4'-Bromo-2'-[(5-chloro-2-pyridyl)carbamoyl]-6'-hydroxyl-1-isopropylpiperidine-4-carboxanilide

ID: ALA3354239

PubChem CID: 10117556

Max Phase: Preclinical

Molecular Formula: C21H24BrClN4O3

Molecular Weight: 495.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)N1CCC(C(=O)Nc2c(O)cc(Br)cc2C(=O)Nc2ccc(Cl)cn2)CC1

Standard InChI:  InChI=1S/C21H24BrClN4O3/c1-12(2)27-7-5-13(6-8-27)20(29)26-19-16(9-14(22)10-17(19)28)21(30)25-18-4-3-15(23)11-24-18/h3-4,9-13,28H,5-8H2,1-2H3,(H,26,29)(H,24,25,30)

Standard InChI Key:  MXSUKUHNZNKHBL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   19.9744   -3.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9732   -4.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6813   -4.5385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3909   -4.1291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3881   -3.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6795   -2.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2666   -2.9016    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.0993   -4.5365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8063   -4.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5147   -4.5343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8051   -3.3097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5114   -5.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2189   -5.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9269   -5.3476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9230   -4.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2149   -4.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2094   -3.3053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9143   -2.8920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9088   -2.0748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6248   -3.2958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6173   -1.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6137   -0.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9051   -0.4416    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1983   -0.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2002   -1.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9026    0.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6091    0.7904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1937    0.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2198   -6.5746    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   25.6286   -4.1140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 10  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
 19 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
 26 28  1  0
 13 29  1  0
 15 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3354239

   4'-Bromo-2'-[(5-chloro-2-pyridyl)carbamoyl]-6'-hydroxy-1-isopropylpiperidine-4-carboxanilide

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: 495.81

Molecular Weight (Monoisotopic): 494.0720

AlogP: 4.51

#Rotatable Bonds: 5

Polar Surface Area: 94.56

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.41

CX Basic pKa: 9.44

CX LogP: 2.67

CX LogD: 2.47

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.53

Np Likeness Score: -1.78

References

1. Ishihara T, Koga Y, Mori K, Sugasawa K, Iwatsuki Y, Hirayama F..  (2014)  Novel strategy to boost oral anticoagulant activity of blood coagulation enzyme inhibitors based on biotransformation into hydrophilic conjugates.,  22  (22): [PMID:25438755] [10.1016/j.bmc.2014.09.059]

Source

Source(1):

• Scientific Literature