(6aR,9aS)-2-(Phenylmethyl)-5,6a,7,8,9,9a-hexahydro-5-methylcyclopent[4,5]imidazo[2,1-b]purin-4(3H)-one

ID: ALA68152

Chembl Id: CHEMBL68152

PubChem CID: 10663562

Max Phase: Preclinical

Molecular Formula: C18H19N5O

Molecular Weight: 321.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C(=O)c2[nH]c(Cc3ccccc3)nc2N2C1=N[C@@H]1CCC[C@@H]12

Standard InChI:  InChI=1S/C18H19N5O/c1-22-17(24)15-16(23-13-9-5-8-12(13)19-18(22)23)21-14(20-15)10-11-6-3-2-4-7-11/h2-4,6-7,12-13H,5,8-10H2,1H3,(H,20,21)/t12-,13+/m1/s1

Standard InChI Key:  ANKLWQVNAVGBNQ-OLZOCXBDSA-N

Alternative Forms

1. Parent:

   

   ALA68152

   2-benzyl-5-methyl-(6aR,9aS)-1,4,5,8-tetrahydrocyclopenta[4,5]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: 321.38

Molecular Weight (Monoisotopic): 321.1590

AlogP: 2.18

#Rotatable Bonds: 2

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: 12.93

CX Basic pKa: 3.26

CX LogP: 2.53

CX LogD: 2.53

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.92

Np Likeness Score: -0.41

References

1. 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]

2. Xia Y, Chackalamannil S, Czarniecki M, Tsai H, Vaccaro H, Cleven R, Cook J, Fawzi A, Watkins R, Zhang H..  (1997)  Synthesis and evaluation of polycyclic pyrazolo[3,4-d]pyrimidines as PDE1 and PDE5 cGMP phosphodiesterase inhibitors.,  40  (26): [PMID:9435906] [10.1021/jm970495b]

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