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

ID: ALA1160979

PubChem CID: 44346451

Max Phase: Preclinical

Molecular Formula: C46H57N5O

Molecular Weight: 696.00

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC1C2CCN(CC2)C1C(c1ccccc1)c1ccccc1)[C@H](Cc1ccc2ccccc2c1)N/C(=N/C1CCCCC1)NC1CCCCC1

Standard InChI:  InChI=1S/C46H57N5O/c52-45(50-43-37-27-29-51(30-28-37)44(43)42(35-16-5-1-6-17-35)36-18-7-2-8-19-36)41(32-33-25-26-34-15-13-14-20-38(34)31-33)49-46(47-39-21-9-3-10-22-39)48-40-23-11-4-12-24-40/h1-2,5-8,13-20,25-26,31,37,39-44H,3-4,9-12,21-24,27-30,32H2,(H,50,52)(H2,47,48,49)/t41-,43?,44?/m0/s1

Standard InChI Key:  ZXWXGXKPUVYKPX-NDWDGEQISA-N

Molfile:  

     RDKit          2D

 52 59  0  0  0  0  0  0  0  0999 V2000
    9.4042   -6.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792   -4.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0000   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1750   -5.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -3.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2417   -6.1000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5042   -4.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0792   -4.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4000   -6.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7500   -5.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6917   -5.1375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4042   -4.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6375   -5.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5292   -5.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6625   -6.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5875   -4.1000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8500   -7.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0750   -6.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2542   -6.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6875   -7.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1125   -7.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1167   -5.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2250   -4.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2625   -8.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0875   -8.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2667   -3.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4875   -7.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667   -5.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0375   -7.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1042   -8.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8250   -6.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9750   -6.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6792   -8.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8625   -8.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5625   -3.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8625   -4.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4625   -5.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1625   -5.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6250   -8.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5375   -7.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2542   -7.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9667   -8.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8167   -8.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417   -8.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -3.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9375   -4.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375   -5.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3917   -5.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3125   -4.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2500   -8.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9125   -5.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5375   -8.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  8  1  0
  3  1  1  0
  4  3  1  0
  5  2  2  0
  6  1  1  0
  7  4  1  0
  8 10  1  0
  9  1  1  0
 10  7  1  0
 11  2  1  0
 12  3  1  0
 13  6  1  0
 14  6  1  0
 10 15  1  6
 16  7  2  0
 17 19  1  0
 18 15  1  0
 19 18  2  0
 20  9  1  0
 21  9  1  0
 22 14  1  0
 23 13  1  0
 24 25  1  0
 25 27  2  0
 26  5  1  0
 27 18  1  0
 28 11  1  0
 29 17  1  0
 30 21  2  0
 31 21  1  0
 32 20  2  0
 33 20  1  0
 34 24  1  0
 35 26  1  0
 36 26  1  0
 37 28  1  0
 38 28  1  0
 39 29  2  0
 40 31  2  0
 41 32  1  0
 42 33  2  0
 43 30  1  0
 44 34  2  0
 45 35  1  0
 46 36  1  0
 47 37  1  0
 48 38  1  0
 49 46  1  0
 50 42  1  0
 51 48  1  0
 52 40  1  0
 12 22  1  0
 12 23  1  0
 43 52  2  0
 41 50  2  0
 24 17  2  0
 44 39  1  0
 51 47  1  0
 45 49  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1160979

   (2S)-N-(2-benzhydryl-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: 696.00

Molecular Weight (Monoisotopic): 695.4563

AlogP: 8.36

#Rotatable Bonds: 10

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: 11.44

CX LogP: 9.20

CX LogD: 5.37

Aromatic Rings: 4

Heavy Atoms: 52

QED Weighted: 0.12

Np Likeness Score: 0.03

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]

Source

Source(1):

• Scientific Literature