ChemFOnt: Showing chemical card for N-Acetyl-D-glucosaminyldiphosphodolichol (CFc000001117)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:41 UTC

Chemfont ID

CFc000001117

Molecule Identification

Common Name

N-Acetyl-D-glucosaminyldiphosphodolichol

Definition

This compound is an intermediate in N-glycan biosynthesis, and the byproduct of N-acetylglucosaminyldiphosphodolichol (EC 2.4.1.141) and UDP-N-acetylglucosamine-dolichyl-phosphate (EC 2.7.8.15). (KEGG) This compound and its corresponding enzymes are implicated in the developmental programmes of a variety of eukaryotes. (PMID: 10024536 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-Acetyl-D-glucosaminyl-diphosphodolichol	HMDB
N-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-2-{[hydroxy({[hydroxy({[(6E)-3,7,11-trimethyldodeca-6,10-dien-1-yl]oxy})phosphoryl]oxy})phosphoryl]oxy}-6-(hydroxymethyl)oxan-3-yl]ethanimidate	HMDB

Chemical Formula

C₂₃H₄₃NO₁₂P₂

Average Molecular Weight

587.5345

Monoisotopic Molecular Weight

587.226048869

IUPAC Name

{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}({[hydroxy({[(6E)-3,7,11-trimethyldodeca-6,10-dien-1-yl]oxy})phosphoryl]oxy})phosphinic acid

Traditional Name

[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy({hydroxy[(6E)-3,7,11-trimethyldodeca-6,10-dien-1-yl]oxyphosphoryl}oxy)phosphinic acid

CAS Registry Number

None

SMILES

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

InChI Identifier

InChI=1S/C23H43NO12P2/c1-15(2)8-6-9-16(3)10-7-11-17(4)12-13-33-37(29,30)36-38(31,32)35-23-20(24-18(5)26)22(28)21(27)19(14-25)34-23/h8,10,17,19-23,25,27-28H,6-7,9,11-14H2,1-5H3,(H,24,26)(H,29,30)(H,31,32)/b16-10+/t17?,19-,20-,21-,22-,23+/m1/s1

InChI Key

OZGJPDIBINDRGZ-GKXPKBPWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-acyl-alpha-hexosamines

Alternative Parents

Substituents

N-acyl-alpha-hexosamine
Farsesane sesquiterpenoid
Sesquiterpenoid
Hexose monosaccharide
Monosaccharide phosphate
Organic pyrophosphate
Monoalkyl phosphate
Monosaccharide
Organic phosphoric acid derivative
Alkyl phosphate
Phosphoric acid ester
Oxane
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic nitrogen compound
Carbonyl group
Primary 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

Source

Endogenous

Endogenous (HMDB: HMDB0001445)

Exogenous

Food

Food (HMDB: HMDB0001445)

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: HMDB0001445)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0001445)

Role

Biological role

Energy source (HMDB: HMDB0001445)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0001445)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1 g/L	ALOGPS
logP	1.3	ALOGPS
logP	1.54	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	1.75	ChemAxon
pKa (Strongest Basic)	-0.78	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	201.31 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	139.28 m³·mol⁻¹	ChemAxon
Polarizability	58.82 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon