3-(biphenyl-4-yl)-2-(1-((R)-2-mercapto-4-(methylthio)butanamido)cyclopentanecarboxamido)propanoic acid

ID: ALA2297564

PubChem CID: 76327684

Max Phase: Preclinical

Molecular Formula: C26H32N2O4S2

Molecular Weight: 500.69

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C26H32N2O4S2/c1-34-16-13-22(33)23(29)28-26(14-5-6-15-26)25(32)27-21(24(30)31)17-18-9-11-20(12-10-18)19-7-3-2-4-8-19/h2-4,7-12,21-22,33H,5-6,13-17H2,1H3,(H,27,32)(H,28,29)(H,30,31)/t21?,22-/m1/s1

Standard InChI Key:  VBTCEOFCVYGVOQ-FOIFJWKZSA-N

Molfile:  

     RDKit          2D

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    8.2767   -2.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.5125   -1.9918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3386   -1.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.3323   -0.5605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5030   -0.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0974   -1.2827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1600   -5.5762    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  0
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 22 25  1  0
 17 31  1  0
 19 32  1  0
 32 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2297564

   2-[[1-[[(2R)-4-methylsulfanyl-2-sulfanylbutanoyl]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: 500.69

Molecular Weight (Monoisotopic): 500.1803

AlogP: 3.95

#Rotatable Bonds: 11

Polar Surface Area: 95.50

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.97

CX Basic pKa: ┄

CX LogP: 4.47

CX LogD: 1.29

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.35

Np Likeness Score: -0.44

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