2-(1-((S)-2-mercapto-3-methylbutanamido)cyclopentanecarboxamido)-3-(3'-(trifluoromethyl)biphenyl-4-yl)propanoic acid

ID: ALA2297550

PubChem CID: 76316776

Max Phase: Preclinical

Molecular Formula: C27H31F3N2O4S

Molecular Weight: 536.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)[C@H](S)C(=O)NC1(C(=O)NC(Cc2ccc(-c3cccc(C(F)(F)F)c3)cc2)C(=O)O)CCCC1

Standard InChI:  InChI=1S/C27H31F3N2O4S/c1-16(2)22(37)23(33)32-26(12-3-4-13-26)25(36)31-21(24(34)35)14-17-8-10-18(11-9-17)19-6-5-7-20(15-19)27(28,29)30/h5-11,15-16,21-22,37H,3-4,12-14H2,1-2H3,(H,31,36)(H,32,33)(H,34,35)/t21?,22-/m0/s1

Standard InChI Key:  ZSJJOBOSYOMLJX-KEKNWZKVSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2297550

   2-[[1-[[(2S)-3-methyl-2-sulfanylbutanoyl]amino]cyclopentanecarbonyl]amino]-3-[4-[3-(trifluoromethyl)phenyl]phenyl]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: 536.62

Molecular Weight (Monoisotopic): 536.1957

AlogP: 4.87

#Rotatable Bonds: 9

Polar Surface Area: 95.50

Molecular Species: ACID

HBA: 4

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.83

CX Basic pKa: ┄

CX LogP: 5.58

CX LogD: 2.33

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.34

Np Likeness Score: -0.53

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