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Lipid IIA (M2MDB005112)

Record Information
Version2.0
Creation Date2015-06-05 09:59:07 -0600
Update Date2015-08-05 16:22:05 -0600
Secondary Accession Numbers
  • ECMDB23844
Identification
Name:Lipid IIA
DescriptionA 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
MOLSDFPDBSMILESInChI
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
Weight:Average: 1536.858
Monoisotopic: 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
Description 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Acylaminosugar
  • Saccharolipid
  • Hexose phosphate
  • N-acyl-alpha-hexosamine
  • Disaccharide phosphate
  • Disaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Beta-hydroxy acid
  • Fatty acid ester
  • Dialkyl phosphate
  • Monoalkyl phosphate
  • Fatty amide
  • Alkyl phosphate
  • Hydroxy acid
  • Phosphoric acid ester
  • Oxane
  • N-acyl-amine
  • Organic phosphoric acid derivative
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • 1,2-aminoalcohol
  • Amino acid or derivatives
  • Carboxamide group
  • Carboxylic acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Primary amine
  • Primary alcohol
  • Primary aliphatic amine
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.029 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count64ChemAxon
Refractivity385.44 m³·mol⁻¹ChemAxon
Polarizability173.16 ųChemAxon
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
undecaprenyl phosphate-4-amino-4-deoxy-L-arabinose + KDO2-Lipid A + 2 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
SMPDB Pathways:Not Available
KEGG Pathways:
  • Cationic antimicrobial peptide (CAMP) resistance eco01503
EcoCyc Pathways:Not Available
Concentrations
Not Available
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 IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Undecaprenyl phosphate-alpha-4-amino-4-deoxy-L-arabinose arabinosyl transferase
General function:
Involved in transferase activity, transferring pentosyl groups
Specific function:
Catalyzes the transfer of the L-Ara4N moiety of the glycolipid undecaprenyl phosphate-alpha-L-Ara4N to lipid A. The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides
Gene Name:
arnT
Uniprot ID:
P76473
Molecular weight:
62542
Reactions
4-amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate + lipid IV(A) = lipid II(A) + di-trans,octa-cis-undecaprenyl phosphate.