2-(1-{Carboxymethyl-[3-(4-chloro-3-sulfamoyl-benzoylamino)-propyl]-carbamoyl}-ethylamino)-4-phenyl-butyric acid hydrochloride

ID: ALA2448079

PubChem CID: 14632307

Max Phase: Preclinical

Molecular Formula: C25H32Cl2N4O8S

Molecular Weight: 583.06

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](N[C@@H](CCc1ccccc1)C(=O)O)C(=O)N(CCCNC(=O)c1ccc(Cl)c(S(N)(=O)=O)c1)CC(=O)O.Cl

Standard InChI:  InChI=1S/C25H31ClN4O8S.ClH/c1-16(29-20(25(35)36)11-8-17-6-3-2-4-7-17)24(34)30(15-22(31)32)13-5-12-28-23(33)18-9-10-19(26)21(14-18)39(27,37)38;/h2-4,6-7,9-10,14,16,20,29H,5,8,11-13,15H2,1H3,(H,28,33)(H,31,32)(H,35,36)(H2,27,37,38);1H/t16-,20-;/m0./s1

Standard InChI Key:  OGHHZHFGNUQZHL-XXRBRTKDSA-N

Molfile:  

     RDKit          2D

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    4.4000   -1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5417   -3.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1167   -5.9542    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.5417   -0.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8292   -4.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1042   -1.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 33 35  1  0
 10 34  1  6
 35 26  1  0
 36 32  2  0
 37 32  1  0
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  9 22  2  0
 40 38  2  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: 583.06

Molecular Weight (Monoisotopic): 582.1551

AlogP: 1.08

#Rotatable Bonds: 15

Polar Surface Area: 196.20

Molecular Species: ZWITTERION

HBA: 7

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.78

CX Basic pKa: 9.43

CX LogP: -1.48

CX LogD: -4.60

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.19

Np Likeness Score: -1.05

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