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

ID: ALA2297562

PubChem CID: 76331358

Max Phase: Preclinical

Molecular Formula: C25H30N2O5S

Molecular Weight: 470.59

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C25H30N2O5S/c1-32-16-21(33)22(28)27-25(13-5-6-14-25)24(31)26-20(23(29)30)15-17-9-11-19(12-10-17)18-7-3-2-4-8-18/h2-4,7-12,20-21,33H,5-6,13-16H2,1H3,(H,26,31)(H,27,28)(H,29,30)/t20?,21-/m1/s1

Standard InChI Key:  FPDVGQSEODEEEQ-BPGUCPLFSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   10.1950  -29.0240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6116  -29.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0239  -29.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2033  -31.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0283  -31.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2851  -30.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9507  -30.2274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8489  -29.0190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6093  -28.3083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2593  -28.3033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0843  -28.3008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8446  -27.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2549  -26.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5005  -29.0141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4962  -27.5851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3700  -29.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9553  -28.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9596  -29.7422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3656  -27.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0807  -26.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4910  -26.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0762  -25.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2470  -25.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8405  -26.1678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4828  -24.7313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3089  -24.7291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7182  -24.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3026  -23.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4733  -23.3063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0678  -24.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1303  -28.3158    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.9510  -26.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3613  -26.1686    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  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2297562

   2-[[1-[[(2R)-3-methoxy-2-sulfanylpropanoyl]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: 470.59

Molecular Weight (Monoisotopic): 470.1875

AlogP: 2.84

#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: 3.93

CX Basic pKa: ┄

CX LogP: 3.41

CX LogD: 0.21

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.40

Np Likeness Score: -0.30

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