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

ID: ALA2297556

PubChem CID: 76313236

Max Phase: Preclinical

Molecular Formula: C27H34N2O4S

Molecular Weight: 482.65

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C27H34N2O4S/c1-18(2)16-23(34)24(30)29-27(14-6-7-15-27)26(33)28-22(25(31)32)17-19-10-12-21(13-11-19)20-8-4-3-5-9-20/h3-5,8-13,18,22-23,34H,6-7,14-17H2,1-2H3,(H,28,33)(H,29,30)(H,31,32)/t22?,23-/m1/s1

Standard InChI Key:  VSWMKFWTWGIJGV-OZAIVSQSSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
   10.1408  -14.2115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5575  -14.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9698  -14.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1491  -16.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9741  -16.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2309  -15.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8966  -15.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7948  -14.2065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2051  -13.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0301  -13.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7904  -12.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2008  -12.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4463  -14.2016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4420  -12.7726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3158  -14.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8966  -13.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9055  -14.9297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0265  -12.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4368  -11.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0221  -10.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1928  -10.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7863  -11.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4287   -9.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2548   -9.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6641   -9.2012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2484   -8.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4192   -8.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0136   -9.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2945  -12.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9153  -12.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0911  -12.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5464  -13.4753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3602  -11.3471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0717  -13.5119    0.0000 S   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 32  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 10 13  1  0
 10 14  2  0
  1 15  1  0
 15 16  1  0
 15 17  2  0
 12 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 12  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 20 23  1  0
 16 29  1  6
 29 30  1  0
 30 31  1  0
 30 33  1  0
 16 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2297556

   2-[[1-[[(2R)-4-methyl-2-sulfanylpentanoyl]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: 482.65

Molecular Weight (Monoisotopic): 482.2239

AlogP: 4.24

#Rotatable Bonds: 10

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: 3.97

CX Basic pKa: ┄

CX LogP: 5.07

CX LogD: 1.89

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.38

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