ATP   Click here for help

GtoPdb Ligand ID: 1713

Synonyms: 5'-ATP | adenosine 5' triphosphate | adenosine triphosphate
PDB Ligand
Compound class: Metabolite
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: atp

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
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
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
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
mevalonate kinase 2.7.1.36 ATP + (R)-mevalonate -> ADP + (R)-5-phosphomevalonate 5-7,9,13,27-28,33
phosphomevalonate kinase 2.7.4.2 ATP + (R)-5-phosphomevalonate = ADP + (R)-5-diphosphomevalonate 11-12
diphosphomevalonate decarboxylase 4.1.1.33 ATP + (R)-5-diphosphomevalonate -> ADP + isopentenyl diphosphate + CO2 + PO34- 24,29-30,36
Pyruvate carboxylase
Acetyl-CoA carboxylase 1
Acetyl-CoA carboxylase 2
Propionyl-CoA carboxylase
sphingosine kinase 1 2.7.1.91 Sphingosine + ATP = sphingosine 1-phosphate + ADP
dihydrosphingosine + ATP = dihydrosphingosine 1-phosphate + ADP
sphingosine kinase 2 2.7.1.91 Sphingosine + ATP = sphingosine 1-phosphate + ADP
dihydrosphingosine + ATP = dihydrosphingosine 1-phosphate + ADP
ceramide kinase 2.7.1.138 ceramide + ATP -> ceramide 1-phosphate + ADP
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 31
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 - 8,17,38
⤷ pEC50 4.2 – 5.6 [8,17,38]
P2Y1 receptor Ligand is endogenous in the given species Hs Agonist Partial agonist 6.1 – 7.8 pIC50 - 32,37
⤷ pIC50 6.1 – 7.8 [32,37]
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 39
⤷ Conc range: 1x10-3 - 3x10-3 M [39]
Voltage: -60.0 mV
Kir6.1 Ligand is endogenous in the given species Mm Activator Agonist - - 1x10-3 39
⤷ Conc range: 1x10-3 M [39]
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 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 Ligand is endogenous in the given species 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 - 34
⤷ pIC50 6.1 [34]
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
Potency order of endogenous ligands at P2Y12 receptor ADP>ATP
Other channel blockers at TRPM4 Intracellular nucleotides including ATP, ADP, adenosine 5'-monophosphate and AMP-PNP with an IC50 range of 1.3-1.9 μM
Potency order of endogenous ligands at P2Y1 receptor ADP>ATP
Potency order of endogenous ligands at P2Y13 receptor ADP>>ATP
Potency order of endogenous ligands at P2Y4 receptor UTP>ATP (at rat recombinant receptors, UTP = ATP)
Potency order of endogenous ligands at P2Y11 receptor ATP>ADP
Potency order of endogenous ligands at P2Y2 receptor UTP > ATP
Targets where the ligand is described in the comment field
Target Comment
TRPM5 TRPM5 is not blocked by ATP. APV206512A and APV206513A are TRMP5 blockers, with IC50s of 15 μM [35]. Steviol glycosides (sweet-tasting organic molecules) act as positive modulators of TRMP5 activity [26].
Ligand mentioned in the following text fields
Adenosine turnover overview
Adenylyl cyclases (ACs) overview
F-type ATPase overview
F-type and V-type ATPases overview
Kinases (EC 2.7.x.x) overview
Maxi chloride channel overview
Mitochondrial nucleotide transporter subfamily overview
Mitochondrial phosphate transporters overview
P2Y receptors overview
V-type ATPase overview
Vesicular nucleotide transporter overview
CFTR comments
Maxi chloride channel comments
NOD-like receptor family comments
Phosphatidylcholine-specific phospholipase D comments
SLC33 acetylCoA transporter comments