3-amino-N-(2-chloro-5-(3-(dimethylamino)propyl)benzyl)-N-cyclopropyl-2-(4-(3-(2,6-dichloro-4-methylphenoxy)propyl)benzyl)propanamide

ID: ALA1093289

PubChem CID: 46883802

Max Phase: Preclinical

Molecular Formula: C35H44Cl3N3O2

Molecular Weight: 645.11

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(Cl)c(OCCCc2ccc(CC(CN)C(=O)N(Cc3cc(CCCN(C)C)ccc3Cl)C3CC3)cc2)c(Cl)c1

Standard InChI:  InChI=1S/C35H44Cl3N3O2/c1-24-18-32(37)34(33(38)19-24)43-17-5-7-25-8-10-27(11-9-25)20-28(22-39)35(42)41(30-13-14-30)23-29-21-26(12-15-31(29)36)6-4-16-40(2)3/h8-12,15,18-19,21,28,30H,4-7,13-14,16-17,20,22-23,39H2,1-3H3

Standard InChI Key:  DYGTZUDCRYLTSM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 43 46  0  0  0  0  0  0  0  0999 V2000
   -4.8061  -18.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8074  -19.6995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0892  -20.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3737  -19.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3769  -18.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0912  -18.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0938  -17.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3819  -17.2190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6627  -17.6315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9509  -17.2144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2316  -17.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2311  -18.4491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5220  -18.8569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1910  -18.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1854  -17.6146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5290  -17.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5360  -16.3812    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.9482  -18.8606    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.0894  -20.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3763  -21.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6584  -20.9402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452  -21.3505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6581  -20.1151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9454  -22.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2318  -20.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5187  -21.3510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5229  -22.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1893  -22.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9084  -22.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9056  -21.3438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1882  -20.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1836  -20.1124    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3564  -22.8897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5314  -22.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3765  -22.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0899  -22.5899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886  -23.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5249  -23.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5256  -24.6480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2346  -25.0623    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2353  -25.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9522  -24.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9108  -18.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  1  0
  2  3  1  0
 21 22  1  0
 10 11  1  0
 21 23  2  0
  5  6  2  0
 22 24  1  0
 11 12  2  0
 22 25  1  0
  6  1  1  0
 25 26  1  0
 12 13  1  0
 26 27  2  0
  1  2  2  0
 27 28  1  0
 13 14  2  0
 28 29  2  0
  6  7  1  0
 29 30  1  0
 14 15  1  0
 30 31  2  0
 31 26  1  0
  3  4  2  0
 31 32  1  0
 33 24  1  0
 34 33  1  0
 24 34  1  0
 15 16  2  0
 16 11  1  0
  7  8  1  0
 20 35  1  0
 16 17  1  0
 35 36  1  0
 28 37  1  0
 12 18  1  0
 37 38  1  0
  8  9  1  0
 38 39  1  0
  3 19  1  0
 39 40  1  0
  4  5  1  0
 40 41  1  0
 19 20  1  0
 40 42  1  0
  9 10  1  0
 14 43  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1093289

   3-amino-N-(2-chloro-5-(3-(dimethylamino)propyl)benzyl)-N-cyclopropyl-2-(4-(3-(2,6-dichloro-4-methylphenoxy)propyl)benzyl)propanamide

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: 645.11

Molecular Weight (Monoisotopic): 643.2499

AlogP: 7.77

#Rotatable Bonds: 16

Polar Surface Area: 58.80

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 9.71

CX LogP: 8.34

CX LogD: 4.57

Aromatic Rings: 3

Heavy Atoms: 43

QED Weighted: 0.16

Np Likeness Score: -0.80

References

1. Chen A, Bayly C, Bezençon O, Richard-Bildstein S, Dubé D, Dubé L, Gagné S, Gallant M, Gaudreault M, Grimm E, Houle R, Lacombe P, Laliberté S, Lévesque JF, Liu S, MacDonald D, Mackay B, Martin D, McKay D, Powell D, Remen L, Soisson S, Toulmond S..  (2010)  Design and optimization of a substituted amino propanamide series of renin inhibitors for the treatment of hypertension.,  20  (7): [PMID:20206513] [10.1016/j.bmcl.2010.02.036]

Source

Source(1):

• Scientific Literature