Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001582
Identification
Name: 4-Amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A
Description:4-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
Synonyms:
  • 4-amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A
Chemical Formula: C181H314N3O103P4
Average Molecular Weight: 4304.2832
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as polysaccharides. These are compounds containing more than ten saccharide units.
Kingdom Organic compounds
Super ClassOrganic Polymers
Class Polysaccharides
Sub ClassNot Available
Direct Parent Polysaccharides
Alternative Parents
Substituents
  • Polysaccharide
  • Saccharolipid
  • Hexose phosphate
  • N-acyl-alpha-hexosamine
  • Fatty acyl glycoside
  • C-glucuronide
  • Alkyl glycoside
  • Glycosyl compound
  • C-glycosyl compound
  • O-glycosyl compound
  • Pyran carboxylic acid or derivatives
  • Pyran carboxylic acid
  • Monoalkyl phosphate
  • Ketal
  • Beta-hydroxy acid
  • Dialkyl phosphate
  • Fatty acid ester
  • Hydroxy acid
  • Pyran
  • Alkyl phosphate
  • Phosphoric acid ester
  • Fatty acyl
  • Organic phosphate
  • Organic phosphoric acid derivative
  • 1,2-aminoalcohol
  • 1,2-diol
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid ester
  • Carboxylic acid salt
  • Secondary alcohol
  • Polyol
  • Organoheterocyclic compound
  • Carboxylic acid
  • Acetal
  • Oxacycle
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Organonitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Amine
  • Primary amine
  • Primary alcohol
  • Primary aliphatic amine
  • Organic anion
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors Not 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 Å2ChemAxon
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:
Pathways: Not Available
Spectra
Spectra:
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

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
Locus Tag:
PA3556
Molecular weight:
61.7 kDa
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.
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
Locus Tag:
PA3827
Molecular weight:
39.2 kDa
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
Locus Tag:
PA3828
Molecular weight:
41.3 kDa
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
Locus Tag:
PA4461
Molecular weight:
26.5 kDa
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
Locus Tag:
PA4459
Molecular weight:
21.4 kDa
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
Locus Tag:
PA0005
Molecular weight:
28.7 kDa

Transporters

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
Locus Tag:
PA3827
Molecular weight:
39.2 kDa
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
Locus Tag:
PA3828
Molecular weight:
41.3 kDa