5-[7-benzyl-5-ethyl-2-methoxy-4-oxo-(7R)-4,5,7,8-tetrahydro-3H-imidazo[2,1-b]purin-3-ylmethyl]-2-methoxybenzonitrile

ID: ALA24228

Chembl Id: CHEMBL24228

PubChem CID: 10205437

Max Phase: Preclinical

Molecular Formula: C26H26N6O3

Molecular Weight: 470.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1C(=O)c2c(nc(OC)n2Cc2ccc(OC)c(C#N)c2)N2C[C@@H](Cc3ccccc3)N=C12

Standard InChI:  InChI=1S/C26H26N6O3/c1-4-30-24(33)22-23(32-16-20(28-25(30)32)13-17-8-6-5-7-9-17)29-26(35-3)31(22)15-18-10-11-21(34-2)19(12-18)14-27/h5-12,20H,4,13,15-16H2,1-3H3/t20-/m1/s1

Standard InChI Key:  OKZLZFAEOLBLDC-HXUWFJFHSA-N

Alternative Forms

1. Parent:

   

   ALA24228

   5-[7-benzyl-5-ethyl-2-methoxy-4-oxo-(7R)-4,5,7,8-tetrahydro-3H-imidazo[2,1-b]purin-3-ylmethyl]-2-methoxybenzonitrile

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

Calculated Properties

Molecular Weight: 470.53

Molecular Weight (Monoisotopic): 470.2066

AlogP: 3.08

#Rotatable Bonds: 7

Polar Surface Area: 95.98

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.20

CX LogP: 4.21

CX LogD: 4.21

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.53

Np Likeness Score: -0.69

References

1. Pissarnitski DA, Asberom T, Boyle CD, Chackalamannil S, Chintala M, Clader JW, Greenlee WJ, Hu Y, Kurowski S, Myers J, Palamanda J, Stamford AW, Vemulapalli S, Wang Y, Wang P, Wu P, Xu R..  (2004)  SAR development of polycyclic guanine derivatives targeted to the discovery of a selective PDE5 inhibitor for treatment of erectile dysfunction.,  14  (5): [PMID:14980684] [10.1016/j.bmcl.2003.12.027]

2. Antunes JE, Freitas MP, Rittner R..  (2008)  Bioactivities of a series of phosphodiesterase type 5 (PDE-5) inhibitors as modelled by MIA-QSAR.,  43  (8): [PMID:18045743] [10.1016/j.ejmech.2007.10.019]

Source

Source(1):

• Scientific Literature