uridine triphosphate   

GtoPdb Ligand ID: 1734

Abbreviated name: UTP
Synonyms: 5'-UTP | uridine 5'-triphosphate
2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 15
Hydrogen bond donors 7
Rotatable bonds 8
Topological polar surface area 293.8
Molecular weight 483.97
XLogP -5.54
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES OC1C(COP(=O)(OP(=O)(OP(=O)(O)O)O)O)OC(C1O)n1ccc(=O)[nH]c1=O
Isomeric SMILES O[C@@H]1[C@@H](COP(=O)(OP(=O)(OP(=O)(O)O)O)O)O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1=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
References
1. Bogdanov YD, Wildman SS, Clements MP, King BF, Burnstock G. (1998)
Molecular cloning and characterization of rat P2Y4 nucleotide receptor.
Br. J. Pharmacol., 124 (3): 428-30. [PMID:9647463]
2. Communi D, Parmentier M, Boeynaems JM. (1996)
Cloning, functional expression and tissue distribution of the human P2Y6 receptor.
Biochem. Biophys. Res. Commun., 222 (2): 303-8. [PMID:8670200]
3. Kennedy C, Qi AD, Herold CL, Harden TK, Nicholas RA. (2000)
ATP, an agonist at the rat P2Y(4) receptor, is an antagonist at the human P2Y(4) receptor.
Mol. Pharmacol., 57 (5): 926-31. [PMID:10779375]
4. Kim HS, Ravi RG, Marquez VE, Maddileti S, Wihlborg AK, Erlinge D, Malmsjö M, Boyer JL, Harden TK, Jacobson KA. (2002)
Methanocarba modification of uracil and adenine nucleotides: high potency of Northern ring conformation at P2Y1, P2Y2, P2Y4, and P2Y11 but not P2Y6 receptors.
J. Med. Chem., 45 (1): 208-18. [PMID:11754592]
5. Lazarowski ER, Watt WC, Stutts MJ, Boucher RC, Harden TK. (1995)
Pharmacological selectivity of the cloned human P2U-purinoceptor: potent activation by diadenosine tetraphosphate.
Br. J. Pharmacol., 116 (1): 1619-27. [PMID:8564228]
6. White PJ, Webb TE, Boarder MR. (2003)
Characterization of a Ca2+ response to both UTP and ATP at human P2Y11 receptors: evidence for agonist-specific signaling.
Mol. Pharmacol., 63 (6): 1356-63. [PMID:12761346]