SID22401700

ID: ALA1547940

PubChem CID: 5889878

Max Phase: Preclinical

Molecular Formula: C21H21NO5

Molecular Weight: 367.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)/C=C/C(=O)OCC(=O)NC(c1ccccc1)c1ccccc1

Standard InChI:  InChI=1S/C21H21NO5/c1-2-26-19(24)13-14-20(25)27-15-18(23)22-21(16-9-5-3-6-10-16)17-11-7-4-8-12-17/h3-14,21H,2,15H2,1H3,(H,22,23)/b14-13+

Standard InChI Key:  IAIQVESVEHEGDS-BUHFOSPRSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    3.5387   -2.5997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1098   -1.7747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2532   -3.8372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3966   -1.7747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1111   -3.0122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3953   -3.0122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6808   -2.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0336   -3.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6808   -1.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1098   -2.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0336   -3.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0336   -1.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7481   -2.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3953   -1.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8242   -3.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7481   -4.2497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0336   -0.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4626   -3.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3953   -0.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4626   -3.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6808   -0.1247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2532   -3.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9677   -2.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6821   -3.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3966   -2.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1111   -1.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1111   -0.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0
  1 22  1  0
  2 10  2  0
  3 22  2  0
  4 25  1  0
  4 26  1  0
  5 25  2  0
  6  7  1  0
  6 10  1  0
  7  8  1  0
  7  9  1  0
  8 11  2  0
  8 13  1  0
  9 12  2  0
  9 14  1  0
 10 15  1  0
 11 16  1  0
 12 17  1  0
 13 18  2  0
 14 19  2  0
 16 20  2  0
 17 21  2  0
 18 20  1  0
 19 21  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1547940

   4-O-[2-(benzhydrylamino)-2-oxoethyl] 1-O-ethyl (E)-but-2-enedioate

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: 367.40

Molecular Weight (Monoisotopic): 367.1420

AlogP: 2.55

#Rotatable Bonds: 8

Polar Surface Area: 81.70

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.40

CX Basic pKa: ┄

CX LogP: 3.48

CX LogD: 3.48

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.57

Np Likeness Score: -0.71

References

1. PubChem BioAssay data set, 

2. 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(2):

• PubChem BioAssays
• Winzeler Lab Plasmodium Screening Data