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

ID: ALA2297561

PubChem CID: 76309557

Max Phase: Preclinical

Molecular Formula: C24H28N2O5S

Molecular Weight: 456.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C(Cc1ccc(-c2ccccc2)cc1)NC(=O)C1(NC(=O)[C@H](S)CO)CCCC1

Standard InChI:  InChI=1S/C24H28N2O5S/c27-15-20(32)21(28)26-24(12-4-5-13-24)23(31)25-19(22(29)30)14-16-8-10-18(11-9-16)17-6-2-1-3-7-17/h1-3,6-11,19-20,27,32H,4-5,12-15H2,(H,25,31)(H,26,28)(H,29,30)/t19?,20-/m1/s1

Standard InChI Key:  IPKPCECYBQKZCG-GFOWMXPYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    3.1075  -29.2115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5241  -29.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9364  -29.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1158  -31.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9408  -31.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1976  -30.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8632  -30.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7614  -29.2065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218  -28.4958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1718  -28.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9968  -28.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7571  -27.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1674  -27.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4130  -29.2016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4087  -27.7726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2825  -29.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8678  -28.5008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8721  -29.9297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2781  -27.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9932  -27.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4034  -26.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9887  -25.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1595  -25.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7529  -26.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3953  -24.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2214  -24.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6307  -24.2012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2151  -23.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3858  -23.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9803  -24.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0428  -28.5033    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8635  -27.0718    0.0000 O   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
 17 19  1  6
 13 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 13  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 22 25  1  0
 17 31  1  0
 19 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2297561

   2-[[1-[[(2R)-3-hydroxy-2-sulfanylpropanoyl]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: 456.56

Molecular Weight (Monoisotopic): 456.1719

AlogP: 2.19

#Rotatable Bonds: 9

Polar Surface Area: 115.73

Molecular Species: ACID

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.93

CX Basic pKa: ┄

CX LogP: 2.77

CX LogD: -0.44

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.37

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