ContaminantDB: Uridine diphosphate-N-acetylgalactosamine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 05:13:31 UTC

Update Date

2026-04-05 14:35:02 UTC

Accession Number

CHEM034791

Identification

Common Name

Uridine diphosphate-N-acetylgalactosamine

Class

Small Molecule

Description

Uridine diphosphate-N-acetylgalactosamine (UDP-GalNAc) is a sugar donor metabolite, transferring N-acetylgalactosamine (GalNAc, an O-glycan) from UDP-GalNAc to serine and threonine residues, forming an alpha anomeric linkage in a reaction catalyzed by enzymes known as UDP-N-acetylgalactosamine: polypeptide N-acetylgalactosaminyltransferases; addition of GalNAc to serine or threonine represents the first committed step in mucin biosynthesis. O-glycans impart unique structural features to mucin glycoproteins and numerous membrane receptors, and resistance to thermal change and proteolytic attack in a number of diverse proteins. O-linked carbohydrate side chains function as ligands for receptors; lymphocyte and leukocyte homing and as signals for protein sorting. (PMID: 12634319) Animal studies suggest that overactivity of the hexosamine pathway, resulting in increased UDP-hexosamines [i.e.: UDP-N-acetylgalactosamine (UDP-GalNAc)] is an important mechanism by which hyperglycemia causes insulin resistance. However, to date, human studies concerning the role of the hexosamine pathway in hyperglycemia-induced insulin resistance are scarce and restricted to measurements of glutamine fructose-6-phosphate amidotransferase (GFAT) enzyme activity. Both positive and negative correlations between GFAT activity in human muscle tissue from patients with type 2 DM and glucose disposal rate have been reported. (PMID: 12414889) [HMDB]

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Uridine diphosphoric acid-N-acetylgalactosamine	Generator
UDP-N-Acetyl-D-galactosamine	HMDB
UDP-N-Acetyl-delta-galactosamine	HMDB
UDP-N-Acetylgalactosamine	HMDB
Uridine 5'-diphospho-N-acetylgalactosamine	HMDB
Uridine diphosphate-N-acetyl-D-galactosamine	HMDB
Uridine diphosphate-N-acetyl-delta-galactosamine	HMDB
Uridine diphospho-2-acetamido-2-deoxy-D-galactose	HMDB
Uridine diphospho-2-acetamido-2-deoxy-delta-galactose	HMDB
Uridine diphospho-N-acetylgalactosamine	HMDB
Uridine diphosphoacetylgalactosamine	HMDB
Uridine pyrophosphate 2-acetamido-2-deoxy-a-D-galactopyranosyl ester	HMDB
Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-D-galactopyranosyl ester	HMDB
Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-delta-galactopyranosyl ester	HMDB
Uridine pyrophosphate N-acetyl-a-D-chondrosamine ester	HMDB
Uridine pyrophosphate N-acetyl-alpha-D-chondrosamine ester	HMDB
Uridine pyrophosphate N-acetyl-alpha-delta-chondrosamine ester	HMDB
Uridine pyrophosphoacetylgalactosamine	HMDB
Pyrophosphoacetylglucosamine, uridine	MeSH, HMDB
UDP Acetylglucosamine	MeSH, HMDB
Uridine diphospho-N-acetylglucosamine	MeSH, HMDB
Acetylgalactosamine, UDP	MeSH, HMDB
diphospho-N-Acetylglucosamine, uridine	MeSH, HMDB
Uridine diphosphate N acetylgalactosamine	MeSH, HMDB
Uridine diphosphate N acetylglucosamine	MeSH, HMDB
Uridine diphosphate N-acetylglucosamine	MeSH, HMDB
Diphosphate N-acetylglucosamine, uridine	MeSH, HMDB
UDPGNAc	MeSH, HMDB
Uridine diphosphate N-acetylgalactosamine	MeSH, HMDB
Acetylglucosamine, UDP	MeSH, HMDB
N-Acetylgalactosamine, uridine diphosphate	MeSH, HMDB
UDP Acetylgalactosamine	MeSH, HMDB
Uridine pyrophosphoacetylglucosamine	MeSH, HMDB
Uridine diphospho N acetylglucosamine	MeSH, HMDB
Diphosphate N-acetylgalactosamine, uridine	MeSH, HMDB
N-Acetylglucosamine, uridine diphosphate	MeSH, HMDB
N-[2-({[({[3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidate	Generator, HMDB

Chemical Formula

C₁₇H₂₇N₃O₁₇P₂

Average Molecular Mass

607.354 g/mol

Monoisotopic Mass

607.082 g/mol

CAS Registry Number

7277-98-7

IUPAC Name

[({[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid

Traditional Name

{[5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid

SMILES

CC(=O)NC1C(O)C(O)C(CO)OC1OP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1O)N1C=CC(=O)NC1=O

InChI Identifier

InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)

InChI Key

LFTYTUAZOPRMMI-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine nucleotide sugars

Direct Parent

Pyrimidine nucleotide sugars

Alternative Parents

Substituents

Pyrimidine nucleotide sugar
Pyrimidine ribonucleoside diphosphate
Pentose phosphate
Pentose-5-phosphate
N-acyl-alpha-hexosamine
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Organic pyrophosphate
Pyrimidone
Monoalkyl phosphate
Hydropyrimidine
Monosaccharide
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Vinylogous amide
Acetamide
Tetrahydrofuran
Heteroaromatic compound
Urea
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Lactam
Azacycle
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organopnictogen compound
Organooxygen compound
Alcohol
Primary alcohol
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	13 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-5.3	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	1.74	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	300.41 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	117.56 m³·mol⁻¹	ChemAxon
Polarizability	51.59 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f96-5924660000-c11cc7fa21a050c0f373	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-03fu-5926205000-cdab8d90ff64fb776a15	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-05e9-8897100000-095b6091bd84d37fd58b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000l-2900000000-82a9c4130de4b3125fd7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000l-2900000000-4d24529e74ad2fa21c05	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0f79-1930010000-55436553b484e5220f19	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1490000000-ac1c456c4492cae878a2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0910010000-188f1b92ae056d7c7cd0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-3921000000-ce6262fadd328364b376	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-5910000000-b91dd47ef36e2cad815b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-06ri-9502321000-f502248d5c26ca57aecb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ox-9605010000-08fa474eedca91ebd68f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06tf-5911000000-55e7efddb090fc85714a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bt9-0000095000-b04755a1d58b54039931	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08fr-4201191000-b741fdd379d9a2afcc61	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053u-5719010000-abc6f96328a6d0fbfbb8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0000914000-04cfea1597e2554c0ff8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-1412944000-aafe333f4e24af5bf092	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0h3r-9231000000-e1c43f13a820bf095dda	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0259722

FooDB ID

FDB021933

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

1134

ChEBI ID

Not Available

PubChem Compound ID

1167

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Uridine diphosphate-N-acetylgalactosamine (CHEM034791)

Structure for CHEM034791: Uridine diphosphate-N-acetylgalactosamine