ATP   Click here for help

GtoPdb Ligand ID: 1713

Synonyms: 5'-ATP | adenosine 5' triphosphate | adenosine triphosphate
PDB Ligand
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 17
Hydrogen bond donors 7
Rotatable bonds 8
Topological polar surface area 308.56
Molecular weight 507
XLogP -5.53
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES OC1C(COP(=O)(OP(=O)(OP(=O)(O)O)O)O)OC(C1O)n1cnc2c1ncnc2N
Isomeric SMILES O[C@@H]1[C@@H](COP(=O)(OP(=O)(OP(=O)(O)O)O)O)O[C@H]([C@@H]1O)n1cnc2c1ncnc2N
InChI InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
InChI Key ZKHQWZAMYRWXGA-KQYNXXCUSA-N
Natural/Endogenous Targets
Target
GPR17
IP3R1
P2X1
P2X2
P2X3
P2X4
P2X5
P2X6
P2X7
P2Y11 receptor
P2Y13 receptor
P2Y1 receptor
P2Y2 receptor
P2Y4 receptor
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
phosphomevalonate kinase 11-12
diphosphomevalonate decarboxylase 24,28-29,34
Pyruvate carboxylase
mevalonate kinase 5-7,9,13,26-27,32
Acetyl-CoA carboxylase 1
Acetyl-CoA carboxylase 2
Propionyl-CoA carboxylase
sphingosine kinase 1
sphingosine kinase 2
ceramide kinase
Cofactor in Enzyme Reactions
Enzyme Reference
diphosphomevalonate decarboxylase 23-24
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Peroxisomal membrane protein
Vesicular nucleotide transporter 30
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
P2Y4 receptor Hs Antagonist Antagonist 6.2 pKd - 19
pKd 6.2 [19]
P2Y1 receptor Ligand is endogenous in the given species Hs Antagonist Antagonist 4.8 pKi - 10
pKi 4.8 [10]
GPR17 Ligand is endogenous in the given species Hs Agonist Agonist 7.4 pEC50 - 4
pEC50 7.4 (EC50 3.7x10-8 M) [4]
P2Y2 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 6.6 – 7.1 pEC50 - 17,20-21
pEC50 6.6 – 7.1 [17,20-21]
P2Y4 receptor Ligand is endogenous in the given species Rn Agonist Partial agonist 5.7 – 6.3 pEC50 - 3,17,19
pEC50 5.7 – 6.3 [3,17,19]
P2Y4 receptor Ligand is endogenous in the given species Hs Agonist Agonist 5.4 pEC50 - 1
pEC50 5.4 (EC50 4.3x10-6 M) [1]
P2Y11 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 4.2 – 5.6 pEC50 - 8,17,36
pEC50 4.2 – 5.6 [8,17,36]
P2Y1 receptor Ligand is endogenous in the given species Hs Agonist Partial agonist 6.1 – 7.8 pIC50 - 31,35
pIC50 6.1 – 7.8 [31,35]
P2Y13 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 5.4 pIC50 - 22
pIC50 5.4 [22]
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
KNa1.2 Ligand is endogenous in the given species Rn Gating inhibitor - - - < 5x10-3 2
Conc range: < 5x10-3 M [2]
Kir6.1 Ligand is endogenous in the given species Mm Gating inhibitor Antagonist - - 1x10-3 - 3x10-3 37
Conc range: 1x10-3 - 3x10-3 M [37]
Voltage: -60.0 mV
Kir6.1 Ligand is endogenous in the given species Mm Activator Agonist - - 1x10-3 37
Conc range: 1x10-3 M [37]
Voltage: -60.0 mV
P2X1 Ligand is endogenous in the given species Hs Agonist Agonist 7.3 pEC50 - 17
pEC50 7.3 (EC50 5.6x10-8 M) [17]
P2X3 Ligand is endogenous in the given species Hs Agonist Agonist 6.5 pEC50 - 17
pEC50 6.5 (EC50 3.4x10-7 M) [17]
P2X4 Ligand is endogenous in the given species Hs Agonist Agonist 5.9 – 6.3 pEC50 - 17-18
pEC50 6.3 (EC50 5x10-7 M) [17]
pEC50 5.9 (EC50 1.259x10-6 M) [18]
P2X5 Ligand is endogenous in the given species Rn Agonist Agonist 6.0 pEC50 - 17
pEC50 6.0 (EC50 1x10-6 M) [17]
P2X6 Ligand is endogenous in the given species Rn Agonist Agonist 6.0 pEC50 - 17
pEC50 6.0 (EC50 1x10-6 M) [17]
P2X2 Ligand is endogenous in the given species Rn Agonist Agonist 5.8 pEC50 - 16
pEC50 5.8 (EC50 1.4x10-6 M) [16]
P2X4 Mm Agonist Agonist 5.6 – 6.0 pEC50 - 17-18
pEC50 6.0 (EC50 1x10-6 M) [17]
pEC50 5.6 (EC50 2.511x10-6 M) [18]
P2X4 Rn Agonist Agonist 5.3 pEC50 - 18
pEC50 5.3 (EC50 5.011x10-6 M) [18]
P2X7 Ligand is endogenous in the given species Hs Agonist Agonist 3.1 pEC50 - 17
pEC50 3.1 (EC50 7.8x10-4 M) [17]
TRPM4 Ligand is endogenous in the given species Mm Channel blocker Antagonist 6.1 pIC50 - 33
pIC50 6.1 [33]
Voltage: 100.0 mV
TRPM4 Ligand is endogenous in the given species Hs Channel blocker Antagonist 5.8 pIC50 - 25
pIC50 5.8 [25]
Voltage: 100.0 mV
TRPM4 Ligand is endogenous in the given species Hs Gating inhibitor Antagonist 4.9 pIC50 - 25
pIC50 4.9 [25]
Voltage: 100.0 mV
Kir6.2 Mm Gating inhibitor Antagonist - - - 14-15
[14-15]
Voltage: -60.0 mV
IP3R1 Ligand is endogenous in the given species Hs Activator (cytosolic ATP) - - - -
< mM range
RyR1 Ligand is endogenous in the given species Hs Activator (cytosolic ATP) - - - -
endogenous; mM range
RyR2 Ligand is endogenous in the given species Hs Activator (cytosolic ATP) - - - -
endogenous; mM range
RyR3 Ligand is endogenous in the given species Hs Activator (cytosolic ATP) - - - -
endogenous; mM range
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Targets where the ligand is described in the comment field
Target Comment
Ligand mentioned in the following text fields