(R)-3-(2-(4-chlorophenyl)-2-fluoroethyl)-5-((7-methyl-6-oxo-6,7-dihydro-1H-purin-1-yl)methyl)-1,3,4-oxadiazol-2(3H)-one

ID: ALA4863686

PubChem CID: 134540805

Max Phase: Preclinical

Molecular Formula: C17H14ClFN6O3

Molecular Weight: 404.79

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1cnc2ncn(Cc3nn(C[C@H](F)c4ccc(Cl)cc4)c(=O)o3)c(=O)c21

Standard InChI:  InChI=1S/C17H14ClFN6O3/c1-23-8-20-15-14(23)16(26)24(9-21-15)7-13-22-25(17(27)28-13)6-12(19)10-2-4-11(18)5-3-10/h2-5,8-9,12H,6-7H2,1H3/t12-/m0/s1

Standard InChI Key:  RSSHXKVUURRAKX-LBPRGKRZSA-N

Molfile:  

 
     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   17.3671  -13.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0768  -12.9820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0739  -12.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3653  -11.7540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6591  -12.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6558  -12.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8782  -11.9167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4009  -12.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8835  -13.2378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3669  -14.2086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6342  -14.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7851  -13.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4922  -12.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2374  -13.3057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7833  -12.6975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3736  -11.9904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5745  -12.1617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7047  -11.2433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5961  -12.7816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0754  -12.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8883  -12.2039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2194  -12.9480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0315  -13.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5116  -12.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1739  -11.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3629  -11.5405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3246  -12.4532    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.7419  -11.3738    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  1 10  2  0
  9 11  1  0
  2 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 16 18  2  0
 15 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 24 27  1  0
 20 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4863686

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 404.79

Molecular Weight (Monoisotopic): 404.0800

AlogP: 1.69

#Rotatable Bonds: 5

Polar Surface Area: 100.74

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.89

CX LogD: 1.89

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.50

Np Likeness Score: -1.34

References

1. Villemure E, Terrett JA, Larouche-Gauthier R, Déry M, Chen H, Reese RM, Shields SD, Chen J, Magnuson S, Volgraf M..  (2021)  A Retrospective Look at the Impact of Binding Site Environment on the Optimization of TRPA1 Antagonists.,  12  (8.0): [PMID:34413952] [10.1021/acsmedchemlett.1c00305]

2. Terrett JA, Chen H, Shore DG, Villemure E, Larouche-Gauthier R, Déry M, Beaumier F, Constantineau-Forget L, Grand-Maître C, Lépissier L, Ciblat S, Sturino C, Chen Y, Hu B, Lu A, Wang Y, Cridland AP, Ward SI, Hackos DH, Reese RM, Shields SD, Chen J, Balestrini A, Riol-Blanco L, Lee WP, Liu J, Suto E, Wu X, Zhang J, Ly JQ, La H, Johnson K, Baumgardner M, Chou KJ, Rohou A, Rougé L, Safina BS, Magnuson S, Volgraf M..  (2021)  Tetrahydrofuran-Based Transient Receptor Potential Ankyrin 1 (TRPA1) Antagonists: Ligand-Based Discovery, Activity in a Rodent Asthma Model, and Mechanism-of-Action via Cryogenic Electron Microscopy.,  64  (7.0): [PMID:33749283] [10.1021/acs.jmedchem.0c02023]

Source

Source(1):

• Scientific Literature