4-Amino-5-phenyl-1-[4-(tetrahydropyran-4-ylmethyl)piperazin-1-yl]pentan-1-one hydrochloride

ID: ALA1083974

PubChem CID: 46237033

Max Phase: Preclinical

Molecular Formula: C21H34ClN3O2

Molecular Weight: 359.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.N[C@@H](CCC(=O)N1CCN(CC2CCOCC2)CC1)Cc1ccccc1

Standard InChI:  InChI=1S/C21H33N3O2.ClH/c22-20(16-18-4-2-1-3-5-18)6-7-21(25)24-12-10-23(11-13-24)17-19-8-14-26-15-9-19;/h1-5,19-20H,6-17,22H2;1H/t20-;/m0./s1

Standard InChI Key:  UROQTVCYJTZFSA-BDQAORGHSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    5.2000   -0.9042    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1171   -1.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8329   -1.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5488   -1.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2605   -1.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2608   -2.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1171   -0.4990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4054   -1.7365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3105   -1.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0264   -1.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0264   -2.5615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3105   -2.9740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4054   -2.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7381   -2.9740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8970   -2.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1665   -3.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4705   -2.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5031   -1.7599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2336   -1.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9315   -1.8187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5464   -2.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8312   -2.5591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1168   -2.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1198   -3.7968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8351   -4.2079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5474   -3.7964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9764   -1.3240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  1
  2  7  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  8 13  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 15 20  1  0
 14 17  1  0
 11 14  1  0
  2  8  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 21 26  2  0
  6 21  1  0
  5 27  1  0
M  END

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: 359.51

Molecular Weight (Monoisotopic): 359.2573

AlogP: 1.91

#Rotatable Bonds: 7

Polar Surface Area: 58.80

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.83

CX LogP: 1.36

CX LogD: -1.72

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.81

Np Likeness Score: -0.82

References

1. Fattori D, Porcelloni M, D'Andrea P, Catalioto RM, Ettorre A, Giuliani S, Marastoni E, Mauro S, Meini S, Rossi C, Altamura M, Maggi CA..  (2010)  Structure-activity relationships of 6-methyl-benzo[b]thiophene-2-carboxylic acid (1-[(S)-1-benzyl-4-[4-(tetrahydropyran-4-ylmethyl)piperazin-1-yl]butylcarbamoyl]cyclopentyl)amide, potent antagonist of the neurokinin-2 receptor.,  53  (10): [PMID:20408549] [10.1021/jm100176s]

Source

Source(1):

• Scientific Literature