N-(2-(hydroxyamino)-2-oxoethyl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide

ID: ALA4780842

PubChem CID: 162663406

Max Phase: Preclinical

Molecular Formula: C22H23N3O4

Molecular Weight: 393.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CNC(=O)c1ccc(C#Cc2ccc(CN3CCOCC3)cc2)cc1)NO

Standard InChI:  InChI=1S/C22H23N3O4/c26-21(24-28)15-23-22(27)20-9-7-18(8-10-20)2-1-17-3-5-19(6-4-17)16-25-11-13-29-14-12-25/h3-10,28H,11-16H2,(H,23,27)(H,24,26)

Standard InChI Key:  KKQPPDLVGMTMLX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   23.0281   -2.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0269   -3.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7418   -3.9653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7400   -2.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3121   -3.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5920   -4.3709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8736   -4.7765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1661   -4.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4482   -4.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4397   -5.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1553   -6.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8703   -5.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7219   -5.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0109   -5.5718    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0175   -4.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3106   -4.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5903   -4.7316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5815   -5.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2930   -5.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4554   -2.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4602   -3.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1678   -2.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8843   -2.7142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.1637   -1.4803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5968   -2.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3133   -2.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0257   -2.2911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3174   -3.5322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7422   -2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3 21  1  0
 20  4  1  0
  4  1  2  0
  2  5  1  0
  5  6  3  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 10 13  1  0
 13 14  1  0
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4780842

   ---

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: 393.44

Molecular Weight (Monoisotopic): 393.1689

AlogP: 1.15

#Rotatable Bonds: 5

Polar Surface Area: 90.90

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.76

CX Basic pKa: 6.77

CX LogP: 1.46

CX LogD: 1.45

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.40

Np Likeness Score: -1.23

References

1. Furuya T,Shapiro AB,Comita-Prevoir J,Kuenstner EJ,Zhang J,Ribe SD,Chen A,Hines D,Moussa SH,Carter NM,Sylvester MA,Romero JAC,Vega CV,Sacco MD,Chen Y,O'Donnell JP,Durand-Reville TF,Miller AA,Tommasi RA.  (2020)  N-Hydroxyformamide LpxC inhibitors, their in vivo efficacy in a mouse Escherichia coli infection model, and their safety in a rat hemodynamic assay.,  28  (24): [PMID:33160146] [10.1016/j.bmc.2020.115826]

Source

Source(1):

• Scientific Literature