(Z)-2-chloro-5-(2-(4-(diethylamino)-2-hydroxybenzylidene)hydrazinyl)benzoic acid

ID: ALA599409

PubChem CID: 135976298

Max Phase: Preclinical

Molecular Formula: C18H20ClN3O3

Molecular Weight: 361.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)c1ccc(/C=N\Nc2ccc(Cl)c(C(=O)O)c2)c(O)c1

Standard InChI:  InChI=1S/C18H20ClN3O3/c1-3-22(4-2)14-7-5-12(17(23)10-14)11-20-21-13-6-8-16(19)15(9-13)18(24)25/h5-11,21,23H,3-4H2,1-2H3,(H,24,25)/b20-11-

Standard InChI Key:  XLANBBIVLZYAFC-JAIQZWGSSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    8.5488   -6.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8343   -6.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8343   -5.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5488   -5.1513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2633   -5.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2633   -6.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5488   -7.6263    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.1199   -6.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4054   -6.3888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1199   -7.6263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5488   -4.3263    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8343   -3.9138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8343   -3.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5488   -2.6763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5488   -1.8513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9778   -1.8513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9778   -2.6763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2633   -1.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2633   -3.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8343   -1.4388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6922   -1.4388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6922   -0.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4067   -1.8513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1212   -1.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4067   -0.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0
 12 13  2  0
  1  2  2  0
 13 14  1  0
 14 15  2  0
  1  7  1  0
 16 17  1  0
  3  4  2  0
  2  8  1  0
  8  9  1  0
 14 19  1  0
 15 18  1  0
 18 16  2  0
 17 19  2  0
  4  5  1  0
 15 20  1  0
  8 10  2  0
 16 21  1  0
  2  3  1  0
 21 22  1  0
  4 11  1  0
 21 23  1  0
  5  6  2  0
 23 24  1  0
 11 12  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA599409

   ---

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: 361.83

Molecular Weight (Monoisotopic): 361.1193

AlogP: 4.04

#Rotatable Bonds: 7

Polar Surface Area: 85.16

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.46

CX Basic pKa: 5.93

CX LogP: 2.43

CX LogD: 1.30

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.51

Np Likeness Score: -1.54

References

1. Podvinec M, Lim SP, Schmidt T, Scarsi M, Wen D, Sonntag LS, Sanschagrin P, Shenkin PS, Schwede T..  (2010)  Novel inhibitors of dengue virus methyltransferase: discovery by in vitro-driven virtual screening on a desktop computer grid.,  53  (4): [PMID:20108931] [10.1021/jm900776m]

Source

Source(1):

• Scientific Literature