ChemFOnt: Showing chemical card for LPS core (CFc000008387)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:07 UTC

Chemfont ID

CFc000008387

Molecule Identification

Common Name

LPS core

Definition

2386

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	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

Chemical Formula

C₁₇₅H₃₁₇N₅O₁₀₁P₆

Average Molecular Weight

4293.205

Monoisotopic Molecular Weight

4290.824851063

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

Traditional 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

CAS Registry Number

None

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

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

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.

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

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 14754910)

Source

Exogenous

Exogenous (HMDB: HMDB0013471)

Endogenous

Microbe

Process

Naturally occurring process

Biological process

Biochemical pathway

Protein pathway

Succinate Signalling (PathBank: SMP0120917)
Toll-Like Receptor Pathway 2 (PathBank: SMP0120937)

Role

Not Available

Physical Properties

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

External Links

HMDB ID

HMDB0013471

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029471

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

c0338

BioCyc ID

CPD0-2271

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481794

PDB ID

Not Available

ChEBI ID

59309

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for LPS core (CFc000008387)

MOL for CFc000008387 (LPS core)

3D MOL for CFc000008387 (LPS core)

3D SDF for CFc000008387 (LPS core)

3D-SDF for CFc000008387 (LPS core)

PDB for CFc000008387 (LPS core)

3D PDB for CFc000008387 (LPS core)

SMILES for CFc000008387 (LPS core)

INCHI for CFc000008387 (LPS core)

Structure for CFc000008387 (LPS core)

3D Structure for CFc000008387 (LPS core)