom Stereocenter Count0 PubChem
Defined Bond Stereocenter Count0 PubChem
Undefined Bond Stereocenter Count0 PubChem
Covalently-Bonded Unit Count1 PubChem
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra: Not Available
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
ChEBI60364
IAF12601450230
KEGGC06024
PubChem25246208