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

ID: ALA2297560

PubChem CID: 76327683

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)NC(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+/m1/s1

Standard InChI Key:  OGXZPPQKOPSYNJ-APBNVXTGSA-N

Molfile:  

     RDKit          2D

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   17.4664  -20.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8748  -19.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0619  -21.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8791  -21.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.4641  -18.6643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   20.3280  -19.3634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3237  -17.9480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   19.0863  -15.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6836  -16.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3105  -15.1212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1287  -15.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5342  -14.4103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1224  -13.7034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3010  -13.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8993  -14.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2260  -17.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0051  -18.6754    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.0431  -17.9534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8125  -17.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2161  -16.5437    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
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  1 16  1  0
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 13 19  2  0
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 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 13  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 21 24  1  0
 17 30  1  0
 17 31  1  1
 30 32  1  1
 30 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2297560

   2-[[1-[[(2S,3R)-3-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: 3.90

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. 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