Uridine-diphosphate-N-acetylglucosamine

Details

• Internal ID: a8602aa5-0a25-44c7-93b3-076141339565
• Taxonomy: Nucleosides, nucleotides, and analogues > Pyrimidine nucleotides > Pyrimidine nucleotide sugars
• IUPAC Name: [(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate
• SMILES (Canonical): CC(=O)NC1C(C(C(OC1OP(=O)(O)OP(=O)(O)OCC2C(C(C(O2)N3C=CC(=O)NC3=O)O)O)CO)O)O
• SMILES (Isomeric): CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1OP(=O)(O)OP(=O)(O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)CO)O)O
• 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
• InChI Key: LFTYTUAZOPRMMI-CFRASDGPSA-N
• Popularity: 757 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₇N₃O₁₇P₂
• Molecular Weight: 607.40 g/mol
• Exact Mass: 607.08157040 g/mol
• Topological Polar Surface Area (TPSA): 300.00 Ų
• XlogP: -6.60
• Atomic LogP (AlogP): -4.65
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 10

Synonyms

• UDP-N-acetyl-D-glucosamine
• UDP-GlcNAc
• URIDINE-DIPHOSPHATE-N-ACETYLGLUCOSAMINE
• UDP-acetylglucosamine
• UPPAG
• UDP-N-acetyl-alpha-D-glucosamine
• CHEBI:16264
• uridine diphosphate N-acetylglucosamine
• UDP-acetyl-D-glucosamine
• 528-04-1
• Uridine diphospho-N-acetylglucosamine
• (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 diphosphate (non-preferred name)
• UDP-a-D-N-acetylglucosamine
• 91183-98-1
• UDP-alpha-D-N-acetylglucosamine
• Uridine diphosphoacetylglucosamine
• UDP-N-acetyl-glucosamine
• Udpx
• Uridine 5'-diphospho-N-acetylglucosamine
• Uridine diphospho-N-acetyl-D-glucosamine
• 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
• UD1
• Uridine diphosphate N-acetyl-D-glucosamine
• Uridine diphospho-2-acetamido-2-deoxy-D-glucose
• UDP N-acetyl-glucosamine
• UDP-acetyl-delta-glucosamine
• UDP-|A-D-N-acetylglucosamine
• CHEMBL388154
• GTPL1779
• SCHEMBL1521296
• UDP-N-acetyl-delta-glucosamine
• LFTYTUAZOPRMMI-CFRASDGPSA-N
• UDP N-acetyl-alpha-D-glucosamine
• UDP-alpha-delta-N-acetylglucosamine
• DB03397
• Uridine 5'-Diphospho-N-Acetlyglucosamine
• [(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate
• Uridine diphospho-N-acetyl-delta-glucosamine
• Uridine diphosphate N-acetyl-delta-glucosamine
• C00043
• Q312208
• J-700272
• Uridine diphospho-2-acetamido-2-deoxy-delta-glucose
• 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 5'-[3-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl) dihydrogen diphosphate]
• [[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
• {[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9518	95.18%
Caco-2	-	0.8740	87.40%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5171	51.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8277	82.77%
OATP1B3 inhibitior	+	0.9414	94.14%
MATE1 inhibitior	-	0.9219	92.19%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7613	76.13%
P-glycoprotein inhibitior	-	0.4442	44.42%
P-glycoprotein substrate	-	0.6009	60.09%
CYP3A4 substrate	+	0.6526	65.26%
CYP2C9 substrate	-	0.7989	79.89%
CYP2D6 substrate	-	0.8653	86.53%
CYP3A4 inhibition	+	0.5327	53.27%
CYP2C9 inhibition	-	0.8426	84.26%
CYP2C19 inhibition	-	0.7877	78.77%
CYP2D6 inhibition	-	0.8425	84.25%
CYP1A2 inhibition	-	0.8604	86.04%
CYP2C8 inhibition	-	0.6691	66.91%
CYP inhibitory promiscuity	-	0.7107	71.07%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.5003	50.03%
Eye corrosion	-	0.9844	98.44%
Eye irritation	-	0.9400	94.00%
Skin irritation	-	0.7884	78.84%
Skin corrosion	-	0.9344	93.44%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7030	70.30%
Micronuclear	+	0.9700	97.00%
Hepatotoxicity	+	0.6334	63.34%
skin sensitisation	-	0.8557	85.57%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.5453	54.53%
Acute Oral Toxicity (c)	III	0.5363	53.63%
Estrogen receptor binding	+	0.7185	71.85%
Androgen receptor binding	+	0.7626	76.26%
Thyroid receptor binding	-	0.5098	50.98%
Glucocorticoid receptor binding	+	0.5870	58.70%
Aromatase binding	+	0.6443	64.43%
PPAR gamma	+	0.6933	69.33%
Honey bee toxicity	-	0.6942	69.42%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	-	0.4105	41.05%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4518	Q15391	Purinergic receptor P2Y14	810 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.35%	96.09%
CHEMBL2581	P07339	Cathepsin D	95.09%	98.95%
CHEMBL2123	P51582	Pyrimidinergic receptor P2Y4	94.76%	93.39%
CHEMBL226	P30542	Adenosine A1 receptor	93.21%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	92.03%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.82%	91.11%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	86.39%	80.33%
CHEMBL255	P29275	Adenosine A2b receptor	86.11%	98.59%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	85.91%	87.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.32%	89.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.91%	94.33%
CHEMBL5255	O00206	Toll-like receptor 4	84.44%	92.50%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.83%	93.04%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	83.61%	81.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.12%	94.45%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.49%	95.83%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.62%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.24%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.47%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.32%	85.14%

Plants that contains it

• Helianthus tuberosus

Cross-Links

• PubChem: 445675
• LOTUS: LTS0269624
• wikiData: Q312208