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

ID: ALA2448091

PubChem CID: 73348095

Max Phase: Preclinical

Molecular Formula: C33H40Cl2N4O9S

Molecular Weight: 703.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](N[C@@H](CCc1ccccc1)C(=O)O)C(=O)N(Cc1ccccc1)[C@H](CCCCNc1cc(Cl)c(C(=O)O)cc1S(N)(=O)=O)C(=O)O.Cl

Standard InChI:  InChI=1S/C33H39ClN4O9S.ClH/c1-21(37-26(32(42)43)16-15-22-10-4-2-5-11-22)30(39)38(20-23-12-6-3-7-13-23)28(33(44)45)14-8-9-17-36-27-19-25(34)24(31(40)41)18-29(27)48(35,46)47;/h2-7,10-13,18-19,21,26,28,36-37H,8-9,14-17,20H2,1H3,(H,40,41)(H,42,43)(H,44,45)(H2,35,46,47);1H/t21-,26-,28+;/m0./s1

Standard InChI Key:  OUOVFYYRLOLDCD-YRXFTSSVSA-N

Molfile:  

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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: 703.21

Molecular Weight (Monoisotopic): 702.2126

AlogP: 3.81

#Rotatable Bonds: 19

Polar Surface Area: 216.43

Molecular Species: ZWITTERION

HBA: 8

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.71

CX Basic pKa: 9.20

CX LogP: 1.47

CX LogD: -4.99

Aromatic Rings: 3

Heavy Atoms: 48

QED Weighted: 0.10

Np Likeness Score: -0.73

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