ID: ALA335950

Max Phase: Preclinical

Molecular Formula: C31H25N7O2

Molecular Weight: 527.59

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(Cc1cccc2ccccc12)Nc1nc2nn(CCCc3ccccc3)cc2c2nc(-c3ccco3)nn12

Standard InChI:  InChI=1S/C31H25N7O2/c39-27(19-23-14-6-13-22-12-4-5-15-24(22)23)32-31-34-28-25(30-33-29(36-38(30)31)26-16-8-18-40-26)20-37(35-28)17-7-11-21-9-2-1-3-10-21/h1-6,8-10,12-16,18,20H,7,11,17,19H2,(H,32,34,35,39)

Standard InChI Key:  OOTVLKSCGYKBDY-UHFFFAOYSA-N

Molecule Features

Natural Product: No

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

Properties

Molecular Weight: 527.59

Molecular Weight (Monoisotopic): 527.2070

AlogP: 5.70

#Rotatable Bonds: 8

Polar Surface Area: 103.14

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.04

CX Basic pKa:

CX LogP: 6.88

CX LogD: 6.79

Aromatic Rings: 7

Heavy Atoms: 40

QED Weighted: 0.27

Np Likeness Score: -1.48

References

1. Pastorin G, Da Ros T, Spalluto G, Deflorian F, Moro S, Cacciari B, Baraldi PG, Gessi S, Varani K, Borea PA..  (2003)  Pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine derivatives as adenosine receptor antagonists. Influence of the N5 substituent on the affinity at the human A 3 and A 2B adenosine receptor subtypes: a molecular modeling investigation.,  46  (20): [PMID:13678407] [10.1021/jm030852k]

2. Michielan L, Bolcato C, Federico S, Cacciari B, Bacilieri M, Klotz KN, Kachler S, Pastorin G, Cardin R, Sperduti A, Spalluto G, Moro S..  (2009)  Combining selectivity and affinity predictions using an integrated Support Vector Machine (SVM) approach: An alternative tool to discriminate between the human adenosine A(2A) and A(3) receptor pyrazolo-triazolo-pyrimidine antagonists binding sites.,  17  (14): [PMID:19501513] [10.1016/j.bmc.2009.05.038]

3. Giovannoni MP, Vergelli C, Cilibrizzi A, Crocetti L, Biancalani C, Graziano A, Dal Piaz V, Loza MI, Cadavid MI, Díaz JL, Gavaldà A..  (2010)  Pyrazolo[1',5':1,6]pyrimido[4,5-d]pyridazin-4(3H)-ones as selective human A(1) adenosine receptor ligands.,  18  (22): [PMID:20937560] [10.1016/j.bmc.2010.09.043]

4. Cheong SL, Federico S, Venkatesan G, Paira P, Shao YM, Spalluto G, Yap CW, Pastorin G..  (2011)  Pharmacophore elucidation for a new series of 2-aryl-pyrazolo-triazolo-pyrimidines as potent human A3 adenosine receptor antagonists.,  21  (10): [PMID:21511471] [10.1016/j.bmcl.2011.03.073]

5. El Maatougui A, Azuaje J, González-Gómez M, Miguez G, Crespo A, Carbajales C, Escalante L, García-Mera X, Gutiérrez-de-Terán H, Sotelo E..  (2016)  Discovery of Potent and Highly Selective A2B Adenosine Receptor Antagonist Chemotypes.,  59  (5): [PMID:26824742] [10.1021/acs.jmedchem.5b01586]

Source

Source(1):

• Scientific Literature