3-[5-(1-Cyclopropyl-piperidin-4-yl)-[1,3,4]oxadiazol-2-yl]-1-isopropyl-1H-indazole oxalate

ID: ALA5283579

Max Phase: Preclinical

Molecular Formula: C22H27N5O5

Molecular Weight: 351.45

Names and Identifiers

Canonical SMILES:  CC(C)n1nc(-c2nnc(C3CCN(C4CC4)CC3)o2)c2ccccc21.O=C(O)C(=O)O

Standard InChI:  InChI=1S/C20H25N5O.C2H2O4/c1-13(2)25-17-6-4-3-5-16(17)18(23-25)20-22-21-19(26-20)14-9-11-24(12-10-14)15-7-8-15;3-1(4)2(5)6/h3-6,13-15H,7-12H2,1-2H3;(H,3,4)(H,5,6)

Standard InChI Key:  JBYPBTGYEJITPU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   35.7516  -15.0163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0371  -15.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3227  -15.0163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.0371  -16.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3227  -16.6663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.7516  -16.6663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3585  -13.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1361  -13.7613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7587  -13.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6080  -12.4154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8292  -12.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2009  -12.6801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2339  -11.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0397  -11.7266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5032  -11.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4601  -16.1072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4590  -16.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1732  -17.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1715  -15.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8863  -16.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8912  -16.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6780  -17.1799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.1596  -16.5090    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6701  -15.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9373  -17.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3893  -18.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7446  -18.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9203  -15.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7003  -14.7994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6955  -13.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9099  -13.7249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.4293  -14.3948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  2  0
  7  8  1  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 14 13  1  0
 15 14  1  0
 13 15  1  0
 16 17  2  0
 17 18  1  0
 18 21  2  0
 20 19  2  0
 19 16  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 20  1  0
 22 25  1  0
 25 26  1  0
 25 27  1  0
 24 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 28  2  0
 30  7  1  0
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 351.45

Molecular Weight (Monoisotopic): 351.2059

AlogP: 4.01

#Rotatable Bonds: 4

Polar Surface Area: 59.98

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.41

CX LogP: 2.66

CX LogD: 1.61

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.71

Np Likeness Score: -1.35

References

1. Nirogi R, Mohammed AR, Shinde AK, Gagginapally SR, Kancharla DM, Ravella SR, Bogaraju N, Middekadi VR, Subramanian R, Palacharla RC, Benade V, Muddana N, Abraham R, Medapati RB, Thentu JB, Mekala VR, Petlu S, Lingavarapu BB, Yarra S, Kagita N, Goyal VK, Pandey SK, Jasti V..  (2021)  Discovery and Preclinical Characterization of Usmarapride (SUVN-D4010): A Potent, Selective 5-HT₄ Receptor Partial Agonist for the Treatment of Cognitive Deficits Associated with Alzheimer's Disease.,  64  (15.0): [PMID:34251799] [10.1021/acs.jmedchem.1c00703]

Source

Source(1):

• Scientific Literature