3-(biphenyl-4-yl)-2-(1-((R)-2-mercapto-3-phenylpropanamido)cyclopentanecarboxamido)propanoic acid

ID: ALA2297565

PubChem CID: 76334944

Max Phase: Preclinical

Molecular Formula: C30H32N2O4S

Molecular Weight: 516.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C(Cc1ccc(-c2ccccc2)cc1)NC(=O)C1(NC(=O)[C@H](S)Cc2ccccc2)CCCC1

Standard InChI:  InChI=1S/C30H32N2O4S/c33-27(26(37)20-21-9-3-1-4-10-21)32-30(17-7-8-18-30)29(36)31-25(28(34)35)19-22-13-15-24(16-14-22)23-11-5-2-6-12-23/h1-6,9-16,25-26,37H,7-8,17-20H2,(H,31,36)(H,32,33)(H,34,35)/t25?,26-/m1/s1

Standard InChI Key:  FUPIWNOUZITLIJ-FXDYGKIASA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
   13.5871   -6.1511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0038   -6.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4161   -6.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5954   -8.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4204   -8.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6772   -7.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3429   -7.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2411   -6.1461    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0015   -5.4354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6515   -5.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4765   -5.4279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2368   -4.7172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6471   -4.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8927   -6.1412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8883   -4.7123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7621   -6.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3475   -5.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3518   -6.8693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7578   -4.7247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4729   -4.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8831   -3.2885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4684   -2.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6392   -2.5795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2326   -3.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8750   -1.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7011   -1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1104   -1.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6948   -0.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8655   -0.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4599   -1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5225   -5.4429    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.3432   -4.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7570   -3.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3431   -2.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5172   -2.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1070   -3.3089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5234   -4.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  1  0
  6  2  1  0
  2  7  1  0
  7  4  1  0
  3  8  1  0
  3  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 11 14  1  0
 11 15  2  0
  1 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  6
 13 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 13  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 22 25  1  0
 17 31  1  0
 19 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 36 37  2  0
 37 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2297565

   3-(4-phenylphenyl)-2-[[1-[[(2R)-3-phenyl-2-sulfanylpropanoyl]amino]cyclopentanecarbonyl]amino]propanoic acid

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: 516.66

Molecular Weight (Monoisotopic): 516.2083

AlogP: 4.44

#Rotatable Bonds: 10

Polar Surface Area: 95.50

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.99

CX Basic pKa: ┄

CX LogP: 5.47

CX LogD: 2.30

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.30

Np Likeness Score: -0.28

References

1. Tanneeru K, Sahu I, Guruprasad L.  (2013)  Ligand-based drug design for human endothelin converting enzyme-1 inhibitors,  22  (9): [10.1007/s00044-012-0433-z]

2. Umekawa, K K and 5 more authors.  2000-09  Pharmacological characterization of a novel sulfonylureid-pyrazole derivative, SM-19712, a potent nonpeptidic inhibitor of endothelin converting enzyme.  [PMID:11043447]

3. Inguimbert, Nicolas N and 6 more authors.  2002-03-28  Toward an optimal joint recognition of the S1' subsites of endothelin converting enzyme-1 (ECE-1), angiotensin converting enzyme (ACE), and neutral endopeptidase (NEP).  [PMID:11906289]

4. Berger, Yann Y and 6 more authors.  2005-01-27  Endothelin-converting enzyme-1 inhibition and growth of human glioblastoma cells.  [PMID:15658862]

5. Seed, Alison A and 8 more authors.  2012-10-15  The dual endothelin converting enzyme/neutral endopeptidase inhibitor SLV-306 (daglutril), inhibits systemic conversion of big endothelin-1 in humans.  [PMID:22480515]

6. McKinnell, R Murray RM and 13 more authors.  2019-01-10  Discovery of TD-0212, an Orally Active Dual Pharmacology AT1 Antagonist and Neprilysin Inhibitor (ARNI).  [PMID:30655952]

Source

Source(1):

• Scientific Literature