MMV1149524

ID: ALA4548928

PubChem CID: 155549019

Max Phase: Preclinical

Molecular Formula: C22H21ClN2O

Molecular Weight: 364.88

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cccc(NCC2(c3ccnc(-c4ccccc4Cl)c3)CC2)c1

Standard InChI:  InChI=1S/C22H21ClN2O/c1-26-18-6-4-5-17(14-18)25-15-22(10-11-22)16-9-12-24-21(13-16)19-7-2-3-8-20(19)23/h2-9,12-14,25H,10-11,15H2,1H3

Standard InChI Key:  ZPORYJMUJPJJSP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    2.5956   -2.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2778   -3.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5303   -2.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8907   -5.2582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1884   -6.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1858   -7.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8855   -8.2582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5877   -7.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5904   -6.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2867   -8.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0099   -7.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3114   -8.2455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3164   -9.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0199  -10.4998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2817   -9.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3189  -10.3576    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 10  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 24 25  1  0
  7 26  2  0
 26  3  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4548928

   ---

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: 364.88

Molecular Weight (Monoisotopic): 364.1342

AlogP: 5.55

#Rotatable Bonds: 6

Polar Surface Area: 34.15

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.53

CX LogP: 5.00

CX LogD: 5.00

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.62

Np Likeness Score: -0.83

References

1. Antonova-Koch Y, Meister S, Abraham M, Luth MR, Ottilie S, Lukens AK, Sakata-Kato T, Vanaerschot M, Owen E, Jado JC, Maher SP, Calla J, Plouffe D, Zhong Y, Chen K, Chaumeau V, Conway AJ, McNamara CW, Ibanez M, Gagaring K, Serrano FN, Eribez K, Taggard CM, Cheung AL, Lincoln C, Ambachew B, Rouillier M, Siegel D, Nosten F, Kyle DE, Gamo FJ, Zhou Y, Llinás M, Fidock DA, Wirth DF, Burrows J, Campo B, Winzeler EA..  (2018)  Open-source discovery of chemical leads for next-generation chemoprotective antimalarials.,  362  (6419): [PMID:30523084] [10.1126/science.aat9446]

Source

Source(1):

• Winzeler Lab Plasmodium Screening Data