4-(2-(3-(3-acetamidophenyl)-1H-pyrazol-1-yl)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)pyridine 1-oxide

ID: ALA4534321

PubChem CID: 25120500

Max Phase: Preclinical

Molecular Formula: C29H28F2N4O4

Molecular Weight: 534.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1cccc(-c2ccn(C(Cc3cc[n+]([O-])cc3)c3ccc(OC(F)F)c(OCC4CC4)c3)n2)c1

Standard InChI:  InChI=1S/C29H28F2N4O4/c1-19(36)32-24-4-2-3-22(16-24)25-11-14-35(33-25)26(15-20-9-12-34(37)13-10-20)23-7-8-27(39-29(30)31)28(17-23)38-18-21-5-6-21/h2-4,7-14,16-17,21,26,29H,5-6,15,18H2,1H3,(H,32,36)

Standard InChI Key:  QEFVLMGONWRDJH-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 39 43  0  0  0  0  0  0  0  0999 V2000
   32.7399   -7.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7387   -8.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4468   -8.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1564   -8.4627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1536   -7.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4450   -7.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0321   -7.2352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0319   -6.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3241   -6.0095    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.7395   -6.0092    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.0307   -8.8712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0232   -9.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3117  -10.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4973  -10.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8994  -10.7944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8648   -8.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8661   -9.6873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.5719   -8.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2802   -8.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2092  -10.1671    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.4630  -10.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2802  -10.9426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5314  -10.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9839  -11.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1701  -11.5187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6910  -12.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0245  -12.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8418  -13.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3173  -12.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1780  -13.7536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.7010  -14.4172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0372  -15.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8879  -14.3359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.2769   -9.6836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9844  -10.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6924   -9.6812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.6885   -8.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9804   -8.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4013  -10.0877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 14 13  1  0
 15 14  1  0
 13 15  1  0
  4 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 17  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 21 24  1  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 19 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 19  1  0
 36 39  1  0
M  CHG  2  36   1  39  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4534321

   N-[3-[1-[1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(1-oxidopyridin-1-ium-4-yl)ethyl]pyrazol-3-yl]phenyl]acetamide

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: 534.56

Molecular Weight (Monoisotopic): 534.2079

AlogP: 5.36

#Rotatable Bonds: 11

Polar Surface Area: 92.32

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 1.99

CX LogP: 4.38

CX LogD: 4.38

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.21

Np Likeness Score: -1.52

References

1. Jansen C, Kooistra AJ, Kanev GK, Leurs R, de Esch IJ, de Graaf C..  (2016)  PDEStrIAn: A Phosphodiesterase Structure and Ligand Interaction Annotated Database As a Tool for Structure-Based Drug Design.,  59  (15): [PMID:26908025] [10.1021/acs.jmedchem.5b01813]

Source

Source(1):

• Scientific Literature