Uridine 5'-triphosphate

Details

• Internal ID: 68501be5-3887-44aa-940c-b78705bd1222
• Taxonomy: Nucleosides, nucleotides, and analogues > Pyrimidine nucleotides > Pyrimidine ribonucleotides > Pyrimidine ribonucleoside triphosphates
• IUPAC Name: [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
• SMILES (Canonical): C1=CN(C(=O)NC1=O)C2C(C(C(O2)COP(=O)(O)OP(=O)(O)OP(=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)OP(=O)(O)O)O)O
• InChI: InChI=1S/C9H15N2O15P3/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
• InChI Key: PGAVKCOVUIYSFO-XVFCMESISA-N
• Popularity: 4,113 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₅N₂O₁₅P₃
• Molecular Weight: 484.14 g/mol
• Exact Mass: 483.96852877 g/mol
• Topological Polar Surface Area (TPSA): 259.00 Ų
• XlogP: -5.80
• Atomic LogP (AlogP): -2.50
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

• uridine triphosphate
• 63-39-8
• Uteplex
• DTXSID0041147
• INS-316
• UT0S826Z60
• [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
• Magnesium UTP
• UTP, Magnesium
• Triphosphate, Uridine
• Mg UTP
• Magnesium Uridine Triphosphate
• Triphosphate, Magnesium Uridine
• (((2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl)methoxy-hydroxyphosphoryl) phosphono hydrogen phosphate
• RefChem:901473
• DTXCID8021147
• (((((((2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)phosphonic acid
• 200-558-7
• Uridine 5'-(tetrahydrogen triphosphate)
• UTP
• 5'-UTP
• Uridine 5'-triphosphoric acid
• INS316
• H4utp
• uridine-5'-triphosphate
• BRN 0071520
• UTP;Uridine 5'-triphosphate
• CHEMBL336296
• ((2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl tetrahydrogen triphosphate
• Uridine 5'-triphosphate tris salt
• uridine5'-triphosphate
• EINECS 200-558-7
• UNII-UT0S826Z60
• uridintriphosphat
• ara UTP
• 3h-uridine triphosphate
• Spectrum_001697
• Diquafosol Impurity 42
• Spectrum2_000525
• Spectrum3_001596
• Spectrum4_000851
• Spectrum5_001167
• araUridine-5'-triphosphate
• bmse000295
• orb63225
• SCHEMBL76682
• BSPBio_003192
• KBioGR_001481
• KBioSS_002177
• 4-24-00-01222 (Beilstein Handbook Reference)
• DivK1c_000269
• SPBio_000509
• GTPL1734
• orb1821475
• orb1821476
• orb1821477
• orb1821478
• orb2646541
• uridine 5''-triphosphoric acid
• CHEBI:15713
• KBio1_000269
• KBio2_002177
• KBio2_004745
• KBio2_007313
• KBio3_002692
• 5''-UTP
• NINDS_000269
• BDBM50118213
• MSK166651
• URIDINE TRIPHOSPHATE [WHO-DD]
• AKOS016011172
• URIDINE 5'-TRIPHOSPHATE [MI]
• CS-7777
• DB04005
• NU04388
• IDI1_000269
• Uridine mono(tetrahydrogen triphosphate)
• Uridine-5'-(tetrahydrogen triphosphate)
• NCGC00163323-01
• (((2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)triphosphoric acid
• [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] phosphono hydrogen phosphate
• uridine 5''-(tetrahydrogen triphosphate)
• CAS 60102-52-5
• HY-107372
• NS00014367
• C00075
• F85566
• 1-beta-D-Arabinofuranosyluridine-5'-triphosphate,
• Uridine, mono(tetrahydrogen triphosphate) (ester)
• Uridine 5'-(tetrahydrogen triphosphate) (8CI,9CI)
• BRD-A89637065-001-01-0
• DC99D596-4755-4E87-B3AA-F1D6CFEDCE9A
• Q32904692
• Uridine 5'-(tetrahydrogen triphosphate), manganese(2+) salt (1:1) (9CI)
• [(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl (hydroxy-phosphonooxyphosphoryl) hydrogen phosphate
• [[[5-(2,4-Dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxyphosphonic acid
• 2,4(1H,3H)-Pyrimidinedione, 1-[5-O-[hydroxy[[hydroxy(phosphonooxy)phosphinyl]oxy]phosphinyl]-.beta.-D-ribofuranosyl]-
• 61994-38-5

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.9393	93.93%
Caco-2	-	0.8746	87.46%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5668	56.68%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9360	93.60%
OATP1B3 inhibitior	+	0.9431	94.31%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7729	77.29%
P-glycoprotein inhibitior	-	0.6486	64.86%
P-glycoprotein substrate	-	0.9014	90.14%
CYP3A4 substrate	+	0.5509	55.09%
CYP2C9 substrate	-	0.5928	59.28%
CYP2D6 substrate	-	0.8685	86.85%
CYP3A4 inhibition	-	0.9193	91.93%
CYP2C9 inhibition	-	0.9131	91.31%
CYP2C19 inhibition	-	0.8878	88.78%
CYP2D6 inhibition	-	0.9021	90.21%
CYP1A2 inhibition	-	0.8879	88.79%
CYP2C8 inhibition	-	0.8454	84.54%
CYP inhibitory promiscuity	-	0.9549	95.49%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.5300	53.00%
Eye corrosion	-	0.9846	98.46%
Eye irritation	-	0.9608	96.08%
Skin irritation	-	0.7754	77.54%
Skin corrosion	-	0.9309	93.09%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3632	36.32%
Micronuclear	+	0.9800	98.00%
Hepatotoxicity	+	0.7335	73.35%
skin sensitisation	-	0.8445	84.45%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.5669	56.69%
Acute Oral Toxicity (c)	III	0.6451	64.51%
Estrogen receptor binding	+	0.7772	77.72%
Androgen receptor binding	+	0.8376	83.76%
Thyroid receptor binding	+	0.5834	58.34%
Glucocorticoid receptor binding	-	0.4710	47.10%
Aromatase binding	+	0.6966	69.66%
PPAR gamma	+	0.6275	62.75%
Honey bee toxicity	-	0.6980	69.80%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	-	0.5520	55.20%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2123	P51582	Pyrimidinergic receptor P2Y4	39 nM	EC50	via Super-PRED
CHEMBL4714	Q15077	Pyrimidinergic receptor P2Y6	424 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	96.94%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	94.55%	95.93%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	92.75%	80.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.48%	86.92%
CHEMBL2581	P07339	Cathepsin D	89.35%	98.95%
CHEMBL5957	P21589	5'-nucleotidase	87.38%	97.78%
CHEMBL3401	O75469	Pregnane X receptor	87.37%	94.73%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	86.86%	94.01%
CHEMBL255	P29275	Adenosine A2b receptor	84.31%	98.59%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.96%	94.00%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	82.85%	92.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.81%	89.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.50%	91.71%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.10%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.18%	99.23%

Plants that contains it

• Helianthus tuberosus

Cross-Links

• PubChem: 6133
• LOTUS: LTS0092501
• wikiData: Q32904692