P. aeruginosa Metabolome Database: lipid A-core (PAMDB120486)

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

PAMDB120486

Identification

Name:

lipid A-core

Description:

A lipid A oxoanion obtained via deprotonation of the carboxy and phosphate OH groups of lipid A-core.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

Not Available

Chemical Formula:

C₁₆₂H₂₈₂N₂O₈₉P₄

Average Molecular Weight:

3805.865

Monoisotopic Molecular Weight:

3813.7334

InChI Key:

CEMLXOTXCUORFY-UHNYCSQFSA-D

InChI:

InChI=1S/C162H292N2O89P4/c1-7-13-19-25-31-37-38-44-50-56-62-68-108(184)229-90(66-60-54-48-42-35-29-23-17-11-5)72-110(186)237-142-112(164-106(182)71-89(65-59-53-47-41-34-28-22-16-10-4)228-107(183)67-61-55-49-43-36-30-24-18-12-6)149(224-84-102-117(191)141(236-109(185)70-88(173)64-58-52-46-40-33-27-21-15-9-3)111(150(232-102)253-257(220,221)222)163-105(181)69-87(172)63-57-51-45-39-32-26-20-14-8-2)235-104(140(142)250-254(211,212)213)86-227-161(159(207)208)74-98(247-162(160(209)210)73-91(174)113(187)135(248-162)94(177)77-167)139(138(249-161)96(179)79-169)242-156-131(205)144(147(251-255(214,215)216)136(240-156)95(178)78-168)245-157-132(206)145(148(252-256(217,218)219)137(241-157)97(180)82-223-152-127(201)121(195)124(198)133(238-152)92(175)75-165)244-155-130(204)143(118(192)103(234-155)85-225-151-126(200)119(193)114(188)99(80-170)230-151)243-158-146(123(197)115(189)100(81-171)231-158)246-154-129(203)120(194)116(190)101(233-154)83-226-153-128(202)122(196)125(199)134(239-153)93(176)76-166/h87-104,111-158,165-180,187-206H,7-86H2,1-6H3,(H,163,181)(H,164,182)(H,207,208)(H,209,210)(H2,211,212,213)(H2,214,215,216)(H2,217,218,219)(H2,220,221,222)/p-10/t87-,88-,89-,90-,91-,92+,93+,94?,95+,96-,97+,98-,99-,100-,101-,102-,103-,104-,111-,112-,113-,114+,115-,116-,117-,118-,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?,161-,162-/m1/s1

CAS number:

Not Available

IUPAC Name:

Not Available

Traditional IUPAC Name:

Not Available

SMILES:

CCCCCCCCCCCCCC(=O)OC(CC(OC2(C(C(OCC1(OC(OP([O-])([O-])=O)C(NC(=O)CC(O)CCCCCCCCCCC)C(OC(=O)CC(O)CCCCCCCCCCC)C(O)1))OC(C2OP([O-])([O-])=O)COC%12(C([O-])=O)(OC(C(O)CO)C(OC%10(OC(C(CO)O)C(C(OC9(OC(C(COC3(OC(C(CO)O)C(C(O)C3O)O))O)C(C(OC5(C(C(C(C(COC4(OC(CO)C(O)C(O)C(O)4))O5)O)OC6(C(C(C(C(CO)O6)O)O)OC8(C(O)C(C(C(COC7(OC(C(CO)O)C(C(O)C7O)O))O8)O)O)))O))C9O)OP([O-])(=O)[O-]))C%10O)OP([O-])(=O)[O-]))C(OC%11(C(=O)[O-])(OC(C(O)CO)C(O)C(O)C%11))C%12))NC(CC(CCCCCCCCCCC)OC(CCCCCCCCCCC)=O)=O))=O)CCCCCCCCCCC

Chemical Taxonomy

Taxonomy Description

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

-10

Melting point:

Not Available

Experimental Properties:

Not Available

Predicted Properties

Property	Value	Source
Molecular Weight	3808.882 g/mol	PubChem
XLogP3-AA	1.7	PubChem
Hydrogen Bond Donor Count	40	PubChem
Hydrogen Bond Acceptor Count	89	PubChem
Rotatable Bond Count	125	PubChem
Exact Mass	3807.682 g/mol	PubChem
Monoisotopic Mass	3806.679 g/mol	PubChem
Topological Polar Surface Area	1470 A^2	PubChem
Heavy Atom Count	257	PubChem
Formal Charge	-9	PubChem
Complexity	7230	PubChem
Isotope Atom Count	0	PubChem
Defined Atom Stereocenter Count	53	PubChem
Undefined Atom Stereocenter Count	15	PubChem
Defined Bond Stereocenter Count	0	PubChem
Undefined Bond Stereocenter Count	0	PubChem
Covalently-Bonded Unit Count	1	PubChem

Biological Properties

Cellular Locations:

Not Available

Reactions:

lipid A-core + O-Antigens → Lipopolysaccharides + Water
lipid A-core + colanic acid → MLPS + Water
galactosyl-(glucosyl)3-(heptosyl)3-Kdo2-lipid A-bisphosphate + ADP-L-glycero-beta-D-manno-heptose → Hydrogen ion + lipid A-core + ADP

Pathways:

Lipid A-core biosynthesisLIPA-CORESYN-PWY
superpathway of lipopolysaccharide biosynthesisLPSSYN-PWY

Spectra

Spectra:

Not Available

References

References:

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI	62004
PUBCHEM	44229197

lipid A-core (PAMDB120486)

Structure for lipid A-core (PAMDB120486)