Enantiomer-4-(3-Butyl-[1,2,4]oxadiazol-5-yl)-N-(2,2-dimethyl-cyclopentylmethyl)-benzamide

ID: ALA125327

PubChem CID: 9820033

Max Phase: Preclinical

Molecular Formula: C21H29N3O2

Molecular Weight: 355.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCc1noc(-c2ccc(C(=O)NC[C@H]3CCCC3(C)C)cc2)n1

Standard InChI:  InChI=1S/C21H29N3O2/c1-4-5-8-18-23-20(26-24-18)16-11-9-15(10-12-16)19(25)22-14-17-7-6-13-21(17,2)3/h9-12,17H,4-8,13-14H2,1-3H3,(H,22,25)/t17-/m1/s1

Standard InChI Key:  MXHSFPJPOSZOQI-QGZVFWFLSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  1  0  0  0  0  0999 V2000
    4.5542   -6.7167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1042   -6.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4542   -7.6750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0375   -7.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1542   -7.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1750   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6917   -6.0417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167   -6.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2750   -5.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6542   -6.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1667   -5.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2417   -5.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7292   -6.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1375   -6.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167   -6.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6542   -6.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1375   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7667   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -7.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4625   -6.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9667   -5.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6917   -5.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8875   -6.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -6.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167   -6.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -5.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5750   -5.5667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  5  2  0
  4  2  1  0
  5  1  1  0
  6 10  1  0
  7  6  1  0
  8  2  1  0
  9 13  1  0
 10 17  2  0
 11  6  2  0
 12  7  1  0
 13 12  1  0
 14  8  1  0
 15  8  2  0
 16 14  2  0
 17 15  1  0
 18  9  1  0
 19  5  1  0
 20 23  1  0
 21  9  1  0
 22  9  1  0
 23 13  1  0
 24 19  1  0
 25 24  1  0
 26 25  1  0
 13 27  1  1
  4  3  1  0
 10 16  1  0
 20 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA125327

   (s)-4-(3-butyl-1,2,4-oxadiazol-5-yl)-N-(2,2-dimethylcyclopentylmethyl)benzamide

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: 355.48

Molecular Weight (Monoisotopic): 355.2260

AlogP: 4.64

#Rotatable Bonds: 7

Polar Surface Area: 68.02

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.12

CX LogD: 5.12

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.79

Np Likeness Score: -0.62

References

1. Lloyd J, Schmidt JB, Rovnyak G, Ahmad S, Atwal KS, Bisaha SN, Doweyko LM, Stein PD, Traeger SC, Mathur A, Conder ML, DiMarco J, Harper TW, Jenkins-West T, Levesque PC, Normandin DE, Russell AD, Serafino RP, Smith MA, Lodge NJ..  (2001)  Design and synthesis of 4-substituted benzamides as potent, selective, and orally bioavailable I(Ks) blockers.,  44  (23): [PMID:11689063] [10.1021/jm015505u]

Source

Source(1):

• Scientific Literature