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

ID: ALA2297555

PubChem CID: 76320476

Max Phase: Preclinical

Molecular Formula: C27H34N2O4S

Molecular Weight: 482.65

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C27H34N2O4S/c1-2-3-11-23(34)24(30)29-27(16-7-8-17-27)26(33)28-22(25(31)32)18-19-12-14-21(15-13-19)20-9-5-4-6-10-20/h4-6,9-10,12-15,22-23,34H,2-3,7-8,11,16-18H2,1H3,(H,28,33)(H,29,30)(H,31,32)/t22?,23-/m0/s1

Standard InChI Key:  FYKGXPQHPALQCK-WCSIJFPASA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
    2.8116  -13.3281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2283  -14.0448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6406  -13.3256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8199  -15.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6449  -15.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9017  -14.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5674  -14.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4656  -13.3231    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2259  -12.6124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8759  -12.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7009  -12.6049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4613  -11.8942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8716  -11.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1172  -13.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1128  -11.8893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9866  -13.3306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5674  -12.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5763  -14.0464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6974  -11.1804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1076  -10.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6929   -9.7513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8636   -9.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4571  -10.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0995   -9.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9256   -9.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3349   -8.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9192   -7.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0900   -7.6104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6844   -8.3264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0013  -11.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8258  -11.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2619  -11.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7424  -12.6056    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8736  -10.5193    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
 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  1
 30 31  1  0
 31 32  1  0
 17 33  1  0
 32 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2297555

   3-(4-phenylphenyl)-2-[[1-[[(2S)-2-sulfanylhexanoyl]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: 482.65

Molecular Weight (Monoisotopic): 482.2239

AlogP: 4.38

#Rotatable Bonds: 11

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: 5.23

CX LogD: 2.05

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.36

Np Likeness Score: -0.23

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