1.0
2011-09-21 00:05:24 UTC
2015-10-09 22:29:27 UTC
FDB021930
Uridine diphosphate-N-acetylglucosamine
Uridine 5'-diphosphate-GlcNAc (UDP-Glc-NAc )respond to nutrient excess to activate O-GlcNAcylation (addition of O-linked N-acetylglucosamine) in the hexosamine signaling pathway (HSP). O-GlcNAc addition (and removal) is key to histone remodeling, transcription, proliferation, apoptosis, and proteasomal degradation. This nutrient-responsive signaling pathway also modulates important cellular pathways, including the insulin signaling cascade in. Alterations in O-GlcNAc metabolism are associated with various human diseases including diabetes mellitus and neurodegeneration. (PMID: 16317114)
The incidence of type 2 diabetes (non-insulin-dependent diabetes mellitus) has increased to epidemic proportions, being described as a disease of 'chronic overnutrition'. Due to the chemical makeup of UDP-GlcNAc,it is well positioned to serve as a glucose sensor in that it is a high-energy compound that requires and/or responds to glucose, amino acid, fatty acid and nucleotide metabolism for synthesis. UDP-Glc-NAc is the donor substrate for modification of nucleocytoplasmic proteins at serine and threonine residues with N-acetylglucosamine. Elevated levels of O-GlcNAc have an effect on insulin-stimulated glucose uptake. (PMID: 12678487) [HMDB]
(2R,3R,4R,5S,6R)-3-(acetylamino)-4,5-Dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl [(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen diate (non-preferred name)
(2R,3R,4R,5S,6R)-3-(acetylamino)-4,5-Dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl [(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen diic acid (non-preferred name)
[[3-acetylamino-4,5-Dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-oryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]inate
[[3-acetylamino-4,5-Dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-oryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]inic acid
[[3-acetylamino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-phosphoryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]phosphinate
[[3-acetylamino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-phosphoryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]phosphinic acid
N-[2-[[[5-[(2,4-dioxo-1H-Pyrimidin-1-yl)]-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-inoyl]oxy-hydroxy-inoyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide
N-[2-[[[5-[(2,4-dioxo-1H-pyrimidin-1-yl)]-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphinoyl]oxy-hydroxy-phosphinoyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide
UDP-a-D-N-acetylglucosamine
UDP-acetyl-D-glucosamine
UDP-acetyl-delta-glucosamine
UDP-acetylglucosamine
UDP-alpha-D-N-acetylglucosamine
UDP-alpha-delta-N-acetylglucosamine
UDP-GlcNAc
UDP-N-acetyl-D-glucosamine
UDP-N-acetyl-delta-glucosamine
UDP-N-acetyl-glucosamine
UDP-N-acetylglucosamine
UPPAG
Uridine 5'-dio-N-acetlyglucosamine
Uridine 5'-dio-N-acetylglucosamine
Uridine 5'-Diphospho-N-Acetlyglucosamine
Uridine 5'-diphospho-N-acetylglucosamine
Uridine diate N-acetyl-D-glucosamine
Uridine diate N-acetyl-delta-glucosamine
Uridine diate N-acetylglucosamine
Uridine dio-2-acetamido-2-deoxy-D-glucose
Uridine dio-2-acetamido-2-deoxy-delta-glucose
Uridine dio-N-acetyl-D-glucosamine
Uridine dio-N-acetyl-delta-glucosamine
Uridine dio-N-acetylglucosamine
Uridine dioacetylglucosamine
Uridine diphosphate N-acetyl-D-glucosamine
Uridine diphosphate N-acetyl-delta-glucosamine
Uridine diphosphate N-acetylglucosamine
Uridine diphospho-2-acetamido-2-deoxy-D-glucose
Uridine diphospho-2-acetamido-2-deoxy-delta-glucose
Uridine diphospho-N-acetyl-D-glucosamine
Uridine diphospho-N-acetyl-delta-glucosamine
Uridine diphospho-N-acetylglucosamine
uridine diphosphoacetylglucosamine
Uridine pyroate 2-acetamido-2-deoxy-a-D-glucopyranosyl ester
Uridine pyroate 2-acetamido-2-deoxy-alpha-D-glucopyranosyl ester
Uridine pyroate 2-acetamido-2-deoxy-alpha-delta-glucopyranosyl ester
Uridine pyrooacetylglucosamine
Uridine pyrophosphate 2-acetamido-2-deoxy-a-D-glucopyranosyl ester
Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-D-glucopyranosyl ester
Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-delta-glucopyranosyl ester
Uridine pyrophosphoacetylglucosamine
URIDINE-diATE-N-acetylglucosamine
URIDINE-diic acid-N-acetylglucosamine
C17H27N3O17P2
607.3537
607.081569477
[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
udp-N-acetyl-α-D-glucosamine
528-04-1
CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O
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)/t7-,8-,10-,11-,12-,13-,14-,15-,16-/m1/s1
LFTYTUAZOPRMMI-CFRASDGPSA-N
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.
Pyrimidine nucleotide sugars
Organic compounds
Nucleosides, nucleotides, and analogues
Pyrimidine nucleotides
Pyrimidine nucleotide sugars
Aromatic heteromonocyclic compounds
Acetamides
Azacyclic compounds
Carbonyl compounds
Glycosylamines
Heteroaromatic compounds
Hydrocarbon derivatives
Hydropyrimidines
Lactams
Monoalkyl phosphates
Monosaccharide phosphates
N-acyl-alpha-hexosamines
Organic oxides
Organic pyrophosphates
Organonitrogen compounds
Organopnictogen compounds
Oxacyclic compounds
Oxanes
Pentose phosphates
Primary alcohols
Pyrimidine ribonucleoside diphosphates
Pyrimidones
Secondary alcohols
Secondary carboxylic acid amides
Tetrahydrofurans
Ureas
Vinylogous amides
Acetamide
Alcohol
Alkyl phosphate
Aromatic heteromonocyclic compound
Azacycle
Carbonyl group
Carboxamide group
Carboxylic acid derivative
Glycosyl compound
Heteroaromatic compound
Hydrocarbon derivative
Hydropyrimidine
Lactam
Monoalkyl phosphate
Monosaccharide
Monosaccharide phosphate
N-acyl-alpha-hexosamine
N-glycosyl compound
Organic nitrogen compound
Organic oxide
Organic oxygen compound
Organic phosphoric acid derivative
Organic pyrophosphate
Organoheterocyclic compound
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Oxacycle
Oxane
Pentose phosphate
Pentose-5-phosphate
Phosphoric acid ester
Primary alcohol
Pyrimidine
Pyrimidine nucleotide sugar
Pyrimidine ribonucleoside diphosphate
Pyrimidone
Secondary alcohol
Secondary carboxylic acid amide
Tetrahydrofuran
Urea
Vinylogous amide
UDP-amino sugar
Solid
logp
-1.41
logs
-1.72
solubility
1.14e+01 g/l
logp
-5.3
pka_strongest_acidic
1.74
pka_strongest_basic
-3.5
iupac
[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
average_mass
607.3537
mono_mass
607.081569477
smiles
CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(=O)NC1=O
formula
C17H27N3O17P2
inchi
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)/t7-,8-,10-,11-,12-,13-,14-,15-,16-/m1/s1
inchikey
LFTYTUAZOPRMMI-CFRASDGPSA-N
polar_surface_area
300.41
refractivity
117.56
polarizability
50.39
rotatable_bond_count
10
acceptor_count
14
donor_count
9
physiological_charge
-2
formal_charge
0
Amino Sugar Metabolism
SMP00045
map00520
Specdb::NmrTwoD
1013
Specdb::NmrTwoD
1257
Specdb::NmrOneD
1314
Specdb::NmrOneD
143330
Specdb::NmrOneD
143331
Specdb::NmrOneD
143332
Specdb::NmrOneD
143333
Specdb::NmrOneD
143334
Specdb::NmrOneD
143335
Specdb::NmrOneD
143336
Specdb::NmrOneD
143337
Specdb::NmrOneD
143338
Specdb::NmrOneD
143339
Specdb::NmrOneD
143340
Specdb::NmrOneD
143341
Specdb::NmrOneD
143342
Specdb::NmrOneD
143343
Specdb::NmrOneD
143344
Specdb::NmrOneD
143345
Specdb::NmrOneD
143346
Specdb::NmrOneD
143347
Specdb::NmrOneD
143348
Specdb::NmrOneD
143349
Specdb::CMs
864
Specdb::CMs
18397
Specdb::CMs
30938
Specdb::CMs
37405
Specdb::CMs
480484
Specdb::CMs
480485
Specdb::CMs
480486
Specdb::CMs
480487
Specdb::CMs
480488
Specdb::CMs
480489
Specdb::CMs
480490
Specdb::CMs
480491
Specdb::CMs
480492
Specdb::CMs
480493
Specdb::CMs
480494
Specdb::CMs
480495
Specdb::CMs
480496
Specdb::CMs
480497
Specdb::CMs
480498
Specdb::CMs
480499
Specdb::CMs
480500
Specdb::CMs
480501
Specdb::CMs
480502
Specdb::CMs
480503
Specdb::CMs
480504
Specdb::MsMs
6243
Specdb::MsMs
6244
Specdb::MsMs
178665
Specdb::MsMs
178666
Specdb::MsMs
178667
Specdb::MsMs
180984
Specdb::MsMs
180985
Specdb::MsMs
180986
Specdb::MsMs
439118
Specdb::MsMs
439119
Specdb::MsMs
2244737
Specdb::MsMs
2245358
Specdb::MsMs
2246880
Specdb::MsMs
2247428
Specdb::MsMs
2248852
Specdb::MsMs
2249518
Specdb::MsMs
2250855
Specdb::MsMs
2251569
Specdb::MsMs
2429329
Specdb::MsMs
2429330
Specdb::MsMs
2429331
Specdb::MsMs
2505533
Specdb::MsMs
2505534
Specdb::MsMs
2505535
HMDB00290
16264
UD1
#<Reference:0x00005556744e3638>
#<Reference:0x00005556744e3430>
#<Reference:0x00005556744e3278>
#<Reference:0x00005556744e3098>
#<Reference:0x00005556744e28f0>
Anatidae
Type 1
specific
Anatidae
8830
Beefalo
Type 1
specific
Bos taurus X Bison bison
297284
Bison
Type 1
specific
Bison bison
9901
Buffalo
Type 1
specific
Bubalus bubalis
89462
Cattle (Beef, Veal)
Type 1
specific
Bos taurus
9913
Chicken
Type 1
specific
Gallus gallus
9031
Columbidae (Dove, Pigeon)
Type 1
specific
Columbidae
8930
Deer
Type 1
specific
Cervidae
9850
Domestic goat
Type 1
specific
Capra aegagrus hircus
9925
Domestic pig
Type 1
specific
Sus scrofa domestica
9825
Elk
Type 1
specific
Cervus canadensis
1574408
Emu
Type 1
specific
Dromaius novaehollandiae
8790
European rabbit
Type 1
specific
Oryctolagus
9984
Greylag goose
Type 1
specific
Anser anser
8843
Guinea hen
Type 1
specific
Numida meleagris
8996
Horse
Type 1
specific
Equus caballus
9796
Mallard duck
Type 1
specific
Anas platyrhynchos
8839
Mountain hare
Type 1
specific
Lepus timidus
62621
Mule deer
Type 1
specific
Odocoileus
9871
Ostrich
Type 1
specific
Struthio camelus
8801
Pheasant
Type 1
specific
Phasianus colchicus
9054
Quail
Type 1
specific
Phasianidae
9005
Rabbit
Type 1
specific
Leporidae
9979
Rock ptarmigan
Type 1
specific
Lagopus muta
64668
Sheep (Mutton, Lamb)
Type 1
specific
Ovis aries
9940
Squab
Type 1
specific
Columba
8931
Turkey
Type 1
specific
Meleagris gallopavo
9103
Velvet duck
Type 1
specific
Melanitta fusca
371864
Wild boar
Type 1
specific
Sus scrofa
9823
Alpha-1,3-mannosyl-glycoprotein 4-beta-N-acetylglucosaminyltransferase A
Q9UM21
MGAT4A
Alpha-1,3-mannosyl-glycoprotein 4-beta-N-acetylglucosaminyltransferase B
Q9UQ53
MGAT4B
Alpha-1,6-mannosyl-glycoprotein 2-beta-N-acetylglucosaminyltransferase
Q10469
MGAT2
Alpha-1,6-mannosylglycoprotein 6-beta-N-acetylglucosaminyltransferase A
Q09328
MGAT5
Beta-1,3-N-acetylglucosaminyltransferase bGnT-2
Q9NY97
bGnT-2
Beta-1,4-mannosyl-glycoprotein 4-beta-N-acetylglucosaminyltransferase
Q09327
MGAT3
Bifunctional UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase
Q9Y223
GNE
Exostosin-1
Q16394
EXT1
Exostosin-2
Q93063
EXT2
Exostosin-like 1
Q92935
EXTL1
Exostosin-like 2
Q9UBQ6
EXTL2
Exostosin-like 3
O43909
EXTL3
Lactosylceramide 1,3-N-acetyl-beta-D-glucosaminyltransferase
Q9BYG0
B3GNT5
N-acetylglucosamine-1-phosphotransferase subunits alpha/beta
Q3T906
GNPTAB
N-acetyllactosaminide beta-1,3-N-acetylglucosaminyltransferase
O43505
B3GNT1
N-acetyllactosaminide beta-1,6-N-acetylglucosaminyl-transferase, isoform B
Q06430
GCNT2
Phosphatidylinositol N-acetylglucosaminyltransferase subunit A
P37287
PIGA
Phosphatidylinositol N-acetylglucosaminyltransferase subunit C
Q92535
PIGC
Phosphatidylinositol N-acetylglucosaminyltransferase subunit H
Q14442
PIGH
Phosphatidylinositol N-acetylglucosaminyltransferase subunit P
P57054
PIGP
Phosphatidylinositol N-acetylglucosaminyltransferase subunit Q
Q9BRB3
PIGQ
UDP-N-acetylglucosamine transferase subunit ALG13 homolog
Q9NP73
ALG13
UDP-N-acetylglucosamine transporter
Q9Y2D2
SLC35A3
UDP-N-acetylglucosamine--dolichyl-phosphate N-acetylglucosaminephosphotransferase
Q9H3H5
DPAGT1
UDP-N-acetylglucosamine--peptide N-acetylglucosaminyltransferase 110 kDa subunit
O15294
OGT
UDP-N-acetylhexosamine pyrophosphorylase
Q16222
UAP1