3-(2-{Carboxymethyl-[2-(1-carboxy-3-phenyl-propylamino)-propionyl]-amino}-acetylamino)-4-chloro-5-sulfamoyl-benzoic acid hydrochloride

ID: ALA2448088

PubChem CID: 73352660

Max Phase: Preclinical

Molecular Formula: C24H28Cl2N4O10S

Molecular Weight: 599.02

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](N[C@@H](CCc1ccccc1)C(=O)O)C(=O)N(CC(=O)O)CC(=O)Nc1cc(C(=O)O)cc(S(N)(=O)=O)c1Cl.Cl

Standard InChI:  InChI=1S/C24H27ClN4O10S.ClH/c1-13(27-16(24(36)37)8-7-14-5-3-2-4-6-14)22(33)29(12-20(31)32)11-19(30)28-17-9-15(23(34)35)10-18(21(17)25)40(26,38)39;/h2-6,9-10,13,16,27H,7-8,11-12H2,1H3,(H,28,30)(H,31,32)(H,34,35)(H,36,37)(H2,26,38,39);1H/t13-,16-;/m0./s1

Standard InChI Key:  YYUOZBPQFYLAOH-LINSIKMZSA-N

Molfile:  

     RDKit          2D

 41 41  0  0  0  0  0  0  0  0999 V2000
    1.1250   -2.7857    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.9917   -0.9250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.2792   -1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667   -0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167   -0.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0000    0.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2875   -2.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -0.9417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667    0.2958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -1.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5750   -3.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2875   -0.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -2.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1458   -0.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167   -0.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1458   -0.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7042   -1.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9917   -0.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292    0.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292    1.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7125   -0.5125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0000    1.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2875   -3.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4292   -2.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667   -1.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167    1.5333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5625   -0.1125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8583    0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8625   -3.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8583   -1.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417    1.5333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5708   -0.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2875    0.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2875   -0.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2958    1.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0083   -0.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0083    1.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7208    0.2833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7208    1.1083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  3  2  0
  5 17  1  0
  6  4  1  0
  7  5  1  0
  8  3  1  0
  9  8  2  0
 10  6  1  0
 11 14  1  0
 12 10  1  0
 13  9  1  0
 14  7  1  0
 15  9  1  0
 18 16  1  6
 17 12  1  0
 18 11  1  0
 19  2  2  0
 20  2  2  0
 21  5  1  0
 22 21  1  0
 23  2  1  0
 24  7  2  0
 25 13  2  0
 26 12  2  0
 27 16  2  0
 28 22  2  0
 29  4  1  0
 30 18  1  0
 31 13  1  0
 32 16  1  0
 33 22  1  0
 34 30  1  0
 35 34  1  0
 14 36  1  6
 37 35  1  0
 38 35  2  0
 39 37  2  0
 40 38  1  0
 41 40  2  0
  6 15  2  0
 39 41  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: 599.02

Molecular Weight (Monoisotopic): 598.1136

AlogP: 0.60

#Rotatable Bonds: 14

Polar Surface Area: 233.50

Molecular Species: ZWITTERION

HBA: 8

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.50

CX Basic pKa: 8.70

CX LogP: -1.84

CX LogD: -8.48

Aromatic Rings: 2

Heavy Atoms: 40

QED Weighted: 0.18

Np Likeness Score: -0.78

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