P. aeruginosa Metabolome Database: L-Ara4N-modified KDO2-Lipid A (PAMDB001379)

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

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB001379

Identification

Name:

L-Ara4N-modified KDO2-Lipid A

Description:

L-ara4n-modified kdo2-lipid a is a member of the chemical class known as Hexose Oligosaccharides. These are oligosaccharides in which the saccharide units are hexoses.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

α-Kdo-(2→4)-α-Kdo-(2→6)-lipid II_A
α-kdo-(2→4)-α-kdo-(2→6)-lipid iia
a-kdo-(2->4)-a-kdo-(2->6)-lipid a
Alpha-KDO-(2->4)-alpha-KDO-(2->6)-lipid A
L-Ara4n-modified (kdo)2-lipid a
L-Ara4N-modified (KDO)₂-Lipid A
α-kdo-(2->4)-α-kdo-(2->6)-lipid a

Chemical Formula:

C₁₂₀H₂₂₀N₄O₄₅P₂

Average Molecular Weight:

2500.9781

Monoisotopic Molecular Weight:

2499.452484074

InChI Key:

RYVJLJVPSMBXLB-UHFFFAOYSA-N

InChI:

InChI=1S/C120H220N4O45P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-96(135)158-84(66-60-54-48-42-35-29-23-17-11-5)72-98(137)162-112-100(124-94(133)71-83(65-59-53-47-41-34-28-22-16-10-4)157-95(134)67-61-55-49-43-36-30-24-18-12-6)113(160-92(110(112)166-170(149,150)168-115-106(143)101(138)85(121)77-153-115)80-156-119(117(145)146)74-90(104(141)109(164-119)89(131)76-126)163-120(118(147)148)73-87(129)103(140)108(165-120)88(130)75-125)155-79-91-105(142)111(161-97(136)70-82(128)64-58-52-46-40-33-27-21-15-9-3)99(123-93(132)69-81(127)63-57-51-45-39-32-26-20-14-8-2)114(159-91)167-171(151,152)169-116-107(144)102(139)86(122)78-154-116/h81-92,99-116,125-131,138-144H,7-80,121-122H2,1-6H3,(H,123,132)(H,124,133)(H,145,146)(H,147,148)(H,149,150)(H,151,152)

CAS number:

Not Available

IUPAC Name:

2-{[3-({[(5-amino-3,4-dihydroxyoxan-2-yl)oxy](hydroxy)phosphoryl}oxy)-6-{[6-({[(5-amino-3,4-dihydroxyoxan-2-yl)oxy](hydroxy)phosphoryl}oxy)-5-[(1,3-dihydroxytetradecylidene)amino]-3-hydroxy-4-[(3-hydroxytetradecanoyl)oxy]oxan-2-yl]methoxy}-5-{[3-(dodecanoyloxy)-1-hydroxytetradecylidene]amino}-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}-4-{[2-carboxy-6-(1,2-dihydroxyethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-(1,2-dihydroxyethyl)-5-hydroxyoxane-2-carboxylic acid

Traditional IUPAC Name:

2-[(3-{[(5-amino-3,4-dihydroxyoxan-2-yl)oxy(hydroxy)phosphoryl]oxy}-6-[(6-{[(5-amino-3,4-dihydroxyoxan-2-yl)oxy(hydroxy)phosphoryl]oxy}-5-[(1,3-dihydroxytetradecylidene)amino]-3-hydroxy-4-[(3-hydroxytetradecanoyl)oxy]oxan-2-yl)methoxy]-5-{[3-(dodecanoyloxy)-1-hydroxytetradecylidene]amino}-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl)methoxy]-4-{[2-carboxy-6-(1,2-dihydroxyethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-(1,2-dihydroxyethyl)-5-hydroxyoxane-2-carboxylic acid

SMILES:

CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC1C(OP(O)(=O)OC2OCC(N)C(O)C2O)C(COC2(CC(OC3(CC(O)C(O)C(O3)C(O)CO)C(O)=O)C(O)C(O2)C(O)CO)C(O)=O)OC(OCC2OC(OP(O)(=O)OC3OCC(N)C(O)C3O)C(N=C(O)CC(O)CCCCCCCCCCC)C(OC(=O)CC(O)CCCCCCCCCCC)C2O)C1N=C(O)CC(CCCCCCCCCCC)OC(=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

Organooxygen compounds

Class

Carbohydrates and carbohydrate conjugates

Sub Class

Aminosaccharides

Direct Parent

Acylaminosugars

Alternative Parents

Substituents

Oligosaccharide phosphate
Oligosaccharide
Hexacarboxylic acid or derivatives
Acylaminosugar
Saccharolipid
Hexose phosphate
N-acyl-alpha-hexosamine
C-glucuronide
C-glycosyl compound
Glycosyl compound
O-glycosyl compound
Pyran carboxylic acid or derivatives
Pyran carboxylic acid
Beta-hydroxy acid
Fatty acid ester
Ketal
Dialkyl phosphate
Fatty amide
Fatty acyl
Hydroxy acid
N-acyl-amine
Pyran
Alkyl phosphate
Organic phosphate
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Secondary alcohol
Carboxamide group
1,2-diol
Carboxylic acid ester
Secondary carboxylic acid amide
1,2-aminoalcohol
Amino acid
Amino acid or derivatives
Oxacycle
Carboxylic acid amide
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Acetal
Primary amine
Organic oxide
Carbonyl group
Hydrocarbon derivative
Amine
Alcohol
Primary aliphatic amine
Organonitrogen compound
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.0761 mg/mL	ALOGPS
logP	0.62	ALOGPS
logP	17.07	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	1.05	ChemAxon
pKa (Strongest Basic)	9.09	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	41	ChemAxon
Hydrogen Donor Count	22	ChemAxon
Polar Surface Area	774.83 Å²	ChemAxon
Rotatable Bond Count	102	ChemAxon
Refractivity	620.32 m³·mol^-1	ChemAxon
Polarizability	279.18 Å³	ChemAxon
Number of Rings	6	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:

Membrane

Reactions:

KDO2-Lipid A + 4-amino-4-deoxy-α-L-arabinopyranosyl <i>ditrans,octacis</i>-undecaprenyl phosphate > L-Ara4N-modified KDO2-Lipid A + Di-trans,poly-cis-undecaprenyl phosphate

Pathways:

Not Available

Spectra

Spectra:

References

References:

Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882

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	656478
Kegg ID	Not Available
ChemSpider ID	570865
Wikipedia ID	Not Available
BioCyc ID	L-ARA4N-MODIFIED-KDO2-LIPID-A
EcoCyc ID	L-ARA4N-MODIFIED-KDO2-LIPID-A

L-Ara4N-modified KDO2-Lipid A (PAMDB001379)

Structure for L-Ara4N-modified KDO2-Lipid A (PAMDB001379)