ID: ALA168949

Max Phase: Preclinical

Molecular Formula: C22H30N6O4S

Molecular Weight: 474.59

Molecule Type: Small molecule

Representations

Canonical SMILES:  CCCc1nc(C)c2c(=O)[nH]c(-c3cc(S(=O)(=O)N4CCN(C)CC4)ccc3OCC)nn12

Standard InChI:  InChI=1S/C22H30N6O4S/c1-5-7-19-23-15(3)20-22(29)24-21(25-28(19)20)17-14-16(8-9-18(17)32-6-2)33(30,31)27-12-10-26(4)11-13-27/h8-9,14H,5-7,10-13H2,1-4H3,(H,24,25,29)

Standard InChI Key:  AIVNVMRJLJHFCU-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: 474.59

Molecular Weight (Monoisotopic): 474.2049

AlogP: 1.68

#Rotatable Bonds: 7

Polar Surface Area: 112.90

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.93

CX Basic pKa: 5.98

CX LogP: 0.75

CX LogD: 0.72

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.55

Np Likeness Score: -1.58

References

1. Haning H, Niewöhner U, Schenke T, Es-Sayed M, Schmidt G, Lampe T, Bischoff E..  (2002)  Imidazo[5,1-f]triazin-4(3H)-ones, a new class of potent PDE 5 inhibitors.,  12  (6): [PMID:11958981] [10.1016/s0960-894x(02)00030-6]

2. Haning H, Niewöhner U, Schenke T, Lampe T, Hillisch A, Bischoff E..  (2005)  Comparison of different heterocyclic scaffolds as substrate analog PDE5 inhibitors.,  15  (17): [PMID:15993055] [10.1016/j.bmcl.2005.05.090]

3. Antunes JE, Freitas MP, da Cunha EF, Ramalho TC, Rittner R..  (2008)  In silico prediction of novel phosphodiesterase type-5 inhibitors derived from Sildenafil, Vardenafil and Tadalafil.,  16  (16): [PMID:18656371] [10.1016/j.bmc.2008.07.022]

4. Jansen C, Kooistra AJ, Kanev GK, Leurs R, de Esch IJ, de Graaf C..  (2016)  PDEStrIAn: A Phosphodiesterase Structure and Ligand Interaction Annotated Database As a Tool for Structure-Based Drug Design.,  59  (15): [PMID:26908025] [10.1021/acs.jmedchem.5b01813]

Source

Source(1):

• Scientific Literature