ChemFOnt: Showing chemical card for Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate (CFc000007836)

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

CFc000007836

Molecule Identification

Common Name

Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate

Definition

UDP-N-acetyl-β-D-mannosaminouronate + undecaprenyl-N-acetyl-α-D-glucosaminyl-pyrophosphate = undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate + UDP.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronic acid pyrophosphoric acid	Generator
C55-PP-GlcNAc-mannaca	HMDB
Lipid II	HMDB
ManNAcA-glcnac-PP-lipid	HMDB
ManNAcA-glcnac-pyrophosphorylundecaprenol	HMDB
Undecaprenyl-diphospho-N-acetylglucosamine-N-acetylmannosaminuronate	HMDB
Muramyl-nac-(pentapeptide)pyrophosphoryl-undecaprenol	MeSH, HMDB
MPPPUP	MeSH, HMDB
Lipid II, peptidoglycan precursor	MeSH, HMDB

Chemical Formula

C₇₁H₁₁₆N₂O₁₈P₂

Average Molecular Weight

1347.6309

Monoisotopic Molecular Weight

1346.769837942

IUPAC Name

(2S,3S,4R,5S,6R)-5-acetamido-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}-3,4-dihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4R,5S,6R)-5-acetamido-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}-3,4-dihydroxyoxane-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](O)[C@@H]1NC(=O)C

InChI Identifier

InChI=1S/C71H116N2O18P2/c1-48(2)25-15-26-49(3)27-16-28-50(4)29-17-30-51(5)31-18-32-52(6)33-19-34-53(7)35-20-36-54(8)37-21-38-55(9)39-22-40-56(10)41-23-42-57(11)43-24-44-58(12)45-46-86-92(82,83)91-93(84,85)90-71-63(73-60(14)76)65(78)67(61(47-74)87-71)88-70-62(72-59(13)75)64(77)66(79)68(89-70)69(80)81/h25,27,29,31,33,35,37,39,41,43,45,61-68,70-71,74,77-79H,15-24,26,28,30,32,34,36,38,40,42,44,46-47H2,1-14H3,(H,72,75)(H,73,76)(H,80,81)(H,82,83)(H,84,85)/b49-27+,50-29+,51-31+,52-33+,53-35+,54-37+,55-39+,56-41+,57-43+,58-45+/t61-,62+,63-,64-,65-,66+,67-,68+,70-,71-/m1/s1

InChI Key

IGGGNUSEBUZFTR-CDDUTUKUSA-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
Polyprenyl monophosphate
Polyprenyl phosphate skeleton
Disaccharide phosphate
N-acyl-alpha-hexosamine
Disaccharide
Glycosyl compound
O-glycosyl compound
Isoprenoid phosphate
Organic pyrophosphate
Beta-hydroxy acid
Monoalkyl phosphate
Pyran
Alkyl phosphate
Phosphoric acid ester
Oxane
Hydroxy acid
Organic phosphoric acid derivative
Acetamide
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Acetal
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Primary alcohol
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Alcohol
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: HMDB0012306)

Source

Endogenous

Endogenous (HMDB: HMDB0012306)

Animal

Animal (HMDB: HMDB0012306)

Exogenous

Food

Food (HMDB: HMDB0012306)

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: HMDB0012306)

Process

Role

Biological role

Energy source (HMDB: HMDB0012306)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012306)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00099 g/L	ALOGPS
logP	7.45	ALOGPS
logP	12.83	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	1.72	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	306.4 Å²	ChemAxon
Rotatable Bond Count	43	ChemAxon
Refractivity	373.78 m³·mol⁻¹	ChemAxon
Polarizability	154.12 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0012306

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028929

KNApSAcK ID

Not Available

Chemspider ID

35032432

KEGG Compound ID

Not Available

BioCyc ID

C55-PP-GLCNAC-MANNACA

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25245571

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 pyrophosphate (CFc000007836)

MOL for CFc000007836 (Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate)

3D MOL for CFc000007836 (Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate)

3D SDF for CFc000007836 (Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate)

3D-SDF for CFc000007836 (Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate)

PDB for CFc000007836 (Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate)

3D PDB for CFc000007836 (Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate)

SMILES for CFc000007836 (Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate)

INCHI for CFc000007836 (Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate)

Structure for CFc000007836 (Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate)

3D Structure for CFc000007836 (Undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate pyrophosphate)