3-(biphenyl-4-yl)-2-(1-((2R,3S)-2-mercapto-3-methoxybutanamido)cyclopentanecarboxamido)propanoic acid

ID: ALA2297563

PubChem CID: 76313238

Max Phase: Preclinical

Molecular Formula: C26H32N2O5S

Molecular Weight: 484.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@@H](C)[C@@H](S)C(=O)NC1(C(=O)NC(Cc2ccc(-c3ccccc3)cc2)C(=O)O)CCCC1

Standard InChI:  InChI=1S/C26H32N2O5S/c1-17(33-2)22(34)23(29)28-26(14-6-7-15-26)25(32)27-21(24(30)31)16-18-10-12-20(13-11-18)19-8-4-3-5-9-19/h3-5,8-13,17,21-22,34H,6-7,14-16H2,1-2H3,(H,27,32)(H,28,29)(H,30,31)/t17-,21?,22+/m0/s1

Standard InChI Key:  HAGLIWSXXXJOAR-QNGGVGCWSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
   17.5325  -28.9907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9491  -29.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3614  -28.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5408  -30.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3658  -30.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6226  -30.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2882  -30.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1864  -28.9856    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9468  -28.2749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5968  -28.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4218  -28.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1821  -27.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5925  -26.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8380  -28.9807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8337  -27.5518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7075  -28.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2928  -28.2799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2971  -29.7089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7031  -27.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4182  -26.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8285  -26.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4137  -25.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5845  -25.4190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1780  -26.1345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8203  -24.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6464  -24.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0558  -23.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6401  -23.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8108  -23.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4053  -23.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4678  -28.2824    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.2885  -26.8510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6988  -26.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5281  -27.5617    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  0
 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  6
 19 32  1  0
 32 33  1  0
 19 34  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2297563

   2-[[1-[[(2R,3S)-3-methoxy-2-sulfanylbutanoyl]amino]cyclopentanecarbonyl]amino]-3-(4-phenylphenyl)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: 484.62

Molecular Weight (Monoisotopic): 484.2032

AlogP: 3.23

#Rotatable Bonds: 10

Polar Surface Area: 104.73

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.86

CX Basic pKa: ┄

CX LogP: 3.83

CX LogD: 0.59

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.39

Np Likeness Score: -0.12

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