Diadenosine tetraphosphate

ID: ALA339385

Chembl Id: CHEMBL339385

Cas Number: 5542-28-9

PubChem CID: 21706

Max Phase: Preclinical

Molecular Formula: C20H28N10O19P4

Molecular Weight: 836.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Diadenosine Tetraphosphate | Diadenosine tetraphosphate|AppppA|5',5'''-Diadenosine tetraphosphate|Ap4A|5542-28-9|(ppA)2|adenosine(5')tetraphospho(5')adenosine|BIS(ADENOSINE)-5'-TETRAPHOSPHATE|CHEMBL339385|CHEBI:17422|P(1),P(4)-bis(5'-adenosyl) tetraphosphate|Adenosine 5'-tetraphosphate, 5'-ester with adenosine|B4P|P1,P4-Bis(5'-adenosyl) tetraphosphate|102783-36-8|bis(5'-adenosyl)tetraphosphate|A(5')p4(5')A|Diadenosine 5',5'''-P(sup 1),P(sup 2)-tetraphosphate|diadenosine-tetraphosphate|P(1), P(4)Show More⌵

Canonical SMILES:  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

Standard 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

Standard InChI Key:  YOAHKNVSNCMZGQ-XPWFQUROSA-N

Alternative Forms

1. Parent:

   

   ALA339385

   DIADENOSINE TETRAPHOSPHATE

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 836.39

Molecular Weight (Monoisotopic): 836.0483

AlogP: -2.45

#Rotatable Bonds: 14

Polar Surface Area: 433.97

Molecular Species: ACID

HBA: 25

HBD: 10

#RO5 Violations: 3

HBA (Lipinski): 29

HBD (Lipinski): 12

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.59

CX Basic pKa: 5.22

CX LogP: -10.62

CX LogD: -14.17

Aromatic Rings: 4

Heavy Atoms: 53

QED Weighted: 0.06

Np Likeness Score: 0.69

References

1. Verspohl EJ, Blackburn GM, Hohmeier N, Hagemann J, Lempka M..  (2003)  Synthetic, nondegradable diadenosine polyphosphates and diinosine polyphosphates: their effects on insulin-secreting cells and cultured vascular smooth muscle cells.,  46  (8): [PMID:12672257] [10.1021/jm011070z]

2. Jacobson KA, Jarvis MF, Williams M..  (2002)  Purine and pyrimidine (P2) receptors as drug targets.,  45  (19): [PMID:12213051] [10.1021/jm020046y]

3. Hillmann P, Ko GY, Spinrath A, Raulf A, von Kügelgen I, Wolff SC, Nicholas RA, Kostenis E, Höltje HD, Müller CE..  (2009)  Key determinants of nucleotide-activated G protein-coupled P2Y(2) receptor function revealed by chemical and pharmacological experiments, mutagenesis and homology modeling.,  52  (9): [PMID:19419204] [10.1021/jm801442p]

4. Chang CJ, Geahlen RL..  (1992)  Protein-tyrosine kinase inhibition: mechanism-based discovery of antitumor agents.,  55  (11): [PMID:1479375] [10.1021/np50089a001]

5. Eliahu S, Barr HM, Camden J, Weisman GA, Fischer B..  (2010)  A novel insulin secretagogue based on a dinucleoside polyphosphate scaffold.,  53  (6): [PMID:20175517] [10.1021/jm901621h]

6. Krakowiak A, Pęcherzewska R, Kaczmarek R, Tomaszewska A, Nawrot B, Stec WJ..  (2011)  Evaluation of influence of Ap4A analogues on Fhit-positive HEK293T cells; cytotoxicity and ability to induce apoptosis.,  19  (16): [PMID:21757356] [10.1016/j.bmc.2011.06.028]

7. Yelovitch S, Camden J, Weisman GA, Fischer B..  (2012)  Boranophosphate isoster controls P2Y-receptor subtype selectivity and metabolic stability of dinucleoside polyphosphate analogues.,  55  (1): [PMID:22107038] [10.1021/jm2013198]

8. Yanachkov IB, Chang H, Yanachkova MI, Dix EJ, Berny-Lang MA, Gremmel T, Michelson AD, Wright GE, Frelinger AL..  (2016)  New highly active antiplatelet agents with dual specificity for platelet P2Y1 and P2Y12 adenosine diphosphate receptors.,  107  [PMID:26588064] [10.1016/j.ejmech.2015.10.055]

9. Yanachkov IB, Chang H, Yanachkova MI, Dix EJ, Berny-Lang MA, Gremmel T, Michelson AD, Wright GE, Frelinger AL..  (2016)  New highly active antiplatelet agents with dual specificity for platelet P2Y1 and P2Y12 adenosine diphosphate receptors.,  107  [PMID:26588064] [10.1016/j.ejmech.2015.10.055]

10. Kawaguchi M, Sekimoto E, Ohta Y, Ieda N, Murakami T, Nakagawa H..  (2021)  Synthesis of Fluorescent Probes Targeting Tumor-Suppressor Protein FHIT and Identification of Apoptosis-Inducing FHIT Inhibitors.,  64  (13.0): [PMID:34160227] [10.1021/acs.jmedchem.1c00874]

Source

Source(1):

• Scientific Literature