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Diadenosine Tetraphosphate

AlkaPlorer ID: AK030044

Synonym: None

IUPAC Name: [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate

Structure

SMILES: NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N3C=NC4=C(N)N=CN=C43)[C@H](O)[C@@H]2O)[C@@H](O)[C@H]1O

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InChI: InChI=1S/C20H28N10O19P4/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(45-19)1-43-50(35,36)47-52(39,40)49-53(41,42)48-51(37,38)44-2-8-12(32)14(34)20(46-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1

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InChIKey: YOAHKNVSNCMZGQ-XPWFQUROSA-N

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Reference

PubChem CID: 21706

CAS: 117137-55-0

LOTUS: LTS0050301

NPASS: NPC319100

Properties Information

Molecule Weight: 836.391

TPSA？: 433.97

MolLogP？: -2.4463999999999992

Number of H-Donors: 10

Number of H-Acceptors: 25

RingCount: 6

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens Bis(5'-adenosyl)-triphosphatase Inhibition 50.0 % 10.1021/acs.jmedchem.1c00874
Homo sapiens Blood T1/2 0.07333 hr 10.1016/j.ejmech.2015.10.055
Homo sapiens P2X purinoceptor 1 Activity 198.0 % 10.1016/j.ejmech.2015.10.055
Homo sapiens P2X purinoceptor 1 EC50 182.0 nM 10.1021/jm020046y
Homo sapiens P2X purinoceptor 2 EC50 15000.0 nM 10.1021/jm020046y
Homo sapiens P2X purinoceptor 3 EC50 500.0 nM 10.1021/jm020046y
Homo sapiens P2X purinoceptor 4 EC50 1000.0 nM 10.1021/jm020046y
Homo sapiens Plasma T1/2 0.03333 hr 10.1016/j.ejmech.2015.10.055
Homo sapiens Purinergic receptor P2Y12 IC50 250000.0 nM 10.1016/j.ejmech.2015.10.055
Homo sapiens Purinergic receptor P2Y2 EC50 145.0 nM 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 EC50 167.0 nM 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 EC50 170.0 nM 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 EC50 185.0 nM 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 EC50 335.0 nM 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 EC50 345.0 nM 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 EC50 423.0 nM 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 EC50 665.0 nM 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 EC50 720.0 nM 10.1021/jm020046y
Homo sapiens Purinergic receptor P2Y2 EC50 1230.0 nM 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 EC50 81000.0 nM 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 EC50 300000.0 nM 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 EC50 740000.0 nM 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 Efficacy 12.0 % 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 Efficacy 15.0 % 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 Efficacy 68.0 % 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 Efficacy 86.0 % 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 Efficacy 98.0 % 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 Efficacy 100.0 % 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 Efficacy 117.0 % 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 Efficacy 128.0 % 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 Efficacy 149.0 % 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 Efficacy nan None 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 Ratio EC50 2.0 None 10.1021/jm801442p
Homo sapiens Purinergic receptor P2Y2 Ratio EC50 560.0 None 10.1021/jm801442p
Homo sapiens Tyrosine-protein kinase SRC IC50 46000.0 nM 10.1021/np50089a001
Rattus norvegicus Plasma T1/2 0.04983 hr 10.1016/j.ejmech.2015.10.055
Rattus norvegicus Plasma T1/2 0.07333 hr 10.1021/jm901621h
Rattus norvegicus Pyrimidinergic receptor P2Y4 EC50 3000.0 nM 10.1021/jm020046y
Rattus norvegicus Rattus norvegicus Radioactivity 21.5 % 10.1021/jm011070z
Rattus norvegicus Rattus norvegicus Radioactivity 26.5 % 10.1021/jm011070z
Rattus norvegicus Rattus norvegicus Radioactivity 31.6 % 10.1021/jm011070z
None ADMET Activity 92.8 % 10.1016/j.bmc.2011.06.028
None ADMET Activity 95.0 % 10.1016/j.bmc.2011.06.028
None ADMET Drug degradation 17.0 % 10.1021/jm2013198
None ADMET Stability 95.0 % 10.1016/j.bmc.2011.06.028
None ADMET T1/2 0.03333 hr 10.1021/jm901621h
None Unchecked IC50 1000.0 nM 10.1021/np50089a001
None Unchecked Radioactivity 52.4 % 10.1021/jm011070z
None Unchecked Radioactivity 54.9 % 10.1021/jm011070z
None Unchecked Radioactivity 61.3 % 10.1021/jm011070z
None Unchecked Radioactivity 70.0 % 10.1021/jm011070z

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT021381 Nc1nc2c(ncn2[C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3cnc4c(N)ncnc43)[C@H](O)[C@@H]2O)[C@@H](O)[C@H]1O MNXR137164
AKRT021792 Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3cnc4c(N)ncnc43)[C@H](O)[C@@H]2O)[C@@H](O)[C@H]1O R00126
AKRT021874 Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3cnc4c(N)ncnc43)[C@H](O)[C@@H]2O)[C@@H](O)[C@H]1O RXN0-5208
AKRT021876 Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(O)(O)=S)[C@@H](O)[C@H]1O>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3cnc4c(N)ncnc43)[C@H](O)[C@@H]2O)[C@@H](O)[C@H]1O enzymemap_91499
AKRT021879 Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OS(=O)(=O)O)[C@@H](O)[C@H]1O>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3cnc4c(N)ncnc43)[C@H](O)[C@@H]2O)[C@@H](O)[C@H]1O R01618
AKRT022129 Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3cnc4c(N)ncnc43)[C@H](O)[C@@H]2O)[C@@H](O)[C@H]1O>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O R00184
AKRT022130 Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3cnc4c(N)ncnc43)[C@H](O)[C@@H]2O)[C@@H](O)[C@H]1O>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O R00125
AKRT022131 Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3cnc4c(N)ncnc43)[C@H](O)[C@@H]2O)[C@@H](O)[C@H]1O>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O R00184
AKRT022132 Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3cnc4c(N)ncnc43)[C@H](O)[C@@H]2O)[C@@H](O)[C@H]1O>>Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O MNXR132130