P. aeruginosa Metabolome Database: 4-Amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A (PAMDB001582)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB001582

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

🔍MOL SDF PDB SMILES InChI View Structure

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 Description

This compound belongs to the class of organic compounds known as polysaccharides. These are compounds containing more than ten saccharide units.

Kingdom

Organic compounds

Super Class

Organic Polymers

Class

Polysaccharides

Sub Class

Not 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:

Property	Value	Source

Predicted Properties

Property	Value	Source
logP	1.99	ChemAxon
pKa (Strongest Acidic)	0.22	ChemAxon
Physiological Charge	-8	ChemAxon
Hydrogen Acceptor Count	97	ChemAxon
Hydrogen Donor Count	47	ChemAxon
Polar Surface Area	1718.14 Å²	ChemAxon
Rotatable Bond Count	139	ChemAxon
Refractivity	1020.58 m³·mol^-1	ChemAxon
Number of Rings	15	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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

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

Links

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	Not Available
Pubchem Compound ID	46173480
Kegg ID	Not Available
ChemSpider ID	57
Wikipedia ID	Not Available
BioCyc ID	CPD0-2293
EcoCyc ID	CPD0-2293

Enzymes

Protein Details

• 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
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.

Protein Details

• 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
Locus Tag:: PA3827
Molecular weight:: 39.2 kDa

Protein Details

• 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
Locus Tag:: PA3828
Molecular weight:: 41.3 kDa

Protein Details

• 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
Locus Tag:: PA4461
Molecular weight:: 26.5 kDa

Protein Details

• 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
Locus Tag:: PA4459
Molecular weight:: 21.4 kDa

Protein Details

• 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
Locus Tag:: PA0005
Molecular weight:: 28.7 kDa

Transporters

Protein Details

• 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
Locus Tag:: PA3827
Molecular weight:: 39.2 kDa

Protein Details

• 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
Locus Tag:: PA3828
Molecular weight:: 41.3 kDa

4-Amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A (PAMDB001582)

Structure for 4-Amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A (PAMDB001582)

Enzymes

Reactions

Transporters