1-[2-(1-Carboxy-3-phenyl-propylamino)-6-(4-chloro-3-sulfamoyl-benzoylamino)-hexanoyl]-pyrrolidine-2-carboxylic acid hydrochloride

ID: ALA2448085

PubChem CID: 73357214

Max Phase: Preclinical

Molecular Formula: C28H36Cl2N4O8S

Molecular Weight: 623.13

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.NS(=O)(=O)c1cc(C(=O)NCCCC[C@H](N[C@@H](CCc2ccccc2)C(=O)O)C(=O)N2CCC[C@H]2C(=O)O)ccc1Cl

Standard InChI:  InChI=1S/C28H35ClN4O8S.ClH/c29-20-13-12-19(17-24(20)42(30,40)41)25(34)31-15-5-4-9-21(26(35)33-16-6-10-23(33)28(38)39)32-22(27(36)37)14-11-18-7-2-1-3-8-18;/h1-3,7-8,12-13,17,21-23,32H,4-6,9-11,14-16H2,(H,31,34)(H,36,37)(H,38,39)(H2,30,40,41);1H/t21-,22-,23-;/m0./s1

Standard InChI Key:  VGGBMAATHKTAAR-RGRVRPFLSA-N

Molfile:  

     RDKit          2D

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    2.9625   -1.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8250   -1.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  3  5  1  0
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 37 33  1  0
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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: 623.13

Molecular Weight (Monoisotopic): 622.1864

AlogP: 2.01

#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: 1.85

CX Basic pKa: 9.58

CX LogP: -0.27

CX LogD: -3.20

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.18

Np Likeness Score: -0.75

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