Phosphoric acid mono-[5-(6-methylamino-purin-9-yl)-2-phosphonooxymethyl-tetrahydro-furan-3-yl] ester;(MRS-2179)

ID: ALA129841

Chembl Id: CHEMBL129841

Max Phase: Preclinical

Molecular Formula: C11H17N5O9P2

Molecular Weight: 425.23

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: MRS-2179

Synonyms from Alternative Forms(1): MRS-2179

Canonical SMILES:  CNc1ncnc2c1ncn2[C@H]1C[C@H](OP(=O)(O)O)[C@@H](COP(=O)(O)O)O1

Standard InChI:  InChI=1S/C11H17N5O9P2/c1-12-10-9-11(14-4-13-10)16(5-15-9)8-2-6(25-27(20,21)22)7(24-8)3-23-26(17,18)19/h4-8H,2-3H2,1H3,(H,12,13,14)(H2,17,18,19)(H2,20,21,22)/t6-,7+,8+/m0/s1

Standard InChI Key:  CCPLITQNIFLYQB-XLPZGREQSA-N

Alternative Forms

  1. Parent:

    ALA129841

    ---
  2. Alternative Forms:

    ALA129841

    CID 49797715

Associated Targets(Human)

P2RY2 Tclin Purinergic receptor P2Y2 (1109 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2RY4 Tchem Pyrimidinergic receptor P2Y4 (598 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2RY6 Tchem Pyrimidinergic receptor P2Y6 (717 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2RX1 Tchem P2X purinoceptor 1 (328 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2RX3 Tclin P2X purinoceptor 3 (1991 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2RX7 Tchem P2X purinoceptor 7 (5534 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2RY1 Tchem Purinergic receptor P2Y1 (1327 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2RX2 Tchem P2X purinoceptor 2 (190 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2RX4 Tchem P2X purinoceptor 4 (516 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NFE2L2 Tchem Nuclear factor erythroid 2-related factor 2 (95332 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

P2RY1 P2Y purinoceptor 1 (470 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2ry12 Purinergic receptor P2Y12 (121 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2rx2 P2X purinoceptor 2 (106 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
P2rx4 P2X purinoceptor 4 (106 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
pfk 6-phospho-1-fructokinase (7870 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 425.23Molecular Weight (Monoisotopic): 425.0502AlogP: -0.26#Rotatable Bonds: 7
Polar Surface Area: 198.38Molecular Species: ACIDHBA: 10HBD: 5
#RO5 Violations: HBA (Lipinski): 14HBD (Lipinski): 5#RO5 Violations (Lipinski): 1
CX Acidic pKa: 0.85CX Basic pKa: 4.72CX LogP: -3.84CX LogD: -8.31
Aromatic Rings: 2Heavy Atoms: 27QED Weighted: 0.36Np Likeness Score: 0.63

References

1. Moro S, Guo D, Camaioni E, Boyer JL, Harden TK, Jacobson KA..  (1998)  Human P2Y1 receptor: molecular modeling and site-directed mutagenesis as tools to identify agonist and antagonist recognition sites.,  41  (9): [PMID:9554879] [10.1021/jm970684u]
2. Nandanan E, Camaioni E, Jang SY, Kim YC, Cristalli G, Herdewijn P, Secrist JA, Tiwari KN, Mohanram A, Harden TK, Boyer JL, Jacobson KA..  (1999)  Structure-activity relationships of bisphosphate nucleotide derivatives as P2Y1 receptor antagonists and partial agonists.,  42  (9): [PMID:10229631] [10.1021/jm980657j]
3. Camaioni E, Boyer JL, Mohanram A, Harden TK, Jacobson KA..  (1998)  Deoxyadenosine bisphosphate derivatives as potent antagonists at P2Y1 receptors.,  41  (2): [PMID:9457242] [10.1021/jm970433l]
4. Kim YC, Brown SG, Harden TK, Boyer JL, Dubyak G, King BF, Burnstock G, Jacobson KA..  (2001)  Structure-activity relationships of pyridoxal phosphate derivatives as potent and selective antagonists of P2X1 receptors.,  44  (3): [PMID:11462975] [10.1021/jm9904203]
5. Jacobson KA, Jarvis MF, Williams M..  (2002)  Purine and pyrimidine (P2) receptors as drug targets.,  45  (19): [PMID:12213051] [10.1021/jm020046y]
6. Xu B, Stephens A, Kirschenheuter G, Greslin AF, Cheng X, Sennelo J, Cattaneo M, Zighetti ML, Chen A, Kim SA, Kim HS, Bischofberger N, Cook G, Jacobson KA..  (2002)  Acyclic analogues of adenosine bisphosphates as P2Y receptor antagonists: phosphate substitution leads to multiple pathways of inhibition of platelet aggregation.,  45  (26): [PMID:12477353] [10.1021/jm020173u]
7. Kim YC, Gallo-Rodriguez C, Jang SY, Nandanan E, Adams M, Harden TK, Boyer JL, Jacobson KA..  (2000)  Acyclic analogues of deoxyadenosine 3',5'-bisphosphates as P2Y(1) receptor antagonists.,  43  (4): [PMID:10691699] [10.1021/jm9905211]
8. Nandanan E, Jang SY, Moro S, Kim HO, Siddiqui MA, Russ P, Marquez VE, Busson R, Herdewijn P, Harden TK, Boyer JL, Jacobson KA..  (2000)  Synthesis, biological activity, and molecular modeling of ribose-modified deoxyadenosine bisphosphate analogues as P2Y(1) receptor ligands.,  43  (5): [PMID:10715151] [10.1021/jm990249v]
9. Raboisson P, Baurand A, Cazenave JP, Gachet C, Retat M, Spiess B, Bourguignon JJ..  (2002)  Novel antagonists acting at the P2Y(1) purinergic receptor: synthesis and conformational analysis using potentiometric and nuclear magnetic resonance titration techniques.,  45  (4): [PMID:11831909] [10.1021/jm0104062]
10. Costanzi S, Mamedova L, Gao ZG, Jacobson KA..  (2004)  Architecture of P2Y nucleotide receptors: structural comparison based on sequence analysis, mutagenesis, and homology modeling.,  47  (22): [PMID:15481977] [10.1021/jm049914c]
11. Pfefferkorn JA, Choi C, Winters T, Kennedy R, Chi L, Perrin LA, Lu G, Ping YW, McClanahan T, Schroeder R, Leininger MT, Geyer A, Schefzick S, Atherton J..  (2008)  P2Y1 receptor antagonists as novel antithrombotic agents.,  18  (11): [PMID:18445527] [10.1016/j.bmcl.2008.04.028]
12. PubChem BioAssay data set, 
13. PubChem BioAssay data set, 
14. 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]
15. Xu P, Feng X, Luan H, Wang J, Ge R, Li Z, Bian J..  (2018)  Current knowledge on the nucleotide agonists for the P2Y2 receptor.,  26  (2): [PMID:29254895] [10.1016/j.bmc.2017.11.043]
16. Li X, Guo T, Feng Q, Bai T, Wu L, Liu Y, Zheng X, Jia J, Pei J, Wu S, Song Y, Zhang Y..  (2022)  Progress of thrombus formation and research on the structure-activity relationship for antithrombotic drugs.,  228  [PMID:34902735] [10.1016/j.ejmech.2021.114035]
17. Conroy S, Kindon N, Kellam B, Stocks MJ..  (2016)  Drug-like Antagonists of P2Y Receptors-From Lead Identification to Drug Development.,  59  (22): [PMID:27413802] [10.1021/acs.jmedchem.5b01972]