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

ID: ALA2297552

PubChem CID: 76334943

Max Phase: Preclinical

Molecular Formula: C26H32N2O4S

Molecular Weight: 468.62

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C26H32N2O4S/c1-2-8-22(33)23(29)28-26(15-6-7-16-26)25(32)27-21(24(30)31)17-18-11-13-20(14-12-18)19-9-4-3-5-10-19/h3-5,9-14,21-22,33H,2,6-8,15-17H2,1H3,(H,27,32)(H,28,29)(H,30,31)/t21?,22-/m1/s1

Standard InChI Key:  MJEAJLOGMRNZPB-FOIFJWKZSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    3.0075   -6.4823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4241   -7.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8364   -6.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0158   -8.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8408   -8.4698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0976   -7.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7632   -7.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6614   -6.4773    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4218   -5.7666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0718   -5.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8968   -5.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6571   -5.0484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0674   -4.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3130   -6.4724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3087   -5.0434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1825   -6.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7632   -5.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7721   -7.2005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8932   -4.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3034   -3.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8887   -2.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0595   -2.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6529   -3.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2953   -2.1897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1214   -2.1874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5307   -1.4676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1151   -0.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2858   -0.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8803   -1.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1971   -5.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0216   -5.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4578   -4.4013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9383   -5.7597    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  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
 13 19  2  0
 19 20  1  0
 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  6
 30 31  1  0
 31 32  1  0
 17 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2297552

   3-(4-phenylphenyl)-2-[[1-[[(2R)-2-sulfanylpentanoyl]amino]cyclopentanecarbonyl]amino]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: 468.62

Molecular Weight (Monoisotopic): 468.2083

AlogP: 3.99

#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: 4.78

CX LogD: 1.60

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.40

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