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

ID: ALA2297566

PubChem CID: 74988248

Max Phase: Preclinical

Molecular Formula: C25H30N2O4S

Molecular Weight: 454.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(S)C(=O)NC1(C(=O)NC(Cc2ccc(-c3ccccc3)cc2)C(=O)O)CCCC1

Standard InChI:  InChI=1S/C25H30N2O4S/c1-24(2,32)22(30)27-25(14-6-7-15-25)23(31)26-20(21(28)29)16-17-10-12-19(13-11-17)18-8-4-3-5-9-18/h3-5,8-13,20,32H,6-7,14-16H2,1-2H3,(H,26,31)(H,27,30)(H,28,29)

Standard InChI Key:  PJLGFANHDUKQKS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   19.7871   -4.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7913   -5.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5037   -5.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0330   -6.1845    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4496   -6.9011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8620   -6.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0413   -8.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8663   -8.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1231   -7.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7887   -7.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6870   -6.1794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4473   -5.4687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0973   -5.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9223   -5.4612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6826   -4.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0930   -4.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3385   -6.1745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3342   -4.7456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2080   -6.1869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7976   -6.9027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9187   -4.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3290   -3.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9143   -2.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0850   -2.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6785   -3.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3208   -1.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1470   -1.8896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5563   -1.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1406   -0.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3113   -0.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9058   -1.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9683   -5.4762    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
  6  5  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  5 10  1  0
 10  7  1  0
  6 11  1  0
  6 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 14 17  1  0
 14 18  2  0
  4 19  1  0
 19  2  1  0
 19 20  2  0
 16 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 16  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 23 26  1  0
  2 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2297566

   2-[[1-[(2-Methyl-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: 454.59

Molecular Weight (Monoisotopic): 454.1926

AlogP: 3.60

#Rotatable Bonds: 8

Polar Surface Area: 95.50

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.08

CX Basic pKa: ┄

CX LogP: 4.25

CX LogD: 1.13

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.46

Np Likeness Score: -0.26

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