Uridine-5'-diphosphate-glucose

Details

• Internal ID: 3df39001-f7b9-42ef-bd6c-98f5bd4f2112
• Taxonomy: Nucleosides, nucleotides, and analogues > Pyrimidine nucleotides > Pyrimidine nucleotide sugars
• IUPAC Name: [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] hydrogen phosphate
• SMILES (Canonical): C1=CN(C(=O)NC1=O)C2C(C(C(O2)COP(=O)(O)OP(=O)(O)OC3C(C(C(C(O3)CO)O)O)O)O)O
• SMILES (Isomeric): C1=CN(C(=O)NC1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)OP(=O)(O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
• InChI: InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1
• InChI Key: HSCJRCZFDFQWRP-JZMIEXBBSA-N
• Popularity: 1,356 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄N₂O₁₇P₂
• Molecular Weight: 566.30 g/mol
• Exact Mass: 566.05502130 g/mol
• Topological Polar Surface Area (TPSA): 292.00 Ų
• XlogP: -6.30
• Atomic LogP (AlogP): -4.79
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 9

Synonyms

• URIDINE DIPHOSPHATE GLUCOSE
• UDPG
• 133-89-1
• UDP-alpha-D-Glucose
• co-waldenase
• URIDINE-5'-DIPHOSPHATE-GLUCOSE
• UDPglucose
• co-galactoisomerase
• UDP-a-D-Glucose
• UDP-D-glucose
• UDP-Glc
• Uridine diphosphoglucose
• Cogalactoisomerase
• 5'-Diphosphoglucose
• URIDINE-5'-DIPHOSPHOGLUCOSE
• Uridine diphosphate-glucose
• Uridine diphospho-D-glucose
• UNII-V50K1D7P4Y
• Uridine pyrophosphate-glucose
• GLUCOSE-URIDINE-C1,5'-DIPHOSPHATE
• Uridine 5'-diphosphoglucose
• Uridine 5'-diphosphate glucose
• V50K1D7P4Y
• [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] hydrogen phosphate
• CHEBI:46229
• EINECS 205-121-4
• Uridine 5'-diphospho-alpha-D-glucose
• Uridine 5'-pyrophosphate glucose ester
• UDP glucose
• Uridine 5'-(trihydrogen diphosphate), mono-alpha-d-glucopyranosyl ester
• Uridine 5'-(trihydrogen diphosphate), P'-alpha-D-glucopyranosyl ester
• C15H24N2O17P2
• (UDP)glucose
• UDP-delta-glucose
• (UPD)-glucose
• Uridindiphosphoglucose
• Mono-D-glucosyl ester
• UDP-alpha-delta-Glucose
• 5''''-Diphosphoglucose
• C15-H24-N2-O17-P2
• UDP-glucose Disodium Salt
• D07MIE
• D0DP9H
• SCHEMBL454078
• Uridine diphospho-delta-glucose
• CHEMBL375951
• GTPL1783
• Uridine 5'-(trihydrogen diphosphate) P'-alpha-D-glucopyranosyl ester
• Uridine-5''''-Diphosphoglucose
• DTXSID00157902
• HSCJRCZFDFQWRP-JZMIEXBBSA-N
• Uridine 5'-diphospho-a-D-glucose
• COGALACTOISOMERASE [WHO-DD]
• URIDINE-5'-MONOPHOSPHATE GLUCOPYRANOSYL-MONOPHOSPHATE ESTER
• Uridine 5-(trihydrogen diphosphate)
• BDBM50209659
• BDBM50423218
• AKOS040744389
• DB01861
• URIDINE DIPHOSPHATE GLUCOSE [MI]
• Uridine 5'-diphospho-alpha-delta-glucose
• URIDINE DIPHOSPHATE GLUCOSE [WHO-DD]
• C00029
• Q424649
• Uridine 5'-(alpha-D-glucopyranosyl pyrophosphate)
• Uridine 5'-pyrophosphate a-D-glucopyranosyl ester
• Uridine 5'-pyrophosphate a-delta-glucopyranosyl ester
• uridine 5''-[3-alpha-D-glucopyranosyl dihydrogen diphosphate]
• Uridine 5'-(trihydrogen pyrophosphate), mono-D-glucosyl ester
• uridine 5'-[3-alpha-D-glucopyranosyl dihydrogen diphosphate]
• Uridine 5'-(trihydrogen diphosphate) alpha-D-gucopyranosyl ester
• Uridine 5'-pyrophosphate, alpha-D-glucopyranosyl ester (6CI,7CI)
• Uridine 5'-(trihydrogen diphosphate), P'-a-D-glucopyranosyl ester (9CI)
• Uridine 5/'-(trihydrogen diphosphate), mono-alpha-d-glucopyranosyl ester
• URIDINE 5'-(TRIHYDROGEN DIPHOSPHATE), P'-.ALPHA.-D- GLUCOPYRANOSYL ESTER
• URIDINE 5'-(TRIHYDROGEN DIPHOSPHATE), P'-.ALPHA.-D-GLUCOPYRANOSYL ESTER
• Uridine 5'-(trihydrogen pyrophosphate), mono-alpha-D-glucopyranosyl ester (8CI)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9424	94.24%
Caco-2	-	0.8971	89.71%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.4598	45.98%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.9194	91.94%
OATP1B3 inhibitior	+	0.9415	94.15%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.6028	60.28%
P-glycoprotein inhibitior	-	0.5443	54.43%
P-glycoprotein substrate	-	0.8461	84.61%
CYP3A4 substrate	+	0.5982	59.82%
CYP2C9 substrate	-	0.5958	59.58%
CYP2D6 substrate	-	0.8648	86.48%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.8605	86.05%
CYP2C19 inhibition	-	0.8096	80.96%
CYP2D6 inhibition	-	0.8544	85.44%
CYP1A2 inhibition	-	0.8601	86.01%
CYP2C8 inhibition	-	0.7700	77.00%
CYP inhibitory promiscuity	-	0.7607	76.07%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.5043	50.43%
Eye corrosion	-	0.9840	98.40%
Eye irritation	-	0.9436	94.36%
Skin irritation	-	0.7799	77.99%
Skin corrosion	-	0.9323	93.23%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6645	66.45%
Micronuclear	+	0.9700	97.00%
Hepatotoxicity	-	0.5165	51.65%
skin sensitisation	-	0.8497	84.97%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.6077	60.77%
Acute Oral Toxicity (c)	III	0.5164	51.64%
Estrogen receptor binding	+	0.6816	68.16%
Androgen receptor binding	+	0.7976	79.76%
Thyroid receptor binding	-	0.4896	48.96%
Glucocorticoid receptor binding	-	0.4644	46.44%
Aromatase binding	+	0.5739	57.39%
PPAR gamma	+	0.6601	66.01%
Honey bee toxicity	-	0.6692	66.92%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	-	0.4206	42.06%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4518	Q15391	Purinergic receptor P2Y14	350 nM; 588 nM; 670 nM; 910 nM; 400 nM; 261 nM; 354 nM	EC50; EC50; EC50; EC50; EC50; EC50; EC50	PMID: 17407275; via Super-PRED; via Super-PRED; via Super-PRED; PMID: 19902968; PMID: 19502066; PMID: 17088057
CHEMBL4398	P41231	Purinergic receptor P2Y2	10000 nM	EC50	PMID: 19502066
CHEMBL4714	Q15077	Pyrimidinergic receptor P2Y6	1600 nM	EC50	PMID: 19902968

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.29%	96.09%
CHEMBL2123	P51582	Pyrimidinergic receptor P2Y4	95.93%	93.39%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.29%	86.92%
CHEMBL226	P30542	Adenosine A1 receptor	89.86%	95.93%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	89.56%	80.33%
CHEMBL2581	P07339	Cathepsin D	88.27%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.47%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	86.25%	94.73%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	84.01%	92.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.17%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.00%	94.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.68%	95.83%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.80%	97.09%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	80.44%	94.01%

Plants that contains it

• Arabidopsis thaliana
• Glycine max
• Helianthus tuberosus

Cross-Links

• PubChem: 8629
• NPASS: NPC155087
• ChEMBL: CHEMBL375951
• LOTUS: LTS0071938
• wikiData: Q424649