(S)-3-Biphenyl-4-yl-2-{[1-((S)-2-mercapto-3-methyl-pentanoylamino)-cyclopentanecarbonyl]-amino}-propionic acid

ID: ALA3351079

PubChem CID: 118719300

Max Phase: Preclinical

Molecular Formula: C27H34N2O4S

Molecular Weight: 482.65

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C27H34N2O4S/c1-3-18(2)23(34)24(30)29-27(15-7-8-16-27)26(33)28-22(25(31)32)17-19-11-13-21(14-12-19)20-9-5-4-6-10-20/h4-6,9-14,18,22-23,34H,3,7-8,15-17H2,1-2H3,(H,28,33)(H,29,30)(H,31,32)/t18-,22-,23-/m0/s1

Standard InChI Key:  OGXZPPQKOPSYNJ-TZYHBYERSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  1  0  0  0  0  0999 V2000
    5.5931   -1.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0582   -2.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8786   -1.6942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8786   -2.5192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5732   -3.1004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9088   -3.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4239   -4.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3076   -1.6942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5931   -0.4567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7226   -1.6793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7360   -6.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7293   -3.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7594   -5.2752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0715   -6.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9155   -6.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2209   -5.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3076   -2.5192    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.0648   -4.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6034   -4.4353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0221   -1.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8853   -4.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5799   -5.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7071   -3.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6991   -2.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5866   -7.6225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8920   -7.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7365   -1.6942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0221   -0.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0347   -3.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4216   -3.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4510   -1.2817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9221   -8.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2275   -7.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7426   -8.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  1  1  0
  4  3  1  0
  5  2  1  0
  6  5  1  1
  7  6  1  0
  8  1  1  0
  9  1  2  0
 10  2  2  0
 11 15  1  0
  6 12  1  0
 13  7  2  0
 14 11  1  0
 15 22  2  0
 16 21  1  0
  8 17  1  6
 18 12  1  0
 19  7  1  0
  8 20  1  0
 21 18  2  0
 22 18  1  0
 23  4  1  0
 24  4  1  0
 25 14  1  0
 26 14  2  0
 27 20  1  0
 20 28  1  1
 29 24  1  0
 30 23  1  0
 31 27  1  0
 32 25  2  0
 33 26  1  0
 34 33  2  0
 30 29  1  0
 16 11  2  0
 32 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3351079

   ---

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: 3.90

CX Basic pKa: ┄

CX LogP: 5.15

CX LogD: 1.93

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.38

Np Likeness Score: -0.21

References

1. Fink CA, Moskal M, Firooznia F, Hoyer D, Symonsbergen D, Wei D, Qiao Y, Savage P, Beil ME, Trapani AJ, Jeng AY..  (2000)  Design and synthesis of potent thiol-based inhibitors of endothelin converting enzyme-1.,  10  (17): [PMID:10987444] [10.1016/s0960-894x(00)00403-0]

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