(R)-7-Benzyl-5-ethyl-3-(4-hydroxy-benzyl)-2-phenylethynyl-7,8-dihydro-3H,5H-imidazo[2,1-b]purin-4-one

ID: ALA365944

Chembl Id: CHEMBL365944

PubChem CID: 44401892

Max Phase: Preclinical

Molecular Formula: C31H27N5O2

Molecular Weight: 501.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1C(=O)c2c(nc(C#Cc3ccccc3)n2Cc2ccc(O)cc2)N2C[C@@H](Cc3ccccc3)N=C12

Standard InChI:  InChI=1S/C31H27N5O2/c1-2-34-30(38)28-29(36-21-25(32-31(34)36)19-23-11-7-4-8-12-23)33-27(18-15-22-9-5-3-6-10-22)35(28)20-24-13-16-26(37)17-14-24/h3-14,16-17,25,37H,2,19-21H2,1H3/t25-/m1/s1

Standard InChI Key:  DATBCDYXHPVZMS-RUZDIDTESA-N

Alternative Forms

1. Parent:

   

   ALA365944

   (R)-7-Benzyl-5-ethyl-3-(4-hydroxy-benzyl)-2-phenylethynyl-7,8-dihydro-3H,5H-imidazo[2,1-b]purin-4-one

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: 501.59

Molecular Weight (Monoisotopic): 501.2165

AlogP: 4.30

#Rotatable Bonds: 5

Polar Surface Area: 73.96

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.21

CX Basic pKa: 1.25

CX LogP: 6.18

CX LogD: 6.17

Aromatic Rings: 4

Heavy Atoms: 38

QED Weighted: 0.41

Np Likeness Score: -0.41

References

1. Boyle CD, Xu R, Asberom T, Chackalamannil S, Clader JW, Greenlee WJ, Guzik H, Hu Y, Hu Z, Lankin CM, Pissarnitski DA, Stamford AW, Wang Y, Skell J, Kurowski S, Vemulapalli S, Palamanda J, Chintala M, Wu P, Myers J, Wang P..  (2005)  Optimization of purine based PDE1/PDE5 inhibitors to a potent and selective PDE5 inhibitor for the treatment of male ED.,  15  (9): [PMID:15837326] [10.1016/j.bmcl.2005.02.083]

Source

Source(1):

• Scientific Literature