2-{1-[N-Carboxymethyl-N'-(6-chloro-1,1-dioxo-7-sulfamoyl-1,2,3,4-tetrahydro-1lambda*6*-benzo[1,2,4]thiadiazin-3-ylmethyl)-N'-methyl-hydrazinocarbonyl]-ethylamino}-4-phenyl-butyric acid ethyl ester hydrochloride

ID: ALA2448084

PubChem CID: 13851278

Max Phase: Preclinical

Molecular Formula: C26H36Cl2N6O9S2

Molecular Weight: 675.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)[C@H](CCc1ccccc1)N[C@@H](C)C(=O)N(CC(=O)O)N(C)CC1Nc2cc(Cl)c(S(N)(=O)=O)cc2S(=O)(=O)N1.Cl

Standard InChI:  InChI=1S/C26H35ClN6O9S2.ClH/c1-4-42-26(37)19(11-10-17-8-6-5-7-9-17)29-16(2)25(36)33(15-24(34)35)32(3)14-23-30-20-12-18(27)21(43(28,38)39)13-22(20)44(40,41)31-23;/h5-9,12-13,16,19,23,29-31H,4,10-11,14-15H2,1-3H3,(H,34,35)(H2,28,38,39);1H/t16-,19-,23?;/m0./s1

Standard InChI Key:  VPXUDVSJTBGJDJ-GGJOXQNSSA-N

Molfile:  

     RDKit          2D

 45 46  0  0  0  0  0  0  0  0999 V2000
    1.7411   -7.6875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -6.4250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.5292   -6.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1000   -6.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6792   -6.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.9625   -6.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1000   -5.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417   -3.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5542   -3.9542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5250   -5.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2417   -6.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -4.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5542   -4.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792   -5.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9542   -5.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -3.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2375   -4.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -3.5417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1292   -3.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5292   -6.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1000   -6.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3000   -4.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -2.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3000   -3.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6875   -7.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3917   -5.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417   -2.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3917   -6.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4167   -5.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5542   -2.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0208   -3.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6667   -4.7542    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0125   -5.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9792   -2.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7333   -3.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458   -3.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -5.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1292   -4.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0125   -6.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4458   -2.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1625   -3.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7250   -6.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8750   -3.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1625   -2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8750   -2.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  2  1  0
  5  6  1  0
  6 11  2  0
  7  4  1  0
  8  9  1  0
  9 13  1  0
 10  3  2  0
 11  3  1  0
 12  7  1  0
 13 14  1  0
 14  7  1  0
 15  6  1  0
 16  9  1  0
 17 10  1  0
 18 19  1  0
 19  8  1  0
 20  2  2  0
 21  2  2  0
 24 22  1  6
 23 16  1  0
 24 18  1  0
 25  5  2  0
 26  5  2  0
 27  8  2  0
 28  5  1  0
 29 22  2  0
 30 23  2  0
 31 24  1  0
 32 15  1  0
 33 22  1  0
 34 23  1  0
 35 31  1  0
 36 35  1  0
 37 13  1  0
 19 38  1  6
 39 33  1  0
 40 36  1  0
 41 36  2  0
 42 39  1  0
 43 41  1  0
 44 40  2  0
 45 43  2  0
 10 12  1  0
 17 15  2  0
 44 45  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: 675.19

Molecular Weight (Monoisotopic): 674.1595

AlogP: 0.32

#Rotatable Bonds: 14

Polar Surface Area: 217.54

Molecular Species: ACID

HBA: 11

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.04

CX Basic pKa: 4.84

CX LogP: -1.07

CX LogD: -2.73

Aromatic Rings: 2

Heavy Atoms: 44

QED Weighted: 0.14

Np Likeness Score: -0.71

References

1. Barton JN, Piwinski JJ, Skiles JW, Regan JR, Menard PR, Desai R, Golec FS, Reilly LW, Goetzen T, Ueng SN..  (1990)  Angiotensin-converting enzyme inhibitors. 9. Novel [[N-(1-carboxy-3-phenylpropyl)amino]acyl]glycine derivatives with diuretic activity.,  33  (6): [PMID:2342054] [10.1021/jm00168a012]

Source

Source(1):

• Scientific Literature