P. aeruginosa Metabolome Database: α-Kdo-(2→6)-lipid IV<sub>A</sub> (PAMDB110367)

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

PAMDB110367

Identification

Name:

α-Kdo-(2→6)-lipid IV_A

Description:

(KDO)-lipid IV_A deprotonated at both phosphono groups and at the uronic acid carboxy group. It is the major species at pH 7.3.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

3-Deoxy-D-manno-octulosonyl-lipid IV(A)
3-deoxy-α-D-manno-oct-2-ulopyranosyl-(2->6)-2-deoxy-2-{[(3R)-3-hydroxypentadecanoyl]amino}-3-O-[(3R)-3-hydroxytetradecanoyl]-4-O-phosphono-β-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-{[(3R)-3-hydroxytetradecanoyl]amino}-1-O-phosphono-α-D-glucopyranose
(KDO)-lipid IV_A

Chemical Formula:

C₇₆H₁₃₇N₂O₃₀P₂

Average Molecular Weight:

1620.9

Monoisotopic Molecular Weight:

1624.9122642516

InChI Key:

GPNCBCJEDRRCDW-XFULRARUSA-I

InChI:

InChI=1S/C76H142N2O30P2/c1-5-9-13-17-21-25-29-33-37-41-53(80)45-61(86)77-65-71(104-63(88)47-55(82)43-39-35-31-27-23-19-15-11-7-3)68(91)59(102-74(65)108-110(97,98)99)51-100-73-66(78-62(87)46-54(81)42-38-34-30-26-22-18-14-10-6-2)72(105-64(89)48-56(83)44-40-36-32-28-24-20-16-12-8-4)70(107-109(94,95)96)60(103-73)52-101-76(75(92)93)49-57(84)67(90)69(106-76)58(85)50-79/h53-60,65-74,79-85,90-91H,5-52H2,1-4H3,(H,77,86)(H,78,87)(H,92,93)(H2,94,95,96)(H2,97,98,99)/p-5/t53-,54-,55-,56-,57-,58-,59-,60-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,76+/m1/s1

CAS number:

Not Available

IUPAC Name:

Not Available

Traditional IUPAC Name:

Not Available

SMILES:

CCCCCCCCCCCC(O)CC(=O)NC1(C(OP([O-])([O-])=O)OC(C(O)C(OC(CC(O)CCCCCCCCCCC)=O)1)COC2(C(NC(CC(O)CCCCCCCCCCC)=O)C(OC(CC(O)CCCCCCCCCCC)=O)C(C(O2)COC3(C([O-])=O)(O[CH](C(CO)O)C(O)C(O)C3))OP([O-])([O-])=O))

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

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

a small molecule (KDO-LIPID-IVA)

Physical Properties

State:

Not Available

Charge:

-5

Melting point:

Not Available

Experimental Properties:

Not Available

Predicted Properties

Property	Value	Source
Molecular Weight	1620.864 g/mol	PubChem
XLogP3-AA	12.8	PubChem
Hydrogen Bond Donor Count	11	PubChem
Hydrogen Bond Acceptor Count	30	PubChem
Rotatable Bond Count	64	PubChem
Exact Mass	1619.873 g/mol	PubChem
Monoisotopic Mass	1619.873 g/mol	PubChem
Topological Polar Surface Area	524 A^2	PubChem
Heavy Atom Count	110	PubChem
Formal Charge	-5	PubChem
Complexity	2550	PubChem
Isotope Atom Count	0	PubChem
Defined Atom Stereocenter Count	19	PubChem
Undefined Atom Stereocenter Count	0	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:

Pathways:

KDO₂-lipid A and peptidoglycan biosynthesisKDO-PEP-LIPASYN-PWY
superpathway of (Kdo)₂-lipid A biosynthesisKDO-NAGLIPASYN-PWY
Kdo transfer to lipid IV_A (E. coli)KDOSYN-PWY
superpathway of lipopolysaccharide biosynthesisLPSSYN-PWY

Spectra

Spectra:

Not Available

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
ChEBI	60364
IAF1260	1450230
KEGG	C06024
PubChem	25246208

α-Kdo-(2→6)-lipid IVA (PAMDB110367)

Structure for α-Kdo-(2→6)-lipid IVA (PAMDB110367)

α-Kdo-(2→6)-lipid IV_A (PAMDB110367)

Structure for α-Kdo-(2→6)-lipid IV_A (PAMDB110367)