ChemFOnt: Showing chemical card for N-Acetylglucosaminyl-diphosphodolichol (CFc000007806)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:19 UTC

Chemfont ID

CFc000007806

Molecule Identification

Common Name

N-Acetylglucosaminyl-diphosphodolichol

Definition

N-Acetylglucosaminyl-diphosphodolichol is found in the dolichyl-diphosphooligosaccharide biosynthesis pathway. Dolichyl-phosphate reacts with UDP-N-acetyl-D-glucosamine to produce N-acetylglucosaminyl-diphosphodolichol and UMP. UDP-N-acetylglucosamine--dolichyl-phosphate N-acetylglucosaminephosphotransferase catalyzes this reaction. N-acetylglucosaminyl-diphosphodolichol reacts with UDP-N-acetyl-D-glucosamine to produce (N-acetylglucosaminyl)2-diphosphodolichol and UDP. N-acetylglucosaminyldiphosphodolichol N-acetylglucosaminyltransferase catalyzes this reaction.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-Acetyl-D-glucosaminyldiphosphodolichol	HMDB
N-[(2S,3R,4R,5S,6R)-2-({[({[(6E,10E,14E,18E,22E,26E,30E,34E,38E,42E,46E,50E,54E,58E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63-hexadecamethyltetrahexaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62-pentadecaen-1-yl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidate	HMDB

Chemical Formula

C₈₈H₁₄₇NO₁₂P₂

Average Molecular Weight

1473.0558

Monoisotopic Molecular Weight

1472.039852197

IUPAC Name

{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}[({[(6E,10E,14E,18E,22E,26E,30E,34E,38E,42E,46E,50E,54E,58E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63-hexadecamethyltetrahexaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62-pentadecaen-1-yl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid

Traditional Name

[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy({[(6E,10E,14E,18E,22E,26E,30E,34E,38E,42E,46E,50E,54E,58E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63-hexadecamethyltetrahexaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62-pentadecaen-1-yl]oxy(hydroxy)phosphoryl}oxy)phosphinic acid

CAS Registry Number

None

SMILES

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

InChI Identifier

InChI=1S/C88H147NO12P2/c1-67(2)34-19-35-68(3)36-20-37-69(4)38-21-39-70(5)40-22-41-71(6)42-23-43-72(7)44-24-45-73(8)46-25-47-74(9)48-26-49-75(10)50-27-51-76(11)52-28-53-77(12)54-29-55-78(13)56-30-57-79(14)58-31-59-80(15)60-32-61-81(16)62-33-63-82(17)64-65-98-102(94,95)101-103(96,97)100-88-85(89-83(18)91)87(93)86(92)84(66-90)99-88/h34,36,38,40,42,44,46,48,50,52,54,56,58,60,62,82,84-88,90,92-93H,19-33,35,37,39,41,43,45,47,49,51,53,55,57,59,61,63-66H2,1-18H3,(H,89,91)(H,94,95)(H,96,97)/b68-36+,69-38+,70-40+,71-42+,72-44+,73-46+,74-48+,75-50+,76-52+,77-54+,78-56+,79-58+,80-60+,81-62+/t82?,84-,85-,86-,87-,88+/m1/s1

InChI Key

PJOHRMFBCONSHW-HWUFQLITSA-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
Polyprenyl phospho carbohydrate
Dolichyl diphosphate
Polyprenyl monophosphate
Polyprenyl phosphate skeleton
N-acyl-alpha-hexosamine
Hexose monosaccharide
Monosaccharide phosphate
Organic pyrophosphate
Monoalkyl phosphate
Monosaccharide
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Alkyl phosphate
Acetamide
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organic oxide
Organonitrogen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Primary alcohol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0012264)
Membrane (HMDB: HMDB0012264)

Source

Exogenous

Exogenous (HMDB: HMDB0012264)

Food

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)

Endogenous

Endogenous (HMDB: HMDB0012264)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00058 g/L	ALOGPS
logP	9.11	ALOGPS
logP	23.12	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	1.74	ChemAxon
pKa (Strongest Basic)	-1.6	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	55	ChemAxon
Refractivity	448.71 m³·mol⁻¹	ChemAxon
Polarizability	183.42 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

External Links

HMDB ID

HMDB0012264

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB112306

KNApSAcK ID

Not Available

Chemspider ID

35032426

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481397

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for N-Acetylglucosaminyl-diphosphodolichol (CFc000007806)

MOL for CFc000007806 (N-Acetylglucosaminyl-diphosphodolichol)

3D MOL for CFc000007806 (N-Acetylglucosaminyl-diphosphodolichol)

3D SDF for CFc000007806 (N-Acetylglucosaminyl-diphosphodolichol)

3D-SDF for CFc000007806 (N-Acetylglucosaminyl-diphosphodolichol)

PDB for CFc000007806 (N-Acetylglucosaminyl-diphosphodolichol)

3D PDB for CFc000007806 (N-Acetylglucosaminyl-diphosphodolichol)

SMILES for CFc000007806 (N-Acetylglucosaminyl-diphosphodolichol)

INCHI for CFc000007806 (N-Acetylglucosaminyl-diphosphodolichol)

Structure for CFc000007806 (N-Acetylglucosaminyl-diphosphodolichol)

3D Structure for CFc000007806 (N-Acetylglucosaminyl-diphosphodolichol)