N-2-[4-[[1-Adamantanecarbonyl]-1-piperazinyl]-2-oxoethyl]chlorofluoroacetamide

ID: ALA5282572

Max Phase: Preclinical

Molecular Formula: C19H27ClFN3O3

Molecular Weight: 399.89

Names and Identifiers

Canonical SMILES:  O=C(NCC(=O)N1CCN(C(=O)C23CC4CC(CC(C4)C2)C3)CC1)C(F)Cl

Standard InChI:  InChI=1S/C19H27ClFN3O3/c20-16(21)17(26)22-11-15(25)23-1-3-24(4-2-23)18(27)19-8-12-5-13(9-19)7-14(6-12)10-19/h12-14,16H,1-11H2,(H,22,26)

Standard InChI Key:  XWALABJLJRYGAC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -2.3931   -1.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5681   -1.6073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1556   -0.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3307   -0.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0817   -1.6073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0817   -0.1784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9066   -0.1784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3191    0.5359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9066    1.2503    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0817    1.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3307    0.5359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3191    1.9648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9066    2.6792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1441    1.9648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4910    1.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3104    1.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3104    2.3660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8746    3.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6306    2.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6306    1.8903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0771    1.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8688    1.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1441    2.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8056   -2.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3931   -3.0362    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6306   -2.3218    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.8056   -0.8929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
  4  5  2  0
  6  4  1  0
  7  6  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  6 11  1  0
 11 10  1  0
 12  9  1  0
 12 13  2  0
 14 12  1  0
 14 15  1  0
 16 15  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 20 19  1  0
 21 16  1  0
 20 21  1  0
 22 20  1  0
 14 22  1  0
 14 23  1  0
 18 23  1  0
  1 24  1  0
 24 25  1  0
 24 26  1  0
  1 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5282572

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 399.89

Molecular Weight (Monoisotopic): 399.1725

AlogP: 1.52

#Rotatable Bonds: 4

Polar Surface Area: 69.72

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.04

CX Basic pKa: 1.17

CX LogP: 0.84

CX LogD: 0.83

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.73

Np Likeness Score: -1.11

References

1. Mader L, Watt SKI, Iyer HR, Nguyen L, Kaur H, Keillor JW..  (2023)  The war on hTG2: warhead optimization in small molecule human tissue transglutaminase inhibitors.,  14  (2.0): [PMID:36846370] [10.1039/d2md00378c]

Source

Source(1):

• Scientific Literature