4-Amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A (ECMDB21173) (M2MDB001582)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (6)Transporters (2)XML
Proteins (6)
Record Information
Version2.0
Creation Date2012-07-30 14:54:45 -0600
Update Date2015-06-03 17:20:48 -0600
Secondary Accession Numbers
  • ECMDB21173
Identification
Name:4-Amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A
Description4-amino-4-deoxy-l-arabinose modified core oligosaccharide lipid a belongs to the class of Polyhexoses. These are polysaccharides in which the saccharide units are hexoses. (inferred from compound structure)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 4-amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A
Chemical Formula:C181H314N3O103P4
Weight:Average: 4304.2832
Monoisotopic: 4301.837534177
InChI Key:IOAOXSQGQQYOQU-WSFSDJJVSA-E
InChI:InChI=1S/C181H323N3O103P4/c1-8-14-20-26-32-38-39-45-51-57-63-69-116(206)259-95(67-61-55-49-43-36-30-24-18-12-5)73-118(208)267-157-120(184-114(204)72-94(66-60-54-48-42-35-29-23-17-11-4)258-115(205)68-62-56-50-44-37-31-25-19-13-6)164(253-88-110-127(215)156(266-117(207)71-93(194)65-59-53-47-41-34-28-22-16-10-3)119(165(262-110)286-290(246,247)248)183-113(203)70-92(193)64-58-52-46-40-33-27-21-15-9-2)265-112(155(157)285-291(249,250)287-169-137(225)122(210)96(182)85-251-169)90-256-179(176(234)235)75-105(279-181(178(238)239)76-106(278-180(177(236)237)74-97(195)123(211)148(280-180)100(198)79-187)154(152(282-181)103(201)82-190)272-170-141(229)129(217)121(209)91(7)257-170)153(151(281-179)102(200)81-189)273-173-144(232)159(162(283-288(240,241)242)149(270-173)101(199)80-188)276-174-145(233)160(163(284-289(243,244)245)150(271-174)104(202)86-252-167-139(227)132(220)135(223)146(268-167)98(196)77-185)275-172-143(231)158(128(216)111(264-172)89-254-166-138(226)130(218)124(212)107(83-191)260-166)274-175-161(134(222)125(213)108(84-192)261-175)277-171-142(230)131(219)126(214)109(263-171)87-255-168-140(228)133(221)136(224)147(269-168)99(197)78-186/h91-112,119-175,185-202,209-233H,8-90,182H2,1-7H3,(H,183,203)(H,184,204)(H,234,235)(H,236,237)(H,238,239)(H,249,250)(H2,240,241,242)(H2,243,244,245)(H2,246,247,248)/p-9/t91?,92-,93-,94-,95-,96?,97?,98?,99?,100?,101?,102?,103?,104?,105?,106?,107?,108?,109?,110-,111?,112?,119-,120-,121?,122?,123?,124?,125?,126?,127-,128?,129?,130?,131?,132?,133?,134?,135?,136?,137?,138?,139?,140?,141?,142?,143?,144?,145?,146?,147?,148?,149?,150?,151?,152?,153?,154?,155-,156-,157-,158?,159?,160?,161?,162?,163?,164-,165?,166?,167?,168?,169?,170?,171?,172?,173?,174?,175?,179?,180?,181?/m1/s1
CAS number:Not Available
IUPAC Name:2-{[(3S,4R,5R,6R)-3-({[(5-amino-3,4-dihydroxyoxan-2-yl)oxy](hydroxy)phosphoryl}oxy)-5-{[(3R)-3-(dodecanoyloxy)-1-oxidotetradecylidene]amino}-6-{[(2R,3S,4R,5R)-3-hydroxy-5-{[(3R)-3-hydroxy-1-oxidotetradecylidene]amino}-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}-4-[(2-carboxylato-4-{[2-carboxylato-6-(1,2-dihydroxyethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-(1,2-dihydroxyethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-6-(1,2-dihydroxyethyl)-5-{[6-(1,2-dihydroxyethyl)-4-{[6-(2-{[6-(1,2-dihydroxyethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1-hydroxyethyl)-4-({4-[(3-{[6-({[6-(1,2-dihydroxyethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3,5-dihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl}oxy)-3-hydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}-3-hydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}oxane-2-carboxylate
Traditional IUPAC Name:2-{[(3S,4R,5R,6R)-3-{[(5-amino-3,4-dihydroxyoxan-2-yl)oxy(hydroxy)phosphoryl]oxy}-5-{[(3R)-3-(dodecanoyloxy)-1-oxidotetradecylidene]amino}-6-{[(2R,3S,4R,5R)-3-hydroxy-5-{[(3R)-3-hydroxy-1-oxidotetradecylidene]amino}-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}-4-[(2-carboxylato-4-{[2-carboxylato-6-(1,2-dihydroxyethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-(1,2-dihydroxyethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-6-(1,2-dihydroxyethyl)-5-{[6-(1,2-dihydroxyethyl)-4-{[6-(2-{[6-(1,2-dihydroxyethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1-hydroxyethyl)-4-({4-[(3-{[6-({[6-(1,2-dihydroxyethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3,5-dihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl}oxy)-3-hydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}-3-hydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}oxane-2-carboxylate
SMILES:[H][C@@](O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO[C@]2([H])OC([H])(COC3(CC([H])(OC4(CC([H])(OC5(CC([H])(O)C([H])(O)C([H])(O5)C([H])(O)CO)C([O-])=O)C([H])(OC5([H])OC([H])(C)C([H])(O)C([H])(O)C5([H])O)C([H])(O4)C([H])(O)CO)C([O-])=O)C([H])(OC4([H])OC([H])(C([H])(O)CO)C([H])(OP([O-])([O-])=O)C([H])(OC5([H])OC([H])(C([H])(O)COC6([H])OC([H])(C([H])(O)CO)C([H])(O)C([H])(O)C6([H])O)C([H])(OP([O-])([O-])=O)C([H])(OC6([H])OC([H])(COC7([H])OC([H])(CO)C([H])(O)C([H])(O)C7([H])O)C([H])(O)C([H])(OC7([H])OC([H])(CO)C([H])(O)C([H])(O)C7([H])OC7([H])OC([H])(COC8([H])OC([H])(C([H])(O)CO)C([H])(O)C([H])(O)C8([H])O)C([H])(O)C([H])(O)C7([H])O)C6([H])O)C5([H])O)C4([H])O)C([H])(O3)C([H])(O)CO)C([O-])=O)[C@@]([H])(OP(O)(=O)OC3([H])OCC([H])(N)C([H])(O)C3([H])O)[C@]([H])(OC(=O)C[C@@]([H])(CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@]2([H])N=C([O-])C[C@@]([H])(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)OC([H])(OP(O)(O)=O)[C@]1([H])N=C([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
  • Polysaccharide
  • Saccharolipid
  • Acylaminosugar
  • Hexose phosphate
  • N-acyl-alpha-hexosamine
  • Fatty acyl glycoside
  • C-glucuronide
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • C-glycosyl compound
  • Ketal
  • Dialkyl phosphate
  • Fatty acid ester
  • Beta-hydroxy acid
  • Fatty acyl
  • Alkyl phosphate
  • Pyran
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • N-acyl-amine
  • Hydroxy acid
  • Fatty amide
  • Amino acid
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid salt
  • Carboxylic acid ester
  • Carboxamide group
  • Amino acid or derivatives
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Primary amine
  • Primary alcohol
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Organic anion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-8
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
logP1.99ChemAxon
pKa (Strongest Acidic)0.22ChemAxon
Physiological Charge-8ChemAxon
Hydrogen Acceptor Count97ChemAxon
Hydrogen Donor Count47ChemAxon
Polar Surface Area1718.14 ŲChemAxon
Rotatable Bond Count139ChemAxon
Refractivity1020.58 m³·mol⁻¹ChemAxon
Number of Rings15ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + Water + 4-Amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A > ADP + Hydrogen ion + Phosphate + 4-Amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A
Adenosine triphosphate + Water + 4-Amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A > ADP + Hydrogen ion + Phosphate + 4-Amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A
core oligosaccharide lipid A + undecaprenyl phosphate-4-amino-4-deoxy-L-arabinose > 4-Amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A + Undecaprenyl phosphate
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:Not Available
References
References:
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID46173480
Kegg IDNot Available
ChemSpider ID57
Wikipedia IDNot Available
BioCyc IDCPD0-2293
EcoCyc IDCPD0-2293

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.
Protein Details
2. Lipopolysaccharide export system permease protein lptG
General function:
Involved in lipopolysaccharide transport
Specific function:
Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
Gene Name:
lptG
Uniprot ID:
P0ADC6
Molecular weight:
39618
Protein Details
3. Lipopolysaccharide export system permease protein lptF
General function:
Involved in lipopolysaccharide-transporting ATPase acti
Specific function:
Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
Gene Name:
lptF
Uniprot ID:
P0AF98
Molecular weight:
40357
Protein Details
4. Lipopolysaccharide export system ATP-binding protein lptB
General function:
Involved in nucleotide binding
Specific function:
Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane. Probably responsible for energy coupling to the transport system
Gene Name:
lptB
Uniprot ID:
P0A9V1
Molecular weight:
26800
Protein Details
5. Lipopolysaccharide export system protein lptC
General function:
Involved in lipopolysaccharide transmembrane transporter activity
Specific function:
Required for the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
Gene Name:
lptC
Uniprot ID:
P0ADV9
Molecular weight:
21703
Protein Details
6. Lipopolysaccharide export system protein lptA
General function:
Involved in lipopolysaccharide binding
Specific function:
Required for the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane. May act as a chaperone that facilitates LPS transfer across the aquaeous environment of the periplasm. Interacts specifically with the lipid A domain of LPS
Gene Name:
lptA
Uniprot ID:
P0ADV1
Molecular weight:
20127

Transporters

Protein Details
1. Lipopolysaccharide export system permease protein lptG
General function:
Involved in lipopolysaccharide transport
Specific function:
Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
Gene Name:
lptG
Uniprot ID:
P0ADC6
Molecular weight:
39618
Protein Details
2. Lipopolysaccharide export system permease protein lptF
General function:
Involved in lipopolysaccharide-transporting ATPase acti
Specific function:
Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
Gene Name:
lptF
Uniprot ID:
P0AF98
Molecular weight:
40357