Showing Compound LPS core (FDB029471)

Record Information

Version

1.0

Creation date

2011-09-21 01:56:21 UTC

Update date

2015-07-21 06:59:44 UTC

Primary ID

FDB029471

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

LPS core

Description

Lipopolysaccharides (LPS), also known as lipoglycans, are large molecules consisting of a lipid and a polysaccharide joined by a covalent bond; they are found in the outer membrane of Gram-negative bacteria, act as endotoxins and elicit strong immune responses in animals. LPS is the major component of the outer membrane of Gram-negative bacteria, contributing greatly to the structural integrity of the bacteria, and protecting the membrane from certain kinds of chemical attack. LPS also increases the negative charge of the cell membrane and helps stabilize the overall membrane structure. It is of crucial importance to gram negative bacteria, whose death results if it is mutated or removed. LPS is an endotoxin, and induces a strong response from normal animal immune systems. LPS acts as the prototypical endotoxin because it binds the CD14/TLR4/MD2 receptor complex, which promotes the secretion of pro-inflammatory cytokines in many cell types, but especially in macrophages. In Immunology, the term "LPS challenge" refers to the process of exposing a subject to an LPS which may act as a toxin. LPS is also an exogenous pyrogen (external fever-inducing substance). Being of crucial importance to gram negative bacteria, these molecules make candidate targets for new antimicrobial agents. LPS comprises three parts: 1. O antigen (or O polysaccharide). 2. Core polysaccharide. 3. Lipid A LPS Core domain always contains an oligosaccharide component which attaches directly to lipid A and commonly contains sugars such as heptose and 3-deoxy-D-mannooctulosonic Acid (also known as KDO, keto-deoxyoctulosonate).[2] The LPS Cores of many bacteria also contain non-carbohydrate components, such as phosphate, amino acids, and ethanolamine substitutents.(from wiki) This card shows the LPS core component in E.coli. [HMDB]

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Core oligosaccharide	HMDB
Core oligosaccharide lipid a	HMDB
Endotoxin lipopolysaccharide core	HMDB
Endotoxin LPS core	HMDB
Lipopolysaccharide core endotoxin	HMDB
Lipopolysaccharide ra component	HMDB
Ra-LPS	HMDB
core oligosaccharide	hmdb
core oligosaccharide lipid A	hmdb
endotoxin Lipopolysaccharide core	hmdb
endotoxin LPS core	hmdb
Lipopolysaccharide core endotoxin	hmdb
Lipopolysaccharide Ra component	hmdb
LPS core	hmdb

Predicted Properties

Property	Value	Source
logP	1.54	ChemAxon
pKa (Strongest Acidic)	0.4	ChemAxon
Physiological Charge	-10	ChemAxon
Hydrogen Acceptor Count	91	ChemAxon
Hydrogen Donor Count	53	ChemAxon
Polar Surface Area	1673.8 Å²	ChemAxon
Rotatable Bond Count	145	ChemAxon
Refractivity	963.45 m³·mol⁻¹	ChemAxon
Number of Rings	13	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C175H317N5O101P6

IUPAC name

(2R,4R,5S,6R)-5-{[(3S,4R,5R,6R)-5-[({[(2-aminoethoxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]-6-[(1S)-1,2-dihydroxyethyl]-4-{[(3S,4S,5R,6R)-6-[(1S)-2-{[(3S,4R,5S,6R)-6-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxy-5-(phosphonooxy)oxan-2-yl]oxy}-1-hydroxyethyl]-4-{[(3R,4S,5R,6R)-4-{[(2R,3R,4S,5R,6R)-3-{[(3R,4S,5S,6R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-3-hydroxyoxan-2-yl]oxy}-4-{[(2R,4R,5S,6R)-4-{[(2R,4R,5R,6R)-4-{[(2-aminoethoxy)(hydroxy)phosphoryl]oxy}-2-carboxy-6-[(1S)-1,2-dihydroxyethyl]-5-hydroxyoxan-2-yl]oxy}-2-carboxy-6-[(1S)-1,2-dihydroxyethyl]-5-hydroxyoxan-2-yl]oxy}-6-[(1S)-1,2-dihydroxyethyl]-2-{[(2R,3S,4R,5R,6R)-5-[(3R)-3-(dodecanoyloxy)tetradecanamido]-6-{[(2R,3S,4R,5R,6R)-3-hydroxy-5-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-3-(phosphonooxy)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}oxane-2-carboxylic acid

InChI Identifier

InChI=1S/C175H317N5O101P6/c1-8-14-20-26-32-38-39-45-51-57-63-69-118(202)252-98(67-61-55-49-43-36-30-24-18-12-5)77-120(204)261-152-123(180-116(200)76-97(66-60-54-48-42-35-29-23-17-11-4)251-117(201)68-62-56-50-44-37-31-25-19-13-6)160(246-91-112-130(211)151(260-119(203)75-96(192)65-59-53-47-41-34-28-22-16-10-3)122(162(257-112)280-284(236,237)238)179-115(199)74-95(191)64-58-52-46-40-33-27-21-15-9-2)259-114(150(152)277-282(230,231)232)93-248-173(170(224)225)80-107(272-174(171(226)227)78-105(128(209)144(273-174)99(193)81-181)271-175(172(228)229)79-106(276-285(239,240)249-72-70-176)129(210)145(274-175)100(194)82-182)149(148(275-173)103(197)85-185)265-167-142(223)155(159(147(264-167)102(196)84-184)279-287(243,244)281-286(241,242)250-73-71-177)268-166-141(222)154(139(220)143(262-166)104(198)90-245-164-138(219)136(217)156(278-283(233,234)235)146(263-164)101(195)83-183)266-165-140(221)153(131(212)113(258-165)92-247-163-137(218)133(214)125(206)109(87-187)254-163)267-168-158(135(216)127(208)110(88-188)255-168)270-169-157(134(215)126(207)111(89-189)256-169)269-161-121(178-94(7)190)132(213)124(205)108(86-186)253-161/h95-114,121-169,181-189,191-198,205-223H,8-93,176-177H2,1-7H3,(H,178,190)(H,179,199)(H,180,200)(H,224,225)(H,226,227)(H,228,229)(H,239,240)(H,241,242)(H,243,244)(H2,230,231,232)(H2,233,234,235)(H2,236,237,238)/t95-,96-,97-,98-,99+,100+,101+,102+,103+,104+,105-,106-,107-,108-,109-,110-,111-,112-,113-,114-,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?,173-,174-,175-/m1/s1

InChI Key

AAXCQFOXUJMCCW-PETQGJDISA-N

Isomeric SMILES

CCCCCCCCCCCCCC(=O)O[C@H](CCCCCCCCCCC)CC(=O)O[C@@H]1[C@@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[C@H](OC[C@H]2O[C@H](OP(O)(O)=O)[C@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H]2O)O[C@H](CO[C@@]2(C[C@@H](O[C@@]3(C[C@@H](O[C@@]4(C[C@@H](OP(O)(=O)OCCN)[C@H](O)[C@H](O4)[C@@H](O)CO)C(O)=O)[C@H](O)[C@H](O3)[C@@H](O)CO)C(O)=O)[C@H](OC3O[C@H]([C@@H](O)CO)[C@@H](OP(O)(=O)OP(O)(=O)OCCN)[C@H](OC4O[C@H]([C@@H](O)COC5O[C@H]([C@@H](O)CO)[C@@H](OP(O)(O)=O)[C@H](O)[C@@H]5O)[C@@H](O)[C@H](OC5O[C@H](CO[C@H]6O[C@H](CO)[C@H](O)[C@H](O)[C@H]6O)[C@@H](O)[C@H](O[C@H]6O[C@H](CO)[C@H](O)[C@H](O)[C@H]6OC6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6NC(C)=O)[C@H]5O)[C@@H]4O)[C@@H]3O)[C@H](O2)[C@@H](O)CO)C(O)=O)[C@H]1OP(O)(O)=O

Average Molecular Weight

4293.205

Monoisotopic Molecular Weight

4290.824851063

Classification

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Acylaminosugars

Alternative Parents

Substituents

Polysaccharide
Acylaminosugar
Saccharolipid
Hexose phosphate
Fatty acyl glycoside
N-acyl-alpha-hexosamine
C-glucuronide
Alkyl glycoside
C-glycosyl compound
Glycosyl compound
O-glycosyl compound
Organic pyrophosphate
Phosphoethanolamine
Beta-hydroxy acid
Ketal
Fatty acid ester
Dialkyl phosphate
Monoalkyl phosphate
Alkyl phosphate
Pyran
Fatty amide
Hydroxy acid
N-acyl-amine
Fatty acyl
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Acetamide
Secondary carboxylic acid amide
Amino acid or derivatives
Secondary alcohol
Amino acid
Carboxamide group
Carboxylic acid ester
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Primary alcohol
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Primary aliphatic amine
Organonitrogen compound
Primary amine
Organic nitrogen compound
Amine
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Escherichia coli

Biological location:

Biofluid and excreta:

Blood

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-3190100203-6cc73cac6ee8b6f34f63	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01zc-9271311813-15153f67fde929abb801	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006x-9882221311-ce1866014f1c60c8f6d8	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00b9-4091010001-e7a6007021379e3bde15	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9150000010-b9005aa390051477aed9	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-68958ff65e8f5e748306	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-5390000001-8ebe5141e1eab5cf3018	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-6290000000-87d86e5d6a5486d66885	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-2390000000-1fdbe97f25ee14b3fbfb	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002s-6290000000-7794d6721610899d00a8	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004r-6690000000-087ea5541b6888842ac5	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00n0-7890000000-3cbca374d034e492c839	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

C0338

Pubchem Compound ID

53481794

Pubchem Substance ID

Not Available

ChEBI ID

59309

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB13471

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Lipopolysaccharide

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound LPS core (FDB029471)

Structure for FDB029471 (LPS core)