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

ID: ALA2297557

PubChem CID: 76320477

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-/m0/s1

Standard InChI Key:  VSWMKFWTWGIJGV-WCSIJFPASA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
   17.8533  -13.4656    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2700  -14.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6823  -13.4631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8616  -15.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6866  -15.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9434  -14.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6091  -14.6690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5073  -13.4606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9176  -12.7449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7426  -12.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5030  -12.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9133  -11.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1588  -13.4557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1545  -12.0268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0283  -13.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6091  -12.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6180  -14.1839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7390  -11.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1493  -10.6030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7346   -9.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9053   -9.8940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4988  -10.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1412   -9.1730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9673   -9.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3766   -8.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9609   -7.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1317   -7.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7261   -8.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0070  -12.0287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6278  -11.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8037  -11.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2589  -12.7295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0727  -10.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7842  -12.7660    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  1
 29 30  1  0
 30 31  1  0
 30 33  1  0
 16 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2297557

   2-[[1-[[(2S)-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