N-(1-Aza-bicyclo[2.2.2]oct-3-yl)-2-(N',N''-dicyclohexyl-guanidino)-3-naphthalen-2-yl-propionamide

ID: ALA1160968

PubChem CID: 44346306

Max Phase: Preclinical

Molecular Formula: C33H47N5O

Molecular Weight: 529.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC1CN2CCC1CC2)C(Cc1ccc2ccccc2c1)N/C(=N/C1CCCCC1)NC1CCCCC1

Standard InChI:  InChI=1S/C33H47N5O/c39-32(36-31-23-38-19-17-26(31)18-20-38)30(22-24-15-16-25-9-7-8-10-27(25)21-24)37-33(34-28-11-3-1-4-12-28)35-29-13-5-2-6-14-29/h7-10,15-16,21,26,28-31H,1-6,11-14,17-20,22-23H2,(H,36,39)(H2,34,35,37)

Standard InChI Key:  DQUWHEDLZKSAKF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 39 44  0  0  0  0  0  0  0  0999 V2000
    4.1167   -1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9042   -0.7542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3417   -1.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125   -2.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9167   -1.7667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5875   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8375   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0792   -3.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5292   -2.1292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2417   -3.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2417   -1.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5000   -3.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4250   -1.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1292   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9125   -3.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7250   -3.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167   -5.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9542   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0625   -1.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3667   -2.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4750   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9000   -5.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042   -0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5000   -4.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9500   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1250   -5.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7000   -1.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4000   -0.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0000   -2.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3542   -5.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9417   -5.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2292   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6292   -0.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7750   -1.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3750   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -2.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1500   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  6  1  0
  4  3  1  0
  5  1  1  0
  6  5  1  0
  7  4  1  0
  8 10  1  0
  9  1  1  0
 10  7  1  0
 11  7  1  0
 12  6  1  0
 13  3  2  0
 14 16  1  0
 15 12  1  0
 16 15  2  0
 17 22  1  0
 18 11  1  0
 19 11  1  0
 20 18  1  0
 21 19  1  0
 22 24  2  0
 23  2  1  0
 24 15  1  0
 25  9  1  0
 26 14  1  0
 27 17  1  0
 28 23  1  0
 29 23  1  0
 30 25  1  0
 31 25  1  0
 32 26  2  0
 33 27  2  0
 34 30  1  0
 35 29  1  0
 36 28  1  0
 37 31  1  0
 38 37  1  0
 39 35  1  0
 34 38  1  0
 39 36  1  0
 14 17  2  0
  8 21  1  0
 20  8  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1160968

   N-(1-azabicyclo[2.2.2]octan-3-yl)-2-[(N,N'-dicyclohexylcarbamimidoyl)amino]-3-naphthalen-2-ylpropanamide

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: 529.77

Molecular Weight (Monoisotopic): 529.3781

AlogP: 5.16

#Rotatable Bonds: 7

Polar Surface Area: 68.76

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 11.74

CX LogP: 5.63

CX LogD: 2.63

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.34

Np Likeness Score: -0.18

References

1. Salvino JM, Seoane PR, Douty BD, Awad MA, Hoyer D, Ross TM, Dolle RE, Houck WT, Faunce DM, Sawutz DG.  (1995)  Structure activity relationships of non-peptide bradykinin B2 receptor antagonists,  5  (4): [10.1016/0960-894X(95)00035-R]

2. Salvino JM, Seoane PR, Douty BD, Awad MA, Hoyer D, Ross TM, Dolle RE, Houck WT, Faunce DM, Sawutz DG.  (1995)  Structure activity relationships of non-peptide bradykinin B2 receptor antagonists,  5  (4): [10.1016/0960-894X(95)00035-R]

Source

Source(1):

• Scientific Literature