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

ID: ALA2448081

PubChem CID: 73351180

Max Phase: Preclinical

Molecular Formula: C29H41Cl2N5O9S2

Molecular Weight: 702.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)[C@H](CCc1ccccc1)N[C@@H](C)C(=O)N(CC(=O)O)[C@H](CC(C)C)C1Nc2cc(Cl)c(S(N)(=O)=O)cc2S(=O)(=O)N1.Cl

Standard InChI:  InChI=1S/C29H40ClN5O9S2.ClH/c1-5-44-29(39)21(12-11-19-9-7-6-8-10-19)32-18(4)28(38)35(16-26(36)37)23(13-17(2)3)27-33-22-14-20(30)24(45(31,40)41)15-25(22)46(42,43)34-27;/h6-10,14-15,17-18,21,23,27,32-34H,5,11-13,16H2,1-4H3,(H,36,37)(H2,31,40,41);1H/t18-,21-,23+,27?;/m0./s1

Standard InChI Key:  XSCAATRGEATMAN-VKUJUHMGSA-N

Molfile:  

     RDKit          2D

 47 48  0  0  0  0  0  0  0  0999 V2000
   -0.5893   -7.6071    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9897   -6.4218    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2776   -6.0095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7019   -6.0095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2776   -5.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8591   -6.4093    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.1387   -6.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5529   -3.9523    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7019   -5.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9897   -4.7727    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408   -3.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -6.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5529   -4.7768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1262   -5.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4140   -4.7644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4123   -3.5400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1286   -3.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7019   -6.8258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2776   -6.8258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2999   -4.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2651   -3.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2999   -3.9523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8633   -7.2339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5713   -5.9888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2651   -2.7154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8408   -2.7154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5713   -6.8133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8491   -5.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4165   -5.1974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5529   -2.3031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0203   -3.5400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8383   -4.7519    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0120   -5.1974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9772   -2.2989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7324   -3.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4446   -3.5483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1286   -4.7768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4285   -5.9013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0120   -6.0220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4446   -2.7154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1609   -3.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -5.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8366   -6.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7242   -6.4385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8731   -3.5483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1609   -2.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8731   -2.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  2  1  0
  5  3  1  0
  6  7  1  0
  7 12  2  0
  8 13  1  0
  9  4  2  0
 10  9  1  0
 11  8  1  0
 12  4  1  0
 13  5  1  0
 14  7  1  0
 15  9  1  0
 16 17  1  0
 17 11  1  0
 18  2  2  0
 19  2  2  0
 22 20  1  6
 21  8  1  0
 22 16  1  0
 23  6  2  0
 24  6  2  0
 25 21  1  0
 26 11  2  0
 27  6  1  0
 13 28  1  1
 29 20  2  0
 30 25  2  0
 31 22  1  0
 32 14  1  0
 33 20  1  0
 34 25  1  0
 35 31  1  0
 36 35  1  0
 17 37  1  6
 38 28  1  0
 39 33  1  0
 40 36  1  0
 41 36  2  0
 42 38  1  0
 43 38  1  0
 44 39  1  0
 45 41  1  0
 46 40  2  0
 47 45  2  0
 15 14  2  0
 10  5  1  0
 46 47  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: 702.25

Molecular Weight (Monoisotopic): 701.1956

AlogP: 1.89

#Rotatable Bonds: 15

Polar Surface Area: 214.30

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.40

CX Basic pKa: 5.19

CX LogP: 0.94

CX LogD: -0.63

Aromatic Rings: 2

Heavy Atoms: 46

QED Weighted: 0.17

Np Likeness Score: -0.70

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