2-benzyl-5-ethyl-(6aR,9aS)-1,4,5,8-tetrahydrocyclopenta[4,5]imidazo[2,1-b]purin-4-one

ID: ALA446663

Chembl Id: CHEMBL446663

PubChem CID: 10520799

Max Phase: Preclinical

Molecular Formula: C19H21N5O

Molecular Weight: 335.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1C(=O)c2[nH]c(Cc3ccccc3)nc2N2C1=N[C@@H]1CCC[C@@H]12

Standard InChI:  InChI=1S/C19H21N5O/c1-2-23-18(25)16-17(24-14-10-6-9-13(14)20-19(23)24)22-15(21-16)11-12-7-4-3-5-8-12/h3-5,7-8,13-14H,2,6,9-11H2,1H3,(H,21,22)/t13-,14+/m1/s1

Standard InChI Key:  PRCYQPWWULRKLG-KGLIPLIRSA-N

Alternative Forms

1. Parent:

   

   ALA446663

   (11R,15S)-4-benzyl-8-ethyl-1,3,5,8,10-pentazatetracyclo[7.6.0.02,6.011,15]pentadeca-2(6),3,9-trien-7-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: 335.41

Molecular Weight (Monoisotopic): 335.1746

AlogP: 2.57

#Rotatable Bonds: 3

Polar Surface Area: 64.59

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.92

CX Basic pKa: 3.26

CX LogP: 2.89

CX LogD: 2.89

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.94

Np Likeness Score: -0.55

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. Ahn HS, Bercovici A, Boykow G, Bronnenkant A, Chackalamannil S, Chow J, Cleven R, Cook J, Czarniecki M, Domalski C, Fawzi A, Green M, Gündes A, Ho G, Laudicina M, Lindo N, Ma K, Manna M, McKittrick B, Mirzai B, Nechuta T, Neustadt B, Puchalski C, Pula K, Zhang H..  (1997)  Potent tetracyclic guanine inhibitors of PDE1 and PDE5 cyclic guanosine monophosphate phosphodiesterases with oral antihypertensive activity.,  40  (14): [PMID:9216839] [10.1021/jm9608467]

3. 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]

4. Mittal A, Paliwal S, Sharma M, Singh A, Sharma S, Yadav D..  (2014)  Pharmacophore based virtual screening, molecular docking and biological evaluation to identify novel PDE5 inhibitors with vasodilatory activity.,  24  (14): [PMID:24856068] [10.1016/j.bmcl.2014.05.004]

Source

Source(1):

• Scientific Literature