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

ID: ALA5278364

Max Phase: Preclinical

Molecular Formula: C21H28F3N3O3

Molecular Weight: 427.47

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H28F3N3O3/c1-13(21(22,23)24)18(29)25-12-17(28)26-2-4-27(5-3-26)19(30)20-9-14-6-15(10-20)8-16(7-14)11-20/h14-16H,1-12H2,(H,25,29)

Standard InChI Key:  ADZCQZOSAGKWFG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    2.2940    2.4844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0694    2.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8845    2.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2923    1.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4720    1.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4720    2.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0756    3.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2940    3.3558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8845    3.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5952    1.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4114    2.4844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9700    1.7199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9700    3.2488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0874    1.7199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3538    0.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0874    0.1912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4114    0.9556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9700    0.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3538   -0.5731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0874   -1.3374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2365   -0.5731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6777   -1.3374    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5605   -1.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0017   -2.1019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0017   -0.5731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5605   -2.8663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8845   -2.1019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6777   -2.8663    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0017   -3.6307    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1191   -3.6307    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  1  8  1  0
  7  9  1  0
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  5 10  1  0
  1 10  1  0
  1 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 15 14  1  0
 16 15  1  0
 17 12  1  0
 18 17  1  0
 18 16  1  0
 16 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  1  0
 24 27  2  0
 26 28  1  0
 26 29  1  0
 26 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5278364

   ---

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: 427.47

Molecular Weight (Monoisotopic): 427.2083

AlogP: 2.11

#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: 11.08

CX Basic pKa: 1.17

CX LogP: 1.51

CX LogD: 1.51

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.70

Np Likeness Score: -0.99

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