MMV1263282

ID: ALA4514740

PubChem CID: 42145771

Max Phase: Preclinical

Molecular Formula: C22H26N2O3

Molecular Weight: 366.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)Nc1ccc(C(=O)NCC2(c3ccccc3)CC2)cc1

Standard InChI:  InChI=1S/C22H26N2O3/c1-21(2,3)27-20(26)24-18-11-9-16(10-12-18)19(25)23-15-22(13-14-22)17-7-5-4-6-8-17/h4-12H,13-15H2,1-3H3,(H,23,25)(H,24,26)

Standard InChI Key:  KQBKLDIPEPYHNW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    4.9292   -5.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8509   -5.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8889   -6.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 O   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
    1.5548   -3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 N   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
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6024    2.6977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990    0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2472   -0.4261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7472   -0.4237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8004    1.4893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0981    0.7370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3985    1.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4011    2.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1034    3.7370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8030    2.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 12 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 19  1  0
 19 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4514740

   tert-butyl N-[4-[(1-phenylcyclopropyl)methylcarbamoyl]phenyl]carbamate

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: 366.46

Molecular Weight (Monoisotopic): 366.1943

AlogP: 4.50

#Rotatable Bonds: 5

Polar Surface Area: 67.43

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.73

CX Basic pKa: ┄

CX LogP: 4.25

CX LogD: 4.25

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.82

Np Likeness Score: -1.06

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