ChemFOnt: Showing chemical card for Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate (CFc000007837)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:22 UTC

Chemfont ID

CFc000007837

Molecule Identification

Common Name

Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate

Definition

Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate is synthesized on the cytoplasmic side of the membrane. It is then translocated to the periplasmic side of the membrane by the flippase, where assembly of the polysaccharide chains occurs by a block-polymerization mechanism. The polysaccharide chains are then transferred to an as yet unidentified glyceride acceptor to yield ECAPG. Completed ECAPG polymers are then incorporated into the exterior leaflet of the outer membrane (PMID: 12621029 ). Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate + dTDP-4-acetamido-4,6-dideoxy-D-galactose = undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate + dTDP.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronic acid-4-acetamido-4,6-dideoxy-D-galactose pyrophosphoric acid	Generator
C55-PP-GlcNAc-mannaca-fuc4nac	HMDB
Lipid III	HMDB
ManNAcA-glcnac-fuc4nac-PP-lipid	HMDB
ManNAcA-glcnac-fuc4nac-pyrophosphorylundecaprenol	HMDB
Undecaprenyl-diphospho N-acetylglucosamine-N-acetylmannosaminuronate-N-acetamido-4,6-dideoxy-D-galactose	HMDB
Ceramide nonasaccharide	MeSH, HMDB

Chemical Formula

C₇₉H₁₂₉N₃O₂₂P₂

Average Molecular Weight

1534.824

Monoisotopic Molecular Weight

1533.854295851

IUPAC Name

(2S,3S,4R,5S,6R)-5-acetamido-3-{[(2R,3R,4S,6R)-5-acetamido-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-5-acetamido-4-hydroxy-6-{[hydroxy({[hydroxy({[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxy})phosphoryl]oxy})phosphoryl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-4-hydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4R,5S,6R)-5-acetamido-3-{[(2R,3R,4S,6R)-5-acetamido-3,4-dihydroxy-6-methyloxan-2-yl]oxy}-6-{[(2R,3S,4R,5R,6R)-5-acetamido-4-hydroxy-6-{[hydroxy({hydroxy[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxyphosphoryl}oxy)phosphoryl]oxy}-2-(hydroxymethyl)oxan-3-yl]oxy}-4-hydroxyoxane-2-carboxylic acid

CAS Registry Number

None

SMILES

OC[C@H]1O[C@H](OP(=O)(O)OP(=O)(O)OC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)[C@H](NC(C)=O)[C@@H](O)[C@@H]1O[C@@H]1O[C@H](C(=O)O)[C@@H](O[C@H]2O[C@H](C)C(NC(C)=O)[C@H](O)[C@H]2O)[C@H](O)[C@@H]1NC(=O)C

InChI Identifier

InChI=1S/C79H129N3O22P2/c1-50(2)27-17-28-51(3)29-18-30-52(4)31-19-32-53(5)33-20-34-54(6)35-21-36-55(7)37-22-38-56(8)39-23-40-57(9)41-24-42-58(10)43-25-44-59(11)45-26-46-60(12)47-48-97-105(93,94)104-106(95,96)103-78-68(82-64(16)86)70(88)73(65(49-83)99-78)100-77-67(81-63(15)85)71(89)74(75(102-77)76(91)92)101-79-72(90)69(87)66(61(13)98-79)80-62(14)84/h27,29,31,33,35,37,39,41,43,45,47,61,65-75,77-79,83,87-90H,17-26,28,30,32,34,36,38,40,42,44,46,48-49H2,1-16H3,(H,80,84)(H,81,85)(H,82,86)(H,91,92)(H,93,94)(H,95,96)/b51-29+,52-31+,53-33+,54-35+,55-37+,56-39+,57-41+,58-43+,59-45+,60-47+/t61-,65-,66?,67+,68-,69+,70-,71-,72-,73-,74+,75+,77-,78-,79-/m1/s1

InChI Key

PSONHUYFSWYIME-JNYPHZTQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as polyprenyl phospho carbohydrates. These are polyprenyl phosphates with a carbohydrate moiety attached to it.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Polyprenols

Direct Parent

Polyprenyl phospho carbohydrates

Alternative Parents

Substituents

Polyterpenoid
Bactoprenol diphosphate
Polyprenyl phospho carbohydrate
Oligosaccharide phosphate
Polyprenyl monophosphate
Oligosaccharide
Polyprenyl phosphate skeleton
N-acyl-alpha-hexosamine
Glycosyl compound
O-glycosyl compound
Isoprenoid phosphate
Organic pyrophosphate
Monoalkyl phosphate
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Alkyl phosphate
Pyran
Acetamide
Secondary alcohol
Carboxamide group
Secondary carboxylic acid amide
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Acetal
Organopnictogen compound
Alcohol
Organic oxygen compound
Organic nitrogen compound
Primary alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012307)

Source

Endogenous

Endogenous (HMDB: HMDB0012307)

Animal

Animal (HMDB: HMDB0012307)

Exogenous

Food

Food (HMDB: HMDB0012307)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0012307)

Process

Role

Biological role

Energy source (HMDB: HMDB0012307)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012307)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.003 g/L	ALOGPS
logP	6.83	ALOGPS
logP	11.82	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	1.72	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	374.19 Å²	ChemAxon
Rotatable Bond Count	46	ChemAxon
Refractivity	415.75 m³·mol⁻¹	ChemAxon
Polarizability	172.9 Å³	ChemAxon
Number of Rings	3	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

HMDB0012307

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028930

KNApSAcK ID

Not Available

Chemspider ID

35032433

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481400

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate (CFc000007837)

MOL for CFc000007837 (Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate)

3D MOL for CFc000007837 (Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate)

3D SDF for CFc000007837 (Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate)

3D-SDF for CFc000007837 (Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate)

PDB for CFc000007837 (Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate)

3D PDB for CFc000007837 (Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate)

SMILES for CFc000007837 (Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate)

INCHI for CFc000007837 (Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate)

Structure for CFc000007837 (Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate)

3D Structure for CFc000007837 (Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate)