Lipid IIA (PAMDB005112)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB005112
Identification
Name: Lipid IIA
Description:A lipid A derivative in which the phospho group at the anomeric carbon is esterified with a 4-amino-4-deoxy-β-L-arabinopyranosyl group
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 4-amino-4-Deoxy-b-L-arabinopyranosyl 2-deoxy-6-O-(2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-4-O-phosphono-b-D-glucopyranosyl)-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-a-D-glucopyranosyl hydrogen phosphate
  • 4-amino-4-Deoxy-b-L-arabinopyranosyl 2-deoxy-6-O-(2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-4-O-phosphono-b-D-glucopyranosyl)-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-a-D-glucopyranosyl hydrogen phosphoric acid
  • 4-amino-4-Deoxy-beta-L-arabinopyranosyl 2-deoxy-6-O-(2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-4-O-phosphono-beta-D-glucopyranosyl)-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-alpha-D-glucopyranosyl hydrogen phosphate
  • 4-amino-4-Deoxy-beta-L-arabinopyranosyl 2-deoxy-6-O-(2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-4-O-phosphono-beta-D-glucopyranosyl)-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-alpha-D-glucopyranosyl hydrogen phosphoric acid
  • 4-amino-4-Deoxy-β-L-arabinopyranosyl 2-deoxy-6-O-(2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-4-O-phosphono-β-D-glucopyranosyl)-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-α-D-glucopyranosyl hydrogen phosphate
  • 4-amino-4-Deoxy-β-L-arabinopyranosyl 2-deoxy-6-O-(2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-4-O-phosphono-β-D-glucopyranosyl)-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-α-D-glucopyranosyl hydrogen phosphoric acid
Chemical Formula: C73H139N3O26P2
Average Molecular Weight: 1536.858
Monoisotopic Molecular Weight: 1535.912205604
InChI Key: TYGQMXOPLFWYPM-ISFHUDAKSA-N
InChI:InChI=1S/C73H139N3O26P2/c1-5-9-13-17-21-25-29-33-37-41-52(78)45-59(82)75-63-69(98-61(84)47-54(80)43-39-35-31-27-23-19-15-11-7-3)66(87)58(97-72(63)101-104(92,93)102-73-67(88)65(86)56(74)50-94-73)51-95-71-64(76-60(83)46-53(79)42-38-34-30-26-22-18-14-10-6-2)70(68(57(49-77)96-71)100-103(89,90)91)99-62(85)48-55(81)44-40-36-32-28-24-20-16-12-8-4/h52-58,63-73,77-81,86-88H,5-51,74H2,1-4H3,(H,75,82)(H,76,83)(H,92,93)(H2,89,90,91)/t52-,53-,54-,55-,56+,57-,58-,63-,64-,65+,66-,67-,68-,69-,70-,71-,72-,73-/m1/s1
CAS number: Not Available
IUPAC Name:{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-6-[({[(2R,3R,4S,5S)-5-amino-3,4-dihydroxyoxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]-3-hydroxy-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]methoxy}-2-(hydroxymethyl)-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name: lipid iia
SMILES:CCCCCCCCCCC[C@@H](O)CC(=O)N[C@H]1[C@@H](OP(O)(=O)O[C@H]2OC[C@H](N)[C@H](O)[C@H]2O)O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](OP(O)(O)=O)[C@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@H]2NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](O)[C@@H]1OC(=O)C[C@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
  • Hexose phosphate
  • Disaccharide phosphate
  • N-acyl-alpha-hexosamine
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Fatty acid ester
  • Dialkyl phosphate
  • Monoalkyl phosphate
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Hydroxy acid
  • Alkyl phosphate
  • Organic phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Secondary alcohol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • 1,2-aminoalcohol
  • 1,2-diol
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Propargyl-type 1,3-dipolar organic compound
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Primary amine
  • Carbonyl group
  • Organic oxide
  • Primary alcohol
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • 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 Solubility0.029 mg/mLALOGPS
logP4.58ALOGPS
logP10.01ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)0.64ChemAxon
pKa (Strongest Basic)8.79ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area458.1 Å2ChemAxon
Rotatable Bond Count64ChemAxon
Refractivity385.44 m3·mol-1ChemAxon
Polarizability173.16 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
undecaprenyl phosphate-4-amino-4-deoxy-L-arabinose + KDO2-Lipid A + 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate <> alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + Di-trans,poly-cis-undecaprenyl phosphate + Lipid IIA
Pathways:
  • Cationic antimicrobial peptide (CAMP) resistance pae01503
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0329170000-745e3dca9b61fc4d2d93View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-0294050000-5752a53a672d229d7dd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a70-4549110000-3112332694133528dc00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00vi-9372141200-18e000058f99622278c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ou-9054141010-8d1df109070e04f06a7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-9061110014-b68f54f3f7a4b65e3cbcView in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID61735
HMDB IDNot Available
Pubchem Compound ID51351717
Kegg IDC19884
ChemSpider ID26332343
Wikipedia IDNot Available
BioCyc IDNot Available