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

ID: ALA2448087

PubChem CID: 14632298

Max Phase: Preclinical

Molecular Formula: C25H33Cl2N5O9S2

Molecular Weight: 646.14

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](N[C@@H](CCc1ccccc1)C(=O)O)C(=O)N(CCCC1Nc2cc(Cl)c(S(N)(=O)=O)cc2S(=O)(=O)N1)CC(=O)O.Cl

Standard InChI:  InChI=1S/C25H32ClN5O9S2.ClH/c1-15(28-18(25(35)36)10-9-16-6-3-2-4-7-16)24(34)31(14-23(32)33)11-5-8-22-29-19-12-17(26)20(41(27,37)38)13-21(19)42(39,40)30-22;/h2-4,6-7,12-13,15,18,22,28-30H,5,8-11,14H2,1H3,(H,32,33)(H,35,36)(H2,27,37,38);1H/t15-,18-,22?;/m0./s1

Standard InChI Key:  YJWBZRZGVGLYKJ-JNDAYTCCSA-N

Molfile:  

     RDKit          2D

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    7.5622   -7.6371    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9850   -7.2419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8426   -7.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1271   -7.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6963   -6.0065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8386   -3.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8301   -6.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2652   -7.2170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5414   -5.9816    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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    3.9725   -2.2961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7304   -3.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499   -4.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4417   -3.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1273   -4.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4417   -2.7121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1572   -3.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1572   -2.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8685   -3.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8685   -2.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  6  1  0
  5  2  1  0
  6  8  2  0
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  8  3  1  0
  9 13  1  0
 10 14  1  0
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 15 18  1  0
 16  2  2  0
 17  2  2  0
 18 10  1  0
 20 19  1  6
 20 15  1  0
 21  4  2  0
 22  4  2  0
 23 24  1  0
 24 14  1  0
 25  4  1  0
 26 10  2  0
 27 19  2  0
 28 23  2  0
 29 20  1  0
 30 11  1  0
 31 19  1  0
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 33 29  1  0
 34 37  1  0
 35 33  1  0
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 18 38  1  6
 39 35  1  0
 40 35  2  0
 41 39  2  0
 42 40  1  0
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  7  9  1  0
 12 11  2  0
 41 43  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: 646.14

Molecular Weight (Monoisotopic): 645.1330

AlogP: 0.77

#Rotatable Bonds: 14

Polar Surface Area: 225.30

Molecular Species: ZWITTERION

HBA: 9

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.77

CX Basic pKa: 8.86

CX LogP: -1.79

CX LogD: -4.97

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.17

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